The Florida Keys: 49 Must Dos for Your Ultimate Dream Vacation

For the Christmas holidays in 2020, we decided to give a few small gifts but take a big trip. The girls were excited about going to Disney World, Brandon and I? The Florida Keys!

We had a great time, and ever since then, I have thought of going back and spending a week just relaxing and enjoying the area, spending most of my time writing.

Next summer, I’m getting that chance as we celebrate a big milestone for my mother (she’s turning 29 again, y’all).

So, this one will be laid out differently in two aspects. One, we are covering the entire Florida Keys; two, I won’t be covering just places I’ve been but places I want to go. And in June 2025, I’ll update it!

If you’re flying in and have a little extra time before heading down to the Keys, check out Everglades National Park.

Now, let’s get this party started.

Things to Know About the Florida Keys Before You Go

The Florida Keys are a string of tropical islands stretching about 120 miles off the southern tip of Florida, known for their laid-back atmosphere, stunning natural beauty, and vibrant history. Before you embark on your adventure, here are some things to know about the area’s rich past and why it’s a destination worth exploring.

A Fascinating History

The Florida Keys have a deep and diverse history, starting with the Native American tribes that called the islands home as early as 800 ACE. The Calusa and Tequesta tribes were the first to settle, living off the area’s abundant marine life and natural resources.

In 1513, Spanish explorer Juan Ponce de León sailed through the region and named the islands Los Martires—”the martyrs”—due to the islands’ jagged appearance from afar. While the Spanish mapped the Keys to aid in navigating the Florida Straits, they found little value in settling the islands.

It wasn’t until the 19th century that the first permanent settlers, like American merchant John Simonton, established themselves in the area. By 1822, Simonton had purchased the island of Key West, and it became a bustling port town. Key West flourished in the mid-1800s, mainly due to the wrecking industry, profiting from ships wrecked on the surrounding reefs. At its peak, Key West was Florida’s largest city and a hub for trade with Cuba and the Bahamas.

The islands dominated the sponge trade and held a U.S. monopoly for over 50 years.

Why Visit the Florida Keys?

The Florida Keys are one of the most unique destinations in the United States, offering an unparalleled mix of natural beauty, history, and outdoor activities. Here’s why the Keys should be on your travel bucket list:

• Natural Beauty: The turquoise waters and thriving marine ecosystems make the Keys a paradise for nature lovers. The Florida Keys are home to the only living coral reef in the continental United States, providing visitors with world-class opportunities for snorkeling and diving.
• Outdoor Activities: Whether you’re into sailing, kayaking, paddleboarding, or scuba diving, there’s no shortage of water-based activities. Each island offers adventures, from peaceful paddleboard trips through mangroves to heart-pounding deep-sea diving excursions.
• Fishing Haven: The Florida Keys are famous for their fishing, attracting anglers from around the world. You can try everything from deep-sea fishing to tournament fishing or cast a line off a dock for a more laid-back experience.
• Year-Round Sunshine: The Keys boast a sub-tropical climate, making it a year-round destination with warm temperatures. December through March is the prime time to visit, as you’ll avoid the risk of hurricanes while enjoying mild, sunny weather.
• Unique Character: Each region of the Florida Keys has its personality. Whether you’re exploring the quirky charm of Key West, the natural beauty of Islamorada, or the peaceful seclusion of Big Pine Key, you’ll find the Keys offer a vibe that’s worlds away from mainland Florida’s bustling cities and theme parks.
• History & Architecture: Besides their natural splendor, the Florida Keys are rich with historic architecture and cultural experiences. Key West, in particular, is known for its well-preserved 19th-century homes, museums, and lively nightlife.
• Delicious Food: The fresh, local cuisine of the Keys is another highlight. Enjoy seafood caught right off the coast, prepared with a Caribbean twist. Be sure to try signature dishes like conch fritters, spiny lobster, and the world-famous Key lime pie.

When is the Best Time to Visit the Florida Keys?

The Florida Keys are a year-round destination with warm weather and plenty of sunshine. However, each season offers its own unique experiences and considerations. Here’s a breakdown of what you can expect during different times of the year to help you plan your perfect getaway:

Winter (December–March)
Thanks to its pleasant, mild weather and limited rainfall, Winter is the most popular season to visit the Florida Keys. With temperatures averaging in the mid-70s°F, it’s ideal for outdoor activities, including boating, fishing, and exploring the islands.

The winter brings the slightest chance of rain and offers excellent conditions for those escaping colder climates. However, this is also the busiest time of year, with holiday travelers and snowbirds flocking to the islands, so expect higher prices for accommodations and attractions.
Best for: Sunshine seekers, fishing enthusiasts, and those wanting to avoid crowds in other tropical destinations.

Spring (March–June)
Spring is a fantastic time to visit the Florida Keys. The weather warms up, making it ideal for swimming, snorkeling, and wildlife watching. March through May offers fewer crowds compared to winter, and it’s also the perfect time to spot migratory birds and enjoy water activities like paddleboarding or fishing.
By June, the water temperatures rise, and the coral reefs come alive, making it one of the best months for snorkeling or diving. However, June also marks the beginning of hurricane season, so keep an eye on the weather forecast if you’re planning a summer visit.
Best for: Water sports, wildlife watching, and avoiding the winter crowds.

Summer (June–September)
Summer in the Florida Keys is all about warm waters and sunny days. Reminder, though, that hurricane season runs from June through November. The heat and humidity rise in the summer, and afternoon rain showers are common. Conversely, you’ll find fewer tourists and lower prices, especially in September.
For those who don’t mind the heat, summer is a great time to enjoy the island’s slower pace and explore the Keys’ natural beauty without the wintertime crowds.
Best for: Snorkeling, finding travel deals, and beating the crowds.

Fall (September–November)
Fall is another shoulder season that offers some perks for travelers, especially in September and October. September is one of the best times to score deals on hotels and activities, as it’s the least busy month of the year due to the risk of hurricanes.
By October, the weather begins to cool slightly, and one of Key West’s most famous events, Fantasy Fest, kicks off, bringing in a lively crowd. This is an excellent time to experience the quirky side of the Keys, but keep in mind that the festival brings travelers from all over, so plan accordingly.
Best for: Budget travelers, festival-goers, and those seeking a quiet island getaway in September.

Best Time to Go
If you’re looking for the perfect combination of pleasant weather, manageable crowds, and lower prices, late spring (April through early June) is the best time to visit the Florida Keys. You’ll enjoy warmer temperatures without the peak-season prices of winter, and it’s an ideal time for snorkeling, swimming, and exploring the islands’ outdoor beauty.

For holiday travelers, Christmas and New Year’s are also magical times to visit, offering a festive atmosphere and the chance to start a new tradition. However, be prepared for higher hotel rates and busy streets during the holiday season.

How to Get to the Florida Keys

Now that you’ve picked the time to visit let’s talk about how to get to the Florida Keys! Your route will depend on your budget, timeframe, and where you’re starting from. Whether flying in or taking a scenic drive, getting to the Keys is part of the adventure!

Flying to the Florida Keys

If you’re short on time or prefer flying, the Keys have two airports: Key West International Airport (EYW) and Florida Keys Marathon International Airport.

Flying directly into Key West is the easiest way to get to the southernmost part of the Keys. Direct flights are available from New York City, Asheville, Tampa, and Indianapolis. However, Key West flights tend to be pricier, so if you want to save, consider flying into Miami (MIA) or Fort Lauderdale (FLL) instead.

Driving to the Florida Keys

The Overseas Highway is the iconic 113-mile road connecting Miami to Key West. If you’re driving from Miami, it typically takes about four hours to reach Key West (though it didn’t take us that long on a holiday week), but traffic can sometimes slow you down, so plan for a little extra time—trust me, the ocean views and mangroves along the way make it worth it!

The highway begins at US-1 in Florida City, so if you’re coming from North or Central Florida, you’ll want to take the Florida Turnpike south to Exit 4 (Homestead/Key West), connecting you directly to Route US-1.

Keep in mind that speed limits are strictly enforced throughout the Keys, especially in areas like Big Pine Key, which is a Key Deer Refuge. Slow down and enjoy the drive!

Pro Tip: If you plan to explore the Upper and Lower Keys, consider booking one-way flights: fly into Miami or Fort Lauderdale and out of Key West. This way, you only have to do the entire drive once!

What To Pack for the Florida Keys?

Packing for the Florida Keys is about preparing for sun, sand, and water-based activities. Here’s a handy list of must-haves to ensure you’re ready for adventure in the islands.

• Swimsuit: Whether lounging by the pool or diving into the ocean, a swimsuit is a must-have. You might want to pack more than one, so you’ll always have a dry option ready.
• Beach Bag: You’ll need a sturdy beach bag to carry your essentials, such as towels, sunscreen, and snacks, for your day out on the sand. Look for a waterproof or sand-resistant option to keep your belongings safe and clean.
• Light-Colored Clothing: Light-colored, breathable clothing is perfect for the warm, sunny weather in the Keys. Think lightweight cotton or linen shirts, shorts, and dresses that keep you cool while exploring.
• Quick-Dry Clothing: Quick-dry clothing is essential when you’re moving between the beach and town. Pack a few moisture-wicking shirts, shorts, or cover-ups to make transitions from the water to dry land more comfortable.
• Reusable Water Bottle: Stay hydrated under the tropical sun with a reusable water bottle. Many accommodations and parks have refill stations, so you can save money and avoid single-use plastics.
  I will forever and always recommend Hydroflasks. 😉
• Comfortable Shoes: Comfortable shoes are a must, especially if you plan on walking around town or exploring nature trails. Flip-flops are perfect for the beach, but bring a pair of breathable sneakers or sandals with support for exploring.
• Lip Balm with SPF: The sun can be harsh on your lips, so bring a lip balm with SPF protection to prevent dryness and chapping.
• Water-Resistant Phone Case: You’ll want to capture all the memories on your phone, so a water-resistant case is a good idea to protect it from splashes, sand, or unexpected rain showers.
• Portable Charger: With all the photo ops and map checking, your phone’s battery can drain quickly. A portable charger ensures you stay powered up all day, especially if you’re out on a boat or away from outlets.
• Sunscreen (reef-safe): Protect your skin from the sun’s rays with a high-SPF sunscreen. Make sure it’s reef-safe if you plan on snorkeling or diving—this protects the coral reefs and marine life.
• Sunglasses and Hat: The Florida sun is intense, so pack a good pair of UV-protective sunglasses and a wide-brimmed hat to shield your face and eyes.
• Water Shoes: If you plan on exploring rocky beaches or paddleboarding, pack a pair of water shoes for extra comfort and protection.
• Snorkeling Gear: While many places offer gear rentals, bringing your own equipment (such as a mask, snorkel, and fins) can ensure a more comfortable fit and save you time.
• Insect Repellent: While the breeze often keeps mosquitoes at bay, it’s always wise to have some insect repellent on hand, especially during the summer or when exploring mangroves.
• Light Jacket or Sweater: The evenings in the Keys can get breezy, especially near the water, so it’s a good idea to bring a light jacket or sweater when the temperature dips at night.
• Dry Bag: If you’re going on boating or kayaking excursions, a dry bag will keep your valuables (like your phone, wallet, and camera) safe from water damage.
• Small First Aid Kit: To prepare for minor mishaps, pack a small kit with bandages, antiseptic wipes, pain relievers, and any personal medications.

Now that we’ve covered the basics, Let’s dive right in. We will cover the four major cities, with things to do based on distance from that location, starting closest to the mainland and moving outwards towards Key West/Cuba.

Key Largo

Where to stay

Hampton Inn- Manatee Bay

When choosing a place to stay in Key Largo, you can’t go wrong with the Hampton Inn. I am a huge fan of Hilton hotels because you know what to expect: comfort, quality, and consistent service. The Hampton Inn in Key Largo is no exception.

Conveniently located just 59 miles south of Miami International Airport, the Hampton Inn is an ideal spot to start your Florida Keys adventure. It’s just a short walk from to John Pennekamp Coral Reef State Park, home to the only living coral reef in North America.

The Hampton Inn’s lush, tropical setting on Florida Bay offers more than just proximity to the park—it’s also a perfect spot to watch the Florida sunset. With its laid-back island vibe, this hotel is a relaxing retreat after a day of exploring.

The rooms have a comfortable island feel and feature either a king-size bed or two full-size beds. They have all the modern amenities you need for a great stay, including an LCD flat-panel TV with free premium cable, complimentary high-speed wireless internet, a refrigerator, microwave, wet bar, and coffee maker.

Playa Largo Resort & Spa

Playa Largo Resort and Spa is a perfect choice in Key Largo if you’re looking for a luxurious escape with a tropical flair while still being budget-friendly. Tucked away on 14.5 acres of secluded beachfront, this resort is about laid-back elegance and oceanfront relaxation. The moment you step onto the property, you’re surrounded by dense foliage and sweeping views of Florida Bay, creating a peaceful oasis that’s worlds away from the everyday hustle.

One of the highlights of Playa Largo is its phenomenal pool. It’s the kind of place where you can spend an entire day unwinding in the warm sun, sipping a tropical drink from the sand bar, and dipping in and out of the crystal-clear waters. The pristine white sand beach just beyond the pool also invites you to relax or explore, offering all the joys of the ocean right at your doorstep.

Regarding dining, Playa Largo offers an impressive range of options right on-site. From the beach shack restaurant for casual, toes-in-the-sand dining to the ceviche bar where you can enjoy fresh seafood, there’s something for every palate. The full-service diner offers comfort food with a twist, making it easy to indulge without leaving the resort.

The resort spa lounge provides the perfect sanctuary for those needing a little pampering. After a morning of watersports or an afternoon exploring Key Largo’s natural beauty, you can retreat to the spa for a rejuvenating experience. Whether enjoying a massage, facial, or just some downtime in the serene atmosphere, it’s the perfect way to cap off a day in paradise.

Playa Largo’s mix of adventure and relaxation continues with their on-site watersports—kayaking, paddleboarding, and more are at your fingertips, making it easy to stay active and connected to the natural surroundings.

This sun-drenched tropical oasis is the perfect spot to slow down, reconnect, and enjoy Key Largo’s beauty.

Condo: It’s Island Time

For a home-away-from-home experience in the Florida Keys, Island Time at Ocean Pointe in Tavernier is a fantastic option. This recently renovated, super cute 2-bedroom condo in a gated resort can sleep up to six guests and offers the perfect blend of comfort and luxury. The decor is a vibrant mix of mid-century modern and tropical colors, reflecting the lively spirit of the Keys.

Ocean Pointe’s 60-acre resort offers plenty, including a Junior Olympic pool, a private beach, and an oversized hot tub for relaxing evenings. Active guests will enjoy the on-site tennis and pickleball courts, while the nearby marina is perfect for evening strolls. Nature lovers will appreciate the condo’s balcony, which overlooks a nature conservation area with an osprey nest.

Inside, the condo features a fully equipped kitchen, an open floor plan, and a cozy living room with a custom queen sleeper sofa. For added convenience, you’ll also find an HDTV with cable, free WiFi, and an in-unit washer/dryer. With 24-hour security and local managers ready to assist, Island Time offers a worry-free retreat in the heart of the Keys.

Entire Home: New Mariners Club Listing

The New Mariner’s Club offers an ideal blend of comfort and convenience for those seeking a luxurious, resort-style stay in Key Largo. This gated, private community is ideally located on the island’s ocean side, giving you direct access to world-class snorkeling, diving, and fishing. The townhouse is in a prime spot, nestled between two pristine pools and just steps from the marina and community center.

What got me about this place was its amenities. The resort boasts two pools, including the most significant oceanfront pool in the Florida Keys, a jacuzzi grotto, and a fully equipped fitness center. There are pickleball, tennis, and basketball courts, a game room, and tiki huts for lounging in the sun.

They also have a 200-foot pier that leads straight to the ocean, where you’ll find Molasses Reef, a top-rated dive reef in North America. The 43-slip marina accommodates boats up to 60 feet and offers direct ocean access for your adventures at sea.

John Pennekamp Coral Reef State Park

While all these options are great, I will always be slightly biased towards staying at a campground or somewhere in nature. However, I recommend booking your stay reasonably far in advance, as the campgrounds book quickly. For my van lifers out there- the Florida Keys has a fairly strict no overnight camping/parking rule.

John Pennekamp Coral Reef State Park’s campground offers 47 sites for tent and RV campers, each equipped with water, electric hookups (30 amp, 50 amp, and 110 volts), a picnic table, and a grill. There’s a dump station for RVs, and the Main Restroom provides hot showers and ADA-compliant facilities. Pets are welcome, and reservations are recommended, especially during winter when sites book up months in advance.

Campers can access many outdoor activities, including fishing in designated areas (with a Florida saltwater fishing license) and swimming at one of three beach areas. Canon Beach is especially unique, with remnants of an early Spanish shipwreck just 100 feet offshore, perfect for a quick snorkel.

Where to eat

Bayside Grille & Sunset Bar

Before leaving the islands to head back to Texas, we stopped here to grab a bite to eat. It’s been almost four years, and I don’t remember the food that much. What I remember is that the scenery was very nice. We sat outside near the water, and Brandon got some great pictures of the boats. I also remember that he bought a drink for us to share, and it was very delicious—the perfect kind of drink for the Florida Keys.

C & C Wood-fired Eats

If you’re looking for something different from the usual Florida Keys dining experience, C&C Woodfired Eats should be at the top. I am putting it on mine, anyway.

The first restaurant in Key Largo to feature a Neapolitan wood-burning oven (which you know I love), C&C offers a mouthwatering selection of wood-fired pizzas, house-made specialties, and fresh, carefully chosen ingredients that set it apart from the crowd.

While the menu may have an Italian influence, it’s tailored to be unique to Key Largo, offering something for every palate. And while I may be a pizza girl, the wood-fired steaks sound equally as delicious.

One of the highlights is their rotating selection of artisan cheeses and meats used to create cheese boards. These selections change with availability and seasonality, ensuring each visit feels fresh and exciting. The best part? You can even take your cheese board home to enjoy later!

For adults, C&C boasts an impressive and ever-changing selection of wines, craft beers, and adult beverages, all hand-picked for variety and quality. Whether you’re there for a glass of wine with your pizza or to try something new, the drink menu never disappoints.

Key Largo Conch House

For an authentic taste of the Florida Keys, stop by Key Largo Conch House. Family-owned and operated since 2004, this second-generation seafood restaurant has gained recognition for its commitment to fresh, local ingredients and its charming, laid-back atmosphere. The restaurant’s Key West-inspired vibe, complete with a fun sign showing how far you are from various destinations, adds to its unique appeal.

The Conch House has earned its place in the spotlight, having been featured on The Travel Channel, Food Network, Emeril’s Florida, and more. Known for serving only the best seasonal produce and seafood from local farmers and markets, every dish is fresh and flavorful, no matter when you visit.

Whether you’re in the mood for a latte, cappuccino, or espresso, the Conch House only serves Segafredo coffee, ensuring that even your caffeine fix is top-notch. The caring and dedicated staff are committed to providing an excellent dining experience, making the Conch House a must-visit for delicious, locally sourced food in a warm and welcoming setting.

What to do

Start by Visiting the Florida Keys Visitor Center

As you enter the Florida Keys, your first stop should be the Florida Keys Visitor Center in Key Largo. After crossing the stunning Jewfish Creek Bridge, you’ll find the center right where the road bends—an easy and convenient stop on your adventure.

This friendly spot is packed with information to help you plan your time in the Keys. From recommendations on where to go and what to see to tips on securing discounts, the Visitor Center is a great resource. It’s also a fun photo opportunity with a couple of beach chairs perfect for capturing those “Welcome to the Keys” moments.

If you stop in, say hi to Dave, a well-loved employee who’s always ready to offer his expert advice and make your visit even better.

Visit Christ of the Deep

For visitors looking to experience the underwater beauty of Key Largo, John Pennekamp Coral Reef State Park is the perfect spot. As the first undersea park in the U.S., it offers one of the best snorkeling opportunities right from the beach—no boat needed! For those with a Florida State Parks Pass, entry is free, and if not, it’s just $8 per vehicle, a cheaper option than snorkeling tours.

Established in 1963, the park spans approximately 70 nautical square miles and is home to mangrove swamps, tropical hammocks, and stunning coral reefs. The park is best known for its diverse marine life and vibrant coral formations, which attract snorkelers, divers, and nature enthusiasts from all over. Visitors can also take a glass-bottom boat tour to see the reefs without getting wet or get closer by scuba diving or snorkeling.

If you prefer to stay above water, canoeing and kayaking through the park’s waters are popular activities, and there are designated areas for fishing. On land, visitors can enjoy walking trails, picnicking, or swimming at the beach. The Visitor Center features a 30,000-gallon saltwater aquarium and regularly shows nature videos. The park even provides free Wi-Fi at the Concession and Dive Shop buildings.

Named after John D. Pennekamp, a Miami newspaper editor who played a crucial role in preserving the park, the area has been a treasure of the Florida Keys for decades. With its coral reefs, marine life, and tropical vegetation, John Pennekamp Coral Reef State Park is a must-visit destination in Key Largo.

See the Birds at the Florida Keys Wild Bird Sanctuary

If you’re an animal lover, the Florida Keys Wild Bird Center in Key Largo is a heartwarming and educational stop. This not-for-profit organization is dedicated to rescuing, rehabilitating, and releasing native and migratory wild birds that have been harmed or displaced. The center’s mission extends to providing a permanent home for birds that cannot be released and educating the public about the importance of protecting these fragile species and the unique ecosystems of the Florida Keys.

At the Laura Quinn Wild Bird Sanctuary, you’ll encounter over 100 permanent resident birds, including hawks, owls, pelicans, and more. The sanctuary is open every day from sunrise to sunset, and admission is free, though donations are gladly accepted to help support their work.

The center’s history is a testament to one woman’s passion for wildlife. Laura Quinn began her journey by rescuing and rehabilitating birds from behind her oceanfront home and eventually expanded to the 5.5-acre sanctuary that stands today. Her legacy continues to inspire the center’s efforts to protect and care for the birds of the Florida Keys.

This is a free, family-friendly activity where you can learn about local wildlife, enjoy a peaceful walk, and even closely examine some rescued birds. It’s a beautiful way to give back to the community and support the center’s vital work for Florida’s native bird population.

Islamorada

Where to stay

La Jolla Hotel

For those looking to experience the charm of “Old Florida,” La Jolla Resort in Islamorada is the perfect bayside retreat. Located at Mile Marker 82, this budget-friendly hotel offers a laid-back, local vibe with updated accommodations and a touch of retro-inspired style. It’s an excellent option for budget travelers or anyone wanting a more authentic Keys experience.

With six colorful, recently renovated buildings, La Jolla offers a variety of rooms and suites, each designed to make you feel like you’ve stepped back in time. The resort may not have all the frills of some of the larger properties. Still, it more than makes up for it with its complimentary amenities, including kayak, paddle board, and bicycle rentals available on a first-come, first-served basis.

One of the best parts of staying at La Jolla Resort is its bayside location, which gives you front-row access to stunning Islamorada sunsets. With a small, outdoor freshwater pool, a peaceful atmosphere, and proximity to local attractions, La Jolla Resort is an ideal choice for fishermen, families, or couples looking to embrace the simple beauty of the Florida Keys.

ocean-view condo with 2 balconies

For a serene and peaceful escape in Islamorada, this tropical oceanfront condo offers stunning water views and gentle breezes from not one but two private balconies. Located on the top floor, this condo is the perfect place to unwind and take in the beauty of the Florida Keys.

On-site, you’ll have access to various amenities, including a community pool, a waterfront café, and Ocean Pointe’s private beach, just a short walk away. Whether you’re into deep-sea fishing, visiting the nearby Laura Quinn Wild Bird Sanctuary, or snorkeling at John Pennekamp Coral Reef State Park, this condo provides easy access to the area’s best activities.

Inside, the condo is bright and airy, with coastal decor reflecting the beauty of the surrounding waters. The well-equipped kitchen makes it easy to prepare meals to enjoy at the cozy dining table, while the living area is perfect for relaxing with a movie after a day of adventure. You’ll have all the essentials, including central air-conditioning and a private washer/dryer to refresh your clothes before heading out for another fun day.

Lady blue yacht

For an unforgettable stay in the Florida Keys, why not spend your vacation aboard the Lady Blue Yacht? This one-of-a-kind rental in sunny Marathon offers a private, cool indoor space and an outdoor “salt life” experience. Whether lounging inside or taking in the fresh ocean breeze outside, Lady Blue offers a unique way to enjoy the Keys.

You’ll likely spot manatees, dolphins, and other marine life from the deck, making it a perfect spot for animal lovers and those who want a closer connection to the sea. The central location in the Florida Keys puts you close to many local attractions, but the real highlight is the peaceful experience of staying on the water.

Encore Fiesta Key Camping

Fiesta Key RV Resort is a fantastic option for a perfect blend of relaxation and adventure. Located on a 28-acre island parcel, this resort is surrounded by stunning Gulf of Mexico views. It offers a variety of ways to stay, whether you’re hooking up your RV, checking into one of the resort’s rentals, or staying in the on-site hotel.

The resort has a laid-back, tropical feel and is packed with full amenities. Unplug and unwind as you explore the on-site marina, pool, spa, and beach bar. While there’s no cable TV, you won’t miss it with so much to see and do, from sunset views to fun activities. If you need to stay connected, there’s free Wi-Fi in the community center.

Fiesta Key is close to several popular attractions, including Long Key State Park, the Dolphin Research Center, and Bud ‘N’ Mary’s famous fishing marina.

Where to eat

Starbucks

Now, other than going to two reserve roasteries (in New York and Chicago), I typically do not recommend going to a Starbucks. However, their sign makes me want to go in. I mean, it’s the last Starbucks for 80 miles. What’s a girl to do?!

cafe mocha

But if you’re a mom-and-pop coffee shop enthusiast, Café Mocha is a must-visit in Islamorada. It’s the first coffee shop in the area that offers latte art. This might seem like a small detail, but it says a lot—the milk is properly steamed, and the barista takes extra care to craft something special for every customer. It’s more than just a cup of coffee; it’s an experience.

Located in the charming Village Square at Trading Post, Café Mocha features a cute, ocean-blue espresso machine and a cozy space, complete with a heart-shaped chair perfect for snapping Instagram-worthy photos. They also offer seasonal drinks, so there’s always something new to try.

Village Square has several unique small businesses, including Miss Monroe Boutique, Bad Boy Burrito, and Urbn Grdn. Whether you’re shopping for clothes, grabbing a bite, or even attending a morning yoga class in the garden, Café Mocha is the perfect coffee stop during your day in Islamorada.

Islamorada shrimp shack

If you want some of the best seafood in the Florida Keys, head to the Islamorada Shrimp Shack. This family-owned gem has been serving delicious, homemade recipes since 2011 and has become a staple for locals. Run by the mother-daughter team of Jill and Morgan, the Shrimp Shack brings their family’s best dishes straight from their kitchen to your plate.

The restaurant gained national attention when featured on Diners, Drive-Ins, and Dives in 2016. Guy Fieri couldn’t get enough of their shrimp fritters and ‘Senator’ style local catch—both must-try dishes if you’re a seafood lover.

Be sure to also try their locally famous Shrimp and Grits, a crowd favorite. If you prefer something other than seafood, the Chicken Continental is equally tasty. With made-to-order food and a friendly team of ‘Shrimpettes’ serving you with a smile, the Islamorada Shrimp Shack is a must-visit spot for some mouthwatering seafood and cocktails.

Tiki Bar

For a classic Keys experience, visit the Tiki Bar at Three Waters Resort and Marina. Reopening this fall, this poolside favorite is the perfect spot to relax with a tropical cocktail, whether hopping out of the pool or just looking to soak in the laid-back island vibes.

Open daily for lunch and dinner, the Tiki Bar offers a tempting menu of tacos, island-inspired seafood specialties, and classic American bar bites. Of course, no meal is complete without a slice of authentic Key Lime Pie, served beneath the swaying palms for that perfect Florida Keys touch.

If you’re a local, ask about the Conch card for extra perks!

What to do

Florida Keys Farmers Market

If you are planning to stay in the Florida Keys for a while and are looking for somewhere to cook, be sure to check out the farmers’ market.

Every Sunday, the Florida Keys Farmers Market brings fresh, local, and sustainable shopping to Islamorada. Located at Mile Marker 81, this outdoor market is a vibrant spot where residents and visitors can enjoy paradise while supporting local vendors. Free parking and live music make it the perfect way to spend a laid-back Sunday.

The market features various offerings, including artisan cheeses, select meats, fresh and local seafood, and organic produce. You’ll also find unique crafts, plants, orchids, baked goods, and fresh farm stand juices. Something new is offered each week, and the market showcases rotating chefs, artists, and vendors, making every visit special.

Pets are welcome on a leash, so bring your furry friends along.

Be sure to check out the colorful murals by Miami artist DaveL as you stroll through this outdoor oasis. Just look for the giant mermaid and enjoy a fun, fresh day at the Florida Keys Farmers Market.

Windley Key Fossil Reef Geological State Park

Located at Mile Marker 85.5, Windley Key Fossil Reef Geological State Park offers a fascinating look into the geological and historical roots of the Florida Keys. Once a quarry used by Henry Flagler in the early 1900s to construct the famous Overseas Railroad, the park now displays exposed sections of fossilized coral that date back millennia.

Visitors can explore the quarry and see some of the original machinery used to extract Keystone, a decorative stone made from fossilized coral. This Keystone can still be seen in landmarks like the Hurricane Monument at Mile Marker 82 in Islamorada, built using stone from this quarry.

Anne’s Beach

Located at Mile Marker 73.5 on Upper Matecumbe Key, Anne’s Beach is one of the few natural sandy beaches in the Florida Keys—and the best part? It’s free!

This charming beach park features two parking lots connected by a 1,300-foot boardwalk that winds through the mangroves. Six pavilions offer picturesque picnic spots.

After Hurricane Irma in 2017, the beach and boardwalk were rebuilt for $1.6 million, and today, it’s a beautiful place to explore. The water here is shallow, perfect for wading rather than swimming. Many visitors enjoy simply sitting in the sand flats and letting the water lap over them.

Anne’s Beach is also a popular spot for windsurfing, and if you visit on a breezy day, you can watch windsurfers swoop and glide across the water. The beach is dog-friendly, though pets must be kept on a leash.

Parking can be tricky, but there’s an additional lot about a block south of the beach that also serves the long bridge to Craig Key, a popular spot for fishing and strolling.

Named after local environmentalist Anne Eaton, who played a key role in preserving this stretch of beach, Anne’s Beach offers a peaceful, natural spot to enjoy the beauty of the Keys.

Morada Way Arts & Cultural District

Founded in 2011, the Morada Way Arts and Cultural District (MWACD) has become the cultural hub of the Upper Keys.

Located within a six-block corridor between the Green Turtle Inn and the Hurricane Monument, this lively downtown area is home to a thriving community of galleries, restaurants, and studio spaces. It’s the only true “Main Street” between Miami and Key West, offering a safe and vibrant gathering space for locals and visitors.

The MWACD’s mission is to foster an environment where artists can thrive, providing affordable studio and gallery spaces for emerging and established artists. The district channels arts and culture into surrounding parks, bike paths, and local businesses, making it a cornerstone of creativity in Islamorada.

Whether you’re visiting for one of their popular arts and cultural events or just exploring the area’s galleries and restaurants, Morada Way is the perfect place to experience the artistic pulse of the Florida Keys.

Robbie’s Marina

Brandon, the girls, and I had a great time at Robbie’s Marina, home to the world-famous tarpon feeding!

If you’re looking for fun things to do in Islamorada, Robbie’s offers a little of everything. Whether you’re feeding massive tarpon by hand, enjoying water sports, or browsing the local shops for handcrafted souvenirs, there’s something for everyone at this lively marina.

The excitement starts on the dock, where, for just $1, you can watch the fishy frenzy as Tarpon leaps out of the water. For $6, grab a bucket of bait and join in the fun—trust us, once you get started, you’ll want more than one bucket! It was thrilling for us to watch the giant fish compete with pelicans for snacks!

When ready for a break, head to the waterfront deck to enjoy fresh seafood and one of their signature cocktails. Whether you choose the famous Trailer Trash Bloody Mary or a local draft beer, you’ll have a front-row seat to the tarpon feeding show.

Marathon

Where to stay

Faro Blanco Resort and Yacht Club

During our trip to the Keys, Brandon, the girls, and I spent a night at Faro Blanco Resort & Yacht Club in Marathon, and we really enjoyed our stay. While we didn’t take advantage of many amenities, the room was spacious and perfect for the four of us. We had a bed, Breanna had her own, and Vaeh, in her usual way, chose to sleep on the sofa without even pulling it out.

We visited during Christmas, and the tree in the lobby was absolutely gorgeous, adding to the festive feel of our stay.

Faro Blanco offers a lot as for the hotel itself. It’s part of the Curio by Hilton collection, and with four outdoor pools, a marina, and a poolside bar, it’s a great place to relax. The hotel also features a 24-hour health club, and guests can enjoy drinks at the beach or dine at one of four restaurants, including El Farito, for breakfast. The staff is friendly and helpful, and for a reasonable fee, the hotel is dog-friendly.

The Cabins at Bonefish Bay

If you’re looking for a unique, family-friendly stay in Marathon, the Cabins at Bonefish Bay are a fantastic choice. With a 10/10 rating on hotels.com, these cozy yet spacious cabins offer the perfect blend of comfort and convenience.

Each cabin has full bathrooms, kitchens, and flat-screen TVs, giving guests all the amenities of home while enjoying the natural beauty of the Keys. The property includes access to a boat ramp and dock space for those bringing boats or water toys, plus a big pool, free bikes, and kayaks for guests to use during their stay. With free WiFi, parking, and a quiet location set back from the road, you’ll have all the privacy you need to relax and enjoy your time in the Keys.

Located just minutes from Sombrero Beach, the cabins provide a peaceful retreat yet are close to everything Marathon offers.

Curry Hammock State Park

For those looking to experience the natural beauty of the Florida Keys, Curry Hammock State Park is a hidden gem. As the largest undeveloped parcel of land between Key Largo and Big Pine Key, the park offers a peaceful retreat with spacious campsites, breathtaking sunrises, and a pristine beach.

The park’s 28 campsites include electrical service, water, picnic tables, charcoal grills, and hammock posts. Some sites offer ocean views and beach access is available between sites 13 and 15. The campground also features a bathhouse with hot showers and a fire pit for campers on the west end of the beach.

Curry Hammock is known for its rich ecosystem, protecting large areas of mangrove swamps, rockland hammocks, and seagrass beds essential to the Keys. The park is a haven for wildlife, especially during the fall when it hosts record numbers of peregrine falcons.

There is plenty to keep you active, whether paddling on calm days, kiteboarding on windy days, or exploring the Overseas Heritage Trail by bike or foot. The park also offers kayak, SUP, bike rentals, and ranger-led tours for those looking to dive deeper into the local environment.

Where to eat

Georgie’s Coffee Shop

If you’re a coffee lover with a soft spot for dogs, Georgie’s Coffee Shop is a must-visit on your way through the Keys. Located at Mile Marker 59.3, this cute, dog-themed coffee spot serves specialty Cuban coffee, homemade pastries, and empanadas in a cozy, welcoming environment.

Though the shop is relatively new, it’s already making waves for its clean, upscale interior and friendly staff. Iced coffees are a popular choice (though they don’t have cold brew), and their key lime beignets and meat-filled empanadas are standout menu items.

bongo’s botanical beer garden

In my head I’m saying, “Oh yeah, this is so happening.”

For a truly unique experience in Marathon, Bongo’s is a must-visit. This laid-back oasis offers a tropical garden seating area, tiki bar, and a one-of-a-kind cable park lagoon where you can watch wakeboarders of all ages practicing their skills.

Bongo’s is known for its tiki cocktails, crafted with fresh, local ingredients and garnished with fruit from their on-site gardens. The food is served from a permanent food truck on the property, offering a rotating menu of Caribbean and Polynesian-inspired bowls and wraps, small plates, and daily specials. Everything is beautifully prepared with fresh, healthy ingredients.

A favorite among locals, Bongo’s also features over 20 craft beers on tap, signature cocktails, and plenty of relaxing spaces to kick back, like their hammock chairs. Whether strolling through the botanical garden or playing lawn games, it’s the perfect spot to unwind and enjoy a taste of the Keys.

Castaway Waterfront Restaurant And Sushi Bar

A local favorite in Marathon, the Castaway Waterfront Restaurant and Sushi Bar offers a diverse menu perfect for breakfast, lunch, and dinner. Known for its blend of southern seafood, sushi, steaks, and Asian-influenced cuisine, The Castaway has something for everyone. With a full bar and 32 beers on tap, it’s an excellent spot for casual meals and special nights out.

The Castaway has a long history, dating back to 1951, when it was originally known for serving beer and shrimp steamed in beer, a favorite among the local shrimpers. It was featured on Diners, Drive-ins, and Dives, further solidifying its reputation as a must-visit in the Keys.

If you’re dining here, book a reservation a day or two in advance, especially for dinner.

What to do

Turtle hospital

Since opening in 1986, the Turtle Hospital has been dedicated to rehabilitating injured sea turtles and returning them to their natural habitat. With a mission that includes educating the public, conducting important research into diseases affecting sea turtles, and working toward environmental legislation, The Turtle Hospital has become vital to protecting sea turtles in the Keys and beyond.

The hospital has successfully treated over 3,000 sea turtles and offers guided 90-minute educational programs daily, rain or shine. During these programs, guests get a behind-the-scenes look at the hospital facilities and rehabilitation area. You’ll learn how the hospital treats turtles with ailments like fibropapillomatosis, shell damage, and entanglement injuries, and at the end of the tour, you can even feed some of the permanent residents. While it is a non-interactive experience, meaning no direct handling of the turtles, it must still be incredibly educational and rewarding.

Reservations are highly recommended, and the $35/ adult admission fees help support their work.

Seven Mile Bridge

The Seven Mile Bridge is not only a key connection between Key Vaca in the Middle Keys and Little Duck Key in the Lower Keys, but it’s also a breathtaking drive and one of the most iconic landmarks in the Florida Keys. Spanning 6.79 miles, this bridge offers incredible views of the Gulf of Mexico and the Florida Strait.

This location has two bridges: the older bridge, built by Henry Flagler as part of the Overseas Railroad in the early 1900s, and the modern bridge, constructed from 1979 to 1982. Though damaged by hurricanes, the older bridge is now used for fishing and as access to Pigeon Key, while the new bridge serves as the primary route for vehicles along US 1.

Brandon, the girls, and I spent a lot of time on and around the bridge during our trip. We drove over the vehicle bridge multiple times and stopped on numerous occasions. Once, we went kayaking in the crystal blue waters, and another time, we made a special New Year’s Eve dinner with the stunning sunset as a backdrop.

And for the pedestrian bridge? This is where we fished most of the time we were there.

Interesting Tip: This stretch of road was used for the movie 2 Fast 2 Furious.

Key West

Where to stay

Hampton Inn Key West

The Hampton Inn in Key West is an excellent choice for a stay that combines comfort and convenience. Located just half a mile from Key West International Airport and only two minutes from Smathers Beach, the hotel offers a free local shuttle to get you around easily. Popular attractions like Fort Zachary Taylor, Mallory Square, and the Southernmost Point are all within a five-mile radius.

Guests can enjoy various amenities, including a complimentary hot breakfast, free Wi-Fi, free parking, and a heated outdoor pool with ocean views. The pool area features a fire pit and a bar and grill, making it the perfect spot to unwind after exploring.

The guest rooms are designed for relaxation, offering mini-fridges, microwaves, HDTVs, and laptop-sized safes. Many rooms also feature ocean views, giving you a stunning backdrop for your stay, and the hotel is pet-friendly.

parrot key hotel and villas

Step into a tropical paradise at Parrot Key Hotel & Villas, where white sand terraces, glimmering pools, and lush native landscaping surround the most spacious accommodations in Key West. Whether you’re staying in a room, suite, or villa, you’ll be immersed in the serene beauty of this intimate hideaway, located just a complimentary shuttle ride away from Duval Street and Smathers Beach.

The hotel offers a true taste of island life, with The Grove Kitchen & Bar serving up classic local flavors and island-inspired cocktails poolside. With four stunning pools, onsite watersports, and white-sand sunbathing terraces, Parrot Key is the perfect place to relax and enjoy the laid-back charm of the Keys.

Guests rave about the helpful staff, the well-maintained pools, and the overall relaxing atmosphere.

Dog-friendly Key West Cottage

For those looking to be close to the action in Key West while still enjoying a quiet retreat, this dog-friendly Key West cottage is the perfect choice. Located just off Duval Street, this three-bedroom, two-bathroom cottage offers easy access to Key West’s best attractions, including bars, restaurants, and the Ernest Hemingway Home and Museum, all within walking distance.

The cottage features a private enclosed yard where you can relax in the hot tub, and inside, you’ll find a well-appointed kitchen, flatscreen TV with cable, and free WiFi to stay connected. With off-street parking and the ability to bring your furry friend along, this cottage is perfect for families or groups wanting to explore downtown Key West with ease.

This is the kind of place that feels perfect for sitting and writing for hours—it’s a quiet, charming retreat similar to what I dream about when staying in Key West.

Catchlight House with Private Pool

If you’re traveling to Key West with a large group or extended family, the Catchlight House offers a stunning space designed for comfort and relaxation. This brand-new 6-bedroom, 6.5-bath home is perfect for an unforgettable island getaway. Located just minutes from downtown Key West, it features a private pool, plenty of space for everyone to unwind, and the convenience of a self-check-in process.

The house is beautifully decorated with island-inspired décor and modern furnishings, with large windows that let in plenty of natural light. Each bedroom is a tranquil retreat, featuring plush bedding and en-suite bathrooms for maximum privacy. With a variety of room layouts, including a bunk room for the kids and multiple king beds, there’s enough space for everyone to relax comfortably.

For those who love the water, boating is encouraged! The home offers access to a private dock in an exclusive marina that accommodates boats up to 40 feet. Additionally, the gated community of Key Haven Estates is close to everything Key West has to offer, from local parks and kayak tours to the island’s best restaurants, including Hogfish Grill and Roostica.

With amenities like a private washer/dryer, pet-friendly accommodations, and parking for two vehicles, the Catchlight House is the perfect home base for your Key West vacation.

Boyd’s campground

For a classic Key West camping experience, Boyd’s Key West Campground has been welcoming guests since 1963. Founded by Boyd and Elsie Hamilton, this campground has been run by the Hamilton family for over three generations and is a beloved part of the Key West community.

Located at the end of the Overseas Highway, Boyd’s offers a warm welcome to campers of all kinds, from those in Class A RVs to tent campers. With waterfront views, the pool and tiki hut, and a slice of paradise, this campground feels like a tropical escape where you’re treated like family.

The campground is full of amenities, including a boat ramp, picnic pavilion, laundry facilities, and Elsie’s Garden with a Wi-Fi hotspot. The pool area is a highlight, with tropical vibes, palm trees, and regular activities like aerobics classes, movie nights, and themed parties during the winter months.

Where to eat

Cuban coffee queen

As soon as we arrived in Key West, our first stop had to be Cuban Coffee Queen—it was high on my bucket list on our last trip!

Located in Market Square, the coffee shop is famous for its bold flavors and its vibrant mural, which makes for a perfect photo op. Whether you’re snapping a pic of yourself or just the mural, it’s a must-do while you’re there.

I ordered the Café Con Leche, a traditional Cuban espresso served with steamed milk, and it was everything I hoped for. If you want to really embrace the local tradition, order the Cuban breakfast—toasted pan cubano that’s dunked in your coffee. It’s the perfect way to start your day.

The atmosphere was lively, and I probably saw the most amount of chickens in this area, which made me smile. Between the strong Cuban coffee, the bustling market, and the quirky charm, Cuban Coffee Queen was a fantastic introduction to Key West.

Kermit’s Key Lime Shoppe

During our last trip to Key West, we made sure to stop at Kermit’s Key Lime Shop, and let me tell you—we truly fell in love with this place. From the moment we walked in, the aroma of Key Lime filled the air, and we knew we were in for a treat. We grabbed a full Key Lime pie, which was perfectly tart, and couldn’t resist picking up some seasoning and BBQ sauce as well. In fact, we loved the BBQ sauce so much that we’ve ordered a second bottle since.

Kermit’s Key Lime Shop has been a Key West staple for over 30 years, started by Kermit Carpenter in a humble stand selling smoothies. Over the years, it’s grown into a beloved local spot with two locations on the island—one on Elizabeth Street and the other on Duval Street. Famous for their Key Lime pie on a stick (dipped in Belgian chocolate!), Kermit’s is a must-visit for anyone looking to enjoy a true taste of the Florida Keys.

Kermit’s is a stop you can’t miss. We certainly couldn’t leave without taking home a little slice of Key West—and you shouldn’t either!

sloppy Joe’s

When you step into Sloppy Joe’s, you’re not just entering a bar—you’re entering a piece of Key West history. From its wild beginnings during the Great Depression to its strong connection with Ernest Hemingway, Sloppy Joe’s has seen it all. This one is on the forefront of our next to the Florida Keys this June.

Originally opened by Joe Russell in 1933, Sloppy Joe’s started off as a speakeasy and quickly became a local favorite, especially among the fishing crowd and adventurous rumrunners of the day. It was Hemingway’s favorite watering hole, and he even helped name it after a bar he frequented in Havana.

Over the years, it’s grown into a Key West institution with its lively atmosphere, large drinks, and the kind of laid-back, come-as-you-are vibe that makes it one of the most iconic spots in town.

Whether you’re sipping on a drink, soaking up the ambiance, or checking out the Hemingway memorabilia, Sloppy Joe’s is a must-visit if you want to experience a little bit of Key West’s rich and rowdy past.

Blue Haven Key West

With roosters wandering the grounds, colorful art scattered everywhere, and a canopy of tropical trees shading the outdoor dining area, it’s clear that Blue Haven is all about embracing the island lifestyle. The restaurant is whimsical and charming, but don’t let the decor fool you—the food here is as serious as it gets.

Opened in 1992 by Suanne and Richard, two free spirits with a love for fresh, Caribbean-inspired cuisine, this spot has become a Key West staple. Nestled in the historic Bahama Village, Blue Heaven is famous for its alfresco dining, live entertainment, and unforgettable dishes. The menu features a mix of American, Caribbean, and vegetarian offerings, with standout dishes like miso-marinated eggplant salad, pan-sautéed yellowtail, and their famous Caribbean shrimp deglazed with Red Stripe.

The history of the property is just as colorful as the ambiance. In its past lives, it was a cockfighting arena, bordello, and even a spot for Friday night boxing matches refereed by none other than Ernest Hemingway. Today, it’s a gathering place where locals and visitors alike can enjoy a meal, a drink, and a bit of the quirky Key West magic.

And if you’re lucky, you might just spot Chef David, the culinary genius behind it all, who has a passion for farm-to-table cooking and working with seasonal ingredients.

What to do

Dry Tortugas National Park

Dry Tortugas National Park offers a rare and exciting camping experience, and I’m looking forward to visiting next year. It’s a unique destination that’s only accessible by boat or seaplane, and the island’s remote setting is what makes it so appealing. Plus, it’s home to the massive Fort Jefferson and some of the most pristine coral reefs in the Florida Keys, which makes it perfect for snorkeling and birdwatching.

If you’re interested, they do have camping available at Dry Tortugas. Naturally, the camping is primitive, but that’s part of the charm. It’s first-come, first-served, and while the individual campsites can accommodate up to six people, there’s also an overflow area if the main campsites are full. The good news is everyone will get a spot. You’ll be surrounded by the incredible scenery, with no distractions from cell service or Wi-Fi—just pure natural beauty.

They recommend you bring supplies, including fresh water and charcoal for cooking, since compressed gas is not allowed on the ferry. For camping, the National Park Service provides basics like picnic tables, grills, and hooks to keep food off the ground. Composting toilets are also available, but they are closed for part of the day, so it’s essential to plan ahead.

Check out Duval Street

Duval Street is the heart of Key West’s vibrant atmosphere, stretching from the Gulf of Mexico to the Atlantic Ocean. Named after Florida’s first territorial governor, William Pope Duval, this iconic street is famous for its lively energy and rich history.

Known for its lively nightlife, Duval Street is home to historic watering holes like the previously mentioned Sloppy Joe’s Bar, where Ernest Hemingway once hung out, and Captain Tony’s Saloon, another favorite spot for locals and visitors alike.

The street is also lined with restaurants, offering everything from casual bites at the original Margaritaville to fine dining at spots like Nine One Five Bistro. As you stroll along the street, you can shop for Key West memorabilia or unique art pieces, taking in the relaxed yet energetic vibe of the area.

Duval Street is the center of many festivals and events throughout the year, like the Key West Food & Wine Festival and the rowdy Lobsterfest. Whether it’s the famous Conch Republic Independence Festival or the extravagant 10-day Halloween celebration, there’s always something happening that draws crowds to this lively street.

Visit the Southernmost Point and Mile Marker Zero

One of the must-see stops in Key West is the famous Mile Marker 0. This iconic sign marks the end (or beginning) of U.S. Route 1, the longest north-south road in the United States, stretching 2,369 miles from Key West to Fort Kent, Maine.

Visitors flock to Mile Marker 0 to snap a picture, capturing when they’ve reached the southernmost point of the U.S. highway system. Standing there is a reminder that you’ve reached the end of the road, far from the mainland hustle, and embraced the carefree spirit of the Florida Keys.

Another popular spot to visit is the Southernmost Point Buoy, which signifies the southernmost point in the continental U.S. This large, 12-foot-tall, brightly painted concrete buoy, installed in 1983, draws crowds from all over the world, with people lining up for a chance to take a photo. The buoy marks where you’re only 90 miles from Cuba, and it’s become one of Key West’s most iconic photo opportunities. Fun fact: Before the buoy, a simple sign marked this spot!

The Southernmost Point Buoy has been through a lot, including being battered by hurricanes like Irma in 2017, but it has since been restored to its colorful glory by local artist Danny Acosta. The buoy is a proud symbol of Key West, attracting thousands of visitors each day during peak season, all eager to commemorate their trip to the furthest point south in the continental U.S.

Watch the Sunset at the Sunset Celebration at Mallory Square

The Sunset Celebration at Mallory Square is one of the most iconic and beloved events in Key West, drawing crowds of locals and visitors every evening to watch the sun sink into the Gulf of Mexico. It’s not just about the sunset; it’s a lively arts festival that kicks off two hours before the sun sets, turning Mallory Square into a vibrant gathering space full of energy and entertainment. From magicians and jugglers to musicians, food vendors, and local artisans selling handmade crafts, there’s something for everyone to enjoy.

This tradition has deep roots in Key West’s history, with legends like Tennessee Williams saying that the first “sunset celebration” started with applauding the sun as it disappeared. Since the 1960s, this nightly event has become a must-do experience for visitors, with the phrase “See you at Sunset!” embodying the laid-back, festive spirit of the island. As the sky turns shades of pink, orange, and red, the crowds watch in awe, celebrating yet another beautiful day in paradise.

At Mallory Square, street performers showcase daring acts like sword swallowing and fire juggling alongside artists and psychics, offering a little something extra to the experience. The evening’s soundtrack includes local musicians playing island tunes, adding to the relaxed vibe. You can grab a bite from one of the many food carts or browse unique souvenirs and crafts as you explore.

The Sunset Celebration at Mallory Square is a unique Key West tradition that combines nature, art, and community to keep people coming back night after night.

 Fort Zachary Taylor Historic State Park

Fort Zachary Taylor Historic State Park is one of Key West’s best-kept secrets, offering a blend of rich history and natural beauty. It’s a quieter alternative to the more bustling areas of Key West, making it perfect for those who want to explore without the usual crowds.

The park is divided into two main areas: the historic Civil War-era fort, a serene beach with picnic areas, a small café, and plenty of relaxing space.

The fort is fascinating to explore, with well-preserved structures and history from the Civil War to World War II. You can climb to the top for panoramic views, wander through the rooms and passageways, and even walk around the fort’s moat.

The beach area is just as appealing. It’s one of the few natural beaches in Key West, offering clear waters, shaded picnic spots, and plenty of amenities like lounge chairs, umbrellas, and showers. It’s a refreshing and quiet spot compared to the busier tourist areas.

For a unique experience, the park also features nature trails, including a hammock trail where you can relax under the trees. It’s a perfect spot for a picnic or to hang up a hammock and enjoy the natural beauty of the Keys.

Ernest Hemingway Home & Museum

The Ernest Hemingway Home & Museum is a must-see destination in Key West, especially for literary enthusiasts and history buffs.

This Spanish colonial home at 907 Whitehead Street was purchased by Hemingway in 1931 and became his residence for eight years. It’s now a major tourist attraction, drawing visitors who want to walk the same grounds where the famous author lived and wrote some of his most iconic works. The lush tropical gardens, the historic photographs, and the carefully restored rooms — including Hemingway’s custom-made bed and his writing bungalow — provide a fascinating glimpse into his life.

One of the museum’s highlights are the cats, descendants of Hemingway’s original pet, Snowball. These polydactyl cats have become a beloved part of the property, roaming freely and adding to the unique charm of the estate.

Visitors can explore the house’s interior, including Hemingway’s writing studio, where he penned masterpieces like A Farewell to Arms and To Have and Have Not. The swimming pool, the first in Key West, and the beautiful veranda overlooking the property showcase the luxury that Hemingway and his wife Pauline brought to the house.

Beyond the literary history, the Hemingway House tells stories of the author’s larger-than-life personality. Hemingway was known for his boisterous social life, fishing exploits, and fistfights. The tour delves into these aspects of his time in Key West. Visitors can see where he boxed in the garden, learn about his adventures with friends, and even hear about his stormy relationships and eventual departure from Key West.

Key West first legal rum distillery tour

The Key West First Legal Rum Distillery is a must-visit for any rum lover, and it quickly became one of our favorite unexpected stops during our trip.

Housed in a former Coca-Cola bottling plant, this distillery has an incredible history tied to Key West’s rum-running past. Paul Menta, the founder and Master Distiller, turned his love of the island’s rebellious spirit into crafting premium rum.

During the tour, you’ll learn about the history of rum-running in the Florida Keys and the distillation process. We loved hearing about how the distillery produces unique batches influenced by the island’s weather conditions, giving each bottle a unique character. The distillery pays homage to the rumrunners of the past, with mugshots of local bootleggers adorning the walls. It’s a fun, laid-back atmosphere that draws you into the spirit of Key West.

The distillery also offers tastings of its signature blends. One of our favorite finds was the glazed pineapple rum—a deliciously smooth, tropical flavor that we’ve since been enjoying mixed with Dr. Pepper (but don’t tell them!). The tasting was a highlight, with their Chef Distilled line showcasing inventive flavors like Key Lime, Coconut, and Vanilla Creme Brulee.

If you love rum and want to experience a piece of Key West’s colorful past, this is the place to be. With daily tours at 3:00 and 3:30 pm, the distillery is a great stop to see the craftsmanship behind the island’s first legal rum.

Final Thoughts on Visiting the Florida Keys

Key West is a destination like no other, offering a mix of vibrant history, quirky charm, and endless adventure. As you plan your trip, remember to slow down and embrace the laid-back island life that makes this corner of the world so special. Whether you’re here for the food, the fun, or to relax, Key West will welcome you with open arms and plenty of memories waiting to be made.

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