Florida Keys Travel Guide
The Florida Keys have always held a special kind of magic for me, but even before I ever set foot on these sun-drenched islands, I already felt like I knew them—thanks to Jimmy Buffett. As a lifelong Parrothead, his music painted vivid pictures of salty ocean breezes, lazy afternoons with a cold drink in hand, and the kind of carefree island lifestyle that makes all your worries fade with the tide. The first time I watched the sunset from Mallory Square on Key West, I couldn’t help but hear Tin Cup Chalice in my head, capturing that perfect moment where the sky melts into the sea. And when I sat outside at Louie’s Backyard, rum drink in hand, I was living out the words of Trying to Reason with Hurricane Season, feeling that same blend of island tranquility and reflection that Buffett so effortlessly put to music. Here, the rhythm of life slows, the sunsets steal the show, and every conch bar feels like the setting for a Buffett song. Whether you’re sipping a rum cocktail by the water or wandering down Duval Street, the Keys aren’t just a destination—they’re a state of mind.
Islands of the Florida Keys
The Florida Keys stretch about 125 miles from mainland Florida to Key West, forming an island chain of over 800 islands, though only 42 are connected by bridges along the scenic Overseas Highway (U.S. 1). The Keys are divided into three main regions, and each section has its own distinct vibe, making a road trip through the Keys a fantastic way to experience everything from laid-back island living to historic sites and stunning natural beauty.
Upper Keys: Gateway to the Islands
The Upper Keys, including Key Largo and Islamorada, are the first islands you reach when driving south from Miami. This region is famous for world-class diving, snorkeling, and sport fishing.
In the Upper Keys, you’ll find the famous John Pennekamp Coral Reef State Park on Key Largo. This park is the first underwater state park, and home to colorful coral reefs, shipwrecks, and the famous Christ of the Abyss underwater statue.
A little farther down the line, you’ll find Islamorada, which is known as the sport fishing capital of the world and attracts anglers from all over. The vibe of the Upper Keys is perfect for boaters, fishermen, and outdoor adventurers.
Middle Keys: Bridges, Beaches, and Wildlife
The Middle Keys, including Marathon and Grassy Key, offer a balance between natural beauty and historic sites. This region is home to some of the most breathtaking sections of the Overseas Highway, including the famous Seven Mile Bridge.
The Seven Mile Bridge is one of the most iconic bridges in the world, connecting Marathon to the Lower Keys. The original bridge, built by Henry Flagler’s Overseas Railroad, is now a scenic walking and biking path.
The Middle Keys are also a great place to learn more about the sea life of the region, with the Dolphin Research Center on Grassy Key (a marine sanctuary) and The Turtle Hospital (rehabilitation facility) on Marathon, just before the Seven Mile Bridge. The vibe on the Middle Keys is great for family, with a little bit of everything.
Lower Keys: Remote and Relaxing
The Lower Keys start after the Seven Mile Bridge with Bahia Honda Key and continue to Key West, offering a more secluded, laid-back island experience before reaching the bustling southernmost city.
Bahia Honda State Park is known for having some of the best beaches in the Florida Keys. It’s always been my favorite location in the Keys for a beach day, with its clear, turquoise waters. There’s also the National Key Deer Refuge on Big Pine Key and Looe Key Reef, which is part of the Florida Keys National Marine Sanctuary. The vibe of the Lower Keys (until Key West) is remote and nature-filled.
Key West: The Southernmost Island
The final stop in the Florida Keys, Key West, is known for its colorful history, lively nightlife, and quirky island charm. It’s where history, literature, and a free-spirited attitude blend seamlessly. Key West is a mix of historic charm and lively nightlife, perfect for those who love a blend of culture, history, and fun. I’ll be diving into more about Key West later in this post.
Wildlife Sanctuaries: Protecting the Keys’ Natural Wonders
The Florida Keys are home to some of the world’s most unique and fragile marine ecosystems. Two standout organizations work tirelessly to protect and rehabilitate the area’s incredible wildlife:
The Turtle Hospital (Marathon)
If you’ve ever wanted to see sea turtles up close while also supporting a great cause, this is the place to go. The Turtle Hospital rescues, rehabilitates, and releases injured sea turtles while educating visitors on the threats these creatures face.
When visiting The Turtle Hospital, you’ll get a guided tour through their rehabilitation tanks, where you can see turtles recovering from injuries caused by boats, fishing nets, and disease. Many of the turtles treated here suffer from fibro papillomatosis, a virus linked to pollution that causes tumors on their bodies. The hospital surgically removes these growths, giving many of them a second chance at life. Others struggle with “bubble butt syndrome” (when turtles become buoyant due to air trapped in their shells, often caused by boat strikes), resulting in them being unable to dive and live on their own.
Pro Tip: Book a tour in advance—this place is popular!
Dolphin Research Center (Grassy Key)
Unlike some commercialized dolphin attractions, the Dolphin Research Center (DRC) focuses on education, research, and providing a safe home for dolphins that can’t survive in the wild. The DRC is home to several dolphins who were injured, orphaned, or deemed non-releasable due to past captivity. They also conduct studies on dolphin intelligence and behavior that contribute to conservation efforts.
At the DRC, you can observe rescued dolphins (and sea lions) in natural lagoon enclosures, learn more about dolphin communication through interactive sessions, and even have a swimming experience with the dolphins that follow unforced and ethical principles. This is a great stop for animal lovers who want to experience dolphins in a more ethical, research-based setting rather than a traditional marine park.
The End of the Road: Key West
What to do in Key West
Conch Train Tour: A Fun & Easy Way to Explore Key West
The Conch Train Tour is one of the most iconic and entertaining ways to see Key West, especially if it’s your first visit. This open-air train-style trolley takes visitors on a 90-minute narrated journey through the island’s most famous landmarks, historic neighborhoods, and hidden gems.
Starting at Mallory Square, the tour winds through Old Town, passing by sights like the Hemingway House, Southernmost Point, and the Key West Lighthouse. Along the way, the guides share fascinating stories about Key West’s pirate history, famous residents, and quirky island traditions. It’s a great way to get a feel for the city’s layout while learning some fun historical tidbits.
The tour is especially popular for those who prefer a relaxed, no-walking option for sightseeing. Plus, with the hop-on, hop-off option, you can use it as transportation to explore at your own pace. Whether you’re short on time or just want a fun and easy way to experience the island, the Conch Train Tour is a classic Key West activity that never disappoints!
Hemingway House Tour: A Glimpse Into a Literary Legend’s Life
The Ernest Hemingway Home & Museum is one of Key West’s most beloved historic attractions, offering visitors a chance to step inside the world of one of America’s greatest writers. Hemingway lived in this beautiful Spanish colonial home during the 1930s, writing some of his most famous works, including To Have and Have Not and A Farewell to Arms.
As you tour the home, you’ll see Hemingway’s writing studio, where he spent early mornings crafting his novels, and his personal artifacts that paint a picture of his adventurous, rugged lifestyle. One of the biggest draws, however, is the colony of six-toed cats that roam the property. These cats are descendants of Hemingway’s original pet, Snow White, and have become an iconic part of the home’s charm. Whether you’re a literature lover or just curious about Key West’s history, the Hemingway House is a fascinating stop that brings the past to life.
Rum Tours in Key West: A Taste of the Islands
Key West has a rich rum history, and a visit isn’t complete without sampling some locally crafted varieties. The island’s rum distilleries take pride in using Caribbean-inspired recipes, Florida sugarcane, and barrel aging techniques to create smooth, flavorful spirits. Whether you’re a rum enthusiast or just curious about the process, a rum tour and tasting is a great way to experience the island’s laid-back, tropical vibe.
One of the most well-known distilleries is Papa’s Pilar Rum Distillery, named after Ernest Hemingway’s beloved boat, Pilar. The distillery, located inside a historic brick warehouse, offers guided tours where visitors can learn about Hemingway’s adventures, the art of rum blending, and sample their award-winning dark and blonde rums. Another excellent option is the Key West First Legal Rum Distillery, which emphasizes handcrafted, small-batch rums and even allows guests to bottle their own. If you prefer a casual experience, many bars in Key West offer rum flights and signature cocktails like the classic Rum Runner or a Hemingway Daiquiri, made with grapefruit juice and maraschino liqueur – or just get a dark rum float on a Classic Lime Daiquiri – my favorite!
Where to eat in Key West
Key West is a paradise for seafood lovers and those who appreciate a good meal with a side of island charm. Here are some of my favorite spots:
- Blue Heaven – Laid-Back Charm with the Best Key Lime Pie in the Florida Keys. A visit to Key West isn’t complete without a stop at Blue Heaven. This quirky, open-air restaurant is famous for its island-style brunch, live music, and resident roosters wandering around the patio.
- Seven Fish – Best Romantic Dinner Spot in the Florida Keys. Tucked away from the craziness of Duval Street, Seven Fish is a cozy, intimate spot that’s perfect for a date night or a special meal. The menu focuses on fresh, locally caught seafood prepared with simple yet elegant flavors.
- Louie’s Backyard – Cocktails with Ocean Views. If you want a relaxing waterfront meal away from the hustle of downtown, Louie’s Backyard is the place to be. Sitting outside on their deck overlooking the ocean is an experience in itself.
- Half Shell Raw Bar – Laid-Back Seafood & Oysters. This casual waterfront spot is ideal for fresh seafood, happy hour drinks, and a relaxed, no-frills atmosphere. Great if you’re in the mood for something low-key but delicious. Pro Tip: Happy Hour (4:30-6:30 PM) is the best time to visit for great deals on seafood and drinks.
- Cuban Coffee Queen – Authentic Cuban Coffee. In Cuban culture, coffee is more than just a drink—it’s a ritual. What truly sets Cuban coffee apart is the way sugar is added. Instead of simply stirring sugar into brewed espresso, it’s beaten into the first few drops of coffee to create a thick, frothy layer called espuma. This creates a smooth, caramel-like texture and enhances the coffee’s natural flavors, balancing its strong, slightly bitter notes. Get a Café Cubano or Café con Leche to really experience this delicious drink!
Where to stay in Key West
If you’re looking for an authentic Key West stay that isn’t a chain hotel, the Historic Key West Inns are a fantastic option. They provide charming, boutique accommodations in prime locations—close to everything but still quiet enough for a restful night.
My Personal Picks:
- Ella’s Cottages (formerly Merlin Guesthouse): Cozy, romantic, and tucked away from the crowds.
- Fitch Lodge (formerly Albury Court Hotel): Great for a convenient, walkable stay without being right on Duval Street.
Best For:
✔️ Romantic Getaways – Perfect for couples seeking a more intimate, historic setting.
✔️ Girls’ Trips – Ideal for small groups who want easy access to nightlife but a peaceful place to retreat.
💡 Family Travel Tip: While Key West is amazing for adults, families may prefer staying in the Middle or Upper Keys, where activities are more budget-friendly and not focused on drinking and fine dining.
Bucket List: Dry Tortugas National Park
If you’re looking for a bucket-list adventure in the Florida Keys, Dry Tortugas National Park is a must-visit. Located about 70 miles west of Key West, this remote national park is one of the most stunning and historically rich destinations in Florida. With its crystal-clear waters, vibrant coral reefs, and the massive 19th-century Fort Jefferson, it’s a place that feels completely untouched by time.
The centerpiece of the Dry Tortugas is Fort Jefferson, one of the largest brick forts in the U.S. (built with over 16 million bricks!). It was originally constructed in the mid-1800s to protect the Gulf of Mexico shipping lanes but was never fully completed. During the Civil War, it served as a Union military prison, with its most famous prisoner being Dr. Samuel Mudd, the physician who treated John Wilkes Booth after Lincoln’s assassination.
Dry Tortugas National Park is about 99% water, making it a dream destination for snorkelers, divers, and nature lovers. The surrounding coral reefs are among the healthiest in Florida, offering incredible opportunities to see sea turtles, vibrant fish, nurse sharks, and even shipwrecks.
Getting to the Dry Tortugas
Since Dry Tortugas is one of the most remote national parks in the U.S., getting there requires some planning. There are only two ways to get there:: by ferry or by seaplane. When I went, I took the ferry (Yankee Freedom III). It’s the more affordable option, but it is a long ride (2 hours and 15 minutes each way from Key West), so it makes for a very full day excursion, with limited time on the island. Pro Tip: bring Dramamine if you’re at all prone to motion sickness!
A seaplane is the other option, which takes only 40 minutes, but is significantly more expensive. You’ll get more time to explore the island, and if you get seasick, it might a better option.
Camping in Dry Tortugas
If you want a truly unique experience, you can camp overnight on Garden Key and have the island nearly to yourself once the day-trippers leave. However, camping here requires serious preparation:
- You must bring everything with you—food, water, camping gear, and any supplies you’ll need, as there are no stores, running water, or amenities.
- Only a few permits are issued daily, so reservations are required.
- The experience is incredible—waking up to an empty beach, snorkeling without crowds, and seeing the fort lit up under the stars.
Dry Tortugas isn’t just another beach stop in the Florida Keys—it’s a journey back in time and a natural wonder rolled into one. Whether you choose to visit for the day or camp overnight, this remote paradise offers an escape from the crowds of Key West and a glimpse of Florida’s wild and historic side.
Getting to the Florida Keys
Since there’s no perfect way to get to Key West, here’s what you need to know about each option:
✈️ Flying Direct to Key West
✔️ Quick and easy but pricier.
✔️ Small, hassle-free airport.
❌ Limited flight options.
🚌 Shuttle from Miami to Key West
✔️ No driving stress!
✔️ Comfortable and affordable compared to flying.
❌ Takes longer than driving yourself.
🚗 Driving from Miami/Ft. Lauderdale
✔️ The scenic Overseas Highway drive is one of the most beautiful road trips in the U.S.
✔️ Best if you want to stop in Islamorada, Marathon, or Bahia Honda along the way.
❌ Parking in Key West is a nightmare (and expensive).
Pro Tip: If you drive, take your time on the Overseas Highway! Pull over at scenic spots, visit the old Flagler bridges, and soak in the beauty of the Keys—it’s all part of the experience.
History Lesson: The Overseas Railroad
Before the Overseas Highway was built, the Florida Keys were connected by a railroad—one of the most ambitious engineering projects of the early 20th century. The Overseas Railroad was built by Henry Flagler and opened in 1912 as part of Flagler’s Florida East Coast Railway. This railroad stretched from Miami to Key West, making it possible to travel by train all the way to the southernmost city in the U.S.
The project took seven years to complete, requiring 42 bridges and an extensive network of tracks built over the open ocean, and was one of the greatest engineering achievements of its time, earning the nickname “The Eighth Wonder of the World.”
In 1935, a Category 5 hurricane destroyed large tracks of the railroad (a really tragic story as passengers were trying to evacuate on it at the time), rendering it unusable. Instead of rebuilding the railroad, the state used the infrastructure to create the Overseas Highway (U.S. Route 1). However, you can still see many of the old bridges and railway tracks as you drive down the highway. Some parts, like at the Seven Mile Bridge, now include a pedestrian path for walking, running, and cycling.
The Florida Keys offer an unforgettable blend of history, adventure, and laid-back island charm. Whether you’re road-tripping through the scenic Overseas Highway, sipping Cuban coffee in Key West, or snorkeling the pristine reefs of Dry Tortugas, there’s something for every traveler. These islands aren’t just a getaway—they’re a way of life, best enjoyed at a slow, easy pace with the ocean breeze in your hair and a tropical drink in hand.
If you’re planning a trip to the Florida Keys and feeling overwhelmed with options, I’d love to help! As a custom travel planner, I specialize in crafting personalized itineraries that take the stress out of planning, ensuring you make the most of your time in paradise. Reach out today, and let’s turn your dream Keys getaway into reality!