Road Trippin’ Through the Florida Keys

With crystal blue waters, incredible marine life, and a collectively carefree attitude, the Florida Keys feel vastly different from anywhere else in the United States – and that’s exactly the point. Each year, travelers from all over the world flock to this 125-mile stretch of coral islands to escape mainland worries and embrace island life. 

Paradise is surprisingly easy to reach, too. The journey from Miami to the Keys’ southernmost island, Key West, can be tackled in a day, but getting there is half the fun. At each mile marker on Overseas Highway, you’ll encounter something worth pulling over for – seafood shacks overlooking the ocean, kitschy shops with Tommy Bahama-approved decor, bakeries boasting the best Key lime pie, motorcycle bars, historic marinas, and so much more. And just wait until you get on the water. There are coral reefs to snorkel, trophy fish to reel, mangroves to kayak, and endless underwater wonders to explore.

In this Florida Keys travel guide, we journey from Key Largo to Key West in pursuit of awesome experiences for every type of traveler. Add these destinations to your bucket list and hit the road with Independent Collection.


Your introduction to the Florida Keys’ incredible landscapes and eccentric charm begins at Key Largo, the northernmost key, located about an hour and a half drive south from Miami. Key Largo is perfect for those with limited time to spare, so waste not and jump straight into the fun at John Pennekamp Coral Reef State Park, commonly known as Pennekamp. 

Pennekamp is a fascinating underwater park that protects miles and miles of mangrove swamps, seagrass beds, tropical hammocks, and the only living coral reef in the continental U.S. Whether you choose to scuba dive or snorkel, kayak or boat, wildlife sightings are a sure bet. Turtles, shorebirds, colorful fish, and even crocodiles call this glorious place home. Jesus Christ does, too! Yes, divers and snorkelers can baptize themselves in Pennekamp’s crystal blue waters and come face-to-face with Christ of the Abyss, a bronze underwater statue of Jesus with outstretched arms a la Christ the Redeemer in Rio de Janeiro, Brazil. 


From Key Largo, drive south to Islamorada, one of the most popular (and most developed) islands of the Florida Keys. Islamorada is famous for its mesmerizing purple sunsets, excellent seafood, and world-class fishing. In fact, Islamorada is considered the sports fishing capital of the world! Drop anchor at this gorgeous destination and check in to the iconic Islander Resort, an oceanfront resort conveniently located among some of the best restaurants, bars, and experiences you’ll find in all of the Florida Keys. 

There are seemingly endless things to do at the Islander Resort and its sister property, Bayside Villas by Islander Resort – cocktails on a private beach, saltwater pools with ocean views, beach volleyball, walking trails, paddleboarding, snorkeling, even a butterfly garden! 

For those who want to experience it all, book the resort’s “Islander Adventure” package. Your three-night stay in paradise includes a $100 food and drink credit, unlimited access to the resort’s paddleboards, kayaks and bikes, and a complimentary late check-out. 

Best of all, this package includes a $220 credit towards your choice of land or sea adventure. Enjoy a private boat ride to the biggest party in town – the Islamorada sandbar – or choose from experiences like guided snorkel tours, catamaran sails, and a romantic sunset cruise for two!

Before heading out of Islamorada, get to know the island’s small-batch craft breweries and local art scene. (Check out our blog on Islamorada for more!) And, while a bit touristy, a quick trip to Robbie’s is lots of fun. From Robbie’s dock, brave travelers can dangle bait above enormous, hungry tarpon and watch them attack. Don’t worry, your hand won’t get bit off; tarpon lack sharp teeth (but you don’t have to tell your friends that…)


After a few days of seaside bliss, hop back on the road and continue south towards Bahia Honda Key. This leg of your Florida Keys road trip will quickly become your favorite as you cross the Seven Mile Bridge. Running parallel to the historic Overseas Railroad – a retired railroad and engineering marvel that once connected mainland Florida to Key West – the Seven Mile Bridge is flanked by the Atlantic Ocean on one side and the Gulf of Mexico on the other. With nothing but blue sky and turquoise waters surrounding, you’ll feel like you’re floating in the sky. 

To fully appreciate this ethereal view, pull over to Bahia Honda State Park. Equal parts secluded, rustic, and romantic, Bahia Honda has over 500 acres of landscapes to explore. Prop open an umbrella and hang out by the beach, or gear up to snorkel the park’s crystal clear waters. Queen conchs, spiny lobsters, and tropical fish are often spotted here. The historic Old Bahia Honda Bridge is great for a short hike, and you’ll be rewarded with an epic bird’s-eye view of the island with chance sightings of stingrays, dolphins, and sea turtles swimming below. Bahia Honda is also the darkest location for stargazing in the Florida Keys. Adventurous travelers can set up camp overnight and marvel at an interstellar light show, island style.

After Bahia Honda Key, drive towards its neighbor, Big Pine Key, and keep your eyes peeled for Key deer. Yes, like Bambi! Though this endangered species is much smaller and only found in the Lower Florida Keys. Key deer are known to dart across U.S. 1 during morning and evening hours. At the Florida Keys National Wildlife Refuges Complex, you’ll see plenty of Key deer and other wildlife in their natural habitats, even alligators and rattlesnakes. Plan a visit for excellent birdwatching, wildlife photography, guided bike rides and nature trails.


The wild child of the Florida Keys, Key West is just four miles long and two miles wide. But what it lacks in size, it makes up for in character. 

Key West is closer to Cuba than it is to Miami, which is why, perhaps, so many free spirits and creative minds are drawn to Key West living. In fact, Ernest Hemingway, Tennessee Williams, and Judy Blume famously called Key West home. Key West is very LGBTQ+ friendly, too. Today, thousands of travelers are drawn to the island with the promise of beautiful landscapes, awesome water sports, a welcoming community, and a rowdy nightlife scene.

Start your Key West explorations at Parrot Key Hotel & Villas, an award-winning resort that overlooks the Gulf of Mexico. Located just a few minutes’ drive from Key West’s main drag, Parrot Key feels like its own private paradise. It has five acres (!) of tropical gardens, four swimming pools, and tons of on-site water activities like paddleboarding, kayaking, and jet skis. Not to mention a delicious on-site restaurant, where guests can enjoy quintessential Keys specialties like peel-and-eat Florida Pink Shrimp, conch fritters with Key Lime remoulade, and locally-caught mahi. 

Unwind in your tropical oasis at Parrot Key, then take the resort’s complimentary shuttle to Key West’s historic district, Old Town. The area is easily walkable and cyclist friendly, with plenty of bike rentals scattered throughout. Hop on a cruiser and visit historic landmarks like the Key West Lighthouse, Fort Zachary Taylor, Harry S. Truman’s Little White House, and Ernest Hemingway’s home, a residence-turned-museum where six-toed cats keep a watchful eye. 

An otherworldly historic site is also close by: Dry Tortugas National Park, a remote, 100-square-mile park with an impressive fort and fascinating marine life. Snorkeling and scuba diving are a must here! You’ll encounter storied shipwrecks, tons of tropical fish and reef squid, and, on rare occasion, the endangered American crocodile. 

After a day on the water, head back to Key West and catch the sunset at Mallory Square. Come nightfall, there’s no place more exciting than Duval Street. Think of Duval as Key West’s Bourbon Street – rambunctious, cheeky, and loads of fun. Without agenda or time constraints, hop along Duval to discover a range of restaurants and watering holes, from dollar bill-covered dive bars, to frozen daiquiri shacks, to outdoor eateries flanked by kitschy souvenir shops. 

Any time of year is great to visit Key West thanks to the island’s year-round sunshine and lively local community. Of course, some annual events are especially fun-filled. Consider planning your Key West vacation around Fantasy Fest (October 21-30, 2022), the island’s wildly creative, adults-only, Mardi Gras-meets-Halloween party, or visit during the 25th Annual Key West Lobsterfest (August 11-14, 2022), a four-day extravaganza of tasty events like a traditional lobster boil, a lobster-filled street fair, and a decadent all-you-can-eat lobster brunch. The locally-loved Key West BrewFest (September 1-5, 2022) also returns this year for its 11th installment. Explore the islands’ microbreweries with bottomless sips, all for a good cause: the annual event benefits the Key West Sunrise Rotary, which provides scholarships and charitable donations to local non-profit organizations. 

At the end of your Florida Keys adventure, take time to enjoy the journey back to the mainland and pull over to explore whatever catches your eye. Don’t worry if you aren’t able to see it all. After experiencing the Keys, it’s only a matter of time until you come back for more! 

Ready to book your Florida Keys vacation? Learn more about our Florida Keys hotels and resorts here and let the fun begin!