Florida Keys Road Trip
When it comes to one of the most iconic chains of tropical islands — the Florida Keys — one of the best ways to see everything is to take a road trip. Scenic views spread before your eyes, and kitschy shops are fun to visit. Take in some island flavor at a local restaurant, or catch your food yourself on a fishing trip. Hotels and resorts are ready to offer you the ultimate relaxation. Have fun on your road trip!
You begin your trip by leaving the mainland to cross the Overseas Highway, sometimes called "the Highway that Goes to Sea.” It is the proverbial red carpet rolled out for travelers that lets you admire the countless coral and limestone islets that surround you as you cross the dazzling waters. As you enter the Keys, you can practically feel the vibes of relaxation wash over you —you’re on Island Time now! Your only goal now is to relax and enjoy your trip.
Day 1: Key Largo
The first island to welcome you will be Key Largo. While it’s only an hour’s drive from the airport, it’s an entire world away. Home to tropical hardwoods, winding creeks, two state parks, a national park, and a portion of a national marine sanctuary, Key Largo boasts some of the most fascinating botanical scenery in the state. Key Largo's ties to the sea provide you with countless opportunities for adventure including scuba diving, snorkeling, an underwater hotel, sport fishing, eco-tours, beaches, and dolphin encounters. But it isn’t just the sea that welcomes you - the island also offers numerous on-shore attractions, including nature trails and a rehabilitation center for wild birds.
DIVE IN. You can’t visit Key Largo and miss out on its incredible diving opportunities. Explore John Pennekamp Coral Reef State Park, Dagny Johnson Key Largo Hammock Botanical State Park, and all the underwater delights of the Florida Keys National Marine Sanctuary. Several eco-tourism and dive/snorkel services are ready to help you discover these natural wonders. Rainbow Reef Dive Center can help you out, accommodating your every need with a custom fleet that can cater to small or large groups. Listen to the dive masters give detailed briefings of the site en route, while sipping complimentary bottled water and cookies (yum!). There’s also free internet access at the shops and even on the boats, so you can quickly upload your selfies and videos of your dive adventure!
rainbowreef.us
LOCAL FOOD. Since you’ve been driving a while, you’re going to want to stop at a restaurant (or depending on how congested the traffic in Miami was, perhaps you need to stop at a Tiki bar). Now that you’re in the Keys, it’s time to dig into some authentic, local seafood. Key Largo Conch House is a prime example of an island-style seafood restaurant. Start off with a selection from the beer and wine menu, if needed, as well as something like Lobster & Conch Guacamole, move onto the Seafood Paella, and hopefully you’re lucky enough to be there on a day when they’re making their famous Mom's Key Lime Coconut cake —which was featured on “Emeril's Florida”! This restaurant has also been featured on “Man vs. Food,” and other cable specials. The world can’t get enough of it, and neither will you!
keylargoconchhouse.com
REST EASY. There’s no need to drive tired! There are plenty of great resorts and hotels in Key Largo to get you rested and ready for the next day of driving. Seeing as you’re on a road trip through the Keys, chances are that you’re the kind who truly likes to experience the local flavor and immerse yourself in the culture. Azul del Mar is the most exclusive all adult hotel in Key Largo, and has been featured as one of Travel and Leisure’s “World’s Greatest Hotels, Resorts and Spas” and voted “Best Hidden Gem in The United States” by TripAdvisor users. Even with all of these awards, the hotel avoids any flashiness and instead evokes the desired sense of leisure with lush tropical foliage leading you down to the quiet, private beach.
azulkeylargo.com
Day 2: Islamorada
Eventually, you will make your way to the heart of Islamorada. But Islamorada is more than a singular destination —it’s actually comprised of six islands: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, and the offshore islands of Indian Key and Lignumvitae Key. Along the way, there are tons of fun places to stop along the way to Islamorada. After all, the Keys have been a vacation destination for decades, which means there are a lot of eclectic, kitschy, and colorful local attractions.
SHOP ON. Combine two great road trip activities (selfies and shopping) and throw in a little eclectic flavor and you’ve got a recipe for road trip fun as you stop at local antique shops. Keys Castaway Antiques is a can’t-miss, especially since there’s a big bus full of treasures sitting out front, and has everything to offer from boat motors to silly hats and even couture items! Further down the road, you can hope out of the car to hit up One Drunk Monkey, where you can find one-of-a-kind gifts to take back home. It’s located in the same place as the Rain Barrel Sculpture Gallery, which is chock-full of sculptures large and small, from giant whales to tiny pots. This is yet another can’t-miss spot, since there is a giant, realistic-looking lobster named Betsy sitting out front (picture a monster movie come to life). Talk about some great selfie material!
rainbarrelsculpture.com
FISHY STUFF. This area is best known for its fishing (it is, after all, the “Sport Fishing Capital of the World”). In fact, even if you aren’t an avid fisherman, it is such a great experience that you simply have to try it. Imagine heading out to the open waters with nothing but the sun, sky, waves, and distant islands surround you and nothing on the itinerary but catching some delicious fish (or, not catching fish and instead telling some great stories about “the one that got away”). Islamorada Fishing Guides and Charters keeps it as straightforward as their name when it comes to your fishing experience, offering you the best of the best in professional guides for inshore backcountry, reef and offshore, and night fishing.
ANIMAL FUN. Perhaps you’re more interested in meeting marine animals, rather than catching them. In that case, pay a visit to Theater of the Sea. The theater is a pioneer in animal interactive programs, letting you actually swim with dolphins, sea lions, rays, sharks (don’t worry, they’re friendly!) and meet some sea turtles. One particular experience that you have to try is painting with dolphins. Selfie-alert! Theater of the Sea has been family-owned and operated since 1946, making it one of the oldest marine mammal facilities in the world. The sunlit lagoons and lush, tropical gardens are home to Atlantic bottlenose dolphins, California sea lions, sea turtles, tropical and game fish, sharks, stingrays, alligators, marine invertebrates, and birds.
theaterofthesea.com
RELAXING RESORT. The Drop Anchor Resort & Marina sits majestic on Windley Key, having been a staple resort of the area for over 50 years and still keeping the spirit of Old Florida alive even though their rooms have been recently updated and are kept immaculate for you. The palm trees sway over the pool and beach area, and the oceanside dock and boat ramp are available to guests. Lounge in your lovely guest suite, which is tastefully decorated in a modern take on nautical style and has plenty of room with huge bedrooms, dining areas, and kitchens, or take a snooze in a shaded hammock as you listen to the sound of the waves.
dropanchorresort.com
Day 3: Key West
Prepare for the final drive to Key West! You’ll be passing through several cool areas like Marathon and Big Pine Key, so feel free to stop the car now and then to stretch and have a look around. Once you hit Key West, you will reach a whole new level of chill. This tropical paradise is actually closer to Cuba than it is to Miami, and you can soak in the island-style charm. Palm-lined streets with gingerbread mansions and tin-roofed conch houses were home to many famous faces of history, and the island’s Bahamian and Cuban heritage was, in large part, inspired by Bahamian wreckers, commercial fishermen, spongers, and Cuban cigar makers.
LIVING HISTORY. Now that you’ve taken such a long ride in the car, it’s time to do a bit of walking! Your legs will thank you, and so will your brain, because you’re about to learn some really cool things about Florida Keys history. Key West drew many well-known artistic minds, like Ernest Hemingway, Tennessee Williams, Elizabeth Bishop, and Robert Frost, all of whom discovered solace and inspiration in the island city. In fact, you can visit several of their houses, including The Ernest Hemingway Home & Museum. This palatial estate is not only packed with history and stories of the author’s intriguing life, but also with unbelievable beauty and, shockingly, six-toed cats! (You haven’t truly lived until you’ve taken a selfie with a six-toed cat.)
hemingwayhome.com
FAMOUS STREET. Now that you’ve spent time educating yourself, you can allow yourself a little indulgence. And where better to find indulgence, than the many shops, bars, and restaurants of Duval Street? Once you get there, you’ll see why it inspired The Village People to include it in their hit “Duval Street”: “take a walk down Duval Street, you never know who you’ll meet”. If you’re ready for a refreshing drink, then the first place you need to stop is Hog’s Breath. While its name may not be the most attractive, you’re going to adore the atmosphere, particularly under the canvas roof of the outdoor area. They keep things classic here, with their most popular menu item being their hearty cheeseburger. Top it off with a very indulgent dessert, their Key Lime Shooter, and don’t forget to buy a T-shirt in their gift shop so that everyone can know that you know how to have a good time.
duvalstreet.net
REST STOP. As a perfect little touch to your Keys-long road trip, you could stay in the Southernmost Beach Resort, located in historic Old Town and spanning a breathtaking six acres with Atlantic Ocean views, luxurious, open rooms that overlook the beauty of Key West, and first-class resort service. You may want to plan an extended stay here, since it boasts beautiful sandy beaches, three sparkling pools, four tropical bars, lush garden pathways, relaxing oceanside hammocks, and endless views of the sea and sky from every point, including their popular private pier. At this point, you have reached the ultimate level of chill. Unsurprisingly, this ultra romantic hotel is a picture-perfect location for weddings and also offers romance packages for any adventurous couple —not to mention some of the most picturesque wedding photo backdrops of all time!
southernmostbeachresort.com
Now that your road trip is at its end, you can look back on your trip and mull over your journey. What were your favorite places? You can visit them on the road trip back to the mainland.
