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Writer's pictureAndrew C.

A Road Trip to Paradise - Exploring the Florida Keys

Updated: Oct 8


Stunning turquoise water and aerial view of Florida Keys
Stunning turquoise water and aerial view of Florida Keys

An Invitation From a Dreamer


The Keys and Key West have long been on our list to visit for a while. After we visited the Flagler Museum in Palm Beach, the story, ambition, and legacy of Henry Flagler inspired us to dream and explore. We decided to plan a week-long trip to the southernmost part of the continental United States as an extension of our stay in Florida.


Put your head in the clouds and wheels along the turquoise water, the paradise is simply a car ride away in Florida State. A drive through the Florida Keys and Key West is for sure one of the best scenic road trips in the USA. Instead of going straight to Key West, we suggest exploring many different parts of the coral cay archipelago along the way. the locals call it "Keys Hopping."





Keys Hopping & Connections


Key Largo is both the first island and town of the Florida Keys to be reached from the Overseas Highway to Key West. It was also the location of one of the stations of the famous Overseas Railroad back in the Gilded Age. Surrounded by the shallow warm sea and nature, we had a memorable and romantic sunset dinner in the water at Sol by the Sea at Playa Largo Resort & Spa, enjoying the carefully curated tropical dishes and cocktail menu followed by a relaxing stay at this beachfront resort. The spacious property and well-curated setting were simply perfect for our first stop in The Keys.




Stepping out in a tropical-flavored T-shirt and shorts, we made a stop at the iconic Robbie’s of Islamorada. Robbie's Marina is an eclectic mix of outdoor shops, food vendors, and tarpon feeding. The Hungry Tarpon Restaurant and Bar offers a large menu with a variety of options for the entire family. After a delicious lunch on the sundeck by the water, we grabbed a bucket of fish to feed the tarpon and enjoy watching everyone else getting up close and personal with the huge fish. It was simply a tropical wonderland.


While driving around in warm weather, it is always a good idea to stay hydrated. The Islamorada Brewery & Distillery is a cute stop (Not for the one who drives) that offers legendary Sandbar Sunday beer. The on-site distillery also creates spirits branded as Islamorada Distilling gin, vodka, and dark barrel-aged and spiced rums. To figure out which one would be your favorite, spirits tasting or a beer flight board could help you do the justice. After dark, we put on an evening cape and joined the locals at Chef Michael’s for an elegant evening completed by an extensive menu

featuring creatively inspired Florida Keys cuisine and a variety of freshly caught fish in Islamorada.





Towards The Seven Mile Bridge and Beyond


Marathon is a city where the famous Seven Mile Bridge starts. We settled in the new luxury Isla Bella Beach Resort, charmed by its contemporary glamour by the sea with a crisp palette of blue and white that connects the guests to the private beach, playful prints, modern furniture, contemporary art, and luxury setting. It is a true hidden tropical oasis, that provides guests with a tranquil respite from the world beyond. There is also a marina with watersports including fishing charters, jet ski tours, harbor cruises, kayak, snorkeling, and scuba diving trips, making your stay closer to the nature paradise. It is the perfect place to slow down and unplug.





While exploring the Middle Keys, Keys Fisheries is a must-visit chill spot for conch fritters & other Keys specialties in an open-air fish house overlooking the marina. The locals come in and out of the marina with their jet skis and it becomes a different commute scenery. The annual Stone Crab Eating Contest was happening during our visit and it was intense and a lot of fun. Eating crab surely requires a lot of skills after watching those experts heading their way toward the championship.


We later enjoyed the best sunset view in The Keys at Seven Mile Bridge, a man-made wonder and a major crucial link to all of The Keys. There are two bridges: The modern bridge is open to vehicular traffic; the older one is only to pedestrians and cyclists. The older bridge, originally known as the Knights Key-Pigeon Key-Moser Channel-Pacet Channel Bridge, was constructed from 1909 to 1912 under the direction of Henry Flagler and Clarence S. Coe as part of the Florida East Coast Railway's Key West Extension, also known as the Overseas Railroad. Finally, we got to follow Mr. Flagler's path and his ambition that has left us until today. The bridge was indeed a good inspiration for dreamers. It left its mark on all of us.


We wrapped up the beautiful tropical evening at the Butterfly Café in Tranquility Bay Beachfront Resort and dined on the covered patio with its casual yet sophisticated decor. Besides the remarkable seafood dishes such as horseradish-encrusted Florida grouper, the famous TDF 'To Die For' Sticky Toffee Pudding is something you would not want to miss!





Entering The Conch Republic - Key West


On the 4th day, we finally arrived in Key West, the final stretch of our journey in the Florida Keys. They say Key West is one of the most charming and eccentric towns in the US, and we couldn't agree more! The town is where the tropical meets hippies, historical meets natural, and local meets international. From the charming Lazy Way to the Southernmost Point of the Continental U.S.A., there is plenty of life and variety by the harbor and in the old town neighborhoods.





It is a lot of fun taking the Conch Train to tour the historic center. Dining with the roosters at Blue Heaven was quite an experience. It is an iconic landmark for Floridian-Caribbean cuisine with a funky setting. Try their must-have lobster steak Surf and Turf Benedict and key lime pie. Santiago's Bodega is another hidden gem that is worth note-taking for tapas and sangrias with original artwork by Robert Henry Thompson hanging on the walls.


As seafood lovers, we love the vibe and setting at Half Shell Raw Bar. From the rockabilly-style entrance to the picnic tables surrounded by walls decorated with car license plates, the Half Shell Raw Bar offers a taste of old Key West you can’t experience anywhere else. We spoke with Sandra from the management team, the raw bar was originally built as a shrimp warehouse, and it was established as a restaurant in 1972 as the Key West shrimp industry moved north to Stock Island. As soon as you head inside, you’ll notice the local fisherman unloading the day’s catch into the Half Shell’s Fish Market. They have a long-established relationship with local fishermen, and this is surely our go-to to enjoy the freshest seafood in Key West.





For the stay in Key West, we checked in the contemporary and industrial-looking The Perry Hotel & Marina for a change. It's a fresh twist on the classic island charm. The guest rooms and suites blend contemporary furnishings with rustic touches with the waterfront view of the marina. The property is inspired by Commodore Perry, the father of the United States Navy. The Perry’s spacious, laid-back atmosphere has been thoughtfully cultivated to stay true to the seafaring roots of Old Key West.





Walk The Path of The Legend


Ernest Hemingway once said, " In order to write about life, first you must live it!" For his writing, there were lots of muses and inspirations that came from his real-life experience. The Hemingway Home Museum is a must-see destination in the historical part of Key West. Located by the Key West Lighthouse, which was built by the sea and is now located in the middle of the town, The Hemingway home was built in 1851 in the Spanish Colonial style. The home was in great disrepair when the Hemingways took ownership, but both Ernest and Pauline, his wife at the time, could see beyond the rubble and ruin and appreciated the grand architecture and stateliness of the home. The massive restoration and remodeling they undertook in the early 1930s turned the home into the National Historical Landmark that thousands of tourists visit and enjoy today.


Ernest Hemingway lived a legendary life that was filled with adventures, cultures, and love. The house is still decorated with his furniture and trophies from his travels and journeys in Europe and Africa. The museum also houses two of his most well-known collections, the cats and the wives. It is also one of the first houses to have a swimming pool back in the day. There is a writing room situated on the top floor adjacent to the main building, with a typewriter and a cozy setting filled with books and ideas, this is where many of Hemingway's works started. Throughout the 30s to 50s, Key West has been home to many writers and artists, but none whose presence and influence are as profound as Ernest Hemingway’s. After seeing his house and hearing about his many life chapters, his life was an extraordinary novel in itself.





Experience Paradise in All Dimensions


A visit to Key West will not be complete without spending a day at Fort Zachary Taylor Historic State Park. With the natural white coral sand beach, abundant underwater sea life, lush forest, and the historical Fort from 1845, it is like a little paradise by the doorstep and the perfect place to experience most of what this tropical island life has to offer.





On a sunny and calm day, we hopped on the US First Electric Catamaran with Honest Eco Tours to watch wild Bottlenose Dolphins. The ride was quiet, smooth, and with zero emissions. Founded in 2014 by Biologist Billy Litmer, Honest Eco was formed “to Spread the Value Of Conservation”. It hosts Sustainable Nature Tours with biologists as your tour guides and it is best known for the Dolphin Watch and snorkel trips as they focus on the needs of both the animals and the guests. When we were on board, there were no plastic water bottles around, the solar panels collect and support the energy to manage the operations of the boat. We also learned a great deal of knowledge about sea life and animals during our sailing and snorkeling. After waiting more than two hours, we finally meet a young family of Bottlenose Dolphin. The shallow water in The Keys makes the region a haven for the Dolphins, with no sharks or other predators. It was a feel-good, do-good day with nature and animals up close, everyone felt extra meaningful and memorable.


If you are looking for a relaxing moment in Key West, a lovely sunset sail on a spacious catamaran with Sebago Watersports would be just perfect. Join the folks and crew, and enjoy the tropical breeze, live music, and light food, cruising along the Key West Harbor while chasing the world-famous Key West sunset. It is also an easy way to see the city and harbor from a different perspective.





We also loved the magical moments on the stunning private island of Sunset Key, an island that is privately held among its residents and is accessible only by a shuttle boat that runs from the Margaritaville Marina in Key West. It is considered an exclusive paradise among the paradise. We got to experience one of Florida Keys’ best restaurants at Latitudes inside Sunset Key. Inspired by the warm setting and gorgeous views of the Gulf of Mexico, Latitudes offers an elegant beachfront dining experience that is truly memorable in many ways. The best time is to reserve a table for the golden hours, and enjoy fresh local fish and steaks with a bottle of wine from a well-curated wine list when the sun sets.



When the night falls, Key West is also full of vibrant bars and nightlife scenery along the famous Duval Street. It is also a tropical & safe haven for the LGBTQ community. We stopped by and watched a fun drag race at Aqua Bar and Nightclub, and bumped into our favorite drags from Mykonos. There is also a charming and glittering spot 22&Co bar where you could share your love for the tutus and sip the well-crafted cocktails with guests from all over the world. From morning to night, there was no dull moment that exists in Key West!




For more details and information about The Keys & Key West, please check out fla-keys.com.








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