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Take Another Road: Key West

There is a little island nestled between the Gulf of Mexico and the Atlantic Ocean, a tropical oasis that transports you to a place where time slows down, and your adventurous side revs up. Where you can lobster fish by day and bar hop by night…and where nightmares of deadlines and to-do’s become daydreams of pina coladas and suntans.

This place is real my friends, and it lies just 3.5 hours off the mainland of Florida. Enjoy the breathtaking drive through the Florida Keys and arrive at America’s most tropical getaway – Key West. This tiny haven that truly lives on ‘island time,’ is the perfect destination for a ‘Margaritaville State of Mind’ vacation.

Whether you’re looking to have the ultimate Parrothead holiday, or simply enjoy the island life, here are some places that are guaranteed to keep you in the right state of mind.

Where to Stay

No trip to Key West would be complete without staying at Margaritaville Key West Resort and Marina. Ideally located on the waterfront, the resort hosts breathtaking sunset views, is conveniently located just a few steps from Duval Street, and the beach themed, laidback environment sets the tone for relaxation and fun.

Aside from the perfect location, Margaritaville offers upscale amenities worth indulging in. The pool, only available to guests of the resort, offers both privacy and paradise with its tropical décor. Complete with palm trees and native plants, it’s easy to lose track of time as you lay under the Florida sun.

You can also take a short boat ride to Sunset Key, relax on the exclusive beach and treat yourself to a massage before watching the sunset over the Atlantic Ocean…or is it the Gulf of Mexico?!

Where to Adventure

One of the highlights of Key West is the endless amount of water sports and activities available. From jet skis to sailboats and everything in between, there are numerous tour operators that offer adventure for all fitness levels.

One of the best ways to ensure you fully experience the aquatic beauty of Key West is to spend the day on the water. There is something about the ocean surrounding Key West that makes you feel alive. Maybe it’s the crystal clear turquoise waters or the vast marine life. Or perhaps it’s simply the serenity of watching the sunset over the ocean that refuels your soul. There is a reason Ernest Hemingway spent most of his days aboard his boat in these very waters – and if that had the power to inspire classic American novels, imagine what it can do for your vacation!

Skip the group tours and opt for a private charter you can customize. Laid Back Key West offers personalized excursions; so whether you’re looking to snorkel among sunken ships, troll for kingfish, island hop, or gain creative inspiration – you can do it all!

If you’re feeling extra adventurous – and have the time – take a trip over to the Dry Tortugas. Located 70 miles west of Key West, you can arrive by boat, ferry, or seaplane and spend the day – or a few – exploring this remote island full of history. Home to the impressive Fort Jefferson, as well as breathtaking aquamarine waters abundant with coral and marine life, the Dry Tortugas are a fun-filled getaway for the entire family.

Where to Eat

Cheeseburgers. Mahi. Crepes. Tacos. Conch. Pizza. Stir-fry. Key West Pink Shrimp – I could go on and on. Not only are there endless restaurants to choose from in Key West, but they all seem to delight more than the last; maybe it’s something in the water… or perhaps the tequila! Of all the places to choose, here are a few you must check out.

Located on Caroline Street, and claiming to be the oldest restaurant in Key West, Pepe’s has been delivering up delicious fare since 1909 and remains a favorite breakfast spot among locals and tourist alike. Also open for dinner and serving up prime steaks, Pepe’s is sure to hit the spot day or night.

If you’re looking for a Cheeseburger in Paradise, head over to Margaritaville. Smack dab in the heart of Duval, enjoy a mouthwatering burger and perfect margarita at the very 1st Margaritaville Restaurant, which Jimmy Buffett opened in 1985. Go for the food, stay for the fun.

After a long day and one too many Boat Drinks, shuffle over to Mr. Z’s for one of the best Philly cheesesteaks you’ve ever had. Don’t forget the fries and cheese sauce for a well-rounded midnight snack.

Where to Drink

Finding alcohol in Key West is easier than taking candy from a baby, not to mention more socially acceptable. With the seemingly endless establishments to choose from, there are a few worth prioritizing.

If you’re looking to immerse yourself in Key West, soak up the atmosphere and get a birds-eye view of the hustle and bustle of Duval Street, head over to the Tree Bar for a refreshing cocktail with your choice of freshly squeezed citrus (did someone say vodka grapefruit). Located at the entrance to Ricks Entertainment Complex, this outdoor bar, fittingly marked with a massive tree, was once home to The Snake Pit – one of Jimmy’s hangouts back in the 70’s.

Another great spot along Duval is the unmistakable Willy T’s. Complete with dollar bills covering every inch of real estate, live music, and tourists looking for A Lot to Drink About, Willy T’s is always a good time.

Look out for local artist @jlamsonmusic (you can also find him playing at the Margaritaville restaurant), his interactive personality, rich vocals and ideal song choices make the atmosphere that much more lively and entertaining.

If you’re looking for something slightly off the beaten path and perhaps with a bit of history, head over to First Flight Island Restaurant and Brewery. Located just off Duval on Whitehead Street, what is now the Southernmost Brewery in the United States, was once home to Pan American World Airways, with Pan-Am’s first tickets being sold from this building back in 1927.

Where to Shop

From fine art to shot glasses, you’re sure to find the perfect gift or keepsake while in Key West. Retailers line just about every street, and there is no shortage of unique items to add to your collection.

Souvenir shops are like McDonald’s in Key West – with one about every 50 feet and the unexplainable ability to make you go inside, even though you know you shouldn’t. A lot of these shops, especially the ones on side streets, are located in historic homes, making the store and the items inside even more eclectic.

For a full-service shopping experience, check out The Green Pineapple, which is a wellness center complete with a boutique clothing and accessories shop, a health-conscious cafe, a yoga studio and a spa. With its tropical, welcoming vibe you may go in to browse, but you’ll come out with some unique items, a relaxed outlook, and maybe even a pastry.

If the beach life is rubbing off and you’re thinking of redecorating when you get home, be sure to stop by Fast Buck’s at Home, for all your home furnishing needs (or just some tropical inspiration). With furniture and decor for every room, and styles ranging from industrial to modern to island chic, there is a little something for every taste.

Soaking Up the Island Life

From shopping to snorkeling to bar hopping on Duval, there is so much to see and do in Key West that it is easy to try and squeeze everything in one trip. So whether you choose to spend your days poolside at Margaritaville, knocking ‘um back at Willy T’s, or exploring exotic islands, just remember that this tropical oasis is best explored on island time.

I’m Sarah, and I love exploring our planet and learning from its many wonders. You can follow my adventures and insights on Instagram @sarahthewanderess and my blog Happy Travels and Fins Up!