Florida Staycations: Key West

Sullivan Maley
KEY WEST — Any bonafide Floridian should take in the island gem that is Key West at least once during their time in the Sunshine State. Our nation’s southernmost city boasts a culture reminiscent of New Orleans and Savannahesque southern charm, all wrapped up in a tropical paradise where roosters and six-toed cats roam the streets.

Any good vacation starts with the perfect place to stay, and, in Key West, one won’t find much better accommodations than the Margaritaville Beach House. Hotels along the "Duval Crawl” can be hit-or-miss, often charging steep prices justified by location rather than amenities. But on the island’s southern end, just steps from the Atlantic Ocean, lies Jimmy Buffet’s signature resort, the perfect place to relax and spend your days on island time. This location provides some relief from the noise and commotion of the downtown stretch, but for those looking for a piece of the action, shuttles are provided throughout the day and night to transport guests to the heat of the action.

The hotel’s tropical ambiance is sure to please Parrotheads and family vacationers alike, with hammocks hanging in every palm tree-canopied courtyard and an ice-cold margarita placed in your hand at check-in. Buffet lyrics and imagery adorn the brightly-colored walls of each room for accommodations sure to remind you of your place in paradise, and good time music pumps through all of the public spaces. And while Key West is certainly known for its variety of quality restaurants and eateries, guests can find their five o’clock right on property at the Tin Cup Chalice Bar and Grill, serving a variety of fresh seafood, delicious sandwiches and salads, and a delectable variety of the sort of inventive cocktails one could only expect to find in Key West.

It doesn’t take long in the Conch Republic to see why the island has been a favorite locale of celebrities and tourists alike for most of its history. Key West truly has something for everyone, from historical landmarks and world-renowned fishing and diving to fine dining and a lively bar scene. Visitors can explore sites like the Ernest Hemingway estate and Truman’s Little White House to grow closer to the island’s rich history, or simply opt to take in the area’s natural beauty. 

One of the best methods for the latter is one of Key West’s many evening cruises which allow you to experience a beautiful Florida sunset on the water. I had the pleasure of joining Fury’s Commotion on the Ocean Sunset Sail as a guest of their resident musician Cory Heydon whose band serenade guests with an excellent selection of mellow rock classics as they are wined and dined across the Gulf of Mexico on a beautiful 65-foot catamaran. Quality live music, breathtaking views, and bottomless food and drink at a very reasonable price made for a perfect night in paradise.

Duval Street, the city’s main drag and cultural nucleus, runs from the Gulf of Mexico to the Atlantic Ocean and contains over 40 bars, as well as much of the island’s best dining. Join the famous singalong at Irish Kevin’s, enjoy a rum tasting at Speakeasy Inn’s Rum Bar or head to Flying Monkeys Saloon for their expansive selection of frozen cocktails. 

Thrifty travelers should seek out Duval’s many enticing happy hour specials, the best of which I found to be at Old Town Tavern and Beer Garden, where wine, house liquor, and appetizers are half off (with beer discounted by 25%) twice daily and food is served until 1 a.m. If you’ve ever wondered what might result from carbon-copying the flavor palette of the famous McRib onto a pizza, Old Town Tavern has your answer with their Pig n’ Pickle flatbread, an admittedly curious but surprisingly tasty combination of pickles and ground pork dressed with a tangy mustard seed barbecue sauce. 

The island’s best food and drink aren’t limited to Duval, however. If you want to drink with the locals drop by the Green Parrot or the small tiki bar on the water at fine-dining spot Louie's Backyard—a favorite haunt of Buffet, Hunter S. Thompson, and 92 in the Shade author Thomas McGuane. Pepe’s Cafe on Caroline street serves the best peel-and-eat shrimp I’ve ever had the privilege to consume, along with amazing half-shell oysters and beer prices that can’t be beaten. The rustic institution also serves an excellent cocktail breakfast rivaled only by fellow favorite Blue Heaven. For traditional Cuban coffee or a delicious pressed sandwich, head to 5 Brothers Grocery and Sandwich Shop, where you’re sure to meet a few locals and be ruined on any future Cuban sandwiches you may attempt to enjoy after your trip. 

Of course, one of the central dining questions of a Key West vacation is where to find the best Key Lime pie, and while the island is home to many fine bakeries frequented by locals and tourists alike, I’ve found the best rendition of the dessert to be on the way to Key West in Tavernier at the Blonde Giraffe. Take a box of pies for the road or enjoy a fresh slice in their beautiful butterfly garden on your way out of town.

Sullivan Maley is a sophomore at the University of Southern California’s Annenberg School of Journalism. He is a graduate of St. Stephen’s high school and has done copy editing and social media management for The Bradenton Times since 2018.