Sunday Manifest: Key West, Florida
Located off the southernmost tip of Florida, where the Gulf meets the Atlantic at the end of the 113-mile Overseas Highway, Key West is a unique (and lovely) one-of-a-kind vacation destination—equal parts bustling modern city, laid-back beach town, and subtropical island paradise, all wrapped up in a friendly, edge-of-the-world kind of vibe.
Spanning just two miles by four miles at its widest point, it’s not the largest key in Florida’s archipelago, but it is the most famous—immortalized in stories by Ernest Hemingway and breezy, summer songs by Jimmy Buffet. It’s home to narrow palm-lined beaches set against calm blue water; stunning coral reefs and mangrove forests; historic neighborhoods; and a world-famous bar and party scene.
The island’s history is filled with fascinating tales of settlers and immigrants; pirates, bootleggers, and rum runners; artists and authors; haunted locales; and a symbolic secession from the US in 1982—all of which is woven into the fabric of Key West today.
Because of the island’s size, nothing is ever too far away or too difficult to get to, no matter which neighborhood you’re in. This makes it easy to explore and lose yourself in the sights, sounds, flavors, and fun-loving culture this southern beach city is known for.
Historic Old Town is a great place to start. Laid out in a grid pattern, with rows of pastel conch-style cottages and manor houses, lush landscaping, and some of the island’s most iconic bars and restaurants, it sets the mood for any stay in Key West.
Walk the shaded residential side streets and quiet alleyways or stick to the busy sidewalks around Mallory Square and along Duval Street (where you may cross paths with a few of Key West’s free-roaming chickens). Rent a bike (or take a guided bike tour) around the neighborhood and out to the Southernmost Point Buoy. Or, better yet, make use of the Old Town Trolley for narrated tours and unlimited hop-on/hop-off service for the day.
While in Old Town, pay a visit to the yellow-shuttered Hemingway House Museum across from the Key West Lighthouse for a peek inside the author’s former home and writing studio, and spend time in the gardens with the dozens of cats that live on the property—many of them polydactyl (six-toed) descendants of Hemingway’s own cat, Snowball.
You may also want to tour the nearby Harry S. Truman Little White House (Florida’s only presidential museum); the Tennessee Williams Museum (it’s said the playwright wrote the final draft of A Streetcar Named Desire on the island); and the beautiful Key West Butterfly & Nature Conservatory, if you have the time.
Outside of the historic district, there’s even more to see and do.
Get out on the water for an exciting day of jet skiing, kayaking, fishing, or snorkeling. Spend the afternoon playing and swimming at one of the local beaches. Visit the tropical gardens and Civil War fort at West Martello Tower. Or book an unforgettable half-day seaplane and snorkel excursion to Dry Tortugas National Park—one of North America’s most remote and inaccessible National Parks—where you can tour historic Fort Jefferson, sunbathe on a quiet, white-sand beach, and snorkel the incredible living coral reef (the third largest barrier reef in the world) located just off-shore.
Of course, no trip to Key West is complete without experiencing the island’s amazing cuisine and famed nightlife. Stop in at the legendary Pepe’s Café for fresh seafood and some of the best comfort food on the island. Dine on the garden patio at Blue Heaven, a landmark eatery that’s as famous for its key lime pie and Caribbean-inspired dishes as it is for its funky décor and roosters crowing in the trees. Or enjoy deliciously authentic Cuban food, specialty cocktails, and sunset views at the warm and rustic El Meson de Pepe at Mallory Square. You honestly can’t go wrong with any of them.
Once the sun goes down, head over to the Green Parrot Bar or Sloppy Joe’s for cold drinks, live music, and an authentic Key West dive bar experience. Or try the more upscale Rum Row poolside bar and cigar lounge at the Gates Hotel on the eastern side of the island, if you prefer a more laid-back nightlife scene.
We have a fabulous Sun and Fun Key West Adventure ready to book on our Experiences page. But if this South Florida island destination isn’t on your travel wish list, we’re always happy to curate a custom trip for you wherever you’d like to go.