Closer to Cuba than Miami, the southernmost point in the U.S. is where the eccentricities of a laid-back beach town collide with rich history, vibrant art, and and sunsets so spectacular they’ve earned their own celebration.

This island’s tiny size — only two miles by four — makes it perfect for wandering between world-class adventures and quirky local spots. Here, the streets hum with the spirit of Ernest Hemingway and his six-toed cats, while Jimmy Buffett’s island anthem, Margaritaville, still echoes through its spirited bars and restaurants.

History buffs can step back in time at the Little White House, where President Harry Truman spent many working vacations. It’s a beautiful blend of natural beauty and American history.

But Key West isn’t just about the past — its waters are home to the only living coral reef in North America, making it a playground for divers and snorkelers (who know never to touch the coral!). Take a boat ride to spot dolphins, or chill on a catamaran with the warm breeze in your hair.

No trip is complete without a visit to Mallory Square, where the sunset turns into a nightly festival, complete with street performers, local crafts, and a healthy dose of island spirit. Stroll to the corner of South and Whitehead Street to pose with the famous Southernmost Point buoy, and then hit Duval Street, which comes alive with music, cocktails, and a mix of bars that range from divey to downright legendary.

And don’t get back on the ship without sampling the island’s legendary treat: every variation of Key Lime Pie. Your taste buds will thank you.