Call Center is open from 10AM - 4PM EST

Key West for First Timers

So you’re planning your first trip to Key West?

Well, it’s about time! The Conch Republic offers the perfect tropical island vacation without leaving the United States. Positioned at the southernmost point in the Continental United States, Key West has an offbeat, easygoing energy that’s quick to charm. If you’re a first timer, here’s an essential guide to what you absolutely must do and see.

Go Snorkeling

Key West is home to the third largest barrier reef in the entire world just seven short miles offshore. The best way to discover it is aboard a snorkel excursion with Fury Water Adventures. With a wide variety of trips to choose from including the All Day Water Adventure, the Local’s Eco Tour and the 2 Stop Reef Snorkel trip, two reef stop trip, a classic snorkel trip with Fury is a great option. Departing three times daily, enjoy an hour long sail to the reef aboard a 65-foot catamaran. You’ll learn about the reef’s ecosystem, how to snorkel and get outfitted with your gear. Then, enjoy a full hour to discover coral canyons and colorful tropical fish. On the way back to Key West, it’s all you can drink beer and wine.

Duval Crawl

Duval Street is the heart of Key West’s entertainment district. There are restaurants, shops, art galleries and more bars than we can count. Go for a stroll by day or night and pop into some of Duval’s most famous destinations. Sloppy Joe’s is legendary for live music and a wild good time. Ernest Hemingway frequented it in the 1930s. However, the original location is around the corner on Greene Street at what’s now Captain Tony’s. Go to both! For a more local experience, swing by The Porch and The Other Side off Caroline Street.

Hemingway Home

One of Key West’s most famous historical figures is Ernest Hemingway who called the island home with his second wife Pauline during most of the 1930s. This was Hemingway’s most prolific writing period where he’d spend his early mornings in his writer’s studio and afternoons on the Gulf Stream aboard his beloved fishing boat Pilar. His home, which occupies an entire block on Whitehead Street, is now a museum dedicated to the writer’s life in Key West. You’ll find descendants of his beloved six-toed cat Snowball and fascinating artifacts. Opt for the guided tour from one of the museum’s experts.

Rent Bikes

The best way to get off the beaten path and experience true Key West is by bicycle. You’ll discover charming side streets lined with pastel colored conch cottages, palm trees and bougainvillea vines. A few sights to discover on your ride: the Key West Cemetery, the Southernmost Point and the beaches along the southern end of the island.

Conch Tour Train

To truly get the lay of the land, opt for a tour aboard the Conch Tour Train. The 90-minute trip weaves around Old Town where you’ll see all the sights and learn the quirky history of the island from friendly conductors. They’ll highlight Key West’s unique architecture and the colorful characters who’ve lived here throughout history.

Mallory Square

The sunset is celebrated nightly in Key West at Mallory Square and it is an absolute must for first timers. A cast of characters descend along the harbor to do magic tricks, animal stunts and musical acts. You’ll find vendors selling handmade crafts, mojitos and conch fritters. All of it is set against the backdrop of the setting sun, which is a sight to behold. No two sunsets are alike and they’re all soul-stirringly beautiful.

Eat Conch

They don’t call Key West the Conch Republic for nothing. This is your chance to sample this tasty crustacean in dishes like conch fritters and conch chowder. You’ll find them on almost every menu in Key West. We especially love them at the Conch Republic Seafood Company and BO’s Fish Wagon.

Try Cuban Food

Only 90 miles to Cuba, Key West has strong ties with the Caribbean island nation to the south. A great way to experience Cuban culture in Key West is through its cuisine. Whether it’s a café con leche at Fisherman’s Cafe or a traditional meal of ropa vieja (stewed beef), fried plantains, black beans and yellow rice at El Meson de Pepe or El Siboney, you’ll be delighted by the rich flavors of Cuba in Key West.

Key Lime Pie

Key lime pie is the unofficial dessert of Key West, and like conch fritters, you’ll find it on almost every menu in town. Head to Blue Heaven for homemade pie served with mile high meringue or to Louie’s Backyard for a fine dining experience and lovely Atlantic Ocean views paired with your pie. You can also try Kermit’s Key Lime Pie Shoppe for a wide variety of key lime pies, including the not-to-be-missed frozen key lime pie on a stick dipped in chocolate. They also have frozen strawberry key lime pie dipped in white chocolate. You just can’t go wrong!