Key West Spring Break Crawl: Sunsets and Sailing in Florida

Key West Sunset gathering
Key West crowds gather in Mallory Square to watch the sunset every night. Photo: Shayne Benowitz
With its unique position at the southernmost point in the Continental United States, Key West has an anything goes attitude and a subtropical climate, making it an ideal spring break destination.

Get the All-Inclusive Treatment: Yankee Freedom III
Pay one price for a bundled food or drink experience

As if you're not already far enough off the grid, voyage 70 miles west of Key West aboard the Yankee Freedom III and discover the unspoiled beauty of Dry Tortugas National Park and Fort Jefferson. For $170 per person, your day trip includes breakfast, lunch, a guided tour of the fort and snorkeling along the Florida Straits, the third largest reef in the world.

See the Green Flash: Mallory Square Sunset Celebration
Where to watch the sunset

Gather at Mallory Square for the famous nightly sunset celebration. A group of ragtag street performers -- think, juggling tightrope walkers, sword swallowers and a Frenchmen who's trained his cats to jump through flaming hoops -- serve as the foreground while the sun makes its gradual descent into the Gulf of Mexico. Snack on conch fritters and sip mojitos sold from stands as the sky changes a million shades of pink, purple and gold.

It's 5 o'clock Somewhere -Here: Captain Tony's Saloon
Where to get a great tropical drink

Head to Captain Tony's Saloon, the site of the original Sloppy Joe's bar once frequented by Hemingway. A dark, cool lair just off Duval Street, the walls are covered with license plates, and bras hang from the rafters overhead. Order the Pirates Punch ($7.50), a legendary rum and fruit juice concoction made in 80 gallon batches. The only people who know the actual recipe are the owner and the general manager.

Closer than Disney World: Florida Keys Eco-Discovery Center
A great activity for kids and families

Learn about the delicate ecosystem that makes up the Florida Keys at the interactive Florida Keys Eco-Discovery Center. Through March 26, a special exhibit on botanical art and exploration through Everglades National Park will be on display. It's hands-on learning for the whole family that you can apply throughout your Key West vacation.

Catch Some Rays: Blue Heaven
A place to eat or drink outdoors

A large backyard shaded by palm trees and old sails, Blue Heaven restaurant is a singularly Key West oasis. It's a riot of bougainvillea, pastel-painted bar stools and funky Bahamian-style folk art with a ping-pong table behind the bar. Breakfast is a classic with lobster Benedicts or banana pancakes, and they serve up delicious island fare any time of day. Don't be surprised if one of Key West's famous chickens scurries by your table while you sip a perfectly spiced Bloody Mary.

Planning a Caribbean spring break instead? Check out our island finder >>


Shayne Benowitz is a travel and lifestyle writer who's never so happy than when she's offshore on a boat. Her favorite springtime activity in Key West is snorkeling the reef with her crew at Fury Water Adventures.
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