So, you’re ready to head to the southernmost city for some fun in the sun? There’s no better destination for adventure, from water sports and historical attractions to live music and entertainment venues. Here’s a list of what the locals consider to be some of the top things to do and see while you’re in Key West.
Discover the splendor of The Dry Tortugas
70 miles west of Key West, the Dry Tortugas and Fort Jefferson National Park offer a day of outdoor adventure, centuries of history and one-of-a-kind natural beauty. Hop on the Yankee Freedom for a leisurely ride to this tiny cluster of islands in the middle of the Gulf of Mexico. The sail there is half the fun aboard this expansive catamaran that has several decks for dolphin and sea turtle spotting, an air-conditioned lounge area where you’ll be served a complimentary breakfast and lunch, freshwater showers and a friendly crew. When you arrive, the sight of the massive Fort Jefferson will stun you. It stands in the middle of the island as it has for more than 200 years. This Civil War fortress was used as a prison and held hundreds of inmates including Samuel Mudd, their most infamous criminal. You can tour the fort, walk inside the cells, watch weapon demonstrations and more. Then, hit the beautiful sandy beach, snorkel in the warm shallow waters, grab a kayak and explore the magnificent scenery or just soak in the sun. There are also hundreds of exotic bird species in the area to observe and it’s not uncommon to see wild dolphins, sea turtles and tropical fish.
Throughout its long history, Key West has beckoned souls from all corners of the earth to discover its undeniable allure. Poets, artists, authors, actors, politicians and musicians have flocked to this tiny island paradise and most never turned back. To learn about them and the rich past of Key West, take a ride on the Old Town Trolley Tour. The conductor will guide you to more than 100 different points of interest including the Hemingway House, the Mel Fisher Museum, the Audubon House, Truman Little White House, the Key West Lighthouse, Duval Street, the Oldest House Museum and much more. You’ll have a chance to get off at all of the stops and stay as long as you want, there are trolleys coming and going all day. Step into the world famous Sloppy Joe’s Bar for a cold drink, check out Jimmy Buffet’s Margaritaville and get some souvenirs on Duval Street.
Make a splash in the aqua blue water
Surrounded by gorgeous crystal waters, Key West offers a multitude of things do to in, on and above the water. Whether you’d like to go watch native Key West dolphins play in their natural habitat, parasail 300 feet above the ocean, or tour the backcountry on a jet ski, Key West is the place to do it all.
Most folks who come to Key West have already heard about the island’s magnificent sunset. And a trip here isn’t complete unless you experience it in all its glory, with a glass of champagne in your hand. For the ultimate sunset view, hop on one of the island’s many sunset cruises. The Commotion on the Ocean is the most popular, offering a live concert as you cruise into the beauty of the sunset. If you're looking for a view from the mainland, then check out the Mallory Square Sunset Celebration. It's starts every night about 2 hours before the sunset. You can visit the Dry Tortugas during the day, head back to the hotel for a quick cleanup, then walk down to the end of Duval street and experience this famous tradition.
Release your shady side at the Green Parrot
The ultimate local dive bar, where people come for a cold drink, to catch up on the news of the day and to kick back to the best live music in town. A stop into this 100-year iconic bar is a definite must do. It’s quirky personality, casual ambiance and the fact that everyone who’s anyone in Key West has been here, draws crowds of locals and visitors alike—just keep in mind their mantra, “No Sniveling”. Bands play everyday, music spills out onto the sidewalk and the place is so well known that the famous and infamous have been known to stop in for a cocktail, so on any given day you never know who’ll be sitting on the barstool next to you.
Rock your heart out at Mile 0 Fest
Mile 0 Fest is a new music festival that takes place during winter at the Truman Waterfront Park Amphitheater. If you’re traveling to Key West in February or are considering a winter escape south, this is a “must-see” event, especially for fans of the Red Dirt & Americana scene. The main stages of the festival are located right off of Duval, but throughout the weekend you can catch sporadic acoustic sets at multiple theaters and bars.