3 Days on Key West
Arts & Culture
Key West is a tiny and beautiful island with a huge heart and a rich history - not to mention some amazing cuisine. Famously the southernmost point of the United States, there is really something for everyone to do when you spend time there. Wherever you go, you'll feel a huge sense of community among the locals who have chosen "island life" and you'll never get tired of seeing and hearing that bright blue Gulf of Mexico.
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Where to stay
Kimpton Lighthouse Hotel
A vibrant boutique gem offering personalized service, chic decor, and an intimate atmosphere in the heart of Key West.
$50 hotel / resort credit.
Upgrade & late check-out whenever possible.
Hyatt Centric Key West Resort & Spa
Overlooking the Gulf in Key West, this upscale resort features chic rooms, beach access, a heated outdoor pool and an onsite spa.
Upgrade & extended check-in/out whenever possible.
Simonton Court Hotel
Where historic charm meets modern comfort in the heart of Key West.
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Day 1: Exploring the island
Start your vacation off right with a little wellness and nature! If you’re renting a car, I suggest you head up to Stock Island for outdoor morning yoga in the Key West Tropical Forest & Botanical Garden. The $20 cash admission gets you entry to the gardens as well, so you can spend a few hours out there in tranquility. If you don’t have a car, I suggest a paddle board or kayak in the Gulf to start your day.
When it’s time for lunch, check out the Key West Cuban Coffee Queen kiosk in the Old Town District and then stroll the seaport boardwalk by the water. Careful for those with sensitive stomachs - fishermen often gut terrapin at kiosks right on the boardwalk. You may want to keep your eyes peeled on the water - you may even see a manatee!
At night, get your spook on with the Ghosts & Gravestones ghost tour. This popular attraction takes you through the island for an hour, hitting on famous Key West haunts like Robert the Doll, but also paying tribute to more somber tales of woe associated with the island. In between narratives, you’ll get exclusive nighttime access to the Key West Shipwreck Museum, which has a few secrets up its sleeve.
Finish your night at Kermit’s Key West Key Lime Shoppe for the quintessential key lime pie….or cookies…or popcorn? Kermit’s is your one-stop shop for absolutely anything Key Lime-inspired. Don’t forget to grab souvenirs for your co-workers back home!
Day 2: Literature, history and art
Take a morning walk up Duval over to The Studios of Key West. You might see Judy Blume curating the selections for her independent bookstore, the Key West arm of Books & Books. Even if she isn’t there, maybe you’ll pick up something from their special Key West section, or one of the latest bestsellers from the New York Times. After checking out, be sure to stop into The Studios to see what public art displays are happening - most of the artists are local to the Keys!
Time for a visit to the White House - the Little White House, that is! This living history museum is named for Harry S. Truman, the President who has used this Presidential vacation home the most out of all the Presidents since its construction in 1890. Take a look back into the mid-20th century and learn about Truman’s legacy, as well as Key West’s place in national history.
Local musicians often accompany dinner in Key West, and there's no better place than Hog's Breath Saloon. In fact, check out the wide array of talent up and down Duval Street as the sun sets and sets on the water and the street fills up with nighttime revelers.
Then it’s time to get a little dramatic! Music sets aren’t the only performances you’re bound to experience in Key West - the island is home to multiple professional theaters with eclectic programming of plays and musicals. The Red Barn Theater and Waterfront Theater do familiar titles as well as world premieres, so there’s truly something for everyone.
Day 3: Beach day
Cheese and cured meat for breakfast? Nope, it’s not your typical charcuterie board you’ll find at the breakfast club, too - it’s a pancake charcuterie board! Consisting of pancakes, fresh fruit, and various toppings, this one-of-kind dish will give you the fuel for what’s sure to be a fantastic final day on island time.
And it’s not a Key West trip without a beach day! Time to check out the southernmost state park in the continental U.S.. Fort Zachary Taylor Historic State Park Beach is situated right on the Gulf of Mexico. The park covers 54 acres in total, with the beach on the southern end. Bring your own food (there are grills available!) or make a visit to Cayo Hueso Café for lunch before heading back to your hotel to freshen up for the evening.
Finish out your vacation with a quintessential cruise on the Gulf to see the world-renowned Key West sunset. Whether it’s provided or BYOB, you can sip champagne and eat hors d’oeuvres while you bask in the tropic breezes. You might even spot a dolphin or two waving goodbye to you on the boat!
Need to Know
I believe this is all kid-friendly as well, depending on the sunset cruise you take and how kids will respond to the ghost tour.
For more travel tips, check out Fora Advisor Ashtin Robison’s guide, A Guide to (Mostly) Key West.
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This guide is part of our ongoing series on travel to Florida.