Whether it’s the island weather and the beautiful architecture that drew you to Key West, Florida, or the abundance of historical sites and attractions, this tiny island getaway will jam-pack your itinerary with fun. But don’t feel obligated to take it all in on one trip — after all, you’ll need an excuse to make your way back.
As always, check for travel restrictions and closures before planning your trip.
Friday: Immerse Yourself in History
Centrally located in the Bahama Village district, Key West’s 173-year-old lighthouse is a great place to kick things off, as it offers both breathtaking views of the surrounding Bahamian clapboard-style houses and a ton of history.
Built in 1848 and used by the U.S. Coast Guard through the late 1960s, the lighthouse is a beacon of the city’s maritime history. Walk the 88 steps up to the top and visit the adjoining caretaker’s cottage before heading off for more exploring.
Just east of the lighthouse, you’ll find Duval Street — the 1.25-mile-long strip is lined with boutiques, cafés and restaurants, making it the hub of Old Key West’s shopping district and a center for nightlife.
The city has some incredible Cuban restaurants, like El Meson de Pepe and Frita’s Cuban Burgers, which are a must-try. When visiting Key West, you can’t leave without indulging in a piece (or two) of Key lime pie — so a visit to Blue Heaven or Kermit’s Key West Lime Shop is nonnegotiable.
Once you’ve had your fill (both literally and figuratively), it’s back to exploring the island’s rich history. Head a few blocks west and visit the sprawling 54-acre Fort Zachary Taylor Historic State Park, which is also home to the 170-year-old Civil War-era fort.
Plan to be in Mallory Square for the sunset — it’s a 20-minute walk from the fort. Chances are you won’t be alone, but the views as dusk is settling in are unbeatable.
You saw Duval Street during the day, but make sure to return after dark. The Tiger Bar is a restaurant with two personalities: the Champagne Room, where the wine keeps flowing, and the main bar, where small plates are turned out in a snap.
From here, take a walk down Duval and pop into the many welcoming bars (Sloppy Joe’s, the Rum Bar and the Smallest Bar Inn are a few good places to start). Things get festive after dark in this neighborhood, and it won’t be hard to make new friends.
Saturday: Head Out on the Water
The Historic Seaport is another buzzy center of activity on the island that’s transformed significantly over the years. Having started out as the maritime and economic hub of the city since its founding, the 20-acre port was transformed into a popular destination for visitors nearly 30 years ago with a focus on its access to the water.
Today, peruse the shops and restaurants dotting the blocks surrounding the marina. For those looking for some more adventure off land, there’s a handful of watersport experiences you can book via outfitters, like snorkeling and Jet Skiing.
There are also a handful of charter companies — including Key West Boat Trips and Sebago Watersports — that’ll take you out fishing, kayaking and sailing and cater to both larger groups and more intimate outings.
Book an expedition to go scuba diving or snorkeling with Lost Reef Adventures to explore shipwrecks and reefs. For something a bit more romantic, take a sunset boat tour that won’t require you to slip into a wetsuit.
Round out your busy day at Key West Bight, a marina in the Historic Seaport, and grab dinner at one of the enticing eateries. Conch Republic Seafood Company is a favorite for their incredibly fresh “dock-to-dish” dining.
Sunday: Hit the Beach
On your final day, you’ll want to make some time to visit the beach — you are on an island, after all. And Higgs Memorial Beach Park has both sprawling sandy shores and cultural and historical institutions waiting to be explored.
Stroll along the waterfront while scoping out your beach spot, then spend the afternoon relaxing from your busy trip. If you need a break from the sun and are craving a final dose of history, make sure to leave time to visit West Martello Fort, a historic Civil War-era tower that’s on the National Register of Historic Places, located only steps from the beach.
Next up: the bucolic Key West Tropical Forest & Botanical Gardens, which is only a 10-minute drive away on Stock Island. Open from 10 a.m. to 4 p.m. daily, the gardens specialize in endangered flora from the Florida Keys, Cuba and the Caribbean and have been a favorite among visitors for 85 years.
After a weekend packed with history, culture and plenty of sightseeing, end the trip on a high note — we suggest a seafood dinner you won’t soon forget. While there’s no shortage of phenomenal restaurants on the island, Nine One Five, Little Pearl and Seven Fish are local favorites that serve up some of the island’s best dishes.
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