5 best things to do in Key West!

The best thing about this lifestyle: there’s always another adventure downwind. In this episode, we dropped the lines, said goodbye to Cabbage Key, and began the 17-hour trip to Key West.

We had calm seas at first, but with 12 hours to go, the wind picked up. It was the roughest passage we’ve had yet. Dixie handled the trip like a champ, but by the morning, Emily was feeling sick as a dog, and Cole was running on zero sleep.

The faint outline of the nearby shore had never been so welcome. We were ready to explore Key West and the best it has to offer.

Visiting the area anytime soon? Watch the video and discover 5 fun things to do in Key West!

Fort Zachary Taylor

The words Key West might conjure images of bars, bars and more bars. But there’s much more to this town than stumbling down Duval Street. We took a scooter ride back to the mid-1800s to Fort Zachary Taylor.

The fort was built in 1845 and operated for over 100 years, spanning four wars and the Cuban missile crisis. One particularly infamous inmate of the fort was Dr. Samuel Mudd, the doctor who helped John Wilkes Booth after he assassinated Lincoln. Convicted as a co-conspirator but cleared of the death penalty by one vote, Dr. Mudd was held at Fort Zachary Taylor for a few days, later being moved to Fort Jefferson in the Dry Tortugas.

So much history is tucked away in this 8-square mile island; don’t leave the area without visiting the Truman Annex. This spot served as an army installation and then a naval station from the Spanish American war through WWII. It’s also where President Harry Truman spent 175 days running the country from his ‘Little White House.’ 

The fort offers guided tours, and there’s also a beach, cafe, and the national park to explore.

Sunset Celebration at Mallory Square

Every night, two hours before sunset, vendors, street performers, and local artists all come out for an evening that’s uniquely Key West. The Sunset Celebration is a much-loved gathering at Mallory Square Dock, where tourists make memories and locals remember why they love living here. It’s incredible to watch strangers come together with the same goal: to capture the sunset and take in the final moments of a beautiful day.

Whether you get food and souvenirs or simply a stunning photo of the sunset, you’ll be glad you joined in the fun.

And then, when the sun goes down, the block really wakes up.

Duval Street

If you love live music, Key West’s Duval Street is the place to be. This mile-long stretch runs from the Gulf to the Atlantic and is packed with restaurants, bars, shops, and live music spots, perfect for those wanting a fun night out. 

Grab some BBQ nachos at The Hogs Breath Saloon, or listen to some of the top bands on tour at The Green Parrot Bar, a hundred-year old dive bar on the corner of Duval and Whitehead Street.

The Museum of Art and History at Custom House

After a night out on Duval Street, a quiet morning might be right up your alley. For any history buffs out there, the Museum of Art and History at Custom House is worth a visit.

One exhibit features Henry Flagler’s overseas railroad, an incredible feat of engineering which spanned 153 miles of ocean from Florida’s mainland to Key West. It stood for over 22 years and was considered the 8th Wonder of the World—until ‘the storm of the century’ completely destroyed it in 1935.

Cole’s inner construction geek had a field day at this exhibit! Be sure to add Les Standiford’s book, Last Train to Paradise, to your reading list. 

Kermit’s Key Lime Pie

A visit to Key West is not complete without key lime pie. Even though key limes are no longer grown here, there’s something a little bit magical about the combination of lime juice, sweetened condensed milk, and egg yolks, baked to perfection on a graham cracker crust.

The best key lime pie in Key West is at Kermit’s Key West Key Lime Shoppe, hands down. Opened over 30 years ago, this little gem of a shop sells all things key lime: bottles of juice, sauces, marinades, and, of course, their famous key lime pie.

Here’s a slice of key lime history: the citrus is originally from southeast Asia, but English sailors (nicknamed limeys) brought limes over in barrels of water when they discovered the limes covered up the brackish taste. Plus, the vitamin C helped them not get scurvy. Later they planted the limes all over the world, including in Mexico, Tahiti, and Australia.

Key West used to have large lime groves, but a hurricane wiped them out in the 1950s. Guess what sprang up in their place?

Houses.

We had an amazing time in Key West, made even more special with a visit from Cole’s sister Nicole. You’ll notice in the video we rented scooters and bikes during our time there, which made it much easier to get around. If you’re planning a trip to this beautiful place, we hope a few of these 5 things to do in Key West will make it into your itinerary. 

Already been to Key West? What were your favorite things to do? Drop us a comment below!

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