Things To Do
Sunset Celebration at Mallory Square
Yes, it’s touristy—but you have to do it at least once. Arrive early to claim a good spot and catch the street performers.
Conch Train Tour
A fun way to see the island and learn a ton of quirky history. During the holidays, they also run a special version that takes you around town to see the Christmas lights—it’s a really festive way to experience Key West.
The Hemingway Home and Museum
Tour Ernest Hemingway’s former home, learn about his fascinating life, and meet the famous six-toed cats. This stop is Paul and Sage’s personal favorite—purr-haps because the cats steal the show as much as the history does.
Key West Lighthouse
Climb to the top for breathtaking 360° island views (and maybe a little workout to balance out all the key lime pie). Bonus: it’s one of the best photo spots in town!
Fort Zachary Taylor Historic State Park Beach
This spot has the clearest water in Key West—perfect for swimming, snorkeling, or just lounging with your toes in the sand. History buffs will love exploring the old fort, too.
The Key West Butterfly and Nature Conservatory
Step into a magical tropical paradise filled with hundreds of butterflies (and a few flamingos who love to photobomb). It’s dreamy, peaceful, and very Instagram-worthy.
Capt Tony’s Saloon
The original Sloppy Joe’s - Try your luck tossing a quarter into the big fish’s mouth above the door—legend has it, if you make it, someone buys you a drink. Inside, the walls and ceilings are covered with business cards (and bras). A Key West classic.
Hog's Breath Saloon
The Key Lime shooter can't be missed!
Louie's Backyard
Perfect for a post-dinner cocktail at the oceanfront bar. It’s the spot Jimmy Buffett sang about in Trying to Reason with Hurricane Season.
Irish Kevin's
Sing along, laugh, and enjoy the crowd. Just be ready to belt out “Sweet Caroline.”
Margaritaville Restaurant - Key West
Have a margarita at the original location—but fair warning, they’re stronger than you’d expect!
Schooner Wharf Bar
Known for great live acoustic music and a lively atmosphere right on the water.
El Meson De Pepe's Restaurant & Bar
After sunset, head here for mojitos, salsa music, and dancing in the street. The mojitos are dangerously good—don’t say we didn’t warn you.
Blue Heaven
Legendary food in a quirky outdoor setting, complete with roaming chickens! Their banana pancakes are to die for!
Pepe's Cafe
The oldest restaurant in town—famous for fresh-squeezed mimosas and incredible bread. A must for breakfast lovers.
