Things To Do
The Waterfront Brewery
Large, open air brewery, serving flights + pints of locally crafted ales. The back of the brewery features a large arcade - includes skeeball!
Willie T's
Open air bar and restaurant, typically with live music. The floor-to-ceiling dollar bill wallpaper will let you know you've found it.
DJ's Clam Shack
The Original DJ's Clam Shack - as seen on Diners, Drive-Ins, and Dives (Season 19, Episode 6, if anyone is curious). The lobster roll is hands-down one of the best you can get, and the clam bowls are amazingly delicious.
Old Town Tavern & Beer Garden
A classic pub-style joint with indoor and outdoor seating. Full restaurant menu and centrally located in town.
Speakeasy Inn & Rum Bar
A great little stop-in. Awesome rum specials + custom drinks. Features a resident cat, "Captain". He is grossly overweight and wears a tag stating not to feed him. Guests are expressly told such.
The Key West Butterfly and Nature Conservatory
An extensive butterfly rainforest conservatory in the heart of Key West. Also features numerous species of birds (including flamingoes) that roam the grounds. Tickets can be purchased at the door or reserved online.
Key West Historic Memorial Sculpture Garden
A small garden featuring statues and plaques commemorating the storied histories of Key Wests greatest residents.
Museum of Art & History at the Custom House
An indoor museum featuring the local history of Key West, stationed within the island's old Customs House.
Key West Shipwreck Museum
Family-friendly museum documenting the long history of Key West's ship salvage industry. The watchtower on top (free to access with ticket) provides the best view of Key West in the town.
The Green Parrot
A local legacy. Founded in 1890, and as far as we can tell, last updated 1890. Great island dive-bar atmosphere.
Conch Republic Seafood Company
Boat-accessible, open air restaurant with a large bar and extensive seafood menu. Half price appetizers and buy-one, get-one drinks for happy hour. Kid (and adult) friendly.
Bahia Honda State Park
Once used as a work camp for the Flagler Railroad, this beach provides swimming, camping, kayak rentals, and stunning views. Entrance to the park is free.
Sombrero Beach
Crystal blue, shallow warm waters - one of the prettiest beaches in America. Access is free, though parking at the beach lot is $5.
Porky's Bayside
Full menu, peel & eat shrimp specials, and a great happy hour, plus boat rentals + charters right off the back of the restaurant. A round of mini-golf at the new course next door gets a discount off your restaurant check!
Castaway Waterfront Restaurant & Sushi Bar
A neat little restaurant tucked away in the corner of a neighborhood; outdoor seating literally ends at the water. Lionfish (invasive species) on the menu!
La Niña Restaurant
A cinderblock, no frills, side-of-the-highway building that makes some of the heartiest Cuban breakfasts and strongest coffees that you can find.
Robbie's of Islamorada
Feed giant tarpon with sardines! Fight off Pelicans who want said sardines! See manatees but don't feed them because that would violate Federal Law!
Mangrove Mike's
If you're heading back up to Miami and your head is hurting, be sure to stop by here for a good breakfast. Miles would recommend the "Kitchen Sink", which, as the name implies, is an absolutely diabolical plate of eggs, bacon, hash browns, sausage gravy, and more.
Theater of the Sea
A large animal rehabilitation center that allows you to meet dolphins, seals, and other marine life up close. Parking is free and tours are regularly scheduled throughout the day.