4
Sloppy Joe's Bar
Bar
Open since 1933, this bar offers live music & dancing plus a separate tap room for sports-watching.
$$ $$
4.50 (12.5K reviews)
6
Blue Heaven
American restaurant
Iconic landmark for Floridian-Caribbean cuisine & key lime pie, with a funky setting.
$$ $$
4.60 (9.2K reviews)
7
Sunset Watersports
Tour operator
👍👍 Captain John, Jesse, and Paige were fabulous! We (family of 4) went on the dolphin/snorkeling cruise, and it was well worth it. We saw lots of dolphins, a sea turtle, and the snorkel site was filled with coral and lots of fish. Drinks (soda, water, juice, beer) were included. The snorkel gear and li...
4.70 (9.1K reviews)
8
Smathers Beach
Public beach
Public beach & a spring break destination with showers & volleyball, plus jet ski rentals.
4.20 (8K reviews)
9
Sebago Watersports
Boat tour agency
Popular boat tour agency featuring snorkeling trips, sunset sails & parasailing adventures.
4.70 (6.9K reviews)
11
Two Friends Patio Restaurant
American restaurant
Long-standing mostly outdoor cafe with an old-school American menu plus lively karaoke.
$$ $$
4.50 (5.8K reviews)
12
El Siboney Restaurant
Cuban restaurant
Traditional Cuban home cooking & housemade sangria in a casual, family-friendly setting.
$ $$$
4.60 (5.4K reviews)
14
Hog's Breath Saloon
Pub
Popular pub providing bar food on a covered outdoor patio plus live music & dancing.
$$ $$
4.50 (4.7K reviews)
15
Margaritaville - Key West
American restaurant
Lively joint offers island-inspired fare & margaritas plus a gift shop & live music most nights.
$$ $$
4.20 (4.6K reviews)
16
Irish Kevin's
Irish pub
Lively Irish pub with nightly music, an expansive stout list & an eclectic pub-grub menu.
$$ $$
4.60 (4.5K reviews)
17
Danger Charters
Boat tour agency
👍👍 The Danger trip was amazing! We did a half day snorkel and kayak. We saw a sea turtle, stingray, lion fish and a moray eel while snorkeling. They had better snorkel equipment and a better spot than Fury (we did both tours), and Captain Joe and Sydney were amazing. Small group (3 couples) and we got...
4.90 (4.3K reviews)
19
Caroline's Cafe
American restaurant
American cafe serving po' boys, conch fritters & the like in a circa-1838 house with outdoor seats.
$$ $$
4.50 (4.2K reviews)
20
Schooner Wharf Bar
Bar & grill
Longtime open-air hangout for seafood complemented by live music & dockside views.
$$ $$
4.50 (4.2K reviews)