Best 316 things to do in Summerland Key, FL

Sail a luxury catamaran at sunset with tapas, drinks, and dolphin watching

Sail Key West at sunset with complimentary champagne and drinks

Sail to a Key West sandbar with island-style lunch and drinks

Snorkel the Key West reef with an onboard seafood boil and open bar

Bike Key West with tropical fruit tastings and hidden lanes

Backcountry flats fishing for up to 4 anglers on the ShadowCaster

Fish lesser-fished offshore waters for mutton snapper and grouper on a 6-hour charter

Fish reef, wreck, and inshore waters with gear and license included

Fish and explore Fort Jefferson on a 12-hour Dry Tortugas charter

Fish Key West reefs and wrecks on a 4-hour morning charter

Fish the continental shelf for Broadbill Swordfish from Key West

Follow Hemingway’s Key West with 3 food tastings, 3 drinks, and museum entry

Walk Key West’s historic seaport with 5+ tastings and local seafood favorites

Taste Key West classics on a guided walking tour with 5+ stops

Sip and stroll through Key West bars with 5 craft cocktails and tastings

Walk Key West’s Hemingway haunts with three food tastings

Walk Old Key West’s Jimmy Buffett stops, with Key lime pie and a drink included

Walk Hemingway’s Old Town haunts with a guide in 65 minutes

Explore the USNS Vandenberg on a 2-tank morning wreck dive

Refresh your scuba skills with a pool session and a guided 2-tank reef dive

Dive Key West’s barrier reef on a 2-tank afternoon trip

Boat night dive for certified divers on Wednesday and Saturday nights

Customize your Downtime on a tritoon charter for just 6 guests

Explore Key West's iconic landmarks with a local guide on two wheels