Best 295 things to do in Key West, FL

Cruise to a Gulf swim stop on a tiki boat

Cruise Key West’s seaport by tiki boat with captain-guided local stories

Cruise Key West Harbor at sunset on a tiki boat with a US Coast Guard-certified captain

Cruise Key West Harbor on a tiki boat at sunset

Cruise from Key West to a Gulf swim stop with a captain-led tiki boat ride

Enjoy a four-hour private cruise to mangrove sandbars with snorkeling, paddle boards, and a catered Cuban lunch.

Discover mangrove islands and pristine sandbars on a comfortable 25-ft Sea Ray with captain and fuel included

Spend 5 hours hanging out at a sandbar with a captain and gear for up to 6 guests

Private 6-hour sandbar cruise with lunch for up to 6 guests

Cruise to JewFish Basin Sandbar or Mud Keys for a 2-hour hangout

Private 4-hour Boston Whaler charter with captain for up to 6 guests

Cruise to the sandbar for a 5-hour hangout with lunch for up to 6 guests

Key West sandbar cruise for up to 6 guests with captain and drinks included

Charter a custom houseboat and relax on a remote Key West mooring

Private Key West sunset cruise for up to 6 on the Miss Marie

Rent a 23' center console and fish Key West your way

Cruise by private boat from Key West to Dry Tortugas and tour Fort Jefferson

Build your own private Key West day on the water for up to 6 guests

Enjoy a customizable cruise through Florida Keys sandbars with snorkel gear and coolers included.

Spot playful dolphins and snorkel vibrant reefs on a small-group Key West cruise

Sail into the Key West sunset with fresh sushi and drinks

Private Barefoot II charter for up to 6 to snorkel and relax in the Florida Keys

Boat between Key West waterfront bars on a private 3- or 6-hour charter

Private sandbar and island-hopping charter with 4, 6, or 8-hour options