Best 316 things to do in Summerland Key, FL

Private 2-hour Key West sunset sail with captain and mate

Private 2-hour sail on a 1939 wooden schooner in Key West

Private 4-hour snorkel sail with a swim stop and sunset cruise

Bareboat yacht charter for groups over 6, with snorkel and float gear included

Charter a private motor yacht in Key West with flexible 1.5–8 hour options

Catch the Key West sunset on the historic schooner Malabar X

Private Key West harbor sail with time at the helm

Sail at sunset on a private boat set up for your proposal

Charter a 1939 wooden schooner for a sunset sail from Key West’s Historic Seaport

Book a private Florida Keys backcountry and flats fishing charter

Fish Key West on a fully equipped 24 ft bay boat—ideal for first-time anglers

Fish longer on a 6-hour private charter to reach less-pressured spots

Fish Key West waters on an 8-hour charter for up to 4 anglers

Charter the 54-foot Schooner Valora for a private sail in Key West

Sail a Key West schooner at sunset with drinks, appetizers, and cocktails included

Walk Key West’s haunted Old Town on a private, customizable tour

Cruise Key West on a regular-size step-through e-bike with included helmet and lock

Rent a large step-thru e-bike and explore Key West on your schedule

Snorkel two Key West reef stops with an all-you-can-eat seafood boil and open bar

Ride the 53-foot tiki boat to a Key West sandbar

Sunset catamaran sail with live music, full bar, and appetizers

Snorkel the Florida Keys Reef on a sailing cruise with gear, instruction, and drinks included

Sail to the Florida Keys Reef for an easy morning snorkel

Sail to the dolphin playground on a 2.5-hour Key West catamaran cruise with complimentary drinks