Best 316 things to do in Summerland Key, FL

Paddle at your own pace through serene mangroves and discover Key West’s vibrant marine life.

Customize a 4-hour private tri-toon cruise with a licensed captain in Key West’s backcountry

Customize your Key West backcountry day on a captained tri-toon with a swim deck

Customize a 6-hour captained Manitou tri-toon cruise for up to 10 in Key West

Private 2-hour Key West sunset cruise on a Manitou pontoon for up to 10

Ride a small-group jet ski at sunset and escape the Mallory Square crowds

Ride a jet ski around Key West with scenic stops along the way

Paddle through Key West mangroves with a guide on this 2-hour eco tour

Paddle at your own pace with a 2-hour self-guided paddleboard rental

Pilot a jet ski in a supervised open-water area, ideal for beginners

Private Tiki Boat charter with premium sound, sundeck, and a hired captain

Private Key West tiki boat with sundeck, sound system, and double slide

Paddle mangrove tunnels on a private, guide-led tour

Ride by boat to Dry Tortugas for Fort Jefferson, beach time, and snorkeling

Ride a private charter to Dry Tortugas with a licensed captain

Cruise Key West backcountry, snorkel reefs, and relax at a sandbar on a private charter

Tour Fort East Martello after hours and meet Robert the Doll

Scan the night sky with a military-grade night vision scope in Key West

Catch lobster by hand with 3–8 hour charter options for up to 6 people

See Key West and the Seven Mile Bridge on a 60-minute scenic flight

Fly over the Marquesas Keys and spot marine life from the air

Take a short aerial tour over reefs, shipwrecks, and Key West backcountry

See Key West landmarks and backcountry waters on a 30-minute scenic flight

See Key West landmarks from above on a quick helicopter flight