things to do in Summerland Key, FL

Cruise Key West harbor at sunset with your group and captain

Private light-tackle fishing aboard a 30-foot Jeanneau with a licensed captain

Build a private Key West celebration around your group's ideal day on the water

Private Key West sailing with snorkeling, sandbars, and dolphin searches

Do two guided reef dives with an in-water divemaster

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

Cruise to a Key West sandbar with kayaking, paddleboards, lunch, and drinks

Private sunset sailing with bubbly, wines and a gourmet cheese buffet

Dive the USNS General Hoyt S Vandenberg on a private 2-tank wreck trip

Cast light tackle from Stella Blue in calm nearshore waters

A crewed private charter shaped around your preferences

Snorkel coral reefs and relax at a Key West sandbar

Ride a 28-mile guided jet ski loop around Key West from Opal Key Marina

A discreet, captain-led private escape on Florida Keys waters

Hold a private, personalized farewell at sea with a caring local captain

See Key West landmarks from above on a quick helicopter flight

Book a private reef dive with an in-water divemaster for up to 6 guests

Private 20-minute flight for aerial views of reefs and marine life

Watch the sunset over Seven Mile Bridge from the water

Take in Key West’s sunset with glass-bottom views of marine life

Dive a guided wreck and shallow reef combo in Key West

Dive after dark on a private 2-tank scuba charter with an in-water dive master

See Key West’s sunset from a helicopter, plus a champagne toast

Private 8-hour Key West charter with up to 4 dives