Best 316 things to do in Summerland Key, FL

Swim at a secluded sandbar and watch playful wild dolphins up close, with lunch and unlimited beer and wine included.

Paddle mangrove tunnels then relax on a secluded sandbar with lunch and unlimited drinks

Enjoy unlimited drinks, appetizers, and live music aboard a catamaran while you watch the famous Key West sunset.

Snorkel two reef sites, then cruise back at sunset with drinks after your swim

Spend 6 hours on the water with 11 activities, lunch, and draft beer on the cruise back

Parasail from Casa Marina with an 8–15 minute flight and up to 1 hour on the boat

Boat out to a remote sandbar, then kayak through Key West mangroves

Snorkel Key West’s reef, then sip from the open well bar

6-hour Key West watersports combo with 10 activities plus lunch and drinks

Cruise to spot dolphins, snorkel a reef, then enjoy sunset drinks

Cruise to spot dolphins, then snorkel a Key West reef with drinks on the ride back

All-day Smathers Beach pass with parasail flight and unlimited watersports

Cruise to a secluded Key West sandbar with lunch, kayak tour, and sunset cruise

Explore Key West and Stock Island with a 4-person golf cart

Rent a 6-passenger golf cart to explore Key West roads up to 35 MPH

Ride a jet ski around Key West with 5–6 guided stops

Sail into the Key West sunset with a tropical buffet and open well bar

Sip and sail into the Key West sunset with live music and an open well bar

Snorkel two reef sites, then sail back at sunset

Build your own Key West private boat charter with a licensed local captain

Customize your Key West private charter with a captain and your choice of 3 activities

Sail into the Key West sunset with drinks and hors d'oeuvres included

Sail Key West and snorkel the backcountry on your own private boat

Private sail to a shallow-water anchorage with time to lounge on a Lilypad float