Water Activities in Summerland Key, FL

Light up the sea floor on a guided kayak paddle beneath the stars

Cruise to a Key West sandbar for swimming, relaxing, and wildlife watching

Snorkel Sombrero Reef with gear included on the Marathon Mermaid

Reef fishing for snapper and grouper, with bait and tackle included

Parasail above Key West on a 12-passenger boat with tandem flight options

Charter a private 2-tank dive with an in-water dive master

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

Paddle calm, shallow waters with glass-bottom views of illuminated marine life

Dolphin watch, snorkel, and visit a sandbar on a small-group Key West tour

Paddle clear waters and mangrove tunnels with an eco-guide

Cruise to Fort Jefferson and swim in Dry Tortugas waters

Brunch, drinks, and a swim stop aboard a Key West sail

Sail turquoise waters as Key West’s sunset colors emerge

Customize your day on Key West’s waters with snorkeling, fishing, or island exploring

An evening cruise with champagne, music, and sunset views from the water

Cruise Key West's calm harbor channels on a private sunset charter

Cruise Key West by private boat with snorkel gear and a sandbar stop

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

Backcountry flats fishing for up to 4 anglers on the ShadowCaster

Shape your fishing day around reef, wreck, or offshore waters

Charter COWFISH for a Key West sandbar stop and guided snorkel, with snacks and water included

Choose a 3–6 hour private sandbar charter with floats, snorkel gear, and shade

Customize a private day of fishing, snorkeling, sandbar stops, or island hopping

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