Water Activities in Summerland Key, FL

Private Key West sandbar charter with snorkel gear, drinks, and snacks

Charter a private historic schooner sail with drinks and snacks included

Snorkel Key West’s coral reef, then relax with complimentary margaritas

Explore historic shipwrecks guided by a dive master for an unforgettable 4-hour underwater adventure.

Sip bubbly and sail into the Key West sunset aboard a spacious catamaran

Cruise Key West waters aboard a private captained Boston Whaler

Set your own fishing pace with a private captain

Share a 4-hour fishing charter and meet fellow anglers in Key West

Design a Key West charter around your group’s occasion

Circle Key West by jet ski with guided stops and free-ride time

Cruise 30 miles offshore to snorkel, explore sandbars, and shape your own day

A clothing-optional all-male sailing trip with snorkeling, sandbar, or kayaking

Build your own 3–3.5 hour private boat charter with snorkeling gear, snacks, and drinks

Sail a historic schooner, snorkel and kayak, then cruise into the Key West sunset

Sunset catamaran sail with live music, appetizers, and included drinks

Hunt reef fish alongside a professional divemaster and refine your underwater skills.

Private catamaran sailing with champagne, wines and a gourmet cheese buffet

Spend 8 hours fishing deeper into Key West’s backcountry waters

Circle Key West by jet ski with guided landmark stops and swim time

Split a 4-hour party fishing charter with up to 14 people

Customize a private day on the water with lunch, drinks and watersports

Circle Key West by Yamaha WaveRunner with landmark and sandbar stops

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

See reefs below the surface and relax at a Key West sandbar