Best results for Water Activities in Stock Island, FL

Cruise to a Gulf swim stop on a tiki boat

Cruise Key West’s seaport by tiki boat with captain-guided local stories

Cruise Key West Harbor on a tiki boat at sunset

Cruise from Key West to a Gulf swim stop with a captain-led tiki boat ride

Charter a custom houseboat and relax on a remote Key West mooring

Rent a 23' center console and fish Key West your way

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

Private sandbar and island-hopping charter with 4, 6, or 8-hour options

Choose a 4, 6, or 8-hour private charter to island hop local waters

Choose a 4, 6, or 8 hour sandbar and island-hopping charter from Sunset Key

Enjoy a customizable cruise through Florida Keys sandbars with snorkel gear and coolers included.

Spot playful dolphins and snorkel vibrant reefs on a small-group Key West cruise

Private Barefoot II charter for up to 6 to snorkel and relax in the Florida Keys

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

Fish Key West backcountry waters on a 4-hour charter

Charter The Coolwater for a Key West–style fishing trip for up to 6 people

Adults-only Key West sunset sail with champagne and gourmet cheese

Charter Cowfish for a 4-hour private cruise with any two water activities

Private Key West sunset sail with your music and a flexible start time

Sail Key West waters on a private 4-hour charter for up to six guests

Spend a full day sailing from Key West with up to 6 guests

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

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

Private 4-hour kayak, snorkel, and sail trip for up to 6 in Key West