Best results for Yacht Charters in Big Pine Key, FL

Customize a 4-hour private tri-toon cruise with a licensed captain in Key West’s backcountry

Customize your Key West backcountry day on a captained tri-toon with a swim deck

Ride a private charter to Dry Tortugas with a licensed captain

Explore remote islands, patch corals, and shipwrecks by charter

Cruise to Dry Tortugas to tour Fort Jefferson and swim—captain and first mate included

Private 6-hour sandbar cruise with lunch for up to 6 guests

Private 4-hour Boston Whaler charter with captain for up to 6 guests

Private captained day on the water with lunch, floats, and refreshments

Cruise Key West waters aboard a private captained Boston Whaler

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

Customize your time on the water with snorkeling, fishing, island stops, or a sunset cruise

Explore reefs, wildlife habitats, and private islands on a flexible Key West charter

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

Cruise the Historic Seaport as the sun sets

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

Tailor a private Caribbean sailing charter for your celebration or getaway

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

Bareboat yacht charter for groups over 6, with snorkel and float gear included

Charter a private motor yacht in Key West with flexible 1.5–8 hour options

Relax and explore local sandbars aboard a 37-foot Edgewater

Celebrate with champagne, hors d'oeuvres, and sunset views on a private charter

Explore Fort Jefferson and the Dry Tortugas aboard a private 37-foot boat