Best results for Cudjoe Key Florida

Private Key West sailing with snorkeling, sandbars, and dolphin searches

Private sunset sailing with bubbly, wines and a gourmet cheese buffet

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

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

Sail, snorkel, and explore Key West waters on your private catamaran

Sail, kayak, and snorkel Key West's shallow waters on a private cruise

Sail Key West’s reefs, barrier islands, and mangroves

Tailor a private Caribbean sailing charter for your celebration or getaway

Shape a private yacht charter around your celebration or vacation

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

Paddle the mangroves and snorkel with a small group in the Key West National Wildlife Refuge

Snorkel the reef, visit a sandbar, and sail into sunset on a spacious catamaran

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

Explore mangrove islands by schooner, kayak and snorkel

Enjoy a high-flying 10–12 minute parasail ride with sweeping views of Key West

Snorkel Key West’s vibrant reef aboard a fast catamaran with breakfast and post-trip drinks.

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