Sailing in Big Pine Key, FL

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

Sail Key West's clear waters, kayak mangrove islands, snorkel vibrant reefs, and refuel with a buffet lunch—all in one day.

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

Charter the 54-foot Schooner Valora for a private sail in Key West

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

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

Sip and sail into the Key West sunset with live music and an open well bar

Choose your boat and learn to sail with a private instructor in Key West

Private sail to a shallow-water anchorage with time to lounge on a Lilypad float

Sail past Key West landmarks and relax on a private catamaran cruise at sunset

Customize a private day on the water with snorkeling and onboard lunch

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

Sail into Key West’s sunset with complimentary drinks on board

Private Key West schooner charter with snorkeling, kayaking, drinks, and snacks

Evening catamaran cruise with craft drinks and island music

Sail a Key West schooner at sunset with drinks, appetizers, and cocktails included

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

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

Sail to a local sandbar aboard a captained Hobie Cat

Learn at your own pace with private instruction on the water

Private 2-hour Key West sunset sail with captain and mate

Sail Key West waters your way with snorkeling, kayaking, fishing, and time to unwind

Sail Key West waters with drinks, onboard gear, and a freshwater rinse

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