Sailing in Sugarloaf Key, FL

Sunday sailing with brunch bites and bottomless mimosas

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 into the Key West sunset with drinks and hors d'oeuvres included

Take in Key West's sunset from the water with a hint of piracy

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

Enjoy the Florida Keys with a sailboat all to yourselves

Evening catamaran cruise with craft drinks and island music

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

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

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

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

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

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

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

Unwind on the water with a sail reserved just for your group

Private sailing, ocean scenery, and a setting built around your comfort

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

Sail the Florida Keys privately aboard a classic sailboat