Sunset Sail Key West in Key West, Florida

Sunset Sail Key West — Key West, Florida

Sunset Sail Key West is more than just a private sailing charter — it's the culmination of decades of experience and a lifelong passion for sailing and the unique spirit of Key West. Our top priority is sharing the joy of boatmanship with our guests. We love making new friends and hopefully inspiring a few new sailors along the way. Our mission is to offer authentic sailing experiences, away from the crowds and chaos of party boats and booze cruises. That mission took root early on, around the turn of the century, when a boy named Seth discovered his love for the sea.

Frequently Asked Questions

What types of sailing trips does Sunset Sail Key West offer?
Sunset Sail Key West offers a variety of trips including sunset sails, daysails, and private charters. Popular options include the Schooner Sunset Sail, Private Sunset Sail, Chillout Lilypad Sail, and Key West Daysail. They also offer custom private charters for snorkeling, stargazing, or other desired activities.
What is the pricing and capacity for the different sailing trips?
The Schooner Sunset Sail is a two-hour trip for up to 28 guests priced at $109 per person. The Private Sunset Sail starts from $645 and can accommodate up to 12 guests. The Chillout Lilypad Sail and Key West Daysail also have starting prices of $595 and $395 respectively, with capacity varying by vessel.
What boats does Sunset Sail Key West use for their charters?
Sunset Sail Key West operates with a fleet of three classic sailboats: the schooner "When and If," and two other vessels including the sloop "High Tide." Each boat offers a unique experience and is suited for different types of outings, from intimate private charters to shared sunset sails.
Can I book a private charter for a specific activity like snorkeling or stargazing?
They offer private charters that can be customized for various activities such as snorkeling, stargazing, or simply relaxing while enjoying the sunset. Guests can build their own custom trip to curate a unique experience on the water.