Key West Historic Schooner Sunset Cruise: Champagne Toast

Sail a wooden schooner built for a general, steer into the sunset, raise a glass as the sun hits the water.

The When And If is a historic wooden schooner commissioned by General George Patton in 1939, sailing out of Key West Historic Seaport for a two-hour evening cruise through the Florida Keys National Marine Sanctuary. You board 15 minutes before departure at E dock in front of the Waterfront Brewery, then sail past Mallory Square and the offshore estates while watching for dolphins, sea turtles and marine birds. Champagne and a sunset toast are included, and you can take the wheel and help raise the sails under the captain's guidance if you want to.

Step-by-step itinerary

Sunset cruise aboard historic schooner

• Check in at Key West Historic Seaport
• Board the schooner When And If
• Sail through National Marine Sanctuary
• Spot dolphins, sea turtles, and birds
• Sail past Mallory Square sunset celebration
• View offshore Key West Island from yacht
• Enjoy champagne sunset toast
• Try steering the schooner

The Experience

The schooner leaves from E dock at Key West Historic Seaport—look for the E sign on the dock piling and walk to the end of the long pier, where the varnished wooden masts with flags at the top are hard to miss. Check-in happens directly at the boat 15 minutes before departure. Once aboard, the experienced captain and crew handle the sails, but you're welcome to take the wheel and help raise them yourself if the moment appeals to you. The two-hour sail moves through the Florida Keys National Marine Sanctuary, where sea turtles, bottlenose dolphins and marine birds show up regularly enough that spotting them is part of the rhythm of the evening.

The route passes Mallory Square—where the famous sunset celebration happens onshore—and glides past the offshore island estates of Key West's wealthy residents. As the sun dips toward the horizon, champagne comes out for a sunset toast. Soda, bottled water, select beer and wine are included throughout; bottle service upgrades are available if you want to bring something special. The boat has a restroom on board, and the whole experience is designed to feel unhurried and exclusive—small enough that you're not fighting crowds, substantial enough that the history and the moment land.

What’s included

• Champagne sunset toast.
• soda, bottled water, select beer and wine.
• experienced captain and crew.
• restroom on board.
• opportunity to take the wheel and help raise the sails.

Good to know

Easy physical levelPets welcomePublic transport nearbyInfants must sit on laps

Operated by Sunset Sail Key West

Is this one for you?The crew handles all the sailing if you want to watch and toast—but if you've ever wanted to actually steer a wooden schooner at sunset, this is the boat and the moment to do it.

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Top questions

What is the When And If and why does it matter?

The When And If is a wooden schooner commissioned by General George Patton in 1939. It's a working historic vessel, not a replica, and sailing it is the point of the evening—you're not just watching the sunset from a boat, you're aboard a piece of maritime history.

Can I actually help sail the boat, or is that just marketing?

You can take the wheel and help raise the sails under the captain's guidance. It's optional—the crew handles everything if you'd rather sit back—but the opportunity is real and built into the experience.

What wildlife might I see on the sail?

The route through the Florida Keys National Marine Sanctuary regularly passes sea turtles, bottlenose dolphins and marine birds. Sightings aren't guaranteed, but the sanctuary waters make them common enough that the crew knows where to look.

What's included in the ticket price?

Champagne for the sunset toast, soda, bottled water, select beer and wine are all included. The experienced captain and crew, restroom on board, and the two-hour sail are included. Gratuities and transportation to the seaport are separate.

Where exactly do I board, and how do I find the boat?

Board at E dock at Key West Historic Seaport, in front of the Waterfront Brewery. Look for the E sign on the dock piling and walk to the end of that long pier. The schooner's varnished wooden masts with flags are visible from a distance. Check-in and boarding begin 15 minutes before departure.

Is this suitable for children?

Yes. Children sail at a discounted fare and must be accompanied by an adult. Infants need to sit on an adult's lap. The two-hour sail and hands-on sailing opportunity work for family adventures as well as romantic evenings.