Classic Schooner Sunset Sail with Open Bar

Sail out of Key West's harbor on a traditional wooden schooner and watch the sun drop into the Gulf while the crew pours from a full open bar. This two-hour, nonstop evening sail is about old-fashioned sailing, an open horizon and an easy, unhurried evening.
About this experience
- Duration: 2 hours
- E-ticket · Sent by email
- Group size: Up to 12 guests
- Runs daily · One departure a day, between 4:30 PM and 6:30 PM depending on the season
Highlights
- Sail on a traditional schooner under real canvas, with the crew working the lines the way sailors have for generations
- Enjoy a full open bar with cocktails, spirits, premium beer, wine and champagne for guests 21+
- Watch the sunset from open water, with clear views west and none of the crowds on shore
- Cruise for two hours with no stops, so you can stay on deck from golden hour through the afterglow
- Hear stories and local insight from an English-speaking guide as you sail
- Pay one price that covers the drinks, so there are no bar tabs to worry about
Full description
On land, Key West's sunset means elbowing for a spot on a busy waterfront. Out on a schooner, it means wind, creaking timber and open sky. This sail is for travelers who want the classic version of the experience, aboard the kind of vessel that once carried cargo, sponges and salvaged treasure in and out of this very harbor.
A schooner is a traditional sailing ship with two or more masts and large fore-and-aft sails. It's the classic tall-ship silhouette people picture when they think of old Key West. Once the crew hoists the sails and the engine goes quiet, you'll feel the boat heel gently and pick up speed with the wind. That steady, rhythmic motion is very different from a motorized cruise, and it's a big part of the appeal. Feel free to watch the crew work, and ask questions about how the rig works.
The schooner heads offshore from the historic harbor toward the open Gulf, with the island's waterfront on one side and nothing but horizon on the other. The deck is open-air and spacious, so you can find a spot at the rail, sit back with a drink or move around for photos. The sail runs for two hours with no stops, and the whole trip is about the sail itself and the sunset at the end.
Drinks are included for the full sail. Bartenders serve mixed cocktails, spirits, premium beer, wine and champagne to guests 21 and over, and soda and bottled water are available for everyone. Because it's all in the ticket price, you know exactly what your evening will cost before you board.
As the sun gets low, the light turns gold and the sails glow. When the sun reaches the horizon, watch closely: on very clear evenings, the last sliver sometimes flashes green for a split second. Don't head below or put your camera away once it's gone, though. The richest pinks and purples usually spread across the sky 10 to 20 minutes after sunset, while you're still sailing back toward the harbor lights.
Included
- Two-hour sunset sail on a traditional schooner
- Full open bar with cocktails, spirits, premium beer, wine and champagne (21+)
- Soda and bottled water
- English-speaking guide and crew
Not included
- Gratuities for the crew
- Food and snacks
- Hotel pickup and drop-off
- Parking
Meeting point
201 William St, Key West, FL 33040. The check-in booth is at the far end of William Street, on the waterfront at Key West's historic harbor. Coming from Elizabeth Street, keep the water on your left and follow Lazy Way Lane past the shops. You'll pass a waterfront resort on your right and a popular harbor bar on your left, and the booth will be on your left.
View on Google Maps (opens in a new tab)Important information
- Check your confirmation for the exact check-in time, and allow extra time to park, since downtown parking is paid and fills up before sunset.
- Bring a valid government-issued photo ID. The crew has to verify age before serving alcohol, and the drinking age is 21.
- The sail is nonstop. It's two hours on the water from departure to return, so use the restroom before boarding if you're unsure about facilities on board.
- Eat before you go. Food isn't included, so have a snack beforehand or plan dinner in Old Town after you dock.
- The schooner isn't wheelchair accessible. Infants are welcome, but they must sit on an adult's lap.
- Wear flat, non-slip shoes. Schooner decks can be wet and tilted while under sail.
- Pack for sun and breeze. Bring a hat and sunglasses for the low evening sun, and a light layer for the ride back after dark.
- Departure times follow the sunset. In Key West, sunset ranges from about 5:45 p.m. in late fall to about 8:20 p.m. in early summer, so confirm the time on your ticket.
What's allowed
- Families with children
- Infants, seated on an adult's lap
- Cameras and phones
- Hats, sunglasses and a light jacket
Not allowed
- Alcohol for guests under 21
- Separate seats for infants (lap only)
- Wheelchairs, since the schooner isn't wheelchair accessible
Cancellation policy
With Ticket Assurance, Cancellation up to 24 hours before the scheduled cruise. Without Ticket Assurance, Cancellation up to 48 hours in advance. To cancel, visit Manage Booking or Contact Support.
Frequently asked questions
Is food included?
No. The full open bar is included, but food isn't, so have a snack beforehand or plan dinner in Old Town after you dock.
Can I bring a baby?
Infants are welcome but must sit on an adult's lap. The schooner isn't wheelchair accessible.
Are there stops during the sail?
No. It's two hours on the water from departure to return, so use the restroom before boarding if you're unsure about facilities on board.


