Key West Signature Sunset Cruise: Live Music, Open Bar & Food
Spend two hours on a new three-deck sailing catamaran with an unlimited open bar, plenty of appetizers and a live band as the sun sets over the water. You'll be back on shore early enough to keep the night going in Old Town.
About this experience
- Duration: 2 hours
- E-ticket · Sent by email
- Group size: Up to 75 guests
- Runs daily · One departure a day, between 5:00 PM and 6:30 PM depending on the season
Highlights
- Sail straight out to open water for a clear sunset view, away from the crowds on shore
- Enjoy an unlimited open bar with rum runners, margaritas, draft beer, wine, champagne and mixed drinks
- Graze on appetizers like jerk chicken sliders, barbecue meatballs, hummus and pita, and cheese and veggie trays
- Dance on the upper deck while a live musician plays through sunset
- Help the crew raise the sails, and get a photo at the helm
- Spread out across three decks on one of the newest catamarans sailing out of Key West
Full description
A night out in Key West can get expensive fast once you add up cover charges, cocktails and something to eat. This sunset sail bundles all three into one ticket and adds the best view on the island. When you dock, there's still plenty of evening left for dinner or a stroll down Duval Street.
You'll sail on a modern catamaran with three separate decks, licensed for up to 149 guests. Even on a busy night, you can find a quiet seat by the rail or move up to where the music is. The upper deck is the social hub, with live music and room to dance. The lower levels are more relaxed if you'd rather just sip and watch the water.
This isn't a motor cruise with sails just for show. Once you're clear of the harbor, the crew invites guests to help haul up the sails, which is a fun, hands-on moment that kids and adults both enjoy. Ask the captain and you can have your photo taken at the wheel, too.
The open well bar stays open for the whole trip. It serves Florida Keys favorites like rum runners and frozen margaritas, along with draft beer, wine, champagne and classic mixed drinks. If you prefer top-shelf spirits, you can upgrade to the premium bar for an extra charge. The food is substantial for a sunset cruise, with jerk chicken sliders, barbecue meatballs, hummus with pita, cheese and crackers, and fresh vegetable and meat platters. The menu may vary.
As the sun sinks, the captain holds the boat in position for a clear, unobstructed view, and the music builds as the sky turns orange and pink. Not long after the last light fades, you're back at the dock in the heart of Old Town, close to the bars and restaurants.
Included
- Two-hour sunset sail on a three-deck sailing catamaran
- Unlimited open well bar: rum runners, margaritas, draft beer, wine, champagne and mixed drinks (21+)
- Appetizer spread
- Live music on the upper deck
- Chance to help raise the sails and take a photo at the helm
Not included
- Gratuities for the crew and musician
- Premium bar upgrade for top-shelf spirits (optional, extra cost)
- Transportation to and from the dock
- Parking
Meeting point
Check in at 201 William Street, Key West, FL 33040, on the historic seaport waterfront in Old Town. Please arrive 30 minutes before departure to check in and board.
View on Google Maps (opens in a new tab)Important information
- Transportation isn't included, and parking nearby is paid, so allow extra time near sunset, when the seaport lots fill up.
- Bring a driver's license or other photo ID. You'll need it to be served alcohol, and the drinking age is 21.
- Families are welcome. The boat is stroller friendly, infant seats are available, and children just need to be with an adult.
- Departure times change with the seasons. Departure times follow sunset, which ranges from around 5:45 p.m. in late fall to about 8:20 p.m. in early summer, so check the time on your ticket.
- Choose your deck to match your mood. Head up top for the music and dancing, or stay lower for quieter conversation and photos.
- Plan your evening around the cruise. The cruise ends early enough for a late dinner, so many guests book a table nearby or head straight into Old Town afterward.
- Pace yourself. Two hours of unlimited drinks in the sun can sneak up on you, so alternate with water.
- Bring a light layer. It can get breezy on the open water after dark, especially in winter.
What's allowed
- Kids and families, with an adult present
- Strollers, since the boat is stroller accessible
- Infants, with infant seats available on board
- Service animals
- Cameras and phones
Not allowed
- Alcohol for anyone under 21
- Children on board without an adult
- Wheelchairs, since the boat 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
Can I bring children?
Yes. Families are welcome. The boat is stroller friendly, infant seats are available, and children just need to be with an adult.
What does the open bar include?
An unlimited open well bar with rum runners, margaritas, draft beer, wine, champagne and mixed drinks (21 and over), plus an appetizer spread. A premium bar upgrade for top-shelf spirits is optional at extra cost.
Can I help with the sails?
Yes. Guests get the chance to help raise the sails and take a photo at the helm, and there is live music on the upper deck.
