Key West Christmas Cruise: Schooner America 2.0 with Live Band

Ninety minutes on a decorated schooner: live band, festive lights, hot cocoa and the harbor at dusk.

A 1.5-hour holiday cruise aboard Schooner America 2.0 in Key West harbor, decorated with Christmas lights and staffed with a live band playing seasonal music. You'll sail the waterfront while sipping hot cocoa and holiday treats, with two drinks included. Choose between an evening departure or a daytime option to fit your holiday schedule.

Step-by-step itinerary

Festive holiday sail in Key West

• Board Schooner America 2.0
• Enjoy Christmas lights and decorations
• Listen to live Christmas band
• Sing along to holiday music
• Drink festive hot cocoa
• Eat holiday treats
• Sail around Key West waterfront

The experience

The Schooner America 2.0 is a 105-foot working sailboat strung with festive Christmas lights, and it leaves the Key West waterfront for a sail around the harbor. A live band plays Christmas music throughout the cruise, and you can sing along or simply listen as the boat moves through the water. The pace is unhurried (this is a sightseeing sail, not a racing event), so you'll have time to take in the Key West waterfront and the water around you without rushing.

Two drinks come with your ticket: beer, wine or champagne for guests 21 and older, or non-alcoholic options if you prefer. Hot cocoa and holiday treats are served as part of the cruise. Additional beverages are available for purchase onboard by credit card if you want more. The whole experience runs 90 minutes from departure to return, and you'll need to check in at the ticket booth 30 to 45 minutes before your departure time to get your boarding pass.

The cruise operates in two options: an evening departure and a daytime holiday cruise. Both sail the same route and include the same band, lights and refreshments, so your choice depends on whether you prefer the harbor at dusk or in daylight. Service animals are welcome aboard, and specialized infant seats are available if you're traveling with a baby. The boat is suitable for all fitness levels since you're seated for the entire sail.

What’s included

• Two drinks (beer, wine, champagne for ages 21+, or non-alcoholic options).
• 1.5-hour holiday cruise aboard Schooner America 2.0.
• hot cocoa and holiday treats.

Options for this experience

2 options

Option for a daytime holiday cruiseGuide in English · Available from 22 Dec · 12:30Each ticket includes 2 beverages, with both alcoholic and non-alcoholic choices available. Family option: this is a fun, family-friendly event, and kids sail free! Everyone attending needs a ticket, so please select accordingly at checkout.

Evening OptionGuide in English · Available from 21 Dec · 19:00Each ticket includes 2 beverages, with both alcoholic and non-alcoholic choices available. General admission ticketing: adult tickets apply to all travelers. Select an adult ticket for anyone planning to attend, including infants and children.

You'll see the exact price of each option when you check availability.See dates and prices

Before you book

Days and timesMonday to ThursdayDepartures at 12:30 and 19:00

Book up to1h before

AgesAdult (13 and older) · Child (under 13): free

GroupUp to 75

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated yesterday

Good to know

Low physical effortInfant seats availablePets welcomePublic transport nearby

Operated by Classic Harbor Line

Is this one for you?Choose the evening departure if you want to see the Key West waterfront as the sun sets, or pick the daytime option if you prefer to sail in daylight. Either way, you're on the water for 90 minutes, so plan accordingly if you have other holiday activities scheduled in Key West that day.

Traveler reviews

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Top questions

Can children come?

Yes. Ticket types: Child (under 13): free.

What is the Schooner America 2.0 like?

The Schooner America 2.0 is a 105-foot sailing vessel decorated with Christmas lights for the holiday season. It's a working schooner, so you'll experience an actual sail rather than a motorized cruise, and the live band performs on deck throughout the 90-minute voyage.

Do I need to arrive early to board?

Yes, you must check in at the ticket booth 30 to 45 minutes before your departure time to receive your boarding pass. This gives the crew time to process passengers and prepare for departure.

What drinks and food are included?

Two drinks come with your ticket: beer, wine or champagne for ages 21 and up, or non-alcoholic beverages for all ages. Hot cocoa and holiday treats are also included. If you want more to drink, additional beverages are available for purchase onboard by credit card.

Can I choose between evening and daytime sailings?

Yes, you can book either the evening option or the daytime holiday cruise option at checkout. Both include the same live band, festive decorations, drinks and treats. The difference is the time of day and how the harbor looks when you sail.