Key West Christmas Cruise with Live Band and Drinks in Key West
Key West, United States

Key West Christmas Cruise with Live Band and Drinks

Outty Ranking 55 5.0 · 5 traveler reviews1.5 hoursFrom $98

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September 2026

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Adults

Age 13 and over

2

Children

Age 12 and under

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From, per person$98
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Outty Ranking

55/100

Worth a Look. Our proprietary evaluation. How we score

Traveler rating

5.0/5

Based on 5 traveler reviews. Ratings and reviews provided by Viator and Tripadvisor.

Quick answer

Is Key West Christmas Cruise with Live Band and Drinks worth booking?

Key West Christmas Cruise with Live Band and Drinks is a 1.5-hour experience in Key West, United States, from $98 per person. It scores 55 out of 100 on the Outty Ranking, which we label “Worth a Look, based on a 5/5 rating across 5 reviews. Cancellation is free up to 24 hours before the start time. Same-day spots are currently showing.

Outty Ranking
55 / 100
Rating
5/5 (5)
Duration
1.5 hours
From
$98 per person

Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in K

What you get

    About this experience

    Join us for a family-friendly holiday sail aboard Schooner America 2.0 decorated with festive Christmas lights! Sing along to your favorite Christmas music with our live band and celebrate the holidays and Christmas in Key West. Enjoy a festive hot cocoa and holiday treats as we glide along with water for a fun night in Key West. Our beautiful 105-foot Schooner America 2.0 in full holiday decor that's sure to get you into the Christmas spirit in Key West harbor.

    What's included

    Included

    • Two drinks included. Beer, wine, champagne for ages 21+. Non-alcoholic drinks also available.
    • 1.5-hour holiday cruise aboard Schooner America 2.0
    • Holiday treats

    Not included

    • Additional beverages are available for purchase onboard by credit card
    • Gratuity

    What you'll see and do

    1. Key West

      See the Key West waterfront and enjoy the waters around Key West from a sailboat as we enjoy a festive holiday sightseeing sailboat ride

      Pass by without stopping

    Where it starts and ends

    Meeting point

    Key West

    Check in is located dockside in front of the Schooner Wharf Bar at 202 William Street in Key West, 33040. Our ticket booth is located at the end of William Street near the corner of William St and Greene St. Parking can be found in the municipal lot on Caroline St.

    Hotel pickup

    No pickup: everyone meets at the start point.

    Ends at

    Check in is located dockside in front of the Schooner Wharf Bar at 202 William Street in Key West, 33040. Our ticket booth is located at the end of William Street near the corner of William St and Greene St. Parking can be found in the municipal lot on Caroline St.

    Options you can book

    • Evening Option

      2 drinks included: Each ticket comes with 2 beverages. We have both alcoholic and non-alcoholic options available. General Admission Ticketing: Adult ticketing applies to all travelers. Select an 'adult' ticket for anyone planning to attend including infants/children.

    • Daytime Holiday Cruise Option

      2 drinks included: Each ticket comes with 2 beverages. We have both alcoholic and non-alcoholic options available. Family option: This is a fun family-friendly event. Kids sail free! Everyone attending needs a ticket. Please select accordingly at checkout

    Before you book

    Cancellation
    For a full refund, cancel at least 24 hours before the scheduled departure time.
    Languages
    en
    Ticket
    Mobile Only
    Runs on
    Every day
    Group size
    Up to 10 travelers per booking
    Operated by
    Classic Harbor Line

    Know before you go

    • Service animals allowed
    • Public transportation options are available nearby
    • Specialized infant seats are available
    • Suitable for all physical fitness levels
    • Guests must check in at the ticket booth 30-45 minutes prior to the departure time for boarding passes

    Photos

    Key West Christmas Cruise with Live Band and Drinks in Key West, photo 2Key West Christmas Cruise with Live Band and Drinks in Key West, photo 3Key West Christmas Cruise with Live Band and Drinks in Key West, photo 4Key West Christmas Cruise with Live Band and Drinks in Key West, photo 5Key West Christmas Cruise with Live Band and Drinks in Key West, photo 6Key West Christmas Cruise with Live Band and Drinks in Key West, photo 7

    What travelers are saying

    Outty’s summary of the themes that recur across 5 traveler reviews. Written by us, not quoted from reviewers.

    Photo opportunities

    1 mention

    The views and photo stops come up again and again.

    Traveler reviews

    5 verified traveler reviews for Key West Christmas Cruise with Live Band and Drinks. Ratings and reviews provided by Viator and Tripadvisor.

    5 star
    5
    4 star
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    Sort
    R8051FZdennism · December 2025

    A very special Key West Christmas Cruise.

    Every aspect of this Christmas Cruise was an absolute delight! The boat was stunning and the crew were out outstanding. The icing on the cake was the trio that regaled us with the sounds of the season throughout the cruise. Don't miss this in Key West !

    Response from the operator: Dennis, thank you for joining us on our Cocoa and Carols sail and for taking some time to provide your valuable feedback and recommendation. We are delighted to hear that every aspect of your Christmas cruise was an absolute delight! The holiday trio truly makes the experience special. We hope to have another opportunity to host you on the water! - Classic Harbor Line Key West

    via Tripadvisor

    Michal_L · December 2025

    Awesome Christmas Eve experience!

    Spending Christmas Eve on a schooner ship singing carols was AWESOME! I highly recommend this tour next Christmas.

    via Viator

    V9823ZVwilliama · December 2024

    A quaint Christmas Eve cruise aboard a beautiful boat

    We took the Cocoa and Carols cruise, and what a wonderful way to spend a Christmas Eve! The musicians/singers were terrific and the service from the crew was top-notch!

    Response from the operator: We're thrilled to hear you enjoyed the Cocoa and Carols cruise on Christmas Eve, as it is our newest programming. Wishing you and your family a happy Holidays!

    via Tripadvisor

    Nupur_P · December 2024

    can't miss

    The staff was very friendly, which made the sailing a huge delight. Parking is convenient. Loved the music.

    via Viator

    Carley0807 · December 2024

    AN ABSOLUTE MUST

    Could not recommend this trip enough!! As a local down here, this was the best part of my holiday season, hands down. Definitely check it out!!!

    via Tripadvisor

    Good to know

    Duration
    1.5 hours
    Free cancellation
    Up to 24h before
    Minimum age to book
    All ages
    Availability
    Bookable today
    Runs on
    Every day
    Hotel pickup
    No pickup, meet at start point
    Booked in 30 days
    2
    Verdict
    Worth a Look

    Why this scores 55

    The Outty Ranking is a weighted composite. Here is how this experience performed on each component.

    Traveler sentiment (30% weight)81
    Review evidence (18% weight)23
    Booking momentum (14% weight)17
    Value for money (12% weight)35
    Listing quality (10% weight)73
    Local standing (8% weight)58
    Booking flexibility (8% weight)100

    Key West Christmas Cruise with Live Band and Drinks: questions travelers ask

    Practical detail on this experience, plus the wider planning questions for Key West.

    How much does Key West Christmas Cruise with Live Band and Drinks cost?

    +

    Prices start at $98 per person. The final price depends on the date, the time slot and the number of travelers, and peak weekends in Key West usually price higher than midweek mornings. Live pricing and remaining availability are confirmed on the booking screen before you pay.

    How long does Key West Christmas Cruise with Live Band and Drinks take?

    +

    Plan for about 1.5 hours from start to finish, not counting travel to the meeting point. Most travelers leave another 30 minutes on either side so the rest of the day in Key West is not rushed.

    Is Key West Christmas Cruise with Live Band and Drinks worth it?

    +

    It holds an Outty Ranking of 55 out of 100, which we label "Worth a Look". That score blends traveler sentiment (5/5 across 5 reviews), the depth of that review evidence, recent booking momentum, value for money against comparable last minute in Key West, and how flexible the cancellation terms are.

    Can I cancel or reschedule Key West Christmas Cruise with Live Band and Drinks?

    +

    Yes. Cancel free up to 24 hours before the start time for a full refund. Inside that window the booking is non-refundable, and no-shows are not refunded.

    Is Key West Christmas Cruise with Live Band and Drinks suitable for kids and families?

    +

    Yes, all ages are welcome. Families should still weigh the 1.5-hour running time, and strollers are easier on the earlier, quieter departures.

    How far in advance should I book Key West Christmas Cruise with Live Band and Drinks?

    +

    Around 2 people booked this in the last 30 days, so popular slots go early. Two to three weeks ahead is comfortable in shoulder season, while summer weekends and holidays in Key West can sell out a month out. Same-day spots do open up when other travelers cancel, so it is worth checking if you are already in town.

    What should I bring or wear?

    +

    Bring photo ID, your booking confirmation on your phone, a refillable water bottle and comfortable shoes. Dress for the weather in Key West and add a light layer if any part of the 1.5-hour experience runs outdoors or after sunset.

    Where does Key West Christmas Cruise with Live Band and Drinks start and how do I get there?

    +

    The exact meeting point and directions are on your voucher once you book, and they sit in central Key West within reach of public transport. Arrive 15 minutes early: late arrivals are treated as no-shows by most operators.

    What are the best things to do in Key West?

    +

    Key West is a boat town. The only living coral barrier reef in the continental US sits seven miles offshore, and reef trips, sunset catamarans and backcountry kayak runs are the core bookings, alongside Hemingway house and Duval history walks. Our ranking weighs boat capacity and reef site rotation, which separates the good operators from the party cruises. On Outty we rank every Key West experience on the same 0 to 100 scale, and alongside this one the highest scorers right now include Shark and Wildlife Viewing Adventure in Key West, Southernmost Food & Cultural Walking Tour by Key West Food Tours, Half-Day Trip from Key West with Kayaking, Snorkeling & Sunset. The city page groups everything into most popular, highest reviewed, last minute and family-friendly so you can build a day around what actually delivers.

    When is the best time to visit Key West?

    +

    December to April, dry season and calm reef water. Booking patterns follow the same curve: prices and queues climb in peak weeks, while shoulder season gives you better availability on the top-ranked experiences and more room to change plans.

    How many days do you need in Key West?

    +

    Three full days covers the headline sights without sprinting. A workable rhythm is one anchor experience each morning, such as this one, an unhurried afternoon in a single neighborhood, then a food or nightlife booking in the evening. Five days lets you add a day trip outside the city.

    Do I book through Outty or through the operator?

    +

    Outty ranks and explains the experiences, then hands you to Viator to complete the booking with the operator directly. The price is the same as booking on Viator yourself, and Outty earns an affiliate commission on the referral, which is how the rankings stay free to read.

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