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    1. Local experiences/
    2. Key West, FL/
    3. Dining Experiences/
    4. Dinner Cruises/
    5. Key West Sunset Sip & Sail with Live Music

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    Key West Sunset Sip & Sail with Live Music

    Enjoy unlimited drinks, appetizers, and live music aboard a catamaran while you watch the famous Key West sunset.

    From$69/ person

    Duration

    2 hrs

    Includes

    Unlimited open bar, Appetizers, Live music

    Highlights

    Sail into the warm evening light aboard the Sandie Cat and toast the sunset with unlimited well drinks, appetizers, and live music. Enjoy two relaxing hours on the water as Key West’s skyline glows gold and pink.

    1. Board a spacious new sailing catamaran
    2. Savor unlimited mixed drinks, beer, wine, and champagne
    3. Nosh on tasty appetizers between sips
    4. Dance to live performances by local entertainers
    5. Watch the famed Key West sunset from the water

    What's Included

    1. Unlimited well mixed drinks and soft drinks
    2. Draft beer, margaritas, wine, champagne, rum runners
    3. Appetizers and live music

    Things to know

    Please arrive 45 minutes before departure and bring a photo ID and credit card for check-in. City parking is available for a fee.

    FAQs

    Q: What is included in the open bar?

    A: The open well bar includes unlimited well-mixed drinks, margaritas, rum runners, draft beer, wine, champagne and soft drinks.

    Q: Are appetizers provided, and what kinds?

    A: Yes. Appetizers include Jamaican jerk chicken sliders on Hawaiian rolls, BBQ meatballs, veggie trays, cheese & cracker trays, and pita & hummus.

    Q: Can children join the cruise?

    A: Yes. All ages are welcome. Children under 5 often sail free, and there are youth pricing options for age 6-12.

    Q: Is there a restroom onboard the catamaran?

    A: Yes, the trip on the Sandie Cat includes 2 modern marine restrooms above deck for guest use.

    Cancellation policy

    Customers receive a full refund with 24-hour notice of cancellation. Full refunds are also provided if the operator cancels due to weather or unforeseen circumstances. No-shows are charged the full price.

    Meeting location

    201 William Street, Key West, FL 33040

    Experience provided by Sunset Watersports
    Experience provided by Sunset Watersports

    How can we help?

    We are here to assist with special requests, large groups, last minute needs, and any questions you may have.

    Call or text (650) 414-7338

    Reference #VWKQW9

    Adult

    $69.95

    Ages 13+

    0

    Youth

    $39.95

    Ages 6 - 12

    0

    Handpicked for you, so you can book with confidence

    • Best local prices

    • Flexible cancellation

    • Private and secure

    Each booking directly supports small businesses in our community.

    4.8 stars• 19.2K reviews

    Review summary

    4.8
    Excellent
    19.2K reviews•Google Maps

    Sunset Watersports offers a solid range of activities from parasailing and jet skiing to snorkeling trips and dinner cruises, with most visitors leaving genuinely impressed. The parasailing consistently gets rave reviews, with guests like Wyatt and various captains earning specific shoutouts for making the experience memorable and capturing great photos. The dinner cruises seem to be another winner, with Captain Kristen, Captain Logan, and others praised for their knowledge and service. People love the combination of sunset views, live music, cocktails, and the overall atmosphere. The snorkeling excursions also get strong marks, particularly when captains like Kristen find calm spots on the reef and crews like Kevin, Maggie, Helen, and McKenzie take time to explain everything thoroughly. That said, there are some hiccups worth noting. One detailed review painted a concerning picture of the water adventure park experience, citing inattentive staff more focused on their phones than guest safety, mediocre food (boiled hot dogs and chicken nuggets), and a snorkeling setup that felt underwhelming. Another guest had a truly disappointing sunset sail where the crew couldn't even get the sail up, leading to an hour spent circling near the dock with static-filled music and subpar food and drinks. While these negative experiences seem to be outliers given the overwhelmingly positive feedback, they suggest consistency can vary depending on which activity you book and which crew you get. The jet skiing and parasailing appear to be the safest bets if you're trying to decide what to book.

    What people are saying

    Review 1 of 5
    5/5

    Fabulous evening on the Sandie Cat with friends! Captain and crew were attentive and very friendly. It looked like there was rain all around us, but our wonderful captain steered us between the storms. The boat was not overcrowded at all, and there were plenty of places to stand or sit to enjoy the view. Live music was provided and a wonderful, complete dinner buffet was included too. A nice touch as we boarded the boat – rum punch was premade and ready to grab while we listened to the captains instructions on safety.Would 100% recommend and hope to go again next time we are in Key West.

    Photo of Sally Bartlett

    Sally Bartlett

    October 10, 2025

    Review 1 of 1
    5/5

    Fabulous evening on the Sandie Cat with friends! Captain and crew were attentive and very friendly. It looked like there was rain all around us, but our wonderful captain steered us between the storms. The boat was not overcrowded at all, and there were plenty of places to stand or sit to enjoy the view. Live music was provided and a wonderful, complete dinner buffet was included too. A nice touch as we boarded the boat – rum punch was premade and ready to grab while we listened to the captains instructions on safety.Would 100% recommend and hope to go again next time we are in Key West.

    Photo of Sally Bartlett

    Sally Bartlett

    October 10, 2025

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