Thanksgiving Sunset Dinner Sail in Key West | Holiday Cruise with Dinner, Drinks & Live Music
Thanksgiving Dinner Sail in Key West – Holiday Menu, Live Music & Unlimited Open Well Bar – Very Limited Seating
This Thanksgiving, trade the traditional dining room for a Key West catamaran sailing into the sunset. Step aboard and enjoy a freshly prepared Thanksgiving-themed dinner on the water. Our chefs create a holiday spread that blends classic Thanksgiving favorites with island-inspired flavors found only in the Florida Keys.
As you dine, enjoy unlimited drinks from our open well bar and take in panoramic sunset views of Key West. A talented local musician sets the mood with live tropical music throughout the cruise, creating the perfect island-style atmosphere for your holiday celebration.
There’s no better way to spend Thanksgiving in Key West than with great food, live music, and a world-famous sunset. This special holiday cruise sells out every year due to limited seating, so we recommend reserving your spot early for a Thanksgiving experience you’ll never forget.
Book Now – This Thanksgiving Cruise Sells Out Every Year
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Quick Facts – Thanksgiving Sunset Dinner Sail
- Date: Thanksgiving Day
- Departure: Historic Seaport, Key West
- Duration: 2 hours
- Includes: Dinner, open well bar, live music
- Vessel: Spacious catamaran
- Family-Friendly: Yes
- Tickets: Limited, advance reservations required, this will sell-out
Menu & What’s Included
- Unlimited Open Well Bar
- Live Music
- Turkey sliders with stuffing & cranberry sauce on a Hawaiian rolls
- Honey ham sliders with artesian cheese on Hawaiian rolls
- Sweet potato tots
- Meatballs & gravy
- Holiday cheese & cracker trays
- Veggie & hummus trays
- Thanksgiving dessert
Thanksgiving Sunset Sail FAQ
What is the Thanksgiving Sunset Dinner Sail in Key West?
Our Thanksgiving Sunset Dinner Sail is a special holiday cruise in Key West that combines a scenic sunset sail with a Thanksgiving-themed menu, unlimited open well bar, and live music. Instead of a traditional dining room, you’ll celebrate on the water aboard a comfortable catamaran with views of the Key West coastline and sunset.
What is included with the open well bar on the Thanksgiving Sunset Dinner Sail?
Our Thanksgiving dinner cruise includes an unlimited open well bar featuring house-brand mixed drinks, draft beer, wine, and champagne. Guests can still enjoy popular cocktails like margaritas and rum runners – these are simply prepared with well liquors. A premium cash bar is also available on board for anyone who prefers top-shelf spirits. This full bar service is offered throughout the sail as you enjoy the Key West sunset.
What’s included with the Thanksgiving dinner cruise?
Your Thanksgiving cruise includes a freshly prepared, Thanksgiving-themed meal with holiday favorites and local island-inspired dishes, plus an unlimited open well bar and live entertainment from a local musician. Soft drinks and water are also included.
What time does the Thanksgiving sunset sail depart and how long is it?
The cruise is scheduled from 5pm to 7pm on Thanksgiving Day. Your exact check-in and departure time will be listed in your confirmation email and on your booking voucher. See Key West Sunset Times.
Where does the boat depart from in Key West?
Our Thanksgiving sail departs from the Historic Seaport in downtown Key West. Directions are in the reservation email after booking.
Is the Thanksgiving Sunset Dinner Sail family-friendly?
Yes. The Thanksgiving Sunset Dinner Sail is family-friendly and a great way for families, couples, and groups to celebrate the holiday together on the water. If you are traveling with infants, small children, or older guests, please note this in your reservation so our team can be prepared to assist.
Are drinks included, and what is the open bar?
Yes. Your ticket includes access to an unlimited open well bar for the duration of the cruise. The selection typically includes well cocktails, beer, wine, soft drinks, and water.
What should I wear on the Thanksgiving Sunset Dinner Sail?
We recommend comfortable, casual resort-style clothing suitable for the ocean breeze in the Florida Keys. Light layers are ideal, as it can feel cooler on the water at sunset. Flat, non-slip shoes or sandals are recommended. You may also want to bring a light jacket, sunglasses, and a small bag for personal items. Check the weather day of Thanksgiving.
Will there be live music on the Thanksgiving Sunset Dinner Sail in Key West?
Yes. Our Thanksgiving Sunset Dinner Sail includes live music performed by a local Key West musician. The entertainment is part of what makes this holiday cruise so special.
What is the weather like in Key West on Thanksgiving?
Thanksgiving in Key West typically brings warm, comfortable weather—perfect for a sunset dinner sail. Average temperatures range from 73–80°F, with gentle ocean breezes and lower humidity compared to summer. November is one of the most popular months to visit the Florida Keys because it’s generally sunny, calm, and ideal for boating, sunset cruises, and outdoor activities.
While conditions may vary year to year, Thanksgiving week is historically known for clear skies and smooth sailing weather, making it one of the best times to enjoy a holiday cruise in Key West. Visit The National Weather Service for forecasts.
Don’t want a Thanksgiving sunset sail? What other Key West boat trips do you offer?
If a Thanksgiving sunset sail isn’t what you’re looking for, we offer many other top-rated boat trips in Key West year-round. Popular options include our sandbar charters, reef snorkel & happy hour cruises, mangrove eco tours, tiki boat sandbar trips, jet ski tours, and a great selection of boat rentals you can captain yourself. Give us a call and we can help you find the best trip. 305-422-9811
