ShoreTrips logo Shore Excursions - City Tours - Day Activities


Per Person $97 USD
Child (5 to 12 years old) $73 USD
*Selections and optional choices will be made during checkout


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ShoreTrips says...

Honestly, this sailing was ranked one of the top two sunset sails in all of North America--and I was told it is the only one with real wine!

You know you are in for a good time when the sailing crew brags more about the beverages and hors d'oeuvres than the sail itself. However, we can assure you that both parts of the whole work together for a great time doing exactly what you should be doing in Key West--drinking and eating on the water. The crew is exceptional with the goal of making you comfortable and happy. You will be sailing on a shallow draft schooner, and the cloud of canvas sails are the only thing between you and the stars. If you are looking to make friends, you will be in the company of others who value their food and beverage experience, but you can also make this a romantic evening by finding a secluded spot on board.

Every night, eight different fine wines are served from all over the world--usually four reds, three whites, and a Champagnoise. Special beers are also on the menu. The audience here is an upscale crowd that wants to relax on an intimate vessel. Whether you are enjoying this before a fantastic meal in the city or want to just partake fully in the apps, no problem. Expect an array of imported cheeses, sausage, caprese skewers, and a special brie, green apple, honey drizzled cracker, the captain's favorite.

Soft music in the background sets the mood.

  • This Tour Includes:
  • 65 foot traditional sailing schooner
  • Captain and crew
  • Array of wines from around the world
  • Craft beers, import and domestic
  • Ample hors d'oeuvres
  • Soft music
  • Whomever you invite along!

Days of Operation

Mon - yes
Tue - yes
Wed - yes
Thu - yes
Fri - yes
Sat - yes
Sun - yes

Departures (local time)

  • 4:30 PM (2 hrs) November 5th - January 31st. Please check in 30 minutes prior to departure.
  • 5:00 PM (2 hrs) February 1st - March 11th. Please check in 30 minutes prior to departure.
  • 5:30 PM (2 hrs) October 1st - November 4th. Please check in 30 minutes prior to departure.
  • 6:00 PM (2 hrs) March 12th - April 30th; September 1st - 30th. Please check in 30 minutes prior to departure.
  • 6:30 PM (2 hrs) May 1st - August 31st. Please check in 30 minutes prior to departure.

Transfer / Meeting Instructions

See Special Instructions Specific pick up or taxi instructions will appear on your voucher after you purchase your trip.

Special Instructions

• Departure location is approximately a 5-10 minute walk from the cruise pier, depending on where your ship docks.


• Please alert ShoreTrips in advance of any dietary restrictions or food allergies. We will do our best to accommodate.
• You must be 21 years old to partake in alcoholic beverages.
• These vessels have a maximum of 30 people. They can sail in tandem if you have a private group charter that is larger. Please contact ShoreTrips.
• Calmest waters are May to August.