Set Sail in Style
Treat your team, friends, or family to an unforgettable Key West holiday celebration aboard the classic schooners *When and If* or *Malabar X*. Toast the sunset with boutique wine, nibble from a gourmet cheese platter, and feel the sea breeze as ivory sails fill against the glowing horizon. Perfect for private holiday parties or group celebrations.
-
$1 USD
-
Ages 21+
-
2 Hours
-
Florida, United States
-
Key West
-
- Historic Schooner Yachts
- Gourmet Cheese & Wine
- Sunset Over Key West
- Private Party Option
- Spiced Wine Welcome
- Tandem Yacht Charter
- All-Inclusive Pricing
- Premium Service
-
- Two-hour private sail aboard a historic schooner, spiced wine welcome, boutique wine and beer bar, gourmet cheese platter, and crew service.
-
- Light resort wear or semi-formal attire, camera, and light sweater for evening breeze.
Holiday Party Features
Historic Schooner Yachts
Sail aboard the 1939 *When and If*—built for General George Patton—or the 1930 race-winning *Malabar X*, both beautifully restored classics.
Elegant Seasonal Ambiance
Enjoy a complimentary glass of spiced wine on boarding, with select wines, craft beers, and artisan cheeses served throughout your sunset cruise.
Holiday Party Details
- Highlights
- Description
- Itinerary
- Price & Availability
- Food & Drink
- Instructions
- Restrictions
- Transportation
Highlights
-
Historic Schooner Yachts
-
Gourmet Cheese & Wine
-
Sunset Over Key West
-
Private Party Option
-
Spiced Wine Welcome
-
Tandem Yacht Charter
-
All-Inclusive Pricing
-
Premium Service
Description
Celebrate the holidays in Key West style with a private sunset charter aboard one of two legendary wooden yachts—*When and If* or *Malabar X*. Step aboard to a warm welcome of spiced wine before sailing into golden waters as the sails unfurl. Enjoy a curated selection of boutique wines, local craft beers, and a gourmet cheese platter while the sea breeze mingles with holiday music. Watch the sky shift from coral to indigo as you toast the season under canvas and stars. For larger parties, book both vessels for a tandem or match-race sail and make it a night to remember.
Itinerary
- 4:00 PM – Arrive at the Key West Harbor dock and meet your crew
4:15 PM – Welcome aboard with spiced wine and pre - 4:30 PM – Set sail as the sun dips toward the horizon
5:15 PM – Enjoy wine, beer, and gourmet cheese while mingling on deck
5:45 PM – Sunset toast and optional photo opportunities at sea
6:30 PM – Return to dock beneath twilight skies
Price & Availability
$1,955 per yacht (up to 32 guests).
Duration: 2 hours.
Available for corporate or private holiday events.
Tax and gratuity included.
Optional upgrade: premium sparkling wine package.
Bookings available December 1–31.
Food & Drink
Gourmet cheese platter, boutique wines, select beers, bottled and sparkling water, and spiced wine on arrival.
Instructions
Check in 15 minutes before departure at Key West Bight Marina, 201 William St. Directions provided upon booking.
Restrictions
Guests must be 21+ to drink alcohol. Cruises are weather dependent; rescheduling offered if necessary.
Transportation
Transportation not included. Marina is walkable from most downtown Key West hotels.
Frequently Asked Questions
More Key West Holiday Cruises
-
Holiday At The Farm
Make memories with Santa, animals, and lights in a holiday... More
- 2-Hour Experience in Chapel Hill
- Meet Santa & Craft Gifts
- Includes Farm Admission & Elf Workshop
- All-Ages Holiday Celebration
-
Mid-Century Christmas Experience
Celebrate creativity and Christmas design in a mid-century... More
- 1.5-Hour Tour in Midland
- Explore Mid-Century Holiday Home
- Includes Guided Tour & Displays
- Unique Designer Holiday Experience
-
The Carolina Christmas Train – Family Class: SUMMIT VIEW
Ride through a winter wonderland with Santa, cocoa, and Christmas... More
- 50-Minute Ride in Star, NC
- Meet Santa Onboard
- Includes Hot Cocoa & Cookie
- Nostalgic Holiday Train Ride
Contact Us
-
Christmas Holiday Tours
Fort Collins, CO 80526 -
Meeting locations vary for each tour: You will be sent a meeting location after you book
