Sail Into the Sunset: Unforgettable Holiday Parties Aboard Classic Schooners in Key West
Difficulty
easy
Duration
2 hours
Fitness Level
Suitable for most fitness levels; primarily a seated, relaxed experience with optional light activity if participating in sailing.
Overview
Celebrate the holidays aboard a classic schooner in Key West. Enjoy spiced wine and gourmet cheese while sailing into breathtaking sunsets on a memorable two-hour cruise designed for groups up to 64.
Holiday Party
2 Hrs | Up to 64 Guests | $2,500 per boat
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Adventure Photos
About This Adventure
Treat your team to an unforgettable evening aboard a classic schooner in Key West! Enjoy a stunning sunset while sipping spiced wine and indulging in a gourmet cheese platter. Experience the thrill of sailing on historic yachts, with options for hands-on participation or simply relaxing as the sails catch the wind.
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Show your employees some love and support a truly local family business! Treat your team to a night playing tourist in their home town by doing what Sunset Sail Key West does best - a classic schooner sunset sail.
WHAT"S INCLUDED:
-Tax and Gratuity
- Spiced wine on arrival
- Gourmet cheese platter
- Boutique wine and select beers
- Bottled water and La Croix
Arrive at your ship to a complimentary glass of spiced wine and take your seat as we cast off from the dock to enjoy a beautiful Key West Sunset.
Complimentary boutique wine, select beers and water/sparkling water are available throughout the sail to accompany the offerings from your gourmet cheese platter. An optional beverage upgrade is available to include premium sparkling wine.
Take a turn at the helm, help raise sail or simply relax and enjoy the ride as a cloud of ivory canvas blossoms above the sprung teak deck, the wind fills the sails and the boat leans into her element.
When And If is the gorgeous 1939 transoceanic cruising yacht designed by famed American naval architect John G. Alden and built for General George Patton to sail around the world "When the war is over, and If I live through it."
Malabar X is her stunning senior sister, 1930 racing yacht designed by the same John Alden to win the Newport Bermuda race, which she duly did, winning her class in 1930 and smashing records to take first overall in 1932.
Between the two boats we have capacity for 64 guests as each boat is Coastguard certified for 32. Choose your preferred vessel or split your party up by booking both yachts and enjoy a tandem sail or even a bit of match racing!
Get the season all wrapped up and book your company's Holiday party now.
Adventure Tips
Arrive Early for Best Boarding Experience
Show up at least 15 minutes before departure to receive a safety briefing and choose your ideal spot aboard the schooner.
Dress in Layers for Evening Breezes
Evenings on the water can get cool; bring a light jacket even during warmer months to stay comfortable as the sun dips below the horizon.
Bring a Camera for Sunset Shots
Golden hour on the Gulf creates stunning photo opportunities — keep your camera or phone ready to capture vibrant skies and candid moments.
Participate in Sailing if You Wish
The crew welcomes guests who want a hands-on experience—don’t hesitate to ask about helping with sails or steering for a more immersive outing.
Local Insights
Wildlife
- Look out for playful bottlenose dolphins that often swim alongside the schooner
- Spot pelicans gliding close to the water’s surface during your cruise
History
These classic schooners hark back to Key West’s rich maritime trade in the 19th century, a legacy preserved by local sailing enthusiasts.
Conservation
The operators emphasize eco-friendly practices to protect fragile coral reefs and marine wildlife throughout the waters of Key West.
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Adventure Hotspots in Key West
Frequently Asked Questions
Recommended Gear
Light Jacket or Windbreaker
Evening winds on the water can be chilly during fall, so bring a jacket to stay warm.
fall specific
Comfortable Non-Slip Shoes
Protect your feet and maintain grip on the polished wood decks.
Camera or Smartphone
To capture stunning sunset views and memorable moments aboard.
Sunglasses
Shield your eyes from afternoon sun during summer cruises.
summer specific