2 Hrs | Up to 64 Guests | $2,500 per boat
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.
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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.
Wildlife
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.
Sunset Sail Key West
2 Hrs | Up to 64 Guests | $2,500 per boat
Sunset Sail Key West operates in Key West, Florida, offering a curated collection of sailing experiences aboard classic and historic vessels. The company runs private charters and shared sails that depart from Stock Island and Safe Harbor Marina, featuring the historic schooner yacht Malabar X (a 1930 vessel with record-setting victories) and the 1939 wooden schooner When And If (once owned by General George S. Patton). Guests can choose private sunset sails, day sails, and snorkel-and-sunset combinations tailored to small groups and special occasions. Trips range from 90-minute harbor sails to two- and four-hour private charters, with options to raise sails, take the helm, snorkel vibrant coral nurseries, or relax with boutique beverages.
Private charters allow guests to bring their own drinks and snacks and to customize the itinerary. The operation emphasizes personalized service from experienced captains and crew who guide guest participation in sailing activities while maintaining safety and comfort. The fleet’s historic provenance, open deck experiences, and varied itineraries make it suitable for couples, families, and groups seeking an authentic Key West maritime outing. Sunset Sail Key West supports maritime preservation through interpretive sail experiences on classic schooners and promotes responsible snorkeling around coral nurseries. Booking options include scheduled public sails aboard Malabar X and customizable private charters on multiple vessels. Clear departure locations, defined trip durations, and a range of activities provide transparency for planning. Prospective guests should review trip descriptions and availability when selecting between harbor sails, historic schooner experiences, and snorkel combinations. Reserve early today.
Tours Offered
10
Range of day and sunset sails
Historic Vessels
2
1930 and 1939 schooners
Private Charters
Available
Bring personal drinks and snacks
Trip Durations
90–240 min
From 1.5 to 4 hours
Secure a private charter or join a scheduled schooner sail for an authentic Key West maritime experience—check availability and departure points now.
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.
Light Jacket or Windbreaker
Evening winds on the water can be chilly during fall, so bring a jacket to stay warm.
fall
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