Relax on a private 3-hour sail in the peaceful waters of Key West. Discover hidden coves and enjoy stunning views with Sunset Sail Key West’s chillout experience.
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Difficulty
easy
Duration
3 hours
Fitness Level
Minimal physical effort needed; suitable for all fitness levels including families and older adults.
Wildlife
History
Key West has a rich maritime history dating back to its days as a 19th-century shipping hub and pirate haven.
Conservation
Local companies actively promote reef-safe practices and help protect coral habitats through responsible sailing tours.
Sunset Sail Key West
Relax on a private 3-hour sail in the peaceful waters of Key West. Discover hidden coves and enjoy stunning views with Sunset Sail Key West’s chillout experience.
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 Smooth Boarding
Arriving 15 minutes before your scheduled time helps ensure a relaxed and timely departure.
Bring Reef-Safe Sunscreen
Protect your skin and the delicate marine environment by using eco-friendly sunscreen.
Wear Non-Slip Footwear
Choose shoes with good grip to stay stable on the wet boat deck.
Stay Hydrated
Florida’s sun can be strong even on the water, so drink plenty of water throughout the sail.
Lightweight Clothing
Breathable clothes keep you cool under Florida’s sun during summer sails.
summer
Polarized Sunglasses
Cut glare and protect your eyes while enjoying clear views on the water.
Hat with Wide Brim
Offers sun protection during long hours exposed on the deck.
spring
Water Bottle
Staying hydrated is key when out cruising under the sun.