Experience Key West’s coastal magic aboard historic vessels with Sunset Sail Key West. Private dolphin watching, snorkeling, and sunset sails offer a personalized escape on the island’s crystalline waters.
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Difficulty
easy
Duration
1.5–4 hours
Fitness Level
Suitable for most fitness levels; minimal physical exertion required except optional sail handling.
Wildlife
History
The "When and If" schooner sailed with General Patton in WWII, tying local maritime culture to broader historical events.
Conservation
Sunset Sail Key West practices responsible tourism by educating guests on reef preservation and encouraging zero-waste onboard policies.
Sunset Sail Key West
Experience Key West’s coastal magic aboard historic vessels with Sunset Sail Key West. Private dolphin watching, snorkeling, and sunset sails offer a personalized escape on the island’s crystalline waters.
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.
Book Private Charters in Advance
Sunset Sail Key West specializes in private trips that fill up quickly, especially around holidays and weekends.
Bring Waterproof Camera Gear
Water-resistant cameras or cases are recommended to capture dolphins, reef snorkels, and stunning sunset hues without risk.
Arrive Early for Boarding
Arriving 15 minutes before your scheduled trip ensures a smooth check-in and lets you settle in before departure.
Check Weather and Sea Conditions
Key West can experience sudden afternoon squalls—check forecasts for optimal sailing windows, especially in summer.
Sunscreen
Protect your skin from intense Florida sun exposure during daytime sails.
summer
Light windbreaker
A light jacket helps manage cool breezes when sailing at sunset or in winter months.
fall
Waterproof camera or case
Ideal to capture marine wildlife encounters and sunset colors without worry.
Water shoes or non-slip sandals
Safe footwear helps when boarding or disembarking, especially on dock or wet decks.