Sail into the sunset aboard the charming schooner When and If in Key West. Discover vibrant skies, calm waters, and serene moments on this private boat tour.
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels; minimal physical effort required.
Wildlife
History
The When and If schooner was originally built as a U.S. Coast Guard vessel and now serves as a cherished part of Key West’s maritime heritage.
Conservation
The company emphasizes eco-friendly practices, including use of reef-safe products and efforts to minimize plastic waste during tours.
Sunset Sail Key West
Sail into the sunset aboard the charming schooner When and If in Key West. Discover vibrant skies, calm waters, and serene moments on this private boat tour.
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 Seating
Ensure you get the best spots on deck by arriving at least 15 minutes early.
Bring a Light Jacket
Evenings on the water can be cooler; a light jacket keeps you warm during the sail.
Apply Reef-Safe Sunscreen
Protect your skin and the fragile marine environment with reef-safe sunscreen.
Limit Alcohol Consumption
Enjoy light refreshments but drink responsibly to stay safe while aboard.
Light Jacket
Keeps you warm during cooler evening breezes on the water.
fall
Reef-Safe Sunscreen
Protects your skin and the marine ecosystem during sunny days.
summer
Wide-Brim Hat
Provides extra sun protection during late afternoon before sunset.
summer
Camera or Smartphone
Capture the stunning colors and moments during the sunset sail.