Set sail on a private sunset cruise in Key West and enjoy personalized views of the stunning Florida sunset. This intimate boat tour offers tranquility, beautiful scenery, and unforgettable moments on the water.
More ways to explore the area's outdoor wonders
Hang tight — photos are loading
This usually takes just a second.
Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for most fitness levels; minimal physical activity required
Wildlife
History
Key West's maritime history dates back centuries, and the very waters you'll sail on have witnessed countless historic events and shipwrecks.
Conservation
Sunset Sail Key West practices environmentally friendly navigation to minimize impact on marine life and preserve the area's natural beauty.
Sunset Sail Key West
Set sail on a private sunset cruise in Key West and enjoy personalized views of the stunning Florida sunset. This intimate boat tour offers tranquility, beautiful scenery, and unforgettable moments on the water.
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 the Best Views
Getting to the dock 15-20 minutes before your scheduled departure ensures you can settle in comfortably and enjoy the full experience.
Bring Layers for Temperature Changes
Evening breezes can be cool after sunset, so pack a light jacket or cover-up to stay comfortable throughout the cruise.
Protect Your Camera and Phone
Keep devices safe from splashes and enjoy taking photos of the stunning scenery during the trip.
Book in Advance for Private Experience
Private sunset sails are popular, so reserve your spot early to ensure exclusivity and preferred times.
Sunscreen
Protect your skin from UV rays during daytime preparation for the cruise.
summer
Sunhat or Cap
A wide-brimmed hat shields your face from the sun while on deck.
spring|summer
Light Jacket or Sweater
Bring warmth for the cooler evening temperatures after sunset.
fall|winter
Camera or Smartphone
Capture stunning views of the sunset and surrounding scenery.
all