Experience intimate sunset sails, historic schooner voyages, and private snorkel combos in Key West, Florida.
Choose private sunsets, historic schooner sails, day sails, or snorkel-and-sunset adventures.
Sailing · 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.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Range of day and sunset sails
1930 and 1939 schooners
Bring personal drinks and snacks
From 1.5 to 4 hours
Open the individual experience guide to confirm current availability, pricing, policies, conditions, and inclusions before booking.
The operator provides clear meeting points, departure times, and destination coordinates for all outings.
Personal flotation devices, emergency protocols, equipment checks, and paddling orientations are provided before departure.
Recommended layering, water shoes, sunscreen, and dry bags are detailed in each experience guide.
Guides share rich knowledge of regional flora, fauna, scenic landmarks, and river navigation.
A glimpse into the experiences, natural landscapes, and adventures waiting on your next trip.
Images supplied on the current Sunset Sail Key West listing.
Sunset Sail Key West offers a variety of guided outdoor excursions, scenic routes, rentals, and custom itineraries tailored for families, couples, and adventure enthusiasts.
Yes. Most trips feature comprehensive safety orientations, equipment fittings, and calm routes suited for first-time adventurers. Check the details on individual experience guides for specific age and skill requirements.
Standard safety equipment (such as certified life vests and essential gear) is supplied for each booking. Detailed checklists regarding weather-appropriate attire and personal items are provided prior to departure.
Secure a private charter or join a scheduled schooner sail for an authentic Key West maritime experience—check availability and departure points now.
Unknown · 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.
boat-charters · Key West
Enjoy a private 2-hour sunset sail aboard the classic yacht Malabar X off Key West’s coast. Experience breathtaking views and hands-on sailing fun on this unforgettable maritime adventure.
Unknown · Key West
Set sail on the Malabar X for a private sunset experience in Key West, Florida. Enjoy breathtaking views, peaceful waters, and a personalized adventure at the golden hour.
Unknown · Key West
Sail the scenic waters of Key West Harbor on a private 1.5-hour trip with Sunset Sail Key West. Enjoy peaceful sailing, wildlife sightings, and stunning coastal views.
Unknown · 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.
Unknown · Key West
Discover an unforgettable day with snorkeling and sunset sailing in Key West. Dive into clear waters and end your day with stunning Gulf sunsets on this private, 4-hour adventure.
boat-charters · Key West
Discover the magic of Key West’s waters on a private sunset sail aboard When And If, a 1939 wooden schooner with a fascinating past as General Patton’s own yacht. Experience history, hands-on sailing, and stunning scenery all in one unforgettable evening.
boat-charters · Key West
Experience Key West like never before aboard the 1939 schooner When And If, where history meets hands-on sailing along the Atlantic coast. Raise the sails, steer the helm, or simply relax with a drink as you glide through captivating seascapes.
boat-charters · Key West
Step aboard the 'When And If,' a classic 1939 wooden schooner, for a private two-hour sailing adventure off the coast of Key West. Experience hands-on sailing or relax with stunning Atlantic views framed by historic charm.
boat-charters · Key West
Set sail on the classic schooner Malabar X for a private two-hour daysail near Stock Island, Florida. Experience the thrill of piloting your own vessel with stunning views and local island charm just minutes from Key West.
boat-charters · Key West
Set sail aboard Malabar X for a refreshing two-hour daysail in Key West. Whether you want to relax on deck or take the helm, this classic schooner offers stunning views and sea breezes perfect for an afternoon escape.
boat-charters · Key West
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.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.