Sunset Sail Charters in St. Thomas & St. John

Toast golden hour aboard Kindred Spirit II, a 46′ Leopard sailing catamaran, on a relaxed 2.5-hour private sunset sail. Cruise the calm waters around St. Thomas and St. John with handcrafted cocktails, beer, and wine in hand and a gourmet charcuterie board to share as the sky fills with Caribbean color.

Experience the magic of a Caribbean sunset aboard the 54′ luxury sailing yacht Blue Dream. Cruise the calm waters around St. Thomas and St. John past secluded coves and the coastline of Virgin Islands National Park as the sky lights up in gold, orange, and pink. Relax with a premium open bar and a gourmet charcuterie board at golden hour.

Two-hour Sunset & Harbor Lights Dinner Sail departing from Marriott's Frenchman's Cove. It features spectacular Caribbean sunset views, an open bar, and freshly prepared, island-inspired dinners.

Watch the sky turn over the U.S. Virgin Islands aboard Vibin', a 42′ Aquila power catamaran built for luxury. Take in 360° views from the flybridge, cool off in the air-conditioned salon, and relax across shaded lounges with a top-shelf cocktail and a charcuterie spread as the sun sets in shades of orange, pink, and gold.

Unwind with a snorkel-and-sunset evening aboard Down Time, a stable 32′ World Cat power catamaran. Start with a turtle snorkel at Maho Bay or Scott Beach, swing by Christmas Cove for fresh Pizza Pi, then relax on deck as the U.S. Virgin Islands glow at golden hour.

Wind down with a private 2.5-hour sunset cruise aboard Bama Breeze, a 35′ Scout (fully refit in 2025), departing Compass Point Marina. Cruise the coastline slowly with a drink in hand as the sky turns orange, pink, and purple over the U.S. Virgin Islands.

Toast the evening aboard Sweet Pea, a luxurious 40′ Voyage catamaran, on a two-hour private sunset sail through the U.S. Virgin Islands. Sip champagne and cocktails with hors d'oeuvres as the Caribbean sky turns gold — an intimate evening that feels private even with the whole group aboard.

Unwind into golden hour aboard Sail Meow, a spacious 44′ Leopard catamaran, on an intimate two-hour sunset sail around St. Thomas and St. John. Lounge in sun or shade with a cocktail in hand as warm Caribbean breezes and sunset colors roll across the water.

Wind down with a snorkel-and-sunset evening aboard Bonus Time, a stable 29′ World Cat power catamaran. Start with a turtle snorkel at Maho Bay or Scott Beach, swing by Christmas Cove for fresh Pizza Pi, then relax on deck as golden hour settles over the U.S. Virgin Islands.

Toast the evening aboard Sea Level, a classic 50′ ketch-rigged sailing yacht, on a 2.5-hour private sunset sail from Compass Point Marina. Relax on cushioned deck seating with chilled sparkling wine, South Carolina–style peel-and-eat shrimp, and a premium open bar as the Caribbean sky lights up. Pedro the sailing dog may join you.

Set sail into the sunset aboard VI Cat, a spacious 54′ Gold Coast catamaran, for a two-hour shared dinner cruise off St. Thomas. Cruise Charlotte Amalie Harbor and the coastline as the sky turns gold, with a full island-inspired dinner and drinks served onboard. The only catered sunset dinner sail in the fleet — ideal for date nights and celebrations.

Toast golden hour aboard Salty Viking, a 36′ Aquila power catamaran, on a luxe private sunset cruise through the cays. Enjoy a champagne toast and a generous catered charcuterie spread on deck — or slip in for an evening swim as the Caribbean sun goes down. The islands' most photogenic evening.