THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Set sail on a private sunset cruise around St. Thomas with Happy Island Charters. Enjoy Caribbean views, fresh shrimp, and sparkling wine as the sun dips below the horizon.
Set sail on a private sunset cruise around St. Thomas with Happy Island Charters. Enjoy Caribbean views, fresh shrimp, and sparkling wine as the sun dips below the horizon.
Book with Happy Island Charters
Verified experiences and guided adventures in the surrounding area.
Operated by Happy Island Charters · Charlotte Amalie, St. Thomas
Experience an unforgettable private sunset sail in the stunning waters of St. Thomas, U.S. Virgin Islands, aboard a classic sailing yacht with Happy Island Charters. This exclusive boat tour offers breathtaking Caribbean vistas as the sun dips below the horizon, coloring the sky in hues of orange and pink. Relax on the spacious foredeck with comfortable seating and savor a delicious menu featuring fresh South Carolina shrimp paired with sparkling wine. The friendly crew ensures a smooth and memorable journey, while Pedro, the charming sailing dog, adds a unique touch to the adventure. Whether you're celebrating a special occasion or simply seeking tranquility on the water, this private sailing experience blends relaxation, luxury, and scenic beauty, making it ideal for couples, friends, or families looking for an intimate escape. Make the most of the gentle ocean breeze, panoramic views, and serene ambiance during this 2–3 hour cruise, creating memories that will last a lifetime.
easy.
2–3 hours.
Suitable for all fitness levels; minimal physical effort required mainly for boarding and disembarking.
Yes, children are welcome on the private sunset sail, but parental supervision is required at all times.
Outside food and beverages are not permitted; however, the charter provides a delicious menu and sparkling wine.
In case of severe weather, the charter will reschedule your trip or offer a full refund.
Due to the boat's design, wheelchair access is limited; please contact Happy Island Charters for specific accommodations.
Private charters can accommodate up to 6 guests, ensuring an intimate and personalized experience.
Pedro, the sailing dog, is on board, but outside pets are not permitted for safety reasons.
St. Thomas was an important hub in Caribbean trade during the colonial era and retains many cultural influences from Danish rule.
Happy Island Charters practices eco-friendly sailing techniques to minimize fuel use and supports local marine protection initiatives.
Happy Island Charters is a private boat charter company based in Nazareth, St. Thomas, offering customizable day trips and sunset sails in the U.S. Virgin Islands. The operator focuses on small-group, private experiences that showcase nearby islands, beaches, and marine sites, including Cas Cay and routes around St. John National Park. The fleet includes a 15' RIB with a 70 HP Yamaha engine called the Happy Islander, a 37' Intrepid powerboat named Izulu with twin 300 HP Yamaha engines, and a classic sailing yacht used for sunset sails and full-day charters. Trip options include a private RIB excursion to Cas Cay with snorkeling in mangroves and short hikes; a private sunset sail with a curated menu featuring South Carolina shrimp and sparkling wine; and a full-day sailing charter with a gourmet Caribbean lobster lunch, premium drinks, snorkeling, and extended island exploration. Guests can expect high-quality snorkeling gear, comfortable seating on the yacht foredeck, and the company of Pedro, the sailing dog who joins many trips. Captain Fancy guides customizable itineraries on select trips, and a friendly crew supports onboard service. Charters emphasize private, tailor-made adventures for couples, families, and small groups seeking snorkeling, beach time, and scenic cruising. Reservations are available for private charters originating from Nazareth, St. Thomas, with options that accommodate half-day, full-day, and sunset departures. Booking information, pricing, and seasonal availability are provided upon inquiry; guests can request specific routes, dietary options, and snorkeling instruction when reserving to tailor each private charter to their preferences and needs.
Book with Happy Island Charters