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.
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Difficulty
easy
Duration
2–3 hours
Fitness Level
Suitable for all fitness levels; minimal physical effort required mainly for boarding and disembarking.
Wildlife
History
St. Thomas was an important hub in Caribbean trade during the colonial era and retains many cultural influences from Danish rule.
Conservation
Happy Island Charters practices eco-friendly sailing techniques to minimize fuel use and supports local marine protection initiatives.
Happy Island Charters
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.
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.
Location
Nazareth, St. Thomas
Departures originate in Nazareth
Trips Offered
4 Trip Options
RIB, powerboat, and sailing charters
Featured Vessels
Happy Islander, Izulu, Sailing Yacht
Vessels named in trip descriptions
Onboard Companion
Pedro, the Dog
Pedro often joins sailing trips
Book a RIB excursion, full-day sail, or sunset cruise — customizable itineraries, premium gear, and Pedro the sailing dog included on many trips.
Arrive Early for Check-In
Plan to arrive at the dock at least 15 minutes before departure to complete check-in smoothly.
Wear Light, Breathable Clothing
Choose comfortable clothes made from breathable fabrics to stay cool during the sail.
Bring Seasickness Remedies
If you are prone to seasickness, consider taking medication beforehand or bring ginger candies.
Protect Your Electronics
Use waterproof cases or bags to protect your camera and phone from splashes.
Sunscreen
Protect your skin from strong Caribbean sun exposure during the sail.
summer
Light Jacket
Ideal for cooler breezes, especially during the evening return.
fall
Waterproof Phone Case
Keeps your phone safe from unexpected splashes and saltwater.
Comfortable Non-Slip Shoes
Provides safe footing on wet boat surfaces during boarding and sailing.