THE ADVENTURE COLLECTIVE® · Independent discovery and booking for outdoor travel
Set sail on a private luxury charter with Waypoints in St. Thomas, USVI. Experience world-class sailing, pristine beaches, and unmatched personalized service on crystal clear waters.
Set sail on a private luxury charter with Waypoints in St. Thomas, USVI. Experience world-class sailing, pristine beaches, and unmatched personalized service on crystal clear waters.
Located in the vibrant harbor of Charlotte Amalie, St. Thomas, Waypoints offers an exceptional private sailing charter experience in the heart of the US Virgin Islands. This destination is known for its stunning turquoise waters, protected bays, and lush tropical islands. St. Thomas serves as the perfect gateway to explore the pristine beaches, hidden coves, and coral reefs around the islands. What sets Waypoints apart is their commitment to luxury and professionalism, offering meticulously maintained sailboats and catamarans that blend comfort with adventure, letting you sail in style and ease. Their fleet features high-end amenities such as in-mast furling sails, electric winches, spacious cabins, and comprehensive refrigeration systems that transform an ordinary trip into a yacht charter experience. The company prides itself on personalized service fitting both seasoned sailors and first-timers, with expert staff coordinating provisioning, dive gear rentals, and personalized scheduling to maximize your time on the water. The local waters surrounding St. Thomas include diverse natural features such as Buck Island Marine Reserve with its thriving coral reefs and Green Cay, known for its rich birdlife and protected beaches. These islands provide secluded spots for snorkeling, swimming with turtles, and peaceful anchorage away from the crowds. Checked thoroughly before departure and frequently serviced mid-trip when needed, Waypoints' fleet reliability ensures no interruptions to your itinerary. The staff's attention to detail—from comprehensive pre-trip briefings to thoughtful post-trip checkouts—guarantees a seamless experience. Through years of operation, Waypoints has become a cornerstone of the USVI sailing community and is highly recommended by repeat charterers who appreciate their family-style atmosphere combined with professional quality. Whether you're seeking a relaxing getaway or an active exploration of the Virgin Islands by sea, Waypoints delivers an unforgettable adventure with personalized touches that highlight the beauty and freedom of sailing in this tropical paradise.
Weather in the USVI can change quickly; staying updated helps plan safe and enjoyable sailing days.
essential PriorityProtect the marine environment by using sunscreen that won't harm coral reefs and marine life.
essential PriorityLight, quick-dry fabrics provide comfort on deck and during shore excursions.
info PriorityThough rentals are available, bringing your own mask and fins ensures the best fit and comfort.
warning PriorityProvides grip and protects boat surfaces during sailing.
Protects eyes and skin from strong Caribbean sunlight.
Useful for sudden rain showers typical in tropical climates.
Ensures comfort and hygiene while exploring reefs and marine life.
Spring offers steady trade winds and warm water temperatures, perfect for smooth sailing and vibrant marine life encounters.
Summer brings intense sunshine and warm seas, best enjoyed with early morning or late afternoon sails to avoid midday heat.
Fall features quieter waters and reduced charter rates, though visitors should stay alert for hurricane updates during this season.
Winter delivers pleasant temperatures and steady winds, ideal for cruising and exploring the islands amid festive local culture.
No prior sailing experience is necessary; Waypoints offers thorough training and professional support for bareboat charters.
Boats feature spacious cabins, refrigeration, gas grills, electric winches, and in-mast furling sails for comfort and ease.
Yes, Waypoints coordinates provisioning and dive gear rentals to be delivered directly to your boat before your arrival.
December through May offers the most stable weather, ideal trade winds, and pleasant temperatures for sailing.
Waypoints primarily specializes in bareboat charters but can assist with crew placement upon request.
Bring non-marking deck shoes, sun protection, light clothing, swimwear, and any personal snorkeling equipment.
Tropical seascapesMarine life such as turtles and raysHistoric harbor architecture
Charlotte Amalie
moderate
Half-day to 10+ days
Basic physical fitness needed for handling lines and moving around the boat safely; suitable for most age groups with mobility.
Charlotte Amalie has a rich Danish colonial heritage dating back to the 17th century and served as an important Caribbean port.
Experience Needed: This natural landmark is recommended for those with some outdoor experience.