On The Sea Charters offers private half-day, full-day, sunset, and special-event sails across the USVI and BVI.
Choose from half-day Water Taxi trips, full-day island hops, sunset sails, and event charters like New Year's Eve.
boat-charters · Cruz Bay
Spend a private day island-hopping from Cruz Bay aboard a roomy catamaran with On The Sea Charters. Snorkel vibrant reefs, claim a secluded sandbar, and let a local captain craft an itinerary that fits your group.
On The Sea Charters operates from Smith Bay, St. Thomas, offering private catamaran charters throughout the U.S. and British Virgin Islands. The company specializes in customizable half-day and full-day trips that focus on snorkeling, beach visits, and relaxed island cruising. Popular itineraries include Water Taxi, a half-day private catamaran exploring hidden beaches and vibrant reefs; USVI Private Full-Day and BVI Private Full-Day charters for extended island-hopping; and a BVI - Extended Private Full Day option for larger routes.
Seasonal and special-event trips include the BVI Foxy's Old Year's Night New Years Eve Trip, a private evening charter, and the USVI Sunset Cruise, a 1.5-hour private sail timed for sunset views. More casual options such as Toast to Jost promise all-day relaxation in White Bay, while Golden Hours focuses on scenic sailing, reefs, beaches, and natural rock formations.
Last Day Blues is designed for travelers' final day, combining a relaxed cruise, snorkeling, floating, and a lunch stop at Pizza Pi. All experiences are led by local, experienced captains who guide navigation, snorkeling spots, and island knowledge. Vessels are presented as private catamarans suitable for groups seeking a personalized charter experience.
On The Sea Charters emphasizes flexible, private itineraries that allow guests to snorkel, lounge, and discover secluded spots on a schedule that suits them. Departure point: Smith Bay, St. Thomas.
Departures leave from Smith Bay with tailored routes available for private groups and event-focused sails. Guests can expect snorkeling stops, reef exploration, beach time, and relaxed onboard comfort and personalized service.
“Every outing is organized with local river knowledge, basic safety instruction, and equipment checks before departure.”
Departures from Smith Bay docks
Half-day, full-day, sunset, special events
Flexible cruise lengths available
Expert local captains on board
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 On The Sea Charters listing.
On The Sea Charters 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.
Reserve a private half-day, full-day, sunset, or special-event charter with experienced local captains — secure the preferred date now.
boat-charters · Cruz Bay
Turn a quick stop in Cruz Bay into a three-hour ocean escape: private catamaran charters with local captains, snorkel gear, and secret coves. Perfect for travelers who want a short, memorable taste of St. John’s reefs and beaches.
boat-charters · Cruz Bay
Turn your final day in the U.S. Virgin Islands into a stress-free, sun-soaked cruise. This private charter from Cruz Bay combines snorkeling, floating, lunch at Pizza Pi, and a marina check-in with a quick taxi to the airport.
boat-charters · Cruz Bay
Sail from Cruz Bay aboard Golden Hours, a catamaran charter by On The Sea Charters that mixes reef snorkeling, hidden beaches and coastal rock formations. Perfect for families and small groups looking for an accessible half-day of marine exploration in the U.S. and British Virgin Islands.
boat-charters · Cruz Bay
Spend a full day island-hopping the U.S. and British Virgin Islands aboard the Gato Mundo. Private groups up to 12 can snorkel reefs, stroll secluded beaches, and lean on captains who know the archipelago’s best-hidden coves.
boat-charters · Cruz Bay
Skip the shoreline crowds and spend New Year’s Eve on the water—this private charter from Cruz Bay offers sunset views, Caribbean night air, and a midnight toast under the stars. Perfect for small groups who want an intimate, festive way to ring in the year.
boat-charters · Cruz Bay
Spend a full, unhurried day anchored in White Bay on a private charter—snorkel the reef, float with a cocktail, and hop between legendary beach bars. Toast to Jost simplifies logistics so you can focus on sun, sand, and sea.
boat-charters · Cruz Bay
Spend 90 minutes aboard a private charter from Cruz Bay and watch the Caribbean sky ignite. Small groups (up to 12) get front-row sunset views, bottled water, and the freedom to bring snacks and drinks.
boat-charters · Cruz Bay
Spend a private 6.25‑hour day aboard a catamaran from Cruz Bay, exploring reefs, hidden sandbars, and coastal rock formations with local captains. This flexible private charter is ideal for groups up to 12 who want curated snorkeling, quiet coves, and on‑board comforts.
Click into any experience card above to view current dates, live availability, transparent pricing, cancellation policies, and booking details.