St. John, US Virgin Islands · 2026 Season
On the Sea Charters
St. John's decade-old On the Sea Charters — founded 2015 by Ryan Matthews — running the 32' Cheshire and 33' Gato Mundo power catamarans from the Cruz Bay National Park Dock. Private half-day, full-day, BVI, sunset, and 'Last Day Blues' airport-transfer charters.
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Compare every On the Sea Charters trip
5.0 on Google, 92 reviews
| Trip | Duration | Max guests | From | Departs |
|---|---|---|---|---|
| Private St. John Sunset Cruise with Powerboat | 1.5 Hours | 12 | $450 per charter | Cruz Bay National Park Dock, St. John |
| Half-Day Private USVI Water Taxi & Island Hopping | 3 Hours | 12 | $500 per charter | Cruz Bay National Park Dock, St. John |
| USVI Sunset Sail: Golden Hour Cruise for 12 Passengers | 3.5 Hours | 12 | $695 per charter | Cruz Bay National Park Dock, St. John |
| Private Full-Day USVI Last Day Experience | 7 Hours | 12 | $965 per charter | Cruz Bay National Park Dock, St. John |
| Private Full-Day USVI Tour: Island Hopping & Secluded Beaches | 6.25 Hours | 12 | $1,050 per charter | Cruz Bay National Park Dock, St. John |
| Private Full-Day BVI White Bay Powerboat Charter | 6 Hours | 6 | $1,350 per charter | Cruz Bay National Park Dock, St. John |
| Private Full-Day BVI Powerboat Charter to Jost Van Dyke & The Baths | 8.25 Hours | 12 | $1,450 per charter | Cruz Bay National Park Dock, St. John |
Choose your day on the water
On the Sea Charters – All Tours & Trips
7 charters available
Private Full-Day BVI Powerboat Charter to Jost Van Dyke & The Baths
On the Sea Charters
Explore the British Virgin Islands on a full-day private charter with On The Sea Charters. Island hop through the U.S. and British Virgin Islands visiting secluded beaches, popular
- Boat
- BVI Trips
- Duration
- 8.25 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
USVI Sunset Sail: Golden Hour Cruise for 12 Passengers
On the Sea Charters
Catch the golden hours with On The Sea Charters on a 3.5-hour afternoon cruise through the Virgin Islands. Whether you're looking for a private secluded beach, a popular drinking s
- Boat
- Sunset Sailing
- Duration
- 3.5 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private Full-Day BVI White Bay Powerboat Charter
On the Sea Charters
Spend an unforgettable day anchored in paradise with our White Bay All Day experience. After customs check-in at Great Harbor on Jost Van Dyke, we'll take you directly to the iconi
- Boat
- BVI Trips
- Duration
- 6 Hours
- Up to
- 6 guests
- Stops
- Custom itinerary
Private Full-Day USVI Last Day Experience
On the Sea Charters
Last day blues? Don't want your vacation to end? Let On The Sea Charters give you the best last day. Sleep in, start at 10am, enjoy one last snorkel or just float. Then grab lunch
- Boat
- Private Charters
- Duration
- 7 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private St. John Sunset Cruise with Powerboat
On the Sea Charters
Set sail into the sunset with On The Sea Charters for a leisurely 1.5-hour private cruise on the water. Enjoy breathtaking Virgin Islands sunset views as you relax aboard a comfort
- Boat
- Sunset Sailing
- Duration
- 1.5 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Private Full-Day USVI Tour: Island Hopping & Secluded Beaches
On the Sea Charters
Island hop through the Virgin Islands on a full-day private charter with On The Sea Charters. Whether you are looking for a private secluded beach destination, a popular drinking s
- Boat
- Private Charters
- Duration
- 6.25 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
Half-Day Private USVI Water Taxi & Island Hopping
On the Sea Charters
Island hop through the Virgin Islands with On The Sea Charters. Whether you are looking for a private secluded beach destination, a popular drinking spot, or just a day cruise that
- Boat
- Private Charters
- Duration
- 3 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
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On the Sea Charters was founded on St. John in 2015 by Ryan Matthews — a Florida native, FSU grad, and former Ritz-Carlton St. Thomas intern who worked his way up through St. Thomas maritime jobs (crew, captain, dive instructor) before buying a 26-foot Glacier Bay named '9 Lives' and starting the company. The Cheshire (32') was added in 2019 and Gato Mundo (33') joined the fleet in 2024 — both twin-hulled power catamarans running out of the Cruz Bay National Park Dock.
The trip menu is one of the most complete on St. John: half-day USVI runs at $1,050, full-day trips to Jost Van Dyke's White Bay at $1,350, BVI Full Day at $1,450, the 3.5-hour 'Golden Hours' sunset at $695, and the signature 'Last Day Blues' — snorkel + Pizza Pi lunch + Crown Bay Marina drop-off for a same-day flight — at $965.
What Makes St. John On the Sea Charters Special?
2-Catamaran Fleet
32' Cheshire (added 2019) and 33' Gato Mundo (added 2024) — twin-hulled power catamarans, up to 12 guests each, both berthed at the Cruz Bay National Park Dock.
Founded 2015 by Ryan Matthews
Ryan is a Florida native and FSU grad who came to St. Thomas for a Ritz-Carlton internship, worked through USVI maritime jobs, and launched On the Sea with a 26' Glacier Bay named '9 Lives'.
Cruz Bay National Park Dock
St. John pickup at the National Park Visitor Center dock — the fastest launch to Waterlemon, Lovango, and BVI crossings.
BVI Full Day · $1,450
8-hour full-day BVI trip covering Jost Van Dyke, Norman Island, Tortola, and Virgin Gorda highlights. Up to 12.
Last Day Blues · $965
4-hour signature charter — snorkel + Pizza Pi lunch + drop-off at Crown Bay Marina with showers and taxi coordination to STT airport for your flight home.
Golden Hours Sunset · $695
3.5-hour afternoon-into-sunset cruise — longer than a standard 1.5-hour sunset run, shorter than a full day. The sweet-spot afternoon trip.
Meet the Captains
Ryan Matthews — Founder & Captain
USCG-Licensed Captain · PADI Dive Instructor
Florida native, FSU graduate. Moved to St. Thomas after college for a Ritz-Carlton internship and worked every maritime job the USVI would give him — crew, captain, dive instructor, small vessels to yachts. Moved to St. John, captained for other companies, and in 2015 bought a 26-foot Glacier Bay named '9 Lives' to launch On the Sea Charters. Ten years later he's running a two-boat fleet through hurricane rebuilds and a pandemic and still on the water himself.
On the Sea Captain Team
USCG-Licensed St. John Captains
Ryan's captains run the Cheshire and Gato Mundo alongside him — small crew, all locally-based on St. John, all trained on the same Cruz Bay-to-BVI routes. Repeat guests specifically note the crew's willingness to route around wind and swell to find the calmest water each day.
Trip Pricing at a Glance
| Trip | From |
|---|---|
| Golden Hours (Afternoon → Sunset) | $695 |
| Last Day Blues (Snorkel + Pizza Pi + Airport Drop-off) | $965 |
| USVI Full Day (St. John reefs + hidden coves) | $1,050 |
| White Bay (Jost Van Dyke) BVI Trip | $1,350 |
| BVI Full Day (Jost + Norman + Virgin Gorda area) | $1,450 |
Related St. John Trips
What You Need to Know
- Founded 2015 by Ryan Matthews with a 26' Glacier Bay named '9 Lives' (retired from the fleet).
- 2019: added the 32' Cheshire power catamaran.
- 2024: added the 33' Gato Mundo power catamaran.
- Home dock: Cruz Bay National Park Dock (St. John National Park Visitor Center).
- Passenger capacity: 12 guests per boat.
- Real trip prices: BVI Full Day $1,450 (8 hr) · White Bay JVD $1,350 (6 hr) · USVI Full Day $1,050 (6 hr) · Last Day Blues $965 (4 hr) · Golden Hours sunset $695 (3.5 hr).
- Signature trip: 'Last Day Blues' — snorkel + Pizza Pi + Crown Bay Marina drop-off with showers and taxi to STT airport.
- Also active on Facebook, Instagram, TripAdvisor, and Yelp — one of the most-reviewed small operators on St. John.
What's Included
- USCG-licensed captain
- Ice, bottled water, snorkel equipment, and floats
- Bluetooth sound system
- Freshwater rinse
- Custom itinerary planning based on weather and swell
- Airport-side taxi coordination on 'Last Day Blues' trips
- Fuel included on the White Bay Jost Van Dyke trip (a rare all-in BVI rate)
Pro Tips from the Locals
💡If you're flying out same-day, book 'Last Day Blues' at $965 — it's structured around drop-off at Crown Bay Marina with showers before your STT flight.
💡The 'White Bay All Day' trip includes fuel in the $1,350 rate — one of the few all-in BVI day rates on St. John.
💡Golden Hours is the sweet spot for couples — longer than a standard sunset cruise, shorter than a full day, at $695.
💡Bring reef-safe (non-spray) sunscreen and cash for BVI customs ($75–$85 per person).
💡Passports required for every BVI trip — check your family's expiration dates before booking.
💡Book 4–8 weeks ahead in peak season (Dec–April); Cheshire and Gato Mundo fill fast.
Frequently Asked Questions
On the Sea Charters FAQ
How much do On the Sea Charters trips cost?
On the Sea Charters trips listed on QuestVI range from $450 to $1,450, depending on the trip. See the table above for each trip's price and whether it is per person or per charter.
Where do On the Sea Charters trips depart from?
On the Sea Charters trips depart from Cruz Bay National Park Dock, St. John.
Does On the Sea Charters go to the BVI, and what passport or customs is needed?
Yes — 3 On the Sea Charters trips go to the British Virgin Islands. The operator asks guests to bring: Passports (required for British Virgin Islands). Cash for customs, lunch, souvenirs, and tips.
What's included on On the Sea Charters trips?
Commonly included: Adult snorkel equipment (small - large); Bluetooth sound system; Ice and bottled water; Noodles, floats and dry bag; Freshwater shower; Bottled water. Check each trip page for its full list.
How does booking On the Sea Charters through QuestVI work?
You book on On the Sea Charters's own FareHarbor checkout at the same price as booking direct. QuestVI adds no fee or markup, and our local team is happy to help you choose the right trip.
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