St. Thomas, US Virgin Islands · 2026 Season
Island Buddy
Founded 2015 by Captain Duncan Molesworth — the original Jeep tour crew of St. Thomas plus a four-boat charter fleet (Phoenix, Calico Jack, Flying Tiger, Anne Bonny) with USVI & BVI day trips and the signature Surf & Turf combo.
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Compare every Island Buddy trip
4.9 on Google, 78 reviews
| Trip | Duration | Max guests | From | Departs |
|---|---|---|---|---|
| Full-Day Underwater Scooter Rental | 8 Hours | 1 | $200 per person | Cruz Bay Ferry Dock, St. John |
| Private Half-Day St. Thomas Jeep Tour | 3 Hours | 6 | $325 per charter | St. Thomas |
| Full-Day St. John UTV Rental: Drive Your Own Adventure | 8 Hours | 4 | $369 per charter | St. John |
| Private Full-Day St. Thomas Jeep Tour | 5-7 Hours | 6 | $545 per charter | St. Thomas |
| Private St. John Half or Full-Day Jeep Tour & Snorkel | 3 Hours | 4 | $549 per charter | St. John |
| Private St. John Bronco Tour & Lime Out Tacos | 8 Hours | 4 | $649 per charter | Cruz Bay Ferry Dock, St. John |
| Private Full-Day St. John Surf & Turf: Jeep & Boat Charter | 8 Hours | 4 | $1,100 per charter | St. John |
Choose your day on the water
Island Buddy – All Activities
7 charters available
Private St. John Bronco Tour & Lime Out Tacos
Island Buddy
Hands down the best day trip on St. John! A private island tour with a little (lime) twist. Enjoy a full day in an open-air Bronco exploring St. John highlights — secluded beaches
- Boat
- Jeep Tours/Rentals
- Duration
- 8 Hours
- Up to
- 4 guests
- Stops
- Custom itinerary
Private St. John Half or Full-Day Jeep Tour & Snorkel
Island Buddy
Experience St. John like a local with the original St John Jeep Tour, operating since 2015! Explore off the beaten path in an open-air Bronco with a private guide. Snorkel coral re
- Boat
- Jeep Tours/Rentals
- Duration
- 3 Hours
- Up to
- 4 guests
- Stops
- Custom itinerary
Private Full-Day St. John Surf & Turf: Jeep & Boat Charter
Island Buddy
The ultimate St. John combo experience! Half day private island Jeep tour exploring off the beaten path locations plus half day private boat charter. Start your morning with an ope
- Boat
- Private Charters
- Duration
- 8 Hours
- Up to
- 4 guests
- Stops
- Custom itinerary
Full-Day Underwater Scooter Rental
Island Buddy
Rent your own Underwater Scooter! Zoom across the reef with ease at speeds of up to 4mph for up to an hour. These scooters are perfect for all ages with high and low speed options
- Boat
- Beach Gear / Watersports
- Duration
- 8 Hours
- Up to
- 1 guests
- Stops
- Custom itinerary
Private Half-Day St. Thomas Jeep Tour
Island Buddy
Experience the best of St. Thomas in a private half day jeep tour. Choose a morning or afternoon adventure and explore pristine beaches, panoramic overlooks, and local favorites wi
- Boat
- Jeep Tours/Rentals
- Duration
- 3 Hours
- Up to
- 6 guests
- Stops
- Custom itinerary
Private Full-Day St. Thomas Jeep Tour
Island Buddy
Explore St. Thomas like never before on a private, fully customizable full day jeep tour. Visit stunning beaches, breathtaking viewpoints, and hidden gems across the island with yo
- Boat
- Jeep Tours/Rentals
- Duration
- 5-7 Hours
- Up to
- 6 guests
- Stops
- Custom itinerary
Full-Day St. John UTV Rental: Drive Your Own Adventure
Island Buddy
Explore St. John at your own pace in a 4-seater UTV! Drive yourself through the island's stunning scenery — from Coral Bay to East End beaches, historic ruins, and panoramic overlo
- Boat
- Jeep Tours/Rentals
- Duration
- 8 Hours
- Up to
- 4 guests
- Stops
- Custom itinerary
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Island Buddy is the OG Jeep tour crew of the U.S. Virgin Islands — the very first outfit to run branded Jeep and Bronco tours on St. Thomas, in business since 2015 under founder and captain Duncan Molesworth. They've since built a full four-boat charter fleet, added a St. John Bronco tour, and pioneered the Surf & Turf combo (Jeep + boat, same day).
Pickups are offered on both St. Thomas and St. John. The land side runs on fully-loaded 2022 Ford Broncos — snorkeling, hidden trails, sea turtle beaches, mountain vistas. The sea side runs four charter boats built for USVI & BVI day trips, from an easy 30' 'mini-yacht' to a 12-passenger 38' Statement. Book online or call 305-239-7084.
What Makes St. Thomas Island Buddy Special?
OG Jeep Crew Since 2015
The first branded Jeep tour operator in the USVI — a decade of five-star TripAdvisor reviews on the land side.
Surf & Turf Combo
Signature combo — a private Jeep tour + a boat charter in the same day. One of the most unique itineraries in the USVI.
4-Boat Charter Fleet
Phoenix (30' Mainship), Calico Jack (32' Regulator), Flying Tiger (37' Axopar), Anne Bonny (38' Statement). Every boat is BVI-approved.
Phoenix — Fuel Included
The 30' Mainship 'Phoenix' is Island Buddy's most-booked half-day charter — fuel included, 6 guests, from $765.
'Do It All' Shared Trip
Reef Surfari-branded shared trip — snorkel, Pizza Pi, open bar, sunset — from $99/person adults, $69/kids.
Dual-Island Pickup
Boat pickup available on both St. Thomas and St. John — one operator, both islands.
Meet the Captains
Captain Duncan Molesworth
Founder & Boat Captain
Duncan founded Island Buddy in 2015 as the first branded Jeep tour operator in the USVI, then expanded into boat charters. Based on St. Thomas, he's the operational face of the company — running boats, training captains, and personally responding to guest calls. Featured in The Live Lost's 'Spotlight: Duncan Molesworth — Boat Captain' profile, he's known for building itineraries around the guest's day, not the boat's schedule.
Island Buddy Boat Captains
USCG-Licensed Fleet Captains
The four-boat fleet runs with USCG-licensed captains across Phoenix, Calico Jack, Flying Tiger, and Anne Bonny. Every captain is trained on the same standardized USVI/BVI itinerary map — Trunk Bay, Waterlemon, Christmas Cove, Pizza Pi, Lime Out, Jost Van Dyke, Norman Island, The Baths — and can adjust in real time to sea conditions.
Island Buddy Jeep Guides
Certified Bronco Tour Guides
The Jeep side — the OG business — is run by a small crew of long-tenured St. Thomas locals guiding fully-loaded 2022 Broncos. They know every overlook, every dirt-road cut-through, every empty beach, and every historical stop on both St. Thomas and St. John.
Trip Pricing at a Glance
| Trip | From |
|---|---|
| Phoenix · Half-Day Charter (30' Mainship) | From $765 (fuel incl.) |
| Calico Jack · Full-Day (32' Regulator) | From $900 + fuel |
| Flying Tiger · Full-Day (37' Axopar) | From $1,445 + fuel |
| Anne Bonny · Full-Day (38' Statement) | From $1,400 + fuel |
| BVI Full-Day (any private boat) | Custom quote + fuel + customs |
| Reef Surfari 'Do It All' Shared Trip | $99 adult / $69 child |
| St. Thomas Private Bronco Tour | From $650 |
| Surf & Turf Combo (Jeep + Boat) | From $1,450 |
Related USVI Land & Sea Adventures
What You Need to Know
- Founded 2015 by Captain Duncan Molesworth — the first branded Jeep tour operator in the U.S. Virgin Islands.
- Four-boat fleet: Phoenix (30' Mainship, 6 pax, fuel included), Calico Jack (32' Regulator, 10 pax), Flying Tiger (37' Axopar, 11 pax), Anne Bonny (38' Statement, 12 pax).
- Every boat is BVI-approved for full-day British Virgin Islands crossings.
- Jeep side runs on fully-loaded 2022 Ford Broncos — private custom charters with a guide.
- Signature Surf & Turf combo pairs a private Jeep tour with a boat charter in the same day.
- Reef Surfari 'Do It All' is Island Buddy's shared per-person offering — snorkel + Pizza Pi + open bar + sunset for $99/adult, $69/child.
- Boat pickups available on both St. Thomas and St. John — direct booking at 305-239-7084.
What's Included
- USCG-licensed captain (boat) or certified guide (Jeep)
- Snorkel gear on all boat charters
- Fuel included on Phoenix half-day charters
- Cooler with ice and bottled water
- Custom itinerary planning (private trips)
- Bluetooth sound system
Pro Tips from the Locals
💡Phoenix (fuel included) is the cheapest way to book a private boat in the USVI — great for couples and groups of 4–6.
💡For BVI day trips, Anne Bonny (38' Statement) or Flying Tiger (37' Axopar) handle the crossing best.
💡Surf & Turf is limited-availability — call ahead if you want it on a specific date.
💡St. Thomas Bronco tours are entirely private — the itinerary is yours to build.
💡Cruise-ship guests: call directly if your time in port doesn't match the standard trip windows — Island Buddy often accommodates custom schedules.
💡Bring passports for every guest on any BVI charter.
Frequently Asked Questions
Island Buddy FAQ
How much do Island Buddy trips cost?
Island Buddy trips listed on QuestVI range from $200 to $1,100, depending on the trip. See the table above for each trip's price and whether it is per person or per charter.
Where do Island Buddy trips depart from?
Island Buddy trips depart from Cruz Bay Ferry Dock, St. John; St. Thomas; St. John.
Does Island Buddy go to the BVI, and what passport or customs is needed?
Yes — 2 Island Buddy trips go to the British Virgin Islands.
What's included on Island Buddy trips?
Commonly included: Bottled Water; Cooler with Ice & Drinks; Fuel; Private Guide/Driver; Snorkel Gear; 2 batteries. Check each trip page for its full list.
How does booking Island Buddy through QuestVI work?
You book on Island Buddy'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.
Explore More in St. Thomas
Jeep Tours
Bronco tours on St. Thomas and St. John.
Private Charters
All private boat charters in the USVI.
BVI Trips
Full-day BVI trips aboard Anne Bonny and Flying Tiger.
Shared Excursions
Per-person trips including Reef Surfari 'Do It All'.
Lime Out & Pizza Pi
Signature USVI food stops built into every trip.
Ready to Go?
Book your island buddy experience — we'll help plan the perfect day.