St. John, US Virgin Islands · 2026 Season
Bad Kitty & Calypso Charters
Five-boat power and sail catamaran fleet running Best of the BVI, Jost Van Dyke sails, Lime Out trips, and private charters from St. John and St. Thomas.
Vetted local captains · Secure operator booking
Compare every Calypso Charters trip
4.7 on Google, 103 reviews
| Trip | Duration | Max guests | From | Departs |
|---|---|---|---|---|
| Jost Van Dyke All-Inclusive 18+ Party Boat to BVI | 7 Hours | 49 | $200 per adult | Cruz Bay National Park Dock, St. John |
| Bad Kitty BVI Catamaran Trip: The Baths & Jost Van Dyke | 8 Hours | 49 | $225 per person | Cruz Bay National Park Dock, St. John |
| USVI Private Power Catamaran Charters: Half or Full Day | 3-7 Hours | 6 | $600 per charter | Cruz Bay National Park Dock, St. John |
| Private Power Catamaran Charter: USVI & BVI Day Trips | 3-8 Hours | 12 | $700 per charter | Cruz Bay National Park Dock, St. John |
Choose your day on the water
Bad Kitty & Calypso Charters – All Tours & Trips
4 charters available
Private Power Catamaran Charter: USVI & BVI Day Trips
Calypso Charters
Let our experienced Captain take your group for the perfect day on the water aboard CAT 5, a 36' power catamaran. This spacious and comfortable boat has room for 30 but for the enj
- Boat
- Private Charters
- Duration
- 3-8 Hours
- Up to
- 12 guests
- Stops
- Custom itinerary
USVI Private Power Catamaran Charters: Half or Full Day
Calypso Charters
Charter the USVI aboard a 26' power catamaran! Full-Day Snorkel Trip (7 hours, $900), Half-Day Snorkel Trip (3 hours, $600), or Sunset Cruise (1.5 hours, $375). All prices plus fue
- Boat
- Private Charters
- Duration
- 3-7 Hours
- Up to
- 6 guests
- Stops
- Custom itinerary
Jost Van Dyke All-Inclusive 18+ Party Boat to BVI
Calypso Charters
Put on your party hats! Friday FUNday is an 18+ boat trip to Jost Van Dyke, Sandy Spit, and Willy T. We stop in Great Harbor first to clear customs, then beat the rush to White Bay
- Boat
- BVI Trips
- Duration
- 7 Hours
- Up to
- 49 guests
- Stops
- Custom itinerary
Bad Kitty BVI Catamaran Trip: The Baths & Jost Van Dyke
Calypso Charters
Our first stop is Spanish Town, Virgin Gorda BVI, where we clear customs (all guests MUST have valid passports to enter the BVI). The next stop is The Baths, a unique geological fo
- Boat
- BVI Trips
- Duration
- 8 Hours
- Up to
- 49 guests
- Stops
- Custom itinerary
Swipe to explore →
Bad Kitty & Calypso Charters operates one of the largest and most versatile fleets in the Virgin Islands — five vessels covering everything from a 26-foot private power cat for 6 to a 40-foot sailing catamaran that seats 32 guests. That range lets them handle everything from an intimate half-day sail to a full corporate group trip to the BVI.
Signature trips include Best of the BVI on the Bad Kitty power cats, the weekly Friday BVI FUNday, Lime Out drop-offs, Jost Van Dyke sails on Calypso, sunset cruises, and fully private charters on any of the five boats.
What Makes St. John Bad Kitty & Calypso Charters Special?
5-Boat Fleet
Bad Kitty 1 & 2, Calypso (40' sail), Tropicat (26' power cat), and CAT 5 (36' power cat).
Best of the BVI
Flagship BVI day trips hitting Norman Island, Jost Van Dyke, The Baths, and Willy T.
Lime Out Runs
Direct trips to the Lime Out floating taco bar in Coral Bay, St. John.
Group + Private
Public/shared group departures alongside fully private charters on any vessel in the fleet.
Meet the Captains
Bad Kitty & Calypso Captains
USCG-Licensed Captains + Mates
The Calypso group runs one of the deepest captain benches in the USVI — every boat in the fleet operates with a USCG-licensed captain plus a mate (or full crew on the larger Bad Kitty and Calypso runs). Bad Kitty and CAT 5 captains specialise in fast BVI runs and Willy T / Soggy Dollar stops; the Calypso sail captains focus on Jost Van Dyke and sunset sails.
Trip Pricing at a Glance
| Trip | From |
|---|---|
| Bad Kitty – Best of the BVI (per person) | From $215/person |
| Bad Kitty – Friday BVI FUNday | From $195/person |
| Bad Kitty – Trip to Lime Out | From $150/person |
| Calypso (40' sail) – Jost Van Dyke Sail | From $210/person |
| Calypso – Full or Half Day Sail | From $135/person |
| Calypso – Sunset Sail | From $75/person |
| Tropicat (26' power cat) – Private Half/Full Day | From $1,200 |
| CAT 5 (36' power cat) – Private US or BVI Full Day | From $2,800 |
| Bad Kitty – Private Charter | From $6,500 |
Related BVI & Fleet Trips
What You Need to Know
- Home port: St. John, with pickups also available from St. Thomas depending on the vessel.
- Fleet: Bad Kitty 1 & 2 (identical fast power cats for group BVI trips), Calypso (40' sail catamaran, up to 32 guests), Tropicat (26' power cat, private for 6), and CAT 5 (36' power cat with sundeck and bean bags).
- Shared per-person trips: Best of the BVI, Friday BVI FUNday, Trip to Lime Out, Jost Van Dyke Sail, and Sunset Sail.
- Private charters available on any of the five boats — Tropicat and CAT 5 lean private-only.
- BVI itineraries commonly include The Baths, Norman Island, Willy T, Soggy Dollar Bar, Cane Garden Bay, and Sandy Cay.
- USVI destinations covered include Christmas Cove/Pizza Pi, Water Island, Lovango Cay, and Lime Out.
Pro Tips from the Locals
💡Bad Kitty runs are fast — ideal if you want to hit the most BVI stops in one day.
💡Choose Calypso (the 40' sailing cat) if you'd rather sail than power through the day.
💡Book Tropicat when you have exactly 6 people and want your own private boat.
💡CAT 5's sundeck and bean bags make it the most comfortable private option for lounging groups.
💡Bring passports for any BVI trip — customs fees apply on top of the trip price.
💡Sunset Sail on Calypso is one of the best-value per-person options in the fleet.
Frequently Asked Questions
Calypso Charters FAQ
How much do Calypso Charters trips cost?
Calypso Charters trips listed on QuestVI range from $200 to $700, depending on the trip. See the table above for each trip's price and whether it is per person or per charter.
Where do Calypso Charters trips depart from?
Calypso Charters trips depart from Cruz Bay National Park Dock, St. John.
Does Calypso Charters go to the BVI, and what passport or customs is needed?
Yes — 3 Calypso Charters trips go to the British Virgin Islands. The operator asks guests to bring: Valid passport (BVI charters only). $85 cash per person for BVI Customs.
What's included on Calypso Charters trips?
Commonly included: Ice; Snorkel gear; Water; Beanbag chairs; Continental breakfast; Continental breakfast (breads, fresh fruit, juice, water, soda). Check each trip page for its full list.
How does booking Calypso Charters through QuestVI work?
You book on Calypso 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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