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Calypso - Jost Van Dyke Sail
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Calypso - Jost Van Dyke Sail

5.0(5 reviews)
8 hour(s)
English
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Saint John, Virgin Islands of the United States

Discover calm waters and vibrant marine life on a scenic sail

Explore white bay charm with relaxing beachside moments and gentle waves

Experience smooth sailing powered by steady tradewinds and open horizons

Enjoy island stops filled with shopping strolling and laid back culture

Price start from

124.56

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Set out on a rewarding day of sailing as you glide across the clear waters surrounding St John and make your way toward the British Virgin Islands. Your journey begins with fresh baked breads and fruit served on board before you arrive at a peaceful snorkel spot along the untouched north shore. After exploring the underwater scenery, the sails are raised and the steady tradewinds guide you toward Great Harbor on Jost Van Dyke. While the crew completes the arrival process, you can stroll the shoreline shops, enjoy the relaxed island atmosphere, and perhaps visit the well known Foxys gift shop. The adventure then continues to White Bay, a gentle and inviting stretch of sand where you can swim or wade to shore depending on the conditions. Here you will discover the easygoing charm of island life, whether you choose to relax in a hammock, sample a Painkiller, or enjoy lunch from one of the beachside spots.

As the day slows down, settle into a calm and scenic sail back toward the US Virgin Islands. The return trip offers time to unwind and enjoy the open sea with the warm breeze carrying you home. This experience blends sailing, snorkeling, walking, and quiet moments of island discovery, creating an ideal day for travelers seeking beauty, variety, and a relaxed Caribbean rhythm.

Breakfast 

Open bar

Snorkel gear with instruction

Personal expenses

Gratuities

Weather appropriate clothing

Sunglasses & Sunscreen

Towel

Camera

Travelers with Limited mobility impairments
Families with children
Adventure seekers
Nature enthusiasts
Couples
Groups of friends
Physically fit travelers
Photography lovers
Seniors and mature travelers

Valid passports for each person in your party

Children must be accompanied by an adult

Have a camera ready to capture every special moment

Confirmation will be received at time of booking

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Type in your hotel/accommodation to see how far the attraction or departure point is.

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Activity Provider: Calypso Charters

Customer Reviews

5 reviews
5.0
based on 5 reviews
J

James

June 24, 2025
Google

From the start the crew was welcoming and professional. We were underway on time and they had a basic but fresh fruit and breads available for a breakfast snack. The crew had tons of local knowledge and engaging personalities. The water was a bit rough on the 1st leg but the boat is bad ass and made the trip quickly. This is an engaging tour of swimming in and out to sites, hiking and snorkeling. Open bar after snorkeling was great. Overall the trip was enjoyable a good value as well.

S

Sherrie

June 11, 2025
Google

Greg was the best captain on our chartered tour. If you’re ever in ST John it’s worth looking them up for a charter. Funny, informative and helpful. It was a great day.

S

Sallie

June 10, 2025
Google

We done charters with Bad Kitty twice, on two separate trips to St John, and both times we had a wonderful experience! On our most recent trip, we took our family out on a full day to BVIs, and Capt Greg took great care of us. The boat we were on had shade, which was huge since we had three older family members with us. We asked for a leisurely boat day that included Soggy Dollar and snorkeling, and we got just that. We’ll definitely book with them again on our next visit to St John. Big thanks to Greg for a great boat day!

J

Jana

March 09, 2025
Google

*** Private Charter Review *** Bad Kitty offers group tours on a larger catamaran and some other rentals , but we just did a private charter. AND, if you are in a group of like 6 or more, it’s so worth it - you are on your own schedule and un-rushed. We did a full day + an additional hour in the BVI. HIGHLY Recommend the additional hour if you are going to do the Bathes - it’s an hour to get out there! But it was worth it - a really fun hike down and just beautiful water - if you aren’t trying to do too much in the day you could definitely negotiate spending more time exploring here. Captain Greg was great (we were an older group so we probably were a little boring 😂) but he told us about the various locations, made recommendations and found us some secluded snorkeling spots after lunch. It was THE BEST DAY in the Virgin Islands, just island hopping around and being on the open water. Very friendly, very knowledgeable - he had a bunch of dining and bar recommendations too! It’s no frills and the boat isn’t the newest one out there - but it’s a great value!!! I hope it stays that way - it’s a family run business so that probably helps, but most other charters charge you 50+ per guest over 6 and they are already pricier than Bad Kitty. Bad Kitty only charges you after 8. They also don’t charge you more for going out to the Bathes - I did a lot of comparisons and some will up the charge to go that far out and that doesn’t even include gas! So this was really a great deal for a nice boat with plenty of shade, a wet bar for mixing drinks, plenty of snorkeling gear and noodles and some nice upgrades if you want food and drinks, but they also offer ice and a cooler if you bring your own 😁 I can’t say enough good things, it was a really great experience and a great way to see some of the BVI without being herded around in a large group 🐑 🐑 🐑 Some things to consider for private charters: - All charge a customs fee to go to the BVI: I saw some as low as $75 and some as high as $90 pp - I think this has to do something with what BVI charges charters each year to enter their waters, but this is not unusual and many will ask for your passports up front. If you don’t want to bother with that, stay in the USVI for the day - you will still be able to get to some cool spots! - All charters do expect gratuity for the Captain - standard is 20% gratuity (I suppose you don’t have to give that much, but gee… they hang out with you all day, get you to some hard to reach spots and make sure you are back through US customs before they close at 5 so you aren’t stranded! So you better have a good reason not to give 20% 😉) - You are also responsible for the gas - the further out you go, the more expensive this will be. It was $294 for our day out to the Bathes, then to Norman Island for lunch and a few snorkeling spots (but that is going to be based on the volatile price of gas at the moment - SO DO NOT quote me on that). When I talked to the woman who helped me with the booking, she was able to give me estimates based on where we thought we wanted to go - which was helpful for budgeting :) All-in-all - I can’t recommend them enough!! I plan to be back in the USVI again next year and will be looking these guys up again! And thanks again Captain Greg for a truly wonderful, memorable day!!!

M

Miles

January 15, 2025
Google

Bad Kitty & Calypso Charters has been the highlight of every trip we’ve taken, whether it’s a group outing or a private charter. The crew is amazing, and they always make the experience unforgettable. We’ve recommended it to friends, and every time they come back saying it was the best part of their trip! Booking is super easy with all the details/policies on their website, and their customer service is top-notch. It’s so nice to call and speak to a real person instead of dealing with a robot. If you’re looking for an incredible adventure, this is it!

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+1
Day In a City

Explore More Calypso - Jost Van Dyke Sail

Discover the wonders of Saint John, Virgin Islands of the United States with this unforgettable experience. Set out on a rewarding day of sailing as you glide across the clear waters surrounding St John and make your way toward the British Virgin Islands. Your journey begins with fresh baked breads and fruit served on board before you arrive at a peaceful snorkel spot along the...