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Top St John Sailing Trips

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St John Tours

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St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast - Westin
Likely to Sell Out
Likely to Sell Out
4.9 (203)

St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast - Westin

This one of a kind excursion to Jost Van Dyke allows passengers to spend the most time on the island out of all other group...

8 hours • Free Cancellation
4.9 (203)
from
$199
St. John Days End Sunset Sail with Open Bar from the Westin
4.9 (311)

St. John Days End Sunset Sail with Open Bar from the Westin

As the sun sets our sails rise, and the champagne flows. Experience a Caribbean sunset and celebrate one of nature’s wonders of color under full...

1 hour 30 minutes • Free Cancellation
4.9 (311)
from
$89
Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin St. John
4.9 (346)

Full-Day Lime Out Snorkel Taco Lunch & Open Bar - Westin St. John

Join us for a day of sailing and snorkeling aboard one of our luxury catamarans and enjoy a sun-filled day topped off with lunch at...

6 hours 30 minutes • Free Cancellation
4.9 (346)
from
$149
St. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar - Westin
4.9 (172)

St. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar - Westin

Join us aboard one of our luxury catamarans, as we set sail for the best snorkeling destinations surrounding St. John. Start the day with a...

5 hours • Free Cancellation
4.9 (172)
from
$129
Private Day Charter Classic Sailboat
5.0 (70)

Private Day Charter Classic Sailboat

To maximize your day and our destination options in the National Park, we offer flexible timing allowing for an easy transfer away from the busy...

4 to 5 hours • Hotel pickup offered • Free Cancellation
5.0 (70)
from
$1,395
All Inclusive St. John Boating Adventure
5.0 (79)

All Inclusive St. John Boating Adventure

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful...

5 hours • Hotel pickup offered • Free Cancellation
5.0 (79)
from
$314
Group Sunset Sail St. John
5.0 (32)

Group Sunset Sail St. John

We are a family owned small business; we have a love for true sailing and authentic relationships here in the islands. Looking for more time...

2 hours 30 minutes • Free Cancellation
5.0 (32)
from
$215
SPECIAL - (Up to 4 Passengers) All Inclusive Day Sail
5.0 (3)

SPECIAL - (Up to 4 Passengers) All Inclusive Day Sail

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful...

5 hours
5.0 (3)
from
$1,347
Learn to Sail - Sailing Lessons All Inclusive
5.0 (4)

Learn to Sail - Sailing Lessons All Inclusive

With 20 years of experience sailing here in the US Virgin Islands we have found that our guests value the smaller venue for purists sailing....

5 hours
5.0 (4)
from
$1,395
SPECIAL - All Inclusive Day Sail
5.0 (1)

SPECIAL - All Inclusive Day Sail

We offer an all inclusive day sailing the calm protected waters of the US Virgin Island's National Park. Our small party sails guarantee a peaceful...

5 hours
5.0 (1)
from
$1,550
Turtles Guaranteed! Fuel Price Included. Smooth, Comfortable Ride
5.0 (1)

Turtles Guaranteed! Fuel Price Included. Smooth, Comfortable Ride

We would love to host you all and show you a wonderful day on the water! This itinerary is set to maximize witnessing the beauty...

5 hours • Free Cancellation
5.0 (1)
from
$1,300

Frequently Asked Questions

These answers are based on answers previously given to Cool Destinations customers' questions.

Recent tour reviews
Super nice cruise
New York City
St. John Days End Sunset Sail with Open Bar from the Westin
kimdaveu, Sep 2026
Super nice cruise
Capt & crew were fantastic - super friendly and service oriented. The perfect convenience leaving directly from the Westin's dock. The catamaran was very nice.
Read more
A beautiful sunset and sail
New York City
St. John Days End Sunset Sail with Open Bar from the Westin
B6253GCcheryld, Sep 2026
A beautiful sunset and sail
We had a beautiful sunset sale. The crew was very informative. We enjoyed talking to Ciara and Matt about our adventures on the island. The drinks were very good. I would highly recommend a painkiller whether you want a virgin painkiller or one with booze in it. Overall, it was a really good experience and I would definitely do it again when we come to visit St. John.
Read more
Perfect Day
New York City
St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast – Westin
Barbara_N, Sep 2026
Perfect Day
Great overall experience! Snorkeling, drinks, boat and crew. Loved the sailing. And best snorkeling ever.
Read more
Don’t hesitate to book!
New York City
Group Sunset Sail St. John
Kulmac, Aug 2026
Don’t hesitate to book!
An amazing boat ride with Captain Mike celebrating our 20th wedding anniversary. Great drinks, snacks, and beautiful views throughout. Captain Mike is so informative and fun / just the vibe we were looking for!
Read more
Fun day from start to...
New York City
St. John Jost Van Dyke & Soggy Dollar Snorkel Sail with Breakfast – Westin
Bernadette_B, Aug 2026
Fun day from start to...
Fun day from start to finish. The boat was beautiful and the crew was amazing! Food and drinks were great and plentiful. Snorkel equipment and towels provided. The crew was able to beach the boat so we didn’t even have to get soggy dollars! Would highly recommend
Read more
The captain was extremely...
New York City
St. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar – Westin
Lindsay_R, Aug 2026
The captain was extremely...
The captain was extremely friendly and professional. He was diligent in explaining rules/precautions and made sure everyone was being safe. The staff was friendly, courteous and attentive.
Read more
Great way to spend the day
New York City
Full-Day Lime Out Snorkel Taco Lunch & Open Bar – Westin St. John
Bitsie_H, Aug 2026
Great way to spend the day
Such fun! Snorkeling, slides off boat, great music, fun crew, and Lime Out stop to top off the day. We had a blast!!
Read more
Top notch experience! The...
New York City
Full-Day Lime Out Snorkel Taco Lunch & Open Bar – Westin St. John
Misty_M, Aug 2026
Top notch experience! The...
Top notch experience! The crew was awesome! Time to snorkel and plenty of time for Lime Out. If you’re thinking of doing it just do it! Favorite experience so far!
Read more
Miles Family Sailed with Love..
New York City
St. John PiZZA Pi Snorkel Sail with Beach Stop, Lunch & Open Bar – Westin
Joyia_M, Jul 2026
Miles Family Sailed with Love..
Get Ready to Take Flight on this Wonderful Sail into the Sun for some Fun.. The Pizza and Sides were Captainliousss with a touch of Staffperfect.. The Only Pain, were the PainKillers that Stayed Chilled and Kept Coming. Get Ready too be Thirsty for more and kids friendly, just sit back and let them enjoy Sea of Love🩷
Read more
Sailing adventure
New York City
Private Day Charter Classic Sailboat
Seaside37668293184, Feb 2026
Sailing adventure
Mike was a great captain and host! Mike involved family members with sailing of the boat and was an excellent teacher. We enjoyed sailing with no motor to experience the natural beauty of St John
Read more
Day sail, all inclusive
New York City
SPECIAL – All Inclusive Day Sail
Odyssey62526663900, Jan 2026
Day sail, all inclusive
We had a FANTASTIC sail & snorkel on Morningstar. Captain Mike owns the boat & business and does an excellent job of accommodating guests. He makes you feel welcome and comfortable on his boat. He gauges the kind of ride and experience his guests want and tries to tailor the experience for them. We wanted an aggressive, fast sailing experience. We got it and loved it! Had we wanted a leisurely, smooth sail, I'm confident Captain Mike would have accommodated our wishes. My wife and I would highly recommend Morningstar Sailing and Captain Mike to anyone. We would definitely do it again. We also like the fact that Morningstar has Power Charters. That would make more distant snorkels more feasible and we may do that on our next trip. And if we sail next year, we'd definitely like to do it on Morningstar!
Read more
Powered Charter - Great Way to visit St John!
New York City
All Inclusive St. John Boating Adventure
racheltQ4783KK, Dec 2025
Powered Charter - Great Way to visit St John!
Had an excellent day with Bo on a powered charter. The boat was a comfortable way to get around - my teens especially enjoyed lounging in bean bag chairs in the front of the boat in the sun. Great way to see St John and get to great snorkel spots. Lunch at Lovango Beach Resort was delicious and offered great options for everyone in our group. The boat charter was definitely the highlight of our trip and we would recommend to everyone!
Read more
Amazing way to see St John and the USVI
New York City
Turtles Guaranteed! Fuel Price Included. Smooth, Comfortable Ride
329tysonc, Sep 2025
Amazing way to see St John and the USVI
We spent the day on the Mojo Duex power catamaran with Captain Mike and it was amazing. Not only did we hit 3 great spots for snorkeling but also got a tour of many beautiful spots within the USVI. Captain Mike was extremely accommodating and very knowledgeable about each area we went to. He had the boat stocked with lots of snacks and drinks. I would highly recommend booking your charter with Morningstar and will book again with them on our next trip to St John. You won't be disappointed!
Read more
Great day on the boat!
New York City
All Inclusive St. John Boating Adventure
Pioneer764111, Aug 2025
Great day on the boat!
My family and I had an unforgettable day with Morningstar Sailing and Power Charters in St. John, US Virgin Islands!From start to finish, Captain Mike made our adventure truly special. His expertise as a boat captain and tour guide shone through, blending seamless navigation with fascinating insights into the island’s history that captivated us all.We loved every moment—snorkeling in crystal-clear waters, boating through stunning bays, and swimming alongside sea turtles, which was a magical highlight for the kids and adults alike. Mike’s warm, engaging style and deep knowledge of the area made each stop feel like a personal discovery. He ensured everyone felt safe, comfortable, and included, tailoring the experience to our family’s interests.Morningstar’s boat was pristine, and the itinerary was perfectly paced, giving us ample time to soak in the beauty of St. John. Mike’s passion for the island and his knack for storytelling brought the experience to life.We can’t recommend Morningstar and Captain Mike highly enough—book this charter for a day of adventure, relaxation, and memories that will last a lifetime!
Read more
Come sail away
New York City
Private Day Charter Classic Sailboat
Diane_I, Jun 2025
Come sail away
Captain Mike is the best, thoughtful and attentive to ensure that we had a great time! He even gave my husband a sailing lesson. It was a highlight of our trip.
Read more
Sunset Tour - Westin St John USVI
New York City
St. John Days End Sunset Sail with Open Bar from the Westin
bobsI6069BO, Sep 2026
Sunset Tour - Westin St John USVI
What a great sail and evening on the water. The crew was friendly and helpful. They mingled with the guests and provided some additional sightseeing tips and information. The scenery and views were great. A definite must do!
Read more
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