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All listings in St. John

Incredible sailboat rentals in St. John, U.S. Virgin Islands.

Page 1 of 15 listings

Luxury Sailing Catamaran for up to 12
Sailing in Cruz Bay · 12 guests

Luxury Sailing Catamaran for up to 12

5.0
$350/hour
Instant Book
Sailing Cruise Saint John
Sailing in Cruz Bay · 6 guests

Sailing Cruise Saint John

5.0
$197/hour
Step into a world of refined elegance aboard Fountaine Pajot Alegria 67
Sailing in West End, Tortola · 8 guests

Step into a world of refined elegance aboard Fountaine Pajot Alegria 67

New
$10,000/night
Cruise on one of the most exciting crewed sailing yachts below 70 feet in BVI
Sailing in Freshwater Pond · 6 guests

Cruise on one of the most exciting crewed sailing yachts below 70 feet in BVI

New
$3,666/night
Luxury Sailing Experience  – The Ultimate Caribbean Adventure
Sailing in Cruz Bay · 6 guests

Luxury Sailing Experience – The Ultimate Caribbean Adventure

New
$250/hour

Top Destinations Nearby

Sailing Reviews in St. John

  1. SS

    Simon

    Luxury Sailing Catamaran for up to 12

    Unforgettable Post-Wedding Sail!! We spent a half-day with Aaron on the Catamaran Quest right after our wedding in St. Thomas, and it was easily one of the highlights of our entire trip. From the moment we stepped on board, Aaron made us feel incredibly special. He was super attentive and helpful, ensuring we had everything we needed to just relax and soak in the "just married" bliss. The food and drinks he served were fantastic—well-prepared and exactly what we needed for a day on the water. The boat itself is awesome and very well-equipped with everything you’d want for a comfortable excursion. We did encounter some minor technical issues with the engines during our trip, but Aaron handled it with total professionalism and didn't let it dampen the experience at all. If you are looking for a captain who truly cares about his guests' experience, book with Aaron. Thank you for making our celebration so memorable! PS: Aaron’s mango salsa is to die for - awesome stuff!!

  2. ek

    elizabeth

    Luxury Sailing Catamaran for up to 12

    Our family of 5 had an amazing day with Aaron! He had great communication leading up to our day. Everything about the day was great! He made us feel very at home on his beautiful boat and our day was so much fun! He was a great host!

  3. RB

    Rose

    Sailing Cruise Saint John

    Book now! This was such a memorable experience! From the line of communication, to Shana amazing Mediterranean platter to captain in training Jaya keeping my son company, it was amazing! From pick up to drop off such a wonderful experience. We cannot wait to see them again this time hopefully in Maine!

  4. BR

    Bianca

    Sailing Cruise Saint John

    Our family of four spent the entire day sailing, snorkeling, searching for treasures, and swimming at some of most beautiful beaches in the Virgin Islands. Our sons had a blast. The hospitality was top notch and we plan to return!

  5. KF

    Kroll

    Sailing Cruise Saint John

    We had an incredible day of sailing with Shana and her crew! We enjoyed snorkeling in secluded waters, delicious food and drinks, followed by a beautiful sunset sail back to St.John. Thank you for an unforgettable adventure!

  6. BJ

    Beautiful

    Sailing Cruise Saint John

    Booked with them 3 years ago and still can’t stop thinking of them. I’ve been looking high and low to post my review. Had an amazing time, food was delicious. All above 10/10