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All listings in San Juan

Great sailboat rentals near San Juan, San Juan.

Page 1 of 14 listings

Private San Juan Bay Cruise 37' Sailboat
Sailing in San Juan · 6 guests

Private San Juan Bay Cruise 37' Sailboat

5.0
$195/hour
Private Luxury Sailing Experience out of Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Sailing Experience out of Old San Juan

5.0
$725/hour
Private Sail Classic 1969 Sloop in San Juan, Puerto Rico
Sailing in San Juan · 6 guests

Private Sail Classic 1969 Sloop in San Juan, Puerto Rico

4.9
Superowner
$198/hour
Instant Book
Sunset Cruise in San Juan Puerto Rico
Sailing in San Juan · 6 guests

Sunset Cruise in San Juan Puerto Rico

5.0
Superowner
$353/hour

Sailing Reviews in San Juan

  1. CB

    Claudia

    Private Luxury Sailing Experience out of Old San Juan

    Absolutely beautiful 40-feet sailboat, pristine and immaculate. We were a group of 10 and had a great sunset sail to Old San Juan. Captain William and Manu were superb and made it a memorable experience. Thank you one again! We will repeat.

  2. SA

    Samuel

    Private San Juan Bay Cruise 37' Sailboat

    Captain Luis and Andrea are the real deal! We spent so much time figuring out the best sailing experience and we couldn’t have been more lucky to have found the of them and this sailing experience from San Juan bay watching the sunset and seeing the beauty of the fort and gorgeous old San Juan!!! They are so seasoned and know the waters so well that our ride was just a peaceful incredible magical ride and was the highlight of our trip!!! Trust me, stop looking and hurry and book. They are worth it and the experience will be for a lifetime!!! Thank you again guys for the beautiful evening for my fiance and I

  3. SD

    Sarah

    Private San Juan Bay Cruise 37' Sailboat

    My husband, 2 small kids, and I went on a morning 4 hour sail with Luis and Andrea. Luis and Andrea were kind and always looking out for us enjoying our experience. Our kids had lots of fun and my husband and I were able to relax and enjoy the scenery. I 100% recommend booking a cruise with Captain Luis!

  4. Celena

    Celena

    Private San Juan Bay Cruise 37' Sailboat

    Captain Luis and Andrea provided a beautiful sail by Old San Juan. They anchored for us and my husband and I were also able to jump in and swim. We had a great day on the water. Highly recommend.

  5. JM

    Jason

    Private San Juan Bay Cruise 37' Sailboat

    Captain Luis was awesome. He made our trip one to remember. Highly recommend and will return!

  6. KB

    Katherin

    Private San Juan Bay Cruise 37' Sailboat

    Don’t second guess it. Just book it. Luis and Andrea were great! They were helpful before and during the trip. We had gone for a relaxing trip for my cousin’s bachelorette. They offered a charcuterie tray and some Sangria. I would definitely book again, on another trip to PR (: