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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 Aboard Classic 1969 Sloop in San Juan, Puerto Rico
Sailing in San Juan · 6 guests

Private Sail Aboard 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. BK

    Brian

    Sunset Cruise in San Juan Puerto Rico

    Sailing with Jimbo was the highlight of our trip to San Juan! Can’t say enough about the whole experience. Jimbo gave great historical insights, was an engaging storyteller and most importantly was a great Captain that made the sail both exciting and safe. 10/10 would book again.

  2. Susan

    Susan

    Private San Juan Bay Cruise 37' Sailboat

    Such good people -- beautiful boats and very nice crew! We went snorkeling, swimming and a little light fishing (it wasn't a fishing trip).

  3. RS

    Rabi

    Private San Juan Bay Cruise 37' Sailboat

    John and Nicole as a captain were nicest people. We had great time.

  4. LB

    Leanne

    Private Luxury Sailing Experience out of Old San Juan

    Great day out on the water. The boat was gorgeous and William & David were such wonderful hosts highly recommend!

  5. KP

    Kieta

    Private San Juan Bay Cruise 37' Sailboat

    It was so much fun ! Captain Luis is very informative and made sure we were all safe ! Andrea is absolutely the best !! She made sure we had everything we needed and we took a lot of great photos! Book I promise you will not be disappointed

  6. 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