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All listings in San Juan

Incredible sailboat rentals in San Juan, Puerto Rico.

5.0
(152 Reviews)

Page 1 of 15 listings

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

Private San Juan Bay Cruise 37' Sailboat

5.0
Superowner
$195/hour
Private Luxury Catamaran - Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Catamaran - Old San Juan

5.0
$575/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
All Inclusive 40' Catamaran Sailing Experience - Old San Juan
Sailing in San Juan · 6 guests

All Inclusive 40' Catamaran Sailing Experience - Old San Juan

New
$725/hour

Sailing Reviews in San Juan

  1. GS

    Genevieve

    Private San Juan Bay Cruise 37' Sailboat

    I booked with Captain Luis for my sister’s 30th birthday trip, and we all had the best experience! There were 4 of us in San Juan for a long weekend and this was the highlight of our trip. We felt safe, welcome, and taken care of the whole ride - the captain brought refreshments including Sangria that his wife had made which we all loved. He sailed us around and anchored at a beautiful spot to jump in and swim which was so fun. I highly recommend!

  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. 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 (:

  5. AG

    Ashley

    Private Luxury Catamaran - Old San Juan

    The boat was immaculate and in pristine condition. The captain and crew were so professional and made our trip extra special. The boat was fully stocked with everything we needed. It was the perfect size for our group of 8 adults and was the highlight of our trip!

  6. LM

    Lauren

    Private Luxury Catamaran - Old San Juan

    This was a total highlight of our trip!!! The communication leading up to the charter was awesome and very prompt- all of my questions were answered. The captain (Krista!!) and crew were just amazing- truly had the most wonderful day. The boat is so comfortable, well stocked, and beautiful! They were super chill and worked with us on what we wanted to do and see. 10/10 would recommend and we will be back next time we come to PR!!!