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All listings in San Juan

Incredible sailboat rentals in San Juan, Puerto Rico.

5.0
(112 Reviews)

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
Superowner
$200hour
Quick Sail a 35' Classic 1969 Sloop in San Juan, Puerto Rico
Sailing in San Juan · 6 guests

Quick Sail a 35' Classic 1969 Sloop in San Juan, Puerto Rico

4.9
Superowner
$99person
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
$725hour
Sunset Cruise in San Juan Puerto Rico
Sailing in San Juan · 6 guests

Sunset Cruise in San Juan Puerto Rico

5.0
Superowner
$353hour

Sailing Reviews in San Juan

  1. CF

    Connie

    Private San Juan Bay Cruise 37' Sailboat

    I had my bachelorette party with 6 women in Capt Luis' boat. I wanted a relaxing sailing experience in San Juan, as well as have the option to jump into the water, if we wanted. This was perfect for us. The water was very calm when we went. Capt Luis was good at listening to what the customer wants, and he adjusted to my preferred timeline, and I really liked that. He was very responsive via text, and email. And I would say, after doing my research and messaging a lot of boat companies, his pricing was the most reasonable and he was also the most responsive. My girls and I had a great time! The only thing I would give others a heads up is that the complimentary tapas and drinks that come with a 3-hour booking, is minimal. So if you and your guests are hungry and thirsty bunch, it is best to bring more of your own tapas/drinks. Regardless, I would still book him again as he was very professional and had great communication skills. It was an easy transaction despite my fickle mind.

  2. JW

    Julie

    Private San Juan Bay Cruise 37' Sailboat

    Captain Luis and First Mate Gabi were great! It was rather windy the day we went, so we appreciated their sailing experience. Luis gave us a great tour of San Juan Harbor with lots of historical facts. Gabi was very helpful, taking care of our every need. Luis contacted us the day before with all of the details which were spot on, and we were able to order additional food and drinks so all we had to do was show up. I would highly recommend Captain Luis.

  3. SM

    Samuel

    Private Luxury Sailing Experience out of Old San Juan

    I booked a trip for 12 people, which was the perfect size. The captain was amazing and took us around different areas of San Juan as well as let us dock so we could all go swimming. If you are in San Juan I highly recommend this!!

  4. Madison

    Madison

    Private Luxury Sailing Experience out of Old San Juan

    10/10 experience!! Rented for myself and 6 bridesmaids for my bachelorette and had the best time ever! Service was exceptional and booking process was so easy. This is the boat to book while you’re in Puerto Rico!

  5. Michael

    Michael

    Private San Juan Bay Cruise 37' Sailboat

    Highly recommend this world-class experience. Captain is quite knowledgeable in the history of the Island. The homemade food — and sangria — is delicious. Will book again.

  6. BC

    Brianna

    Quick Sail a 35' Classic 1969 Sloop in San Juan, Puerto Rico

    Our group was raving about this experience for so long after left! What an amazing time and Jimbo made the experience what it was! Educational, fun, relaxing, and exciting all in this 3 hour trip. Couldn’t have been better