The Best Sailboat Rentals in San Juan

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.

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

Private Sail Classic 1969 Sloop in San Juan, Puerto Rico

This is the best sailing charter ever! The day was made for sailing, and we enjoyed every minute of it. This is exactly what we wanted. Thank you!!

Private Luxury Sailing Experience out of 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!

Private San Juan Bay Cruise 37' Sailboat

I had a wonderful experience with Captain Luis. Me and my five friends would absolutely do it again!

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.