The Best Sailboat Rentals Near Roosevelt Roads

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 Tours~ Snorkeling at Icacos & Palomino Islands- Grady White 27'

Absolutely the best experience! We are a family of 4 with 15 year old twins and everyone had the most amazing time! My husband is picky about excursions because he typically captains our own boats and he loved it! Jose was so chill and the best captain we could have asked for! If you want a private experience then this is your route!!!

46' Oyster Sailboat in St. Thomas, Virgin Islands

BOOK NOW! this sail was one of the greatest experiences we have had on the water. The boat was beautiful, comfortable, and sailed like a dream. The food was DELICIOUS! The drinks - amazing! The service was unmatched. Shana and Nicholas made sure to make our day we so special. We found some great snorkeling spots, enjoyed a sail around the islands, and a gorgeous sunset. We feel blessed to have been a part of their sail today - we will be back!! Communication 10/10. On time 10/10. Kind and great hosts 10/10!!!

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!