The Best Sailboat Rentals in San Juan

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 (:

Private San Juan Bay Cruise 37' Sailboat

This was the highlight of our trip to Puerto Rico. Captain Luis was so communicative and friendly from booking to the end of the trip. I booked this experience for a friends bachelorette and it was her favorite part. He provided sangria and a small charcuterie board which was delicious. We asked to swim and he anchored for about an hour for us to enjoy the beautiful waters. Safety was a priority which we appreciated. He and his first mate Andrea were amazing. Andrea is incredible. Captain Luis even danced salsa for us hahaha.

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.

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.

Private San Juan Bay Cruise 37' Sailboat

One of the biggest highlights of our trip and we came here to get married! Captain Luis was an exceptional host and so accommodating. Shortly after starting our voyage it felt like we were just out on the water enjoying a beautiful day with an old friend. This is a must-do experience especially for such a reasonable price. Highly, highly recommended!

Private San Juan Bay Cruise 37' Sailboat

This was, without a doubt, the best part of our 3.5 day trip to San Juan. We knew we wanted to spend one evening doing a boat our around the island, and bonus points if it provided alcohol or allowed us to bring our own. I originally found a similar tour on Viator, but the date was blacked out due to family vacation. I looked through other Viator options and could not find anything that I felt good about--for example, one agency said you can only text, they would not answer any calls for any reason. I searched and searched and finally found GetMyBoat and Captain Luis, and it was everything we asked for and more! First pro: communication! From the beginning, Luis was quick to respond to any and all questions. He communicated the day before the trip, and provided clear instructions (including pictures) on how to find him. Second pro: Experience-- Luis and Gaby treated us like old friends and made sure we were able to what we wanted with our time. (They even sailed a little longer for us) Luis and Gaby started with a quick safety briefing then quickly let us take over as DJ and offered us sangria (which was delicious) and beer. They allowed our group to hang out at the other end of the boat for about an hour uninterrupted. Captain Luis then began telling us about some of the history of Puerto Rico. We had time to swim off the boat, and they took pictures for us. On the way back, Captain Luis and Gaby visited with us , telling us about their lives, asking questions about ours, and providing recommendations for what to do in OSJ and the surrounding area. Drinks were provided the entire time and his wife made us a beautiful charcuterie board. It wasn't small talk, but truly great conversation and laughs! Third pro: Price This tour was the same as viator options BUT IT WAS PRIVATE to our group---win win! No having to worry about other people getting too close, being too rowdy/loud, or rude. It allowed us to relax even more. I simply cannot say enough positive things about the service and fun Captain Luis and Gaby provided. I am a typical Type A lawyer, who has trouble relaxing/turning everything off, but for the three or so hours I was on the boat, I was just a thirty-something year old able to have fun and enjoy the ocean and surroundings. If we are ever able to return to Old San Juan, this would be my first booking.