The Best Sailboat Rentals in Puerto Rico

Private Luxury Sailing Experience out of Old San Juan

The boat is exactly as pictured and is very clean. Captain Willie and crewmate David were great. They ensured we had a great time. I would definitely charter this boat again. If you’re thinking about it, just do it!

Janise Sailing Afternoon Charter - Fajardo, Puerto Rico 🇵🇷

You don’t need to think twice, just simply book. We throughly enjoyed our experience from start to finish. I will definitely be returning. Thank you for having us !

Luxury Sailing Catamaran Charter in Fajardo, Puerto Rico

Amazing day, crew was great, food was spectacular, they kept the drinks flowing, could not ask for a better experience!

Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico

If you are looking for an authentic sailing experience in Puerto Rico, look no further. This is for you! We came in with sailing experience but not in the ocean and not on as large of a boat. He let us sail the entire time and taught us along the way. Jimbo is a very experienced sailor and is looking to give you the sailing experience you are looking for. If I could have given him more than 5 stars I would have!

Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico

This experience was amazing! This was the first time my family experienced a sunset ride on a sailboat and Jimbo made sure the experience was one we'd always remember. Jimbo ensured we were in the know on all safety protocols and during the sail, enlightened us with facts and history about Puerto Rico. Jimbo was personable and accommodating from the beginning to end of our excursion. This was our first, but not our last trip with Jimbo!

Private Sail Aboard Classic 1969 Sloop in San Juan, Puerto Rico

Time out on Jimbo’s sailboat has something for everyone. Whether you want to party, learn to sail or learn about San Juan and its history. We had a great time sailing with Jimbo and learned so much. We’ll definite book again next time we’re in Puerto Rico!