Awesome sailboat rentals in the Caribbean.

Sailing Reviews in Caribbean

1. lb

   lauren

   Lagoon 38 Catamaran trip in St Martin with skipper, departure from Orient bay

   We had a wonderful day on this boat! The captain was great, took us to the best spots for snorkeling and lunch, and we loved leaving from Orient Bay so we didn’t have to sail as long in the rougher waters. Spectacular day all around and highly recommend

2. TL

   Tyler

   Private Luxury Bali 4.0 Catamaran with 3 Cabin from Old San Juan

   Amazing experience! Was the perfect addition to a bachelorette itinerary. Boat was clean, Manuel and Rene were so attentive and friendly. Cant recommend enough!

3. SK

   Sandy

   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!

4. FS

   Felicia

   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!

5. 

   Valerie

   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!

6. JS

   Jess

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

   Jumbo does a great job touring San Juan harbor and the areas just outside of the port. He was great with our kids, teaching them the basics of how to sail his boat. We recommend this as a great way to have fun cruising the areas around old San Juan!