Puerto Rico

Awesome sailboat rentals in Puerto Rico.

Average of 44 reviews in this area.
18 listings

Set sail and experience Puerto Rico from the deck of a sailboat rental.

Puerto Rico is the best place to rent a sailboat. Book a sailboat with a captain if you've never sailed before. Get out on the water and experience the beautiful scenery while enjoying the company of friends and family. From celebrating a special occasion to family vacations, Puerto Rico is the perfect sailboat rental destination.

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GetMyBoat customer reviews for Sailing in Puerto Rico.

  1. AN
    Andrew
    Quick Sail a Classic 1969 Sloop in San Juan, Puerto Rico

    This was a perfect last minute booking. Took the sunset sailboat cruise and couldn’t be happier. Jimbo is extremely humorous and knowledgeable about sailing and Old San Juan history which made the cruise even more enjoyable. We will definitely book another cruise with Jimbo. Highly recommended!

  2. FP
    Felecia
    ❤️ Exclusive Sailing Trips w Spacious Catamaran in Paradisical Puerto Rico ❤️

    This was exactly what we needed! This was our Anniversary trip with our son and daughter n law and their first time to PR. We all had a blast on the Makai and Mik was awesome. Sophie and the co captain were a complete delight! Will definitely use them again!!

  3. SC
    Samuel
    Janise Sailing & Snorkeling Day Charter - Fajardo, Puerto Rico

    We thoroughly enjoyed our private sailing charter trip with Captain Ivan yesterday. Captain Ivan delivers a refined, luxurious and laid-back sailing experience. When we got to the port early, he suggested that we enjoy some drinks at the marina bar, which set the mood with an immersive cultural experience while we waited for the boat. We were greeted by a very friendly, enthusiastic, and laid-back captain, who led us to his beautiful sailing catamaran. It is evident that Captain Ivan takes great pride and cares deeply for his vessel, which features chrome and teak finishes and well-equipped outdoor and indoor seating areas. Almost as soon as we sat down, we were provided with a beautifully presented appetizer plate of cheese and fresh fruit. Though we had the option to play our own music through the boat’s Bluetooth sound system, we were content with the phenomenal island playlist the captain already had going. After thoughtfully asking us about our hopes for our sailing adventure, Captain Ivan skillfully navigated some stormy skies to Piñeros island, making our wish for a white sand beach a reality. Once we arrived, we spent some time lounging on the trampoline net at the front of the boat, where we were brought a second course of appetizers (a charcuterie board). We then enjoyed some snorkeling in the reef near the shore and spent time getting photos on the beautiful beach. First mate Condido made the day a delight and brought the characteristic Puerto Rican hospitality to the entire trip, providing fantastic service of both food and drinks. When we got back from the beach, we found a mixed green salad with Condido’s homemade raspberry vinaigrette waiting for us, while he grilled he amusingly called “chicken of the sea.” As Michelin star-loving foodies, we cannot emphasize enough how incredible this authentically Puerto Rican meal was. It was artfully presented and featured the tastiest grilled chicken we have ever had. We were also impressed at how thoughtfully they accommodated our food allergies. On the return voyage we got an incredible view of the sunset over Fajardo Bay. Though they do offer lovely refreshments and a fun-filled experience, this is not a party boat. If you are looking for a classy, thoughtfully curated, 5-star experience on the beautiful Puerto Rican waters—this is it—and at an incredible value.

  4. LP
    Latisha
    Charter Captain Services

    Jimbo was absolutely wonderful. He educated us on the history of Puerto Rico. He was laid back and friendly. He provided us refreshments and music. The time given allowed us to relax and take on the scenery. I would definitely recommend his services.

  5. MD
    Milana
    Charter 52' Cruising Monohull in Fajardo, Puerto Rico

    We had a great time with Domingo! He was a great host! He was very kind, fun and a fantastic cook! We had a wonderful day! He took us to beautiful places to swim and snorkel. Boat is large and clean. Sailing was very fun. Highly recommend!

  6. JA
    Julio
    Deluxe Adventure Day Sail - Private Sail Charter in Fajardo, Puerto Rico

    Angela was wonderful from the very beginning. Excellent communication about the upcoming trip. She worked with us to make sure my husband and I had the food we wanted and she also made sure our eight year old son had what he likes for his meal. The boat is beautiful and Gio taught us so much, making our trip even more fun and interesting. We have been on other tours and excursions before but this one was the best. We highly recommend it.