Puerto Rico

Awesome sailboat rentals in Puerto Rico.

Average of 56 reviews in this area.
1 - 18 of 19 listings
19 results

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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Search for the perfect experience now and book your dream day out on the water.

GetMyBoat customer reviews for Sailing in Puerto Rico.

  1. EC
    Experience a Beach or Sunset @ Bay of San Juan in Style While Building Moments FULL of Caribbean Flare.

    Luis is a great guide - he was so flexible with our itinerary and brought along snacks and drinks for us. He was so friendly and informational - told us about the sites we passed and knew so much about the Puerto Rico history. He also was an expert fisherman and taught us how to fish - our group of 5 adults had a blast.

  2. PL
    ⛵️ Exclusive Wellness Sailing 🙌 🫐🍉🍍🍇🥭🍹

    We had a wonderful time. Mik and her first mate were amazing. They taught us about sailing, the kids got to fish, and we got to enjoy the waves on the net in the front of the catamaran. They also provided us brunch. Overall it was a very relaxing experience that we would highly recommend everyone should enjoy.

  3. JR
    Experience a Beach or Sunset @ Bay of San Juan in Style While Building Moments FULL of Caribbean Flare.

    Greatest experience you can ever have! We had the pleasure of taking this ride with Captain Luis. He felt more like a friend than anything! He made this boat ride phenomenal! He taught and showed us about the Puerto Rican culture, so well and detailed! I would recommend everyone to book this! You will not regret it!!

  4. ns
    ⛵️ Exclusive Wellness Sailing 🙌 🫐🍉🍍🍇🥭🍹

    Mik was wonderful. A couple of us got sea sick, but Mik and the other crew member really took care of us and made sure that we were okay and comfortable. She was really tentative and flexible as well. All the food she provided was just perfect! Thank you Mik, we had a wonderful time.

  5. MC
    Quick Sail a Classic 1969 Sloop in San Juan, Puerto Rico

    Captain Jimbo was a joy! He made the entire process easy, from booking, to finding the dock, to feeling safe on the boat, and more. He’s a character in all the right ways which made our group laugh and feel comfortable the whole way. Besides the good laughs, the ride was amazing. The weather was perfect for sailing (this was our first time) & it was a great experience seeing the sails go up and the boat just effortlessly glide. Jimbo showed us a few of the historical landmarks of San Juan and gave us a brief history lesson on them all, which was greatly appreciated. Hands down my favorite part of our trip. Captain also let us bring a speaker to play our own music & jammed out with us. 10/10 great experience and worth every penny.

  6. AM
    Experience a Beach or Sunset @ Bay of San Juan in Style While Building Moments FULL of Caribbean Flare.

    My friends and I had an amazing time with captain Luis. He is hands down the best. Recommend him to everyone who is looking for a great boating experience. Thank you captain Luis for making our time memorable here !