Puerto Rico

Awesome sailboat rentals in Puerto Rico.

Average of 11 reviews in this area.
17 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.

Using GetMyBoat to rent your next sailboat.

Experiencing the water has never been easier thanks to GetMyBoat. GetMyBoat allows you to quickly search, compare prices, submit rental inquiries, and pay for your rental or charter from the convenience of your phone or computer. We offer a secure platform for renters to facilitate a seamless rental transaction. For boat owners, we connect millions of renters to their boat and provide the security and safe checks on each rental transaction.

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

GetMyBoat customer reviews for Sailing in Puerto Rico.

  1. LM
    Ludo
    Charter 52' Cruising Monohull in Fajardo, Puerto Rico

    I couldn’t have had a better experience!! The boat was amazing, really well taken care of, Domingo was a perfect captain, he brought us wherever we wanted to, he was really nice and friendly and he cooked us the best lunch we had in Puerto Rico! So delicious! The whole experience was truly memorable. I would book with him again if I go back to PR. Thank you so much Domingo!

  2. LW
    Lea
    Charter 52' Cruising Monohull in Fajardo, Puerto Rico

    By far the nicest experience while in PR! We took my sister on her bachelorette to Puerto Rico and i can say without a doubt that renting Domingo´s boat was the best choice we made during the entire trip! He was so delightful, he took very good care of us,made us an amazing and tasty lunch, gave us recommendations about the destination and was very flexible in general. 100% recommended!

  3. BS
    Blake
    Quick Sail a Classic 1969 Sloop in San Juan, Puerto Rico

    Jimbo went above and beyond! I couldn't recommend him more. My plan was to come to San Juan and get some first hand sailing experience and that is exactly what I got. I went out with him on the Hobie and Pearson a couple times and learned a ton. Jimbo is passionate about sailing, knows a lot, and just loves being on the water. Can't wait to get back out there with him when I return.

  4. NA
    Nathan
    Leopard 43 Sailing Catamaran with USCG Certified Captain and Crew in Ceiba, Puerto Rico

    Great day on the water with a great crew! Service was excellent, food was very good and the boat is comfortable and clean. Really fantastic way to spend a day in PR!

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

    Jim runs a beautiful sailing ship out of San Juan Bay. The boat is in perfect condition and Jim tailors the trip to whatever you want Highly recommend.

  6. NA
    Nathan
    Leopard 43 Sailing Catamaran with USCG Certified Captain and Crew in Ceiba, Puerto Rico

    Beautiful, comfortable boat with a great sound system and excellent food! The captain and crew were great hosts and we enjoyed every minute of our day!