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All listings in San Juan

Incredible sailboat rentals in San Juan, Puerto Rico.

5.0(Average of 73 reviews in this area)
4 listings
Private San Juan Bay Cruise/37 Foot Sailboat/FREE Tapas and Drinks/See Old San Juan/Sunset/Swim
Sailing in San Juan · 6 guests

Private San Juan Bay Cruise/37 Foot Sailboat/FREE Tapas and Drinks/See Old San Juan/Sunset/Swim

5.0
$150hour
Quick Sail a Classic 1969 Sloop in San Juan, Puerto Rico
Sailing in San Juan · 6 guests

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

4.9
Superowner
Best of 2022
$99person
Sunset Cruise in San Juan Puerto Rico
San Juan · 6 guests

Sunset Cruise in San Juan Puerto Rico

5.0
Superowner
Best of 2022
$353hour
Private Luxury Sailing Experience out of Old San Juan
Sailing in San Juan · 12 guests

Private Luxury Sailing Experience out of Old San Juan

5.0
$725hour

Sailing Reviews in San Juan

  1. BS
    Brie
    Private Luxury Sailing Experience out of Old San Juan

    We couldn't have booked a better boat! Our group outing was for a sunset sail for 3.5 hours. The communication prior to the excursion was excellent, the directions to get to the marina location were straightforward, the boat was just as described and was fully equipped with a cooler, fridge, ice, yeti cups and bowls/plates for the food we brought. Krista and Kyle were an amazing captain and crew! They educated us on some of the history of Puerto Rico and took all the photos we could have ever wanted. It did rain a bit during our ride, but that didn't stop us from having fun as we just went under the covered portion of the boat for awhile to hang out. We got to see the sunset, a rainbow, and they even took us out a bit longer than originally planned as we were waiting for a cruise ship to pass by. I would highly recommend this boat, captain and crew—it was certainly the highlight of our trip!

  2. DONALD
    DONALD
    Quick Sail a Classic 1969 Sloop in San Juan, Puerto Rico

    This was absolutely breathtaking!! Our Captin was amazing. And gave us all the privacy we wanted!! Definitely will be using him again!

  3. KJ
    KEMP
    Private San Juan Bay Cruise/37 Foot Sailboat/FREE Tapas and Drinks/See Old San Juan/Sunset/Swim

    was one of best sails we experience. enjoyed the lovely ride as well as the great company and information about San juan

  4. em
    eden
    Private San Juan Bay Cruise/37 Foot Sailboat/FREE Tapas and Drinks/See Old San Juan/Sunset/Swim

    Captain Luis and Rubin really made my birthday experience special. They went above and beyond to make sure we felt comfortable and had a great time. Definitely recommend!!!!

  5. Jasmin
    Jasmin
    Private San Juan Bay Cruise/37 Foot Sailboat/FREE Tapas and Drinks/See Old San Juan/Sunset/Swim

    We had a great time. Luis and his crew member were amazing and my family really enjoyed themselves. The Tapas were delicious as well.

  6. NM
    Natanael
    Private San Juan Bay Cruise/37 Foot Sailboat/FREE Tapas and Drinks/See Old San Juan/Sunset/Swim

    We have an amazing time Captain Luis and his team are very knowledgeable and professional. He will take you to the amazing view of el morro from the water side.They have the local beer and local rum for us and the tapas were delicious. If you want to have a great time book it now sail away to the fun you will have an amazing experience Great Family experience.