Private Sailing Excursion from San Juan

caribbean » puerto rico » puerto rico » puerto rico

From $650.00

51 reviews   (4.65)

Price varies by group size

Lowest Price Guarantee

Pricing Info:

Duration: 3 hours

Departs: puerto rico, puerto rico

Ticket Type: Mobile or paper ticket accepted

Free cancellation

Up to 24 hours in advance.

Learn more


Private, AM. PM. or Sunset, sailing around the Bay and Harbor of Old San Juan, Puerto Rico. (Prices already include all taxes and fees) This sightseeing, sailing tour will pass historical, Old San Juan Forts and views of the Castle and city-scapes .  A truly exclusive, off the beaten path, Private Experience. If desired you can learn the skill of sailing with the optional request of a hands-on lesson always available to everyone. We differentiate ourselves as a stepping stone to the education of chartering. Also, discovering the facts of sailing to inform the client so that by the end of this trip you'll have the answers needed to make the decision of buying, chartering and planning for future ownership. For experienced Sailors we have a Bareboat imitation option where our Captain is simply there to answer questions and for safety.

What's Included



Fuel surcharge


Landing and facility fees


safety gear

What's Not Included

Ground Transportation


Traveler Information

  • TRAVELER: Age: 0 - 99

Additional Info

  • Public transportation options are available nearby
  • Subject to weather conditions. Will match any (USCG certified and fully insured vessel) price in San Juan Bay.
  • Public transportation options are available nearby
  • Subject to weather conditions. Will match any (USCG certified and fully insured vessel) price in San Juan Bay.

Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

What To Expect

Old San Juan
Beginning from a historical fishing dock, you'll get an experience ranging from the industrial bays, loading docks and mechanical wonders to the historical sights, Old San Juan, Forts, the Govoner's Mansion and architecture of the old spanish builders to the open ocean, weather permitting.   The unrivaled experience of wind powered travel, learning the ins and outs of the skill or the wonder of the ocean and the atmosphere through which we travel. Puerto Rico's perpetual summer is our greatest gift. The amazing blue waters that shine in the everlasting summer is nothing short magical on this enchanted isle. You are encouraged to bring your favorite libations.

3 hours • Admission Ticket Free


Simply the Best!
Cecilia_M, 19-08-2022
This was hands down my favorite part of my time in PR. The captain was hospitable, knowledgeable, and just an extreme pleasure all the way around! I learned so much and was able to take the wheel for a bit and sail the boat! Unforgettable moments gives us the memories that lasts forever.
Awesome experience!!
635tamekaa, 18-08-2022
By far, this was the best thing me and my friends did while in Puerto Rico. He was very experienced and knowledgeable. We were able to bring our own drinks and music. He was very laid back and answered questions when we asked. He made us feel very comfortable. We watched the sunset while enjoying ourselves! Thanks again for the wonderful experience!!
Will Remember Forever!
Jules_H, 07-08-2022
Last minute trip to San Juan turned into a vacation we will remember for a lifetime. Luis and Gabriel were amazing Captain and crew and very friendly. If you want a history lesson and boating lesson in one this is the excursion.
Amazing private sail around old San Juan!
Sandeep S, 13-09-2022
“My friend and I thoroughly enjoyed the private sail. Captain Jimbo is a wonderful host, he did everything to ensure we have a good time - from making us comfortable on the boat (we were newbies), getting us through a wonderful sail around the bay, sharing history of Puerto Rico, to even picking a good sparkling rose for us, highly recommend it!
Perfect Sail for friends
Ebony_C, 12-08-2022
Jimbo and Gabby were amazing! Jimbo was very knowledgeable about the island and the history of it. Gabby paid great attention to us and made sure we ate, drank, and just enjoyed our time there. This was a great experience and we would definitely do it again.

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