Free Cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Cancellation Policy
Free Cancellation
June 19100% refund
June 20No refund
You can cancel up to 24 hours in advance of the experience for a full refund.
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.
Any changes made less than 24 hours before the experience’s start time will not be accepted.
Cut-off times are based on the experience’s local time.
This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Morning Private Sailing Tour
2 Adults x $595.00
$1,190.00
Approx Total
$1,190.00
Duration: 3 hours San Juan Harbor: Sailing around the bay and harbor of Old San Juan, Puerto Rico. See the castle, forts and cityscapes!
Afternoon Private Sailing Tour
2 Adults x $595.00
$1,190.00
Approx Total
$1,190.00
Duration: 3 hours San Juan Harbor : Sailing around the bay and harbor of Old San Juan, Puerto Rico. See the castle, forts and cityscapes.
Morning Private Sailing Tour
2 Adults x $595.00
$1,190.00
Approx Total
$1,190.00
Duration: 3 hours San Juan Harbor: Sailing around the bay and harbor of Old San Juan, Puerto Rico. See the castle, forts and cityscapes!
Afternoon Private Sailing Tour
2 Adults x $595.00
$1,190.00
Approx Total
$1,190.00
Duration: 3 hours San Juan Harbor : Sailing around the bay and harbor of Old San Juan, Puerto Rico. See the castle, forts and cityscapes.
Inclusions / Exclusions
Mobile ticket
Offered in: English, Spanish
Coolers
Equipment
Restrooms
Landing and facility fees
Safety gear
Ice
Fuel surcharge
Hotel
Ground Transportation
Overview
Private, AM. PM. or Sunset, sailing around the San Juan 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.
Itinerary
San Juan Bay
Beginning from a historical fishing dock, you'll experience a journey spanning from the industrial bays, loading docks, and mechanical wonders to the historical sights of Old San Juan, the forts, the Governor's Mansion, and the architecture of the old Spanish builders, extending to the open ocean, weather permitting. The unparalleled experience of wind-powered travel allows you to learn the intricacies of the skill and marvel at the wonders 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 are nothing short of magical on this enchanted isle. You are encouraged to bring your favorite libations.
3 hours
Sample Menu
Additional Info
Service animals allowed
Public transportation options are available nearby
Infants are required to sit on an adult’s lap
Suitable for all physical fitness levels
Subject to weather conditions. Will match any (USCG certified and fully insured vessel) price in San Juan Bay.
Free Cancellation
June 19100% refund
June 20No refund
You can cancel up to 24 hours in advance of the experience for a full refund.
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.
Any changes made less than 24 hours before the experience’s start time will not be accepted.
Cut-off times are based on the experience’s local time.
This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
Total review count and overall rating based on Viator and Tripadvisor reviews
5 stars
95
4 stars
3
3 stars
1
2 stars
0
1 star
5
We perform checks on reviews
We had a great experience touring New York City with Jonathan. He's a great tour guide and he made it very memorable and enjoyable. The tour was also super informative and I'm glad to have had a great tour guide during my visit in NYC. Would definitely recommend this tour to anyone looking for a tour her We had a great experience touring New York City with Jonathan. He's a great tour guide and he made it very memorable and enjoyable. The tour was also super informative and I'm glad to have had a great tour guide during my visit in NYC. Would definitely recommend this tour to anyone looking for a tour her We had a great experience touring New York City with Jonathan. He's a great tour guide and he made it very memorable and enjoyable. The tour was also super informative and I'm glad to have had a great tour guide during my visit in NYC. Would definitely recommend this tour to anyone looking for a tour her We had a great experience touring New York City with Jonathan. He's a great tour guide and he made it very memorable and enjoyable. The tour was also super informative and I'm glad to have had a great tour guide during my visit in NYC. Would definitely recommend this tour to anyone looking for a tour her We had a great experience touring New York City with Jonathan. He's a great tour guide and he made it very memorable and enjoyable. The tour was also super informative and I'm glad to have had a great tour guide during my visit in NYC. Would definitely recommend this tour to anyone looking for a tour her We had a great experience touring New York City with Jonathan. He's a great tour guide and he made it very memorable and enjoyable. The tour was also super informative and I'm glad to have had a great tour guide during my visit in NYC. Would definitely recommend this tour to anyone looking for a tour her
Reviews by TravelOne travelers
Showing 1-5 of 95 reviews with 5 stars
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Captain Jimbo is the best!!!!
Published on May, 2025
Captain Jimbo will be part of our wonderful memories of PUERTO RICO. He was a great host learned a lot of history. Exceptional experience!!!!
We sailed!
Published on May, 2025
The views were beautiful, the weather was lovely, and the boat excursion was so fun! Jimbo is a great captain and teacher. This is definitely a choose your own adventure experience, it can be chill or exciting. Our group had a lot of fun!
Familia outing
Published on May, 2025
Awesome experience. Not only did we sail but we learned to sail and applied his teachings while in the bay!
Great communicator, fun and funny, thoroughly enjoyed and was worth EVERY PENNY!!!
10 out of 10
Capt Jimbo
Published on May, 2025
This was a very great experience, Jimbo customize our route for us. He was on a timely manner. He allowed us to bring our own food and drinks and give us the opportunity to get in the water. Would book again thank you!
Captain Jimbo taught my son to sail!
Published on May, 2025
Captain Jimbo was amazing with our two teenage boys who had never been on a sailboat. The first hour he patiently taught them his three rules of sailing. From then on he let them sail the boat. My son says” I really feel like I can sail a boat now”. His friend agrees “ I never knew sailing was so easy “. Jimbo’s sailing lesson was the highlight of our Puerto Rico vacation for this homeschool Mom!
Anne
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