Private Tour
Sail Away: Private Scenic Excursion from San Juan
Overview
Available languages
Mobile ticket
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.
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.
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What To Expect
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.
What‘s Included
coolers
Equipment
restrooms
Landing and facility fees
safety gear
Ice
Fuel surcharge
Hotel
Ground Transportation
Options
Morning Private Sailing Tour
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
Duration: 3 hours
San Juan Harbor : Sailing around the bay and harbor of Old San Juan, Puerto Rico. See the castle, forts and cityscapes.
Private Quickie Sail
Duration: 2 hours
Classic Sailboat
Reviews
151 reviews
Total reviews and rating from Viator & Tripadvisor
Girls Trip - group of 6 sixtyish friends. Last minute booking. Captain Jimbo was amazing. Perfect outing for Sunday!
garymQ1143PH,Mar 8, 2026
- Review from Tripadvisor
5.00Captain Jimbo was very conversational. Several had never sailed before and he explained everything! We even had a pod of dolphins follow us and entertain doing jumps. The whole afternoon was amazing.
Yes!!!
Emily F,Mar 4, 2026
- Review from Viator
5.00This was an amazing tour. Jim was a super friendly and knowledgeable captain, and went out of his way for us to be able to swim. The boat is SO nice and we had the absolute best time!!!
We had an amazing time...
ShaKirah G,Feb 27, 2026
- Review from Viator
5.00We had an amazing time with Captain Jimbo! It was my birthday and he truly made me feel celebrated from start to finish. My friends and I thoroughly enjoyed the whole experience — especially getting the chance to drive the boat, which was definitely a highlight. Everything was fun, smooth, and memorable. When I come back in the near future, I will absolutely be booking again. 10/10 — highly recommend!
An amazing experience
Paul S,Feb 25, 2026
- Review from Viator
5.00It was easy to find and clean. Direction to the dock where easy to follow. Upon arriving we were greeted by Jimbo. We are given and safety briefing and a brief and informative lesson on sailing. The boat was clean and safe. We had an amazing experience.
Excellent experience and...
Warren M,Feb 12, 2026
- Review from Viator
5.00Excellent experience and exactly what we were looking for. A relaxing sailing trip around the San Juan harbour with an experienced and knowledgeable Captain. We did this tour as a group of 6 including two younger children (ages 4 and 6) and they both had a blast! I would highly recommend this to anyone while in San Juan.
Tranquil and full of great vibes
Joel O,Feb 6, 2026
- Review from Viator
5.00The captain is extremely experienced, fluent in english, and very helpful with whatever you need. I would highly recommend.
It was a great time! 2-3...
Paula L,Jan 24, 2026
- Review from Viator
5.00Well worth it! 2-3 hours was just the right amount of time. It rained briefly but was still very enjoyable. I'd definitely do it again!
Beautiful day on the water
Uknowtheone,Jan 22, 2026
- Review from Tripadvisor
5.00Cap’t Jimbo made our day really special. He asked before we went out if we understood the conditions (some rain, windy). We were down and so glad we did. Cap gave us some history of PR, we shared personal stories and he gave my fiancé a fantastic sailing lesson. Overall, it was a fantastic experience and we are so glad we got to spend a few hours out on the water.
Great Experience!
Brianna S,Jan 13, 2026
- Review from Viator
5.00We had an amazing time!!!! Best boat experience yet. Vibes were great and our captain was great!!!!!!
Great time with Captain Jimbo
Jaclyn S,Jan 2, 2026
- Review from Viator
5.00We had a great time with Captain Jimbo sailing out to see old San Juan from the water. Beautiful day. Great fun was had by all!
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Operated by Sail Snorkel Party inc.