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
Private Quickie Sail
Duration: 2 hours
Classic Sailboat
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.
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!
Reviews
143 reviews
Total reviews and rating from Viator & Tripadvisor
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!
Very friendly, very...
Melissa P,,Jan 1, 2026
- Review from Viator
5.00Very friendly, very informative, top notch sail with husband and two daughters (ages 22 and 16). Captain Jimbo was professional and fun.
This was one of our...
Tricia R,,Dec 29, 2025
- Review from Viator
5.00This was one of our favorite excursions well in San juan. Jimbo was amazing and gave us all sorts of information and even allowed our son and daughter to drive the sailboat for a bit. Highly recommend!
So special!
bushytale,,Dec 27, 2025
- Review from Tripadvisor
5.00We decided at the last minute to take this sailing excursion and it was absolutely worth it. Captain Jimbo took care of our party of five (10y - 76y!) We loved that this was 100% personalized. Some of us are prone to motion sickness but we've also been wanting to try sailing. Captain Jimbo taught us how to sail and allowed us to take the helm as much as we wanted to. Being an active crew was super exciting and enjoyable. We spent most of the time in the calmer bay but also got to experience the chops in the open water. Captain Jimbo is very knowledgeable and has a wealth of experience to share. It made our Puerto Rico trip so much more special!
Beautiful, private, and fun trip!
Erin B,,Nov 27, 2025
- Review from Viator
5.00We had such a great time sailing today. We're on a cruise so it was so nice to break away from the crowds and have the sailboat to ourselves (family of 6). My husband loved getting to learn more about sailing and the rest of us loved the adventure. Our captain was so informative and relaxed and did a great job of explaining what to expect. Just a warning- you will likely get wet so bring extra clothes. So glad we did this!
Drive the boat, or relax and enjoy the cruise!
Spencer S,,Nov 11, 2025
- Review from Viator
5.00We had a great time with our bachelorette party of four. Captain Jimbo was incredibly easy going! We brought champagne, dragged off the side of the boat, and he taught us how to sail. You can decide if you want to sit and relax, or take the wheel (literally)! You’re in good hands. Very cool experience, absolutely recommend.
Jimbo was amazing!!!...
Auria C,,Oct 19, 2025
- Review from Viator
5.00Jimbo was amazing!!! Great conversation. Told us history of PR. We had a great time out on the boat! Definitely recommend! 😁
Everything was great. The...
Jamie P,,Oct 13, 2025
- Review from Viator
5.00Everything was great. The captain was very friendly, and since it was our first time on a sailboat he made the experience very nice!
Great Sail!!
Gabby A,,Oct 11, 2025
- Review from Viator
5.00This was such a great experience! If anyone is contemplating, definitely book. Nice sail and we stopped and swam! Nice view of the bay!
Must do!!! Amazing!
Lindsey K,,Sep 4, 2025
- Review from Viator
5.00Our sailing excursion was simply AMAZING!!! My husband and I had an absolute blast enjoying the stunning views and being in awe of the beauty of San Juan. Jimbo was an excellent captain was full of information. He was happy to answer our questions and give us any information we asked about. He was an amazing guide and Captain! We had such an amazing experience that we have already booked him for a second time on our trip. Highly, highly, highly recommend!
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Operated by Sail Snorkel Party inc.