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Private Sailing Excursion from San Juan

Badge of ExcellenceSan Juan, Puerto Rico

From $650.00

per group (up to 6)

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Select Date and Travelers

Reserve Now & Pay Later
Secure your spot while staying flexible
Free cancellation
Up to 24 hours in advance.
  • 3 hours (approx.)
  • Mobile ticket
  • Offered in: English
  • Good for avoiding crowds


This private sailboat charter from San Juan allows you (maximum 6 passengers) to choose your own adventure. Sail around the bay and harbor of Old San Juan with an experienced captain and crew at the helm; you can choose to help sail or just relax and enjoy the ride. Bring whatever you prefer to sip on, as you watch the scenery. Ask any questions you may have about boating or about owning a boat; your crew is there to educate you on potential future boat sailing and ownership. Our prices already include all taxes and fees.
  • Snorkel gear on board for use IF, time and weather permit
  • Cooler with ice if you want to bring your own drinks
  • Choose to help sail or sit back and relax

What's Included

  • restrooms
  • Equipment
  • safety gear
  • coolers
  • Ice
  • Fuel surcharge
  • Landing and facility fees
  • Hotel
  • Ground Transportation

Meeting And Pickup

Meeting point

  • Qué PezCa’o
    Calle Cerra, Parque Central, Villa Pesquera Hoare, San Juan, 00907, Puerto Rico

    We meet on the dock, behind the restaurant, 'Que PezCao!'

End point

This activity ends back at the meeting point.

What To Expect

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Subject to weather conditions. Will match any (USCG certified and fully insured vessel) price in San Juan Bay.
  • Service animals allowed
  • Near public transportation
  • Infants must sit on laps
  • Most travelers can participate
  • This is a private tour/activity. Only your group will participate

Cancellation Policy

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.

about cancellations.

Traveler Photos

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Traveler Tips

Our time was limited in San Juan, so we started the day early, had a wonderful Sail (you can also snorkel) and we were back in town in time to shop and experience San Juan.
Worth every penny and probably one of our favorite excursions in PR.
We arrived an hour early, but he was accommodating and allowed us to set sail early.
49 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 49 reviews
Perfect Sail for friends
Ebony_C, Aug 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.
Will Remember Forever!
Jules_H, Aug 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.
Jimbo is Great!
Michael_P, Jul 2022
Our family had a great sunset cruise with Captain Jimbo. He made it very enjoyable and fun for our entire family. Highly recommend using him for your trip. He also taught our family the basics of sailing a boat and let our family sail the boat, which was very fun for them. Thank you Jimbo!
Perfect sail
Andrea_O, Jun 2022
Captain Jimbo was excellent. Gave great history lesson of the area. Not only sailed in the harbor, but out into the ocean. It was a relaxing 3 hour sail, exactly what we wanted.
Great adventure
Hannah_R, Jun 2022
The captain was very friendly and had alot of knowledge about the island. The best experience was when he taught my kids how to snorkel they loved it.
Great day on the water!!
Key_R, Jun 2022
Jimbo was awesome! He told us alot of history about San Juan. Very interesting! I really enjoyed learning about the the history of this beautiful city. We saw El Morro and just some awesome sights from the water. Loved the sailboat and sailing. This is a must do in my book. Thank you, Jimbo, for a great experience!!
Amazing ocean sail
Madeleine_A, May 2022
Jumbo was an excellent captain. We had a great afternoon on the water, and I got to hone my sailing skills on the open ocean. Not everybody wants to do that, but I’m glad I could! Absolutely would book againn
Awesome Time
Michelle_P, Apr 2022
We had an awesome time. Jimbo and his crew mate were wonderful. It was my husbands birthday and they made it very special. Jimbo was so calm and knowledgeable about sailing. We will come back next time we visit.
Well worth it!
Molly_C, Apr 2022
Such a great day! Jimbo was experienced and knowledgeable and we loved our time on the boat! It was so cool to see the fort from the water as well!
Delightful afternoon well spent
Stacey_M, Mar 2022
Jimbo was great with our group. He gave us the history of the region as we passed through the scenes. He is very knowledgeable in Puerto Evian history & heritage. His boat is perfect for an intimate sailing experience.
A safe variety in a single sailing experience
John_P, Mar 2022
We enjoyed a late morning thru early afternoon sailing excursion with Captain Jimbo. The view of Old San Juan from the harbor is just as magnificent as walking her enchanted streets. Captain Jimbo took us on a thrilling ride just outside the harbor where the swells were easily 12 - 15 feet. Importantly, at all times we felt safe. For this reason, I highly recommend this excursion for anyone looking for variety in their sailing experience.
Sunset sail
Natalie_B, Mar 2022
My daughter learned a little about sailing and a lot about the history of Puerto Rico. Such a fun experience and a lasting memory for sure! Recommend the sunset jaunt. The moon and stars were in full show-off mode.
Fantastic captain
shane_w, Feb 2022
Captain Jumbo was fantastic! Instructed us on sailing the boat Salt of the Earth kinda guy. Very knowledgeable about Puerto Rico history. This is a must if you come to Puerto Rico!
1 traveler found this review helpful
Nice tour
Cornelius_K, Feb 2022
We were four adults and two children 5 and under. All had a good time. Captain extremely friendly both with adults and with children. We had a good time and got a view of San Juan Bay with its fortresses and forts. from multiple angles.
Fantastic sailing trip
Logan_K, Jan 2022
We sailed with Jimbo in January 2022. The trip was fantastic. It was a beautiful day, we were able to soak up the sun and enjoy beverages while Jimbo told us some of the history of Puerto Rico. He is incredibly knowledgeable both about sailing and about the island. He took cues from us, sharing as much or as little as we wished to hear. One of our friends took him up on his offer to sail the boat and learn some of the basic tenets of sailing. We would absolutely take this boat tour again and cannot recommend it highly enough.
Awesome Experience. Highly Recommended.
William_S, Jan 2022
Jimbo was awesome. Great Captian - he really knows the boat very well and it's clear he has been on the water his whole life. The best part was that we wanted to learn how to sail and he was an excellent teacher. He was patient but definitely let us take control when we were ready. There were some folks who just wanted to chill and take it all in and some folks who wanted to get really involved. Jimbo was great at catering to both parties. Everyone had an awesome time and would definitely do it again. Can't recommend it enough!
Fantastic sailing trip!
Julia_B, Nov 2021
Beautiful afternoon out on the water with Capt. Jimbo who is such an expert sailor, patient teacher and knowledgeable tour guide!
Jimbo was a great...
Anthony_U, Sep 2021
Jimbo was a great captain. He shared a lot of cool insights about sailing and some great history about San Juan
1 traveler found this review helpful
Awesome private experience
Derek_M, Aug 2021
Awesome private experience with my family. Jimbo was accommodating for all of us, even our 1 year old. Would absolutely do it again and highly recommend.
Awesome time!
Jamie_S, Jul 2021
Captain jimbo was absolutely amazing. His knowledge of the area was invaluable and the kids loved learning to sail. What a view of the harbor! Highly recommend this experience. Worth every penny and probably one of our favorite excursions in PR.


Product code: 20119P3