Sail Away: Private Scenic Excursion

Embark on a private sailing excursion from San Juan and explore the historic Old Harbour and forts. Learn to sail or enjoy a bareboat experience. Book now!

Duration: 3 hours
Cancellation: 24 hours
Highlights
  • 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…
What's Included
  • coolers
  • Equipment
  • restrooms
  • landing and/or facility fees
  • safety gear
  • Ice
  • Surcharges on fuel
What's Not Included
  • Hotel
  • Ground Transportation
Additional Information

Private, AM, PM, or Sunset sailing around San Juan Bay and the Harbor of Old San Juan, Puerto Rico. (Prices include all taxes and fees) This sightseeing sailing tour will pass historical Old San Juan Forts and offer views of the Castle and cityscapes. A truly exclusive, off-the-beaten-path private experience. If desired, you can learn the skill of…

Location
Qué PezCa'o
We meet on the dock, behind the restaurant, 'Que PezCao!'
Cancellation Policy

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

Customer Ratings
4.8
(126 Ratings)
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1 star
Volivasa
May 21, 2025
Captain Jimbo is the best!!!! - Captain Jimbo will be part of our wonderful memories of PUERTO RICO. He was a great host learned a lot of history. Exceptional experience!!!!
Review provided by Viator
Devone530
May 17, 2025
We sailed! - 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!
Review provided by Tripadvisor
Paul_s
May 16, 2025
Familia outing - 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
Review provided by Viator
Alishotm
May 5, 2025
Capt Jimbo - 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!
Review provided by Tripadvisor
Annedk6261ra
May 2, 2025
Captain Jimbo taught my son to sail! - 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
Review provided by Tripadvisor
796aliyas
May 2, 2025
Amazing Sailing Trip w/ Captain Jimbo! - Our bachelorette party can’t stop raving about our unforgettable sailing trip with Captain Jimbo! He’s an incredible host—fun, knowledgeable, and made everyone feel right at home on the water. Some of us took the chance to learn a bit about sailing (especially my sister, the bride-to-be, who loves picking up new skills), while others kicked back and soaked in the sunshine and ocean breeze. Personally, my favorite part was riding up front as we hit the open ocean and cruised through the waves—absolutely exhilarating! The water was warm, the vibe was perfect, and the timing of the trip couldn’t have been better. I highly recommend sailing with Captain Jimbo to anyone looking for a memorable and unique experience!
Review provided by Tripadvisor
420maggiet
Apr 23, 2025
10/10 experience right in San Juan - Captain Jimbo is the best! We had the best day exploring San Juan from the water with the best hospitality and some history lessons as well! He even found us a safe place to swim in front of the fortress and took lots of photos and videos for us to remember the trip. It’s a must if you’re in San Juan!
Review provided by Tripadvisor
Katierandy
Apr 22, 2025
Amazing sailboat cruise! Jimbo is great!!! - Jimbo was great!!! We had a fantastic time sailing and learning all about Old San Juan. I have 3 teenage boys and Jimbo taught them to sail! It was an experience we will never forget!! We got to see Old San Juan from the ocean… the views were incredible!
Review provided by Tripadvisor
A1032tpjamies
Apr 21, 2025
A Great Experience - We had such a great time learning how to sail with Captain Jimbo! We learned so much about sailing and the island! We had so much fun!!! I would highly recommend this tour.
Review provided by Tripadvisor
Gogwen21
Apr 21, 2025
Can’t Jim rocks - We had a great sail. Capt Jim was a delight and made our day special. He took the time to explain a lot of history of the port and Puerta Rico! He let my daughter sail and taught her some sailing basics. Would definitely recommend a sail with him.
Review provided by Tripadvisor
From $475 (Per Group)
up to 6 guests
1 - Traveler
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).