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
(151 Ratings)
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1 star
Paula_l
Jan 24, 2026
It was a great time! 2-3... - Well 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!
Review provided by Viator
Uknowtheone
Jan 22, 2026
Beautiful day on the water - Cap’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.
Review provided by Tripadvisor
Brianna_s
Jan 13, 2026
Great Experience! - We had an amazing time!!!! Best boat experience yet. Vibes were great and our captain was great!!!!!!
Review provided by Viator
Jaclyn_s
Jan 2, 2026
Great time with Captain Jimbo - We 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!
Review provided by Viator
Melissa_p
Jan 1, 2026
Very friendly, very... - Very friendly, very informative, top notch sail with husband and two daughters (ages 22 and 16). Captain Jimbo was professional and fun.
Review provided by Viator
Tricia_r
Dec 29, 2025
This was one of our... - This 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!
Review provided by Viator
Bushytale
Dec 27, 2025
So special! - We 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!
Review provided by Tripadvisor
Erin_b
Nov 27, 2025
Beautiful, private, and fun trip! - We 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!
Review provided by Viator
Spencer_s
Nov 11, 2025
Drive the boat, or relax and enjoy the cruise! - We 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.
Review provided by Viator
Auria_c
Oct 19, 2025
Jimbo was amazing!!!... - Jimbo was amazing!!! Great conversation. Told us history of PR. We had a great time out on the boat! Definitely recommend! 😁
Review provided by Viator
From $494 (Per Group)
up to 6 guests
1 - Traveler
Cancellation: Free cancellation up to 24 hours before the start of your experience (local time).