Puerto Rico

Authentic Sail by the Bay of San Juan

San Juan, Puerto Rico

From $89.00

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 2 hours (approx.)
  • Mobile ticket
  • Offered in: English


Navigate the seas aboard an authentic sailboat during this excursion in the Bay of San Juan. While most boats these days have noisy motors, this sailboat experience exclusively uses the power of the wind. Enjoy views of Old San Juan from a different perspective and sip on beer or sangria as you sail; you may even encounter local wildlife like dolphins.
  • Avoid crowded tourist boats and ride on a sailboat
  • See landmarks like San Cristobal Castle while you sail
  • Sail sideways as the wind takes you through the bay
  • A small group means more attention from your host

What's Included

  • All taxes, fees and handling charges
  • Beer, Sangria, Rum n Coke
  • Bottled water
  • Local operator not available to take phone calls, please read all information thoroughly
  • Transportation to location

Meeting And Pickup

Meeting point

  • 482 Av. Manuel Fernández Juncos
    482 Av. Manuel Fernández Juncos, San Juan, 00901, Puerto Rico

    Search for SAIL SAN JUAN BAY in ggle or wze maps ***WAIT OUTSIDE BY THE GUARD, STAFF WILL PICK YOU UP ** *** We won't be able to take phone calls or chat ***

End point

This activity ends back at the meeting point.

What To Expect

San Juan Bay

2 hours Admission Ticket Free

San Juan

Admission Ticket Free

Castillo de San Cristobal

Admission Ticket Free

El Canuelo

Admission Ticket Free

La Fortaleza - Palacio de Santa Catalina

Admission Ticket Free

Additional Info

  • Confirmation will be received within 48 hours of booking, subject to availability
  • Infants must sit on laps
  • Not recommended for travelers with back problems
  • No heart problems or other serious medical conditions
  • Not recommended for pregnant travelers
  • Near public transportation
  • Not wheelchair accessible
  • Look for Sail San Juan Bay in Google Maps
  • Dress code is smart casual
  • Not available for phone calls, we may answer relevant texts
  • We depart sharp, we don't make others who arrive on time wait
  • Maximum passenger weight 275
  • We reserve the right of admission. No bad moods.
  • Getting to departure location is your responsibility.
  • Travelers should have a moderate physical fitness level
  • This tour/activity will have a maximum of 6 travelers

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.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Traveler Photos

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Featured review
Absolutely Awesome time!!! Ivan & John are great guys and wonderful sail boat captains and guides! I definitely recommend anyone who is visiting PR do the Old San Juan sail by the bay boat tour.


70 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 70 reviews
Had a great time on the...
Jeanette_H, May 2023
Had a great time on the sailboat! Great captain, fun time. Would recommend. We did the 10:30 am tour.
First and best time sailing ⛵️
Briana_G, May 2023
Everyone should experience a sail boat especially in PR the views and weather were beautiful and relaxing. I loved it and learned some history of the beautiful city. A must do in Puerto Rico with our Captain Joe and his partner!
Awesome Sailing with an Amazing Guide
Heather_R, May 2023
Highly recommend this sail. Joe and his crew member were very knowledgeable of the island and gave us some great recommendations for our trip. The day was gorgeous with a perfect amount of wind! The drinks were delicious and we lucked into being the only 2 passengers.
Response from Host, May 2023
We sail up to 6 per sailboat, and sometimes the daytime sailing trips doesn't get full, so there's a slight possibility to sail with 2 people for price of 2, but usually, you'll need to pay for a private to assure that.
Great way to see old san juan
jeff_d, May 2023
It was great Very basic way to see alot of old san juan. Would recommend to anyone. A little pricey for how short a time.
Amazing experience!
Lanie_J, Apr 2023
I booked this trip for me and my parents and it did not disappoint! By chance we ended up on a private tour and had the opportunity to experience a “sportier” ride…. amazing! The captain was very skilled and highly knowledgeable about the history of the city. He also gave us some great food recommendations! Couldn’t recommend this experience more.
Fun and relaxing!
Fred_S, Mar 2023
Nice sail. Captain Joe and Maria were great! We enjoyed our trip around the harbor and the conversation.
Response from Host, Mar 2023
We agree our staff is great, and the sailing action is very enjoyable. Therefore, you are missing 1 star!!
It was AWESOME!!!
Mark_B, Feb 2023
Awesome Sail!!!! I'd give it a six stars if I could. Sailed for two days. My wife and I sailed both Tuesday and Wednesday on the 10:30 cruise. First day Captain Joe was the skipper and Abraham was the crew (one other passenger). Second day Captain Joe was the skipper and Maria was the crew (no other passengers). Captain Joe was a seasoned sailor that explained the boat and the winds in San Juan Bay. We were under full sail, main and jib, for all but docking and undocking. I was concerned by some reviews of motoring the entire time, this was not an issue for us. Ours was fantastic, the only noise was the wind blowing through our hair. Captain Joe was very informative on the history of San Juan, local attractions, and eateries. We were on a J-30, which is a racing sailboat with limited cockpit space. It seated four adults very comfortably. We had no problem finding the marina. Put in "Sail San Juan Bay" and the Uber Driver or Taxi Driver (we used both) takes you right to the gate. I hope everyone else has just as awesome a time as us.
Beautiful sail with lovely sights
Beth_D, Feb 2023
It was a beautiful day to be on the sea with a kind and experienced sailing captain. We enjoyed it very much. The address and directions to get there, however, made it a challenge to find. Only The kindness of strangers got us there in time.
Response from Host, Feb 2023
Thanks for the 5 stats review. About the address, it very easy, just follow instructions that are included in the booking and recent to text. Find SAIL SAN JUAN BAY in online maps. Very easy!!
A must do!!
Adamah_P, Feb 2023
Very nice and funny. Informative of the Bay Area and educated my friends and I. Drinks were amazing!
Well worth it. Highly recommend!
Stacie_D, Dec 2022
We enjoyed the views, the sail, and Captain Joe's information about the island and San Juan Bay. The strong wind gusts made it thrilling but we felt confident that we were safe.
Great sailboat cruise
vajones7, Dec 2022
We had a wonderful time! Captain Joe and Ivan were great! Learned a lot about sailing and Puerto Rico history!
Great experience! The...
Kayla_F, May 2022
Great experience! The guide gave us great food and activity recommendations for after too! Very informative and fun
Huge disappointment
Jack_G, Apr 2022
We arrived 10 minutes early and they never showed to pick us up. Huge disappointment. I texted to ask where they were and they said they left. Seems unlikely since we were the only group booked for the trip.
Response from Host, Apr 2022
Going to the wrong marina, and thinking you are in the right one and even thinking that you where the only ones . . . . . We recommend to read instructions to find the location and to follow the links included to the right entrance, it worked for the majority who sailed and could get the few ones who couldn't make it to sail and to put a 5 star review like the others. Reading is magical!
Beautiful boat ride and fun!
Kylah_A, Apr 2022
Awesome beautiful experience would do it again! The captain and helper was friendly, funny and awesome! The only thing I recommend is better instructions on pick up spot. they only gave a navigation direction which doesn’t put you in direct location. We had to call the customer service and get better clarification of land mark which we found out was in parking lot of Club nautica which everything was good after that. But overall Loved every bit of it even the Sangria drinks!
Spring break 2022
Jessica_P, Apr 2022
The captain allowing my son to “drive” the sailboat back to the marina. I would definitely do it again…..
Not a true sailing experience
Kurosh_M, Mar 2022
Very nice captain and boat. Problem was that one of the sails wasn’t working so the whole trip was with the motor. Not what we were expecting. Should have been communicated beforehand.
Response from Host, Mar 2022
One of the sailboats needed repairs. And we have been doing sailing trips with only one sail, which is not a problem to the majority of customers. We apologize that the captain didn't told you this, before going out. We sail a lot, more than 150-200 tourist a week, and canceling sailing trips for a minor rigging problem like this, would cause more disappointment than giving a tour with one sail.
Fun adventure in the bay!
Maral_P, Mar 2022
Captain Ivan was great! The intimate sail boat (there were 4 people total) was a wonderful way to see the bay. It was a fun adventure sailing with Captain Ivan and hearing some history of San Juan and his recommendations for things to do and places to see.
Response from Host, Mar 2022
You make our lives shine! Thanks for allow us to sail everyday with amazing 5 stars customers from all over the world. For us, that is a privilege and it's honorable
Amiee_S, Jan 2022
I had the most fabulous time! The captain is amazing. The drinks were great. The views can’t be beat. A must do when traveling to Puerto Rico!
Terrific sailing adventure with Ivan!
Kelley_K, Jan 2022
Sailing with Ivan was amazing, the sunset was spectacular and the conversation was great. Got a sense of the history of the island and some sailing excitement as the wind was fairly strong. This is a true sailing ship, 30' with mainsail and Jib. Sat the four of us very comfortably. I would recommend this to anyone who wants a little more intimate sailing experience. Thanks Ivan for the great time!
Lovely experience!
Arwa_A, Dec 2021
This was my first experience on a sail boat. Really cool! I did the 3 pm one and it was so nice to see the historical sites from a different perspective! The weather was very good and I enjoyed the company of our tour guide and his daughter! May restaurant recommendations were given!

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