Product photo
Product photo
Product photo
Product photo
Product photo
Product photo
Product photo
/ Person
Select date and participants
At least one participant is required. Please adjust and try again.

San Juan Historical Bay Day Sailing Tour

4.5 (124)
San Juan, PR

San Juan Historical Bay Day Sailing Tour

4.5 (124)
San Juan, PR
Please wait, fetching options!
Experience the thrill of authentic sailing in the beautiful Bay of San Juan. Leave behind the noise and crowds as you embark on a journey aboard a real racer-cruiser sailboat. Feel the power of the wind as you glide through the water, taking in the stunning views of old San Juan from a unique perspective. With complimentary drinks and small group sizes, this is the perfect way to create a special and unforgettable moment. Keep your eyes peeled for unexpected encounters with dolphins as you sail along. This is not your typical tourist activity - it's an authentic and immersive experience that will leave you feeling safe, free, and in touch with nature. Book your sail with Sail San Juan Bay and get ready for an adventure like no other.

About this experience

  • Free Cancellation For a full refund cancel at least before the start of your booking
  • 2 hours
  • Suitable for 1-8 Participants
  • Small Group Tour, Private Tour
  • Self Guided Experience
  • Best perspective of old San Juan
  • Opportunity for unforgettable memory
  • Seaward side of historical Old San Juan
  • Preserved Spanish fortresses
  • Oldest fortress in Old San Juan
  • Bottled water
  • All taxes, fees and handling charges
  • Beer, Sangria, Rum n Coke
  • Local operator not available to take phone calls, please read all information thoroughly
  • Transportation to location

Popular Hotels Closeby

More about this experience


Authentic Sail by the Bay of San Juan offers a unique sailing experience that combines culture, nature, and adventure. Unlike other tours, this sailing experience is all about authenticity, allowing you to have a genuine conversation with a local sailor while enjoying the power of the wind and the serenity of the sea. No engine noise, no fake pirates, no crowds – just you and the elements. Step aboard a real racer-cruiser, the Jboat J30, equipped with all the necessary amenities for a comfortable journey. Prepare to embark on a memorable adventure that will give you a different perspective of old San Juan.

What to expect?

During this 120-minute tour, you can expect to sail along the historic Bay of San Juan, immersing yourself in the beauty of the surrounding scenery. Capture breathtaking photos of old San Juan from a unique vantage point and witness the impressive Spanish fortresses that have withstood the test of time. Keep your eyes peeled for surprises from nature, as you may even encounter playful dolphins along the way. This intimate sailing experience allows for small groups, ensuring a personalized and memorable journey.

Who is this for?

This sailing tour is perfect for anyone seeking an authentic and off-the-beaten-path experience. Whether you're a solo traveler, a couple on a romantic getaway, or a group of friends looking to create lasting memories, this tour caters to all. The inclusive nature of the experience means that no one is excluded – everyone can enjoy the tranquility and adventure that come with sailing the Bay of San Juan.

Why book this?

What sets Authentic Sail by the Bay of San Juan apart is its commitment to authenticity. This is not your typical touristy sailing tour; it's a chance to connect with a local sailor and immerse yourself in the culture and beauty of San Juan. With a maximum of only 6 people per sailboat, you'll enjoy a personalized and intimate experience. Leave behind the noise and crowds as you sail sideways and experience real-life sailing. This is your opportunity to create a special moment or turn any moment into an extraordinary one, all while feeling safe and free in the embrace of nature.

Good to know

To join this exceptional sailing experience, search for "SAIL SAN JUAN BAY" on Google or Waze maps and wait outside by the guard. The staff will pick you up and ensure you have a seamless and enjoyable journey. Keep in mind that phone calls or chats during the sailing tour won't be possible, allowing you to disconnect and fully immerse yourself in the experience. Don't miss out on this chance to sail the Bay of San Juan with Sail San Juan Bay – it's an adventure you won't want to miss.


Feedback from previous travelers has been overwhelmingly positive. People rave about the authenticity of the experience, noting how it stands out from other sailing tours in the area. Many highlight the breathtaking views of old San Juan and the thrill of sailing without the noise of engines. Travelers appreciate the small group size, as it allows for a more personalized and attentive experience. The encounters with dolphins also leave a lasting impression, adding an element of surprise and wonder to the journey. Overall, those who have taken part in the Authentic Sail by the Bay of San Juan tour express their satisfaction with the unique and memorable experience it provides.

How long before the event do I need to book?

  • You can book at any time before the event

Vouchers accepted in the following formats

  • Mobile

Is an adult required for the booking?

  • At least one adult or senior required per booking

Your Itinerary

San Juan Bay

From this commercial and historical Bay, the travellers will get the best perspective of old San Juan, and will get the opportunity to get the best photos of this unforgettable memory.

San Juan

Seaward side of historical Old San Juan area

Castillo de San Cristobal

One of the 2 large old Spanish fortresses preserved for the history

El Canuelo

Little Fort located at Goats Island

La Fortaleza - Palacio de Santa Catalina

Oldest fortress in Old San Juan Puerto Rico, Governor's Mansion



4.5 (124)


Learning all the history and all the information...they were extremely pleasant and well versed on local history etc. And the sailing was excellent...his many years of experience shows...had a wonderful day....


This sailboat ride was so much fun. The couple who operate it are very kind, accomodating and knowledgeable, I felt so save with them at the helm. They offered homemade sangria, beer and water. As we navigated the bay they have great historical and geographical information about Old San Juan. I loved when the boat started to keel and all you heard was the sounds of the wind and water. Don't hesitate to book this experience.


We had an absolutely amazing time during our trip! Ivan was wonderful and gave us an informative and very fun tour of the bay.


We had an amazing time! The captain and first mate were incredible, knowledgeable and they make great sangria.


Captain Joe was very knowledgeable, courteous, and made sure that we all had a lot of fun, including my daughter who even got navigate the sailboat!


Very personable Captain and very relaxing sail. Provided interesting facts. Even found us a manatee.


Captain Ivan was fantastic. Very informative and easy going. Will go this again on our next visit had a great afternoon sail. Beautiful sights


I appreciate how we missed our original boat ride, but Joe and his wife took us out anyway. That was very sweet of them!


I Arrived to the excursion at 10:00am, my excursion was at 10:30am. Spoke to the guard who said wait under the bathroom/tent, ( which is across the security guard office) someone will come for you. We waited with no one coming for us. I walked around looking for any one to help me with my excursion because I didnt want to miss my escursion. I contacted Viator and message them. Only to find out that the sail boat left without us. I called the number +17876677778, which says " there is no one to pick up call, please leave message". I left message and explained what happened. I received messages stating that I was late and the sail boat had to leave. The best they can do is re-schedule me for 03pm. Which I agreed, however, I responded to the message " please correct pick up information, because guard does not work for this company and is not responsible for calling anyone pertaining any excursions". The respond I obtained was that I was late and that this is a courtesy reschedule. Again I explained that I arrived at 10:00am. Looking at the reviews I noticed this happened already to someone else in September 2023. Long story short the gentlement texted me to not come at 3pm anymore. I contacted Viator for a refund. I absolutely hate complaining, but these kind of things need to be put out there for the next customer to know. In the future, the owner of Sail Boat needs to put a phone number or email so they know the customer is waiting for the excursion.


My friend and I had a great time! It was too windy to go out to see, so we saw Old San Juan and it was very informative as well as scenic. Would definitely recommend!!
Collected by Evendo, Tripadvisor & Viator
2024-04-12 21:07