San Juan Historical Bay Daytime Sailing Tour
Recommended by 90% of travelers
San Juan, Puerto Rico
- 2 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
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 Meeting Point
Meeting and Pickup
Meeting point
- 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.Itinerary
San Juan Bay (Pass By)
Old San Juan (Pass By)
Castillo De San Cristobal (Pass By)
El Canuelo (Pass By)
La Fortaleza - Palacio de Santa Catalina (Pass By)
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
- Travelers should have a moderate physical fitness level
- Look for SAN JUAN BAY MARINA in Google Maps
- Dress code is smart casual
- we can not take for phone calls, we may answer relevant texts
- We depart sharp, we don't make others to wait
- Maximum passenger weight 275
- We reserve the right of admission. No bad moods.
- Getting to departure location is your responsibility.
- Show up at least 15 mins BEFORE departure time
- BAd reviews come from individuals who never sailed with us, because didn't showed up BEFORE departure time or didn't read our recommendations here, that for manny of us are obvious
- This tour/activity will have a maximum of 6 travelers
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Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Featured review
Maribeth_F
We had the pleasure to Sail with Captain Joe and Carlos. The other couple was a no show so we had the boat to ourselves which made the experience even more special. The weather was beautiful and Joe was very knowledgeable about San Juan’s History. We would recommend this sailing adventure!!
Reviews
4.6
based on 191 reviews
Susan_T, Apr 2026
Captain Joe and Carlos did an awesome job explaining the history of Old San Juan and provided us with some great local food places to try. I would highly recommend this to anyone looking for a sail.
tynisa_c, Apr 2026
Never got to do tour because it was so hard to find needs to give clearer directions, we got lost getting there and got left.So we never got a chance to do this tour
Cheryl_M, Mar 2026
Captain Joe and Abraham were great tour guides. We all had a lot of fun, saw the sites, drank the sangria and enjoyed the sail. We'll be back again!
Maribeth_F, Mar 2026
We had the pleasure to Sail with Captain Joe and Carlos. The other couple was a no show so we had the boat to ourselves which made the experience even more special. The weather was beautiful and Joe was very knowledgeable about San Juan’s History. We would recommend this sailing adventure!!
Albert_U, Feb 2026
Nice time out in the bay on a small sailboat. If you enjoy getting out on the water, and seeing some places you have only seen from land, this could be for you.
Response from Host, Feb 2026
The sailboat is a J30, its a 30 feet racer cruiser with a cabin and perfect size for sailing trip we offer . . . . it is not considered small, but if it would be small it would be even more fun, bit you won't get a toilet for the emergencies
Indra_Q, Feb 2026
It stated, to be at meeting point at 3pm. I arrived at meeting point at 3pm with Uber and they left early.
Would not refund money for tour I didn’t received, even I had a proof of arrival time from Uber App indicating drop off time 3pm. I finally needed to involve AMEX to help me get refund for tour I didn’t receive. I have used boat tours across Europe and never experienced anything like this.
Response from Host, Feb 2026
. . for the rest of you it won't be a problem, because everyone knows that when a movies starts at 3pm, or even taking a plane . . . you'll show up before for not missing it. It is just logic.
The text we have in the description is very clear. It says "show up at least 15mins BEFORE departure time" so apparently the reviewer didn't read anything.
This customer, is not correct. The massive tours in other places, have a fleet of boats departing all the time, so pay in one place and take the next 300 people boat . . . . . . like in disn3y. We are nothing like that. This is n AUTHENTIC sailing trip, very enjoyable and personal, and our business rules are made to keep undesirable ones out.
Sharing a little Sailor's wisdom. "don't live back to back, all stressed up in your vacations, is not about efficiency all the time. On vacations, take a real break an commit to one or few things a day and sleep and breath more"
Terence_M, Feb 2026
The tour was great. Our Captain was great and knowledgeable about the culture and geography. I would definitely recommend.
Marie_F, Jan 2026
Very pleasant sail in/around the harbour. Captain Joe and Abraham were informative and personable. This is a lovely way to spend an afternoon.
Jeff_G, Jan 2026
Very experienced, knowledgeable,and friendly captain and crew.
Meet them at the fence below the Sizzler parking lot near the gated parking area.
Serenate_F, Jan 2026
Joe was amazing and knew a lot of great facts while sailed even showed us a few things on the ship. Also gave us amazing places to go after to eat or visit which was super helpful. Would definitely recommend
Sarah_g, Dec 2025
It's not so much a sailing trip, it's a slow journey around a harbor on a power boat with the main sail partially raised while jib was never unfurled. The hosts were nice, but never intended to actually sail the boat. There was enough wind. The views were partially scenic- we sailed by cruise ship port, a cement yard, saw the Bacardi factory from a distance and learned about a narrow yellow building.
Response from Host, Jan 2026
Withe the experience of about 12 years already we eventually learned, that the majority of people wants to go out sailing weather there's wind or not
In slow wind days, Its NOT TRUE that we run the engine all the time, we always shot down the engine at some point to relax sailing at least a little.
90% of our sailing trips are absolutely under sails with no engine but sometimes, its just required to run the engine, its captains decision
Some people are not easy to satisfy. Our sailing trips, are proven to be enjoyable for along 12 years, for the authentic sailing with the wind, for the historical area, our tales, beers, only 6 per vessel . . so check out our many other 5 stars customer reviews a how they enjoyed it and disregard others who are never satisfied
Yolanda_G, Dec 2025
This was an awesome experience. The captain and his crew were knowledgeable, very helpful and made this sailing trip a relaxing and memorable experience for my family. This is one of the best experiences and much enjoyed getting away from the crowds.
MARTHA_W, Dec 2025
Informative, relaxing, great communication. We had a nice time. It was just two couples and the captain and first mate
Sierra_M, Dec 2025
Our captain was very engaging, pointing out landmarks and interesting sights within the bay. His crewmanwas also knowledgeable. It was a laid back trip with just our group of 4. A new experience for all of us, which we enjoyed very much
William_G, Nov 2025
Excellent cruise. Not a big boat, it was just myself, wife and daugher along with the captain and mate. Our captain was extremely friendly and knowledgeable on PR history, restaurants, sailing, etc. I highly recommend for a relaxing and fun two-ish hours on the bay.
Peggi_S, Nov 2025
Disappointing 😒😒!! Small boat, no space to walk around for pictures 📷, the guide didn't explain anything about the surroundings, the tour was supposed to be in Spanish but he only spoke English. Very disappointing 😪 and very expensive 💰💰. I don't recommend it.
No lo recomiendo!! Bote muy chico, no se puede caminar y nose puede tomar fotos 📷, el precio muy caro 💰💰
Response from Host, Nov 2025
If you are American, just like us the puertorricans, you find this sailing trip expensive, if you are not, probably everything in an island, US Territory, is going to be expensive. Travel responsibly!!
Our description explains the SAILING TRIP VERY specific, in english (the majority of customers speaks english) . . . if you don't READ the description, your expectations may disappoint you.
Our sailboats are 30 feet SAILING VESSELS that goes with the power of te wind. The Jboats brand are one of the best in the whole world, not for walking, not for eating, not for having a cheap massive tourism tour with a crowd . . . . . . this is AUTHENTIC AND PERSONAL. It goes sideways, we DO TELL HISTORICAL FACTS but we are not tour guides.
We invite you to have a pleasant sailing trip with beer and good conversation . . . Sail San Juan Bay
Tammie_B, Sep 2025
Captain Joe and Carlos met me at the gate to the marina. And it was smooth sailing from there. Captain Joe’s sense of humor, hospitality, and historical knowledge made our sail a memorable one. I recommend a hat and lots of sunblock! You’ll have a great time!
Kemara_J, Jul 2025
We were really looking forward to this boat trip, but unfortunately, it didn’t meet our expectations. The boat was much smaller than advertised, which made the experience less comfortable. They also promoted multiple drinks, but we only received two – and they were pretty watered down.
That said, we did enjoy being out on the water, and the captain and co-captain were both incredibly friendly. They shared a lot of interesting history about Puerto Rico, which we really appreciated. Overall, while the staff made the most of it, the trip just didn’t feel worth the price.
Response from Host, Jul 2025
we have a healthy volume of customers, without advertising much, just a true description saying that you will go authentically sailing, sideways aboard a real racer cruiser J30 . . . . we have tried to NOT ADVERTISE but to avoiding false expectations about what a NON TOURISM COMMERCIAL sailing we do, but still we get some creative minds buying this making false expectations on their own.
WE DO AUTHENTIC SAILING, WITH THE WIND, SAILBOATS ARE NOT A COMFY FAMILY ROOM. 46,000 OTHERS, LOVED IT !!
Codie_C, Jun 2025
It was a super fun time. We sailed while our tour guide explained a lot about Old San Juan and other parts of Puerto Rico that we passed.
Kristi_G, Jun 2025
Captain Joe and Abraham made us feel very comfortable on the boat and gave historical information during the tour. The sangria was also very tasty. Highly recommend!
Michele_M, Jun 2025
Our family had an amazing time sailing with captain Ivan. He was very experienced and very informative about the San Juan area. He gave great tips about where to visit as well as warnings of dangerous places to avoid. He took very good care of us and made us feel like we were long time friends of his. He made us feel safe on his boat despite the strong winds tilting the boat throughout our trip. He informed us that in case of rain or severe weather, he will cancel because he wants to make sure all of his passengers have a safe and enjoyable tour. We are very appreciative of captain Ivan’s amazing services!
(P.S.: We were able to park at the marina free of charge, just tell the guard at the gate what you’re there for.)
Lisa_C, May 2025
The experience was amazing with breathtaking views. The captain was very knowledgeable and informative, his love of sailing and the island made the excursion top tier.
Anthony_R, Apr 2025
Nice trip out into the bay with stunning view of the fort. Captain and mate were very pleasant. I enjoyed watched their sailing skills. Would recommend.
Matt_B, Apr 2025
It was such a memorable experience for us! While it was windy (but not dangerous) conditions on the sea, our captain navigated the waters and wind flawlessly due to his decades of experience and even provided exhilarating and fun sailing for my 16- and 11-year-old boys. This was our first time in a sailboat on the open sea, and no doubt, our boys and I will remember this experience for years to come. You worked so hard on the boat, making this a great experience for us! Thank you!
Sofia_D, Mar 2025
Captain Joe and Abraham were kind, wonderful people. They made us feel safe and they were good company!
Karleen_M, Jan 2025
Captain Joe and Marie were fabulous! They were very good at paying attention to every detail, safty and shared their knowledge of the area.
Sharri_R, Jan 2025
We had an exclusive tour of the bay and the city. The captain and first hand Abraham were great very friendly and informative.
Vladimir_R, Jan 2025
What an amazing tour with Captain Ivan! He made the entire experience a wonderful time for our family. He took the time to share the history of the island and other points of interest. Overall he made the tour a very fun experience! I highly recommend this tour. Thank you Captain Ivan!
Lena_H, Dec 2024
Great trip! The wind and weather were perfect for a sail. The captain and Mrs. Maria were very accommodating and told us a few tidbits about San Juan and PR. Very relaxing!!
Christy_J, Dec 2024
Wonderful time with captain Joe and Edgardo. Informative and fun time. Location can be a little confusing as my Google map showed location slightly off but close enough that instructions got us to where they found us.
From $99.00
per personup to 24 hours before the experience starts (local time)
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San Juan Historical Bay Daytime Sailing Tour
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