Historical San Juan Bay Sunset Sailing Tour
San Juan, Puerto Rico
- 2 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
Go sailing and watch the sunset on a cruise from San Juan. Get great photo ops of Puerto Rico’s coastline and enjoy a comfortable sail on the Caribbean Sea. Your captain shares commentary about the region and provides complimentary drinks for your group of no more than six people.
- Take a leisurely sailing cruise in Puerto Rico
- Watch the sun set over the Caribbean Sea
- Keep an eye out for dolphins
- Small-group tour limited to six people
What's Included
- All taxes, fees and handling charges
- Light refreshments
- Non-Alcoholic Beverages
- Bottled water
- Alcoholic BeveragesBeers, Sangria and Rum n Coke
- Local operator does not accept calls or texts, please read all information thoroughly
- Transportation to the Location
Meeting and Pickup
Meeting point
- Parking482 Avenida Manuel Fernández Juncos, PR-1, San Juan, 00910, Puerto Rico
SEARCH FOR: SAN JUAN BAY MARINA in your online 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.Operating hours.5:00 pm
Itinerary
San Juan Bay (Pass By)
Additional Info
- Confirmation will be received within 48 hours of booking, subject to availability
- Not wheelchair accessible
- Near public transportation
- Infants must sit on laps
- Not recommended for travelers with back problems
- Not recommended for pregnant travelers
- No heart problems or other serious medical conditions
- Most travelers can participate
- no heels, or hard soles
- SAN JUAN BAY MARINA is in Google Maps and Waze.
- We will cancel if weather is rough or rainy. You'll get refunded.
- Maximum passenger weight 275
- We reserve the right of admission
- WE WILL PICK UP AT SAN JUAN BAY MARINA PEDESTRIAN GATE
- We don't accept phone calls
- Show up at least 15 minutes earlier, we depart ** SHARP **
- 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
- Maximum weight 275
- 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
Anthony_L
The Captain/ Owner was outstanding. He was a great host on his “ J “ boat. Fantastic views of San Juan Bay and Old San Juan. He got some great photos of my wife and I! Highly recommended this experience.
Reviews
4.5
based on 759 reviews
Christine_S, Apr 2026
Perfect thing to do in San Juan after a day of exploring the usual spots on land. The sunset and time of day is really great for good sailing on awesome racing J 30‘s. Captain Ivan was extremely professional, a very friendly, capable host, a safe sailor even with strong winds, and very knowledgeable about the history of Puerto Rico, San Juan and the Area.
Our whole family agrees that we made some of our favorite memories from this vacation in those few hours on that sailboat. We had already toured el Morro and Old San Juan - but we learned more here!
the icing on the cake was a locals-only dinner restaurant recommendation from Ivan afterward in nearby Ocean Park- husband and kiddos totally happy.
Make sure you pay attention to the instructions when you register for this excursion, not just the 5pm start time! That is when the boats leave.
They mean it—you need to plan AHEAD for traffic and be there at least an hour to 45 minutes prior to sailing time. Ignore the Viator auto reminders that tell you 5pm! That is when they push off the dock.
Stop at the guard shack, if you are early they will send you through the green pedestrian gate, proceed down around to the Sizzler Terrace and where the sailboats are. Hang out near the J30 sailboats Morcilla/Ivana (ask someone)
The crew will show up probably sometime between 4:15-4:25. Do not be late, 5pm is sailing time NOT arrival at the marina time…
Response from Host, Apr 2026
These customers and many others in the same mindset, make our work worth and also make us proud of what we do.
About departing and location, just wait by the green pedestrian gate at San Juan Bay Marina (its the only entrance) we actually don't want you hanging around the marina by us, because we won't pay attention to you there, since we are getting everything ready, as fast as possible. Arriving before departure time, its just logical, show up before the show starts
Cynthia_T, Apr 2026
Captain Joe was very nice, sailing was smooth, the sangria was delicious 😋 my friend and I enjoy it very much
Brantley_S, Mar 2026
Excellent sunset sail. Trip operator did a good job of ensuring safety, and providing a comfortable, engaging tour.
Karl_B, Mar 2026
Garbage experience. I have photo timestamp proof my party and I were there prior to demanded time on the paid ticket. Then to be refused a refund. I also have competitors to state I was there prior to departure time. 1 star reviews are spot on.
Response from Host, Mar 2026
all other customers who REALLY arrived BEFORE departure time sailed. These guys are not saying the truth, our business is to sail people not to leave them. They showed up apparently late, and tried to convince viator to refund, telling all kind of lies
kathleen_c, Mar 2026
Beautiful sail around different landmarks of Puerto Rico in 3/11/26. Our guide was superb, friendly and engaging. Definitely worth doing
Anthony_L, Mar 2026
The Captain/ Owner was outstanding. He was a great host on his “ J “ boat. Fantastic views of San Juan Bay and Old San Juan. He got some great photos of my wife and I! Highly recommended this experience.
Cindy_Z, Mar 2026
My mom and I went on a sunset sail with Captain Ivan and had such a great time! Can’t beat being out on the water in a sailboat watching the sun go down with the salty wind on your face. Captain Ivan shared interesting history and recommendations with us. I will definitely do this again when I’m in Puerto Rico next time!
Ella_H, Mar 2026
Captain Joe was amazing, this whole experience is awesome. Joe feels more like a friend than a your guide, he’s incredibly knowledgeable. His wife and co captain Maria is amazing as well. 10/10 cant recommend enough.
Loutisha_G, Feb 2026
The boat ride was great from beginning to end! We were greeted at the entrance of the Marina which eliminated any confusion on where to go. Both gentlemen were inviting, polite and informative. The sangria was tasty and the captain (I think that’s the correct terminology) was very interactive with the patrons. I 100% recommend this activity while visiting Puerto Rico!
Response from Host, Mar 2026
Thanks Loutisha! It was a pleasure having you sailing with us
Peggy_M, Feb 2026
Very relaxing. You get a history of old San Juan and beautiful views and the sunset was breathtaking. The crew was great
Chris_K, Feb 2026
Ours was a smaller sail boat which made the experience cozy. We really liked it. Our pictures are really clear and nice.
Response from Host, Feb 2026
Both sailboats in our fleet are J30s, 30 feet racer cruisers, the right size, there's not a smaller one. The smaller you get, the more fun actually
Jennifer_V, Feb 2026
What an awesome and amazing adventure! The captain was so engaging and entertaining with facts about Puerto Rico we had a great time - would totally go again!!
Stephanie_L, Feb 2026
Had an incredible experience with Captain Ivan! He was kind, informative, and kept us safe. We saw marine life, learned history of Puerto Rico, and got amazing recommendations!
We had absolutely no problem finding the entrance and were greeted and brought to the boat on time! Instructions where to meet were incredibly clear and easy!
I would recommend this to anyone in or visiting San Juan and will surely be taking this tour when I visit again.
Anyae_J, Feb 2026
It was a great experience and we loved the drinks. Our captain Joe and Carlos were very humorous and taught us a lot about the island.
Candace_D, Jan 2026
The tour was beautiful! We enjoyed the water and sunset while receiving so much history about San Juan from our guide Abraham. He was amazing! Very knowledgeable and made sure we enjoyed ourselves!
Dave_D, Jan 2026
One of the most memorable things ever from all of the trips we’ve made to San Juan. Book it! Don’t delay.
Pallavi_S, Jan 2026
I never got my tour- the tour operators did not provide exact meet up location- we waited over an hour! Do not recommend.
Response from Host, Jan 2026
Not true. This review is the typical anwer from an incompetent. If you are a responsible person, you will be among a whole population of happy 5 stars customers who sailed in the las t 12 years. Book responsibly, do not depend on calling by phone, look for San Juan Bay Marina in maps and arrive BEFORE departure time.
Leslie_C, Jan 2026
We have been in old San Juan and walk the outside wall many times but never seen it from the Ocean. It is a beautiful new perspective and at sunset the temperature was ideal and the light magical. We highly recommend it for Winter, as I am not sure how the timing will work in summer with the sunset.
Hannah_W, Jan 2026
Tour guide was amazing and super friendly and knowledgeable. Was nice talking with the other passengers.
Melissa_O, Jan 2026
Captain Ivan was wonderful. Very personable and knowledgeable about the area. He made us feel like long lost friends. Great recommendations for local food. Gave us plenty of opportunities to take amazing photos.
Kiara_R, Dec 2025
We showed up at 4:50 and there was nobody at the marina bc the don’t allow calls we couldn’t get in touch with nobody and nobody was responding to our text messages we sit there until 5:45 without a response lucky the bathroom was unlocked and it was food trucks with drinks n food lucky we book though a 3party and is trying to get a refund because if we was to book directly with them I doubt we was going to get a refund for them not being a no show
Response from Host, Dec 2025
Our business is to sail not to leave people who paid without sailing. The meeting point is the only pedestrian entrance, not the food truck nor the bathrooms. These guys weren't at the meeting point and we left with the ones who simply showed up BEFORE departure time at the pedestrian gate of San Juan Bay Marina. 43,000 other showed up, the few ones who don't, loose money, loose a sailing trip, loose valuable vacation time . . . . . and they probably are very use to it, loosing.
Arrive earlier than departure time, read our description, don't make phone calls . . . be a winner, let's sail!
Michael_R, Dec 2025
I had imagined a larger boat with more seating but it was fine. Clouds obstructed what might have been a perfect sunset but still nice.
Rita_P, Dec 2025
It was a great sunset tour. Had a nice sangria to celebrate my husband’s 60th birthday trip. The captain and crew were amazing.
Laura_W, Dec 2025
Meeting directions were not good. We were told to go to a green gate. We did. Now they say it was the pedestrian gate. No way to contact them.
Response from Host, Dec 2025
The address is the same that has been used by 43,000 tourists who sailed with us. These winners searched San Juan Bay Marina over the online maps and waited by the green pedestrian gate (its the only entrance)
All 1 stars are the ones who missed the sail because they weren't at the meeting place BEFORE departure time
If you pay for a show, make sure your arrived BEFORE it starts, because it is going to start without you and you will loose your money.
Richard_E, Dec 2025
Find another tour. Stay away from this one. The instructions were incorrect and told us to go to the Guard Shack. The guard had no idea what to tell us. We arrived at 502 and by the time we got to the diock, they were gone. Tried to reach them by phone and they did not answer. Texted the operator and they told us to get over it 4 hours later. Here is what the operator said...
Not showing up, is no reason for refunds. Showing up early is your responsibility. 10 other tourists did showed before departure and sailed happily. We managed to buy a little extra time, to waiting for you to show up at the meeting place, the green pedestrian gate, we departed without you at 5:08pm. The sailboats can only take 6 people, as you probably read, so missing two does has an effect in a micro business.
We would have been happy with a reschedule. Find another tour. Someone that is more tourist friendly.
Response from Host, Dec 2025
** 1 stars means = didn't show up **
Showing up early enough for the "show", will prevent you from missing it. Is impolite to make other responsible ones to wait, for the ones who didn't care enough to show up.
We have sailed 43,000 since 2014, and still we are enjoying taking people sailing by the historical bay of old San Juan, because is about wind, sails, drinks history and happy conversations, among people with good vibes, happy campers kind . . . . . and yes, our business rules strains the irresponsible bad kind that we don't want to sail, The 1 star type.
We go in groups of maximun 6 per sailboat, and that's the reason it feels personal and special. We don't believe on sailing crowds, taking the phone to answer info already posted or explaining directions, we are not tourist trap . . . . we are an authentic sailing trip.
Lisa_S, Dec 2025
What an incredible experience! The sunset sail was intimate, relaxing, and absolutely beautiful. Our captain was interesting, knowledgeable, and genuinely funny—he brought so much personality to the trip and made the whole experience feel special. He also pointed out some fantastic local spots to eat, which we really appreciated. I can’t recommend this sail highly enough. A perfect way to end the day!
Steve_E, Nov 2025
We enjoyed our sail with Ivan. He showed us the sights around San Juan Bay. Was a beautiful night and temps were perfect. The Sangria was not bad either.
Sandra_D, Nov 2025
I had an amazing time on the San Juan Bay sunset sailing tour! Our captain was fantastic! He was knowledgeable, friendly, and had great insights about the area. He also shared some restaurant recommendations. The sail itself was so relaxing and the perfect way to unwind and end the day. Highly recommend this experience to anyone visiting San Juan!
Robert_L, Nov 2025
Fun captain with historical knowledge of the area.
Seating arrangements were 4 seats at the back. 2 seats up front.
Good mixture of calm waters and more adventurous waves. Gorgeous sunset views and an overall authentic sailing experience that did not disappoint. 10/10 will do again!
Kunal_D, Nov 2025
We booked this sailboat experience very last minute on our last day in San Juan and had a wonderful time sailing in the Puerto Rican waters. Our sailor Captain Ivan took our pictures with some really nice backgrounds and gave us a lot of good history of PR. He also offered Rum n Coke, Sangria and beers as a part of the experience. Highly recommend if you are looking for a nice chill evening on the water with Ivan.
From $119.00
per personup to 24 hours before the experience starts (local time)
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Historical San Juan Bay Sunset Sailing Tour
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