San Juan

Sunset Sail by San Juan Historical Bay

San Juan, Puerto Rico

From $93.00

Select Date and Travelers

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


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
  • Beverages
  • Bottled water
  • Alcoholic Beverages
  • Local operator does not accept calls or texts, please read all information thoroughly

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 your online maps. ** WAIT OUTSIDE BY THE GUARD, STAFF WILL PICK YOU UP ** *** We won't be able to take phone calls or chat ***

Start time

05:00 PM

End point

This activity ends back at the meeting point.

What To Expect

San Juan Bay (Pass By)

Castillo San Felipe del Morro (Pass By)

La Fortaleza - Palacio de Santa Catalina (Pass By)

Additional Info

  • Confirmation will be received within 48 hours of booking, subject to availability
  • Not wheelchair accessible
  • Dress code is smart casual, no heels, no hard soles
  • 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
  • SAIL SAN JUAN BAY is in Google Maps and Waze.
  • We depart on time ** SHARP **
  • We will cancel if weather is rough or rainy. You'll get refunded.
  • Maximum passenger weight 275
  • We reserve the right of admission.
  • Look for SAIL SAN JUAN BAY in maps, to find the entrance
  • Maximum weight 275
  • Most travelers can participate
  • 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
Fabulous views of El Morro and Old San Juan. Sunset was magical. Captain Joe and Abraham were wonderful tour guides. Fantastic stories and 30+ years of experience. Excellent refreshments. A lovely way to spend the evening after a late lunch or early dinner!


432 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 432 reviews
No contact with the host
Sabrina_A, May 2023
Impossible to get in contact with the host. Do not recommend this excursion. It shouldn’t be impossible to contact the hosts. Missed the experience and was not able to get a refund.
Response from Host, May 2023
The contact with the host, happens WHERE IS NEEDED. As a captain and as a tour guide, you'd get the best service. To reach the location or any other info, there are better sources, like ggle, web page, your reservation info, captain's texts to repeating the previous . . . . Our operational system is designed to strain people who needs extreme unnecessary attention. We are only 2 captains and couple of mates, who have lost their phones and many family and friends conversations just to answer questions about locations, and what we do over the phone . . . . Over 30,000 other happy customers who did sailed, read info online and reached Sail San Juan Bay like anybody else does, using a map. Responsible ones are majority! I'm glad to say that the toxic kind, don't sail here and use their lack of intellect to write a bad review, when they failed trying to, and to blaming others for their incompetence.
Excellent time! Book it
Jeff_C, May 2023
Amazing experience! Ivan is an excellent captain, super knowledgeable and proud of his home. We had an awesome time. Would def book again.
desire_l, May 2023
The boat ride was relaxing and the tour guide was very nice. The guide told us a lot about the history of old San Juan as well I would definitely recommend this excursion
Andrew_F, May 2023
We had an amazing time! The captain and his mates where very knowledgeable. The other guest we sailed with where quite fun!
Very nice trip
Alan_H, May 2023
It was a very nice experience! They were very accommodating to my pregnant girlfriend and we had a good conversation the whole trip. Super friendly couple , with good sangria, would for sure recommend.
Response from Host, May 2023
Thanks for sailing with us! Regarding pregnant woman, not all pregnant woman can do this, in this case was a very healthy pregnant woman, and she definitely enjoyed the sailing, the wind conditions cooperated to sail smoothly
Great experience and very...
Andrew_S, May 2023
Great experience and very relaxing…even got to steer the sailboat on the way back. Would definitely recommend!
Nice voyage!
Marcia_G, May 2023
We had a wonderful informational voyage with good company, yummy sangria, and clear weather! Definitely recommend!
Great experience!
Janis_W, May 2023
We had the pleasure of taking the sunset sail with Sail San Juan Bay. Booking was easy and finding the pier was not a problem. (Highly recommend taking an Uber) Our captain was knowledgeable and engaging. What a great opportunity to see the bay by sailboat.
Wonderful experience
Derek_B, Apr 2023
Ivan was a great tour guide. We had a wonderful time. Highly recommend the sunset sail. Everything surpassed our expectations.
Would do it over and over
Cathy_W, Apr 2023
We were running a bit late and the captain waiting for us, made us feel right at home and made sure we felt comfortable and we’re enjoying ourselves
Joe and his wife were...
Xavi_C, Apr 2023
Joe and his wife were excellent hosts. Joe was explaining us old histories about PR and himself while his spouse were serving us lovely drinks. A nice calm sail through the bay and we get out a bit to see La Perla from the sea.
Wonderful sunset sail
Shwetha_S, Apr 2023
Wonderful experience! The captain kept the entire sail entertaining with stories and facts about San Juan (and the Bermuda Triangle). They also engage our kids in lively conversations. Would highly recommend.
Peaceful Sunset Sail
marika56, Apr 2023
My mother and I had a wonderful sunset sail. We sailed with 4 young ladies visiting San Juan from New York. The captain and his wife, the crew, shared personal stories and the history of San Juan’s ports and buildings with us. He was sure to take our photos as the sun was setting. The sunset sail was a wonderful excursion. A++
Bermuda Triangle
Michael_A, Apr 2023
Entering the Bermuda Triangle was fun. Initially scared but the water waves and other passengers on the boat made it fun.
Unable to get onto the boat
Patricia_C, Apr 2023
I wasn’t able to get on the boat. It was very unsafe. The description should have included that it was for people in hood, strong physical condition. I was very disappointed. The ship captain was very kind and tried to help, I successfully.
Response from Host, Apr 2023
Reading is as magical, such as the Disney operation she was expecting!. Just by the way we describe this activity any person with disabilities would be discouraged. We have a floating dock that moves a little, and it is required to climb over a railing of 18 inches high. It could be too much for somebody with mobility restrictions, so is not recommended for individuals over 250 that are not agile. It is very vicious to classify us this way, because even though it is her fault for not reading, we REFUNDED full. As I said previously, some people are full of poison and this business has its ways to leave them out
Good ride with pretty views
Benjamin_M, Mar 2023
Hard to hear the tour guide because we sat in the front, but they were kind and the trip was fun. Very pretty!
Response from Host, Mar 2023
We specified to people who seat in the front that one of the advantages is the sense of privacy, drinks will be delivered express to you and you won't hear my broken english . . . this is a five stars for the rest of our imperfect world
Great tour
Lanescia_W, Mar 2023
Good experience, The hosts were very knowledgeable and fun to be around. They let us play music, gave us some drinks, and talked about the history of San Juan.
We had a wonderful time. ...
SarahA_R, Mar 2023
We had a wonderful time. The sailboat was comfortable and the captain very friendly and knowledgeable. This was a great way to spend an evening and the sunset was beautiful!
A Serene Sail
Cait_T, Mar 2023
What a lovely trip around the bay with Captain Ivan. I loved the casual small group experience. I booked this excursion as a solo traveler and it was a great way to learn about Puerto Rico, meet new people, and get authentic local recs!
Sunset sail
Theresa_E, Mar 2023
Captain was very knowledgeable regarding the area and history. Even on a somewhat cloudy day the sunset was very pretty. The sail boat was much smaller than expected and we were glad that several guests did not make the trip as it would have been more uncomfortable. Seating was very uncomfortable.
Response from Host, Mar 2023
We are not a Disney ride with fake sailboats and bucket seats, we are neither the typical mass production tour boat that takes a bunch all packed aboard something that looks like a boat . . . This is real! We actually say that in our activity description, but some people don't read it. This is a real J30 racer cruiser sailing boat, that will take you sideways in an authentic sailing trip, with the wind power, feels personal just up to 6 people. You'll have complimentary drinks listening to the splash of the water, sightseeing historical icons, learning some history having a nice conversation with others in a low voice because there is no engine noise.
Awesome and Relaxing!
Allison_B, Feb 2023
Captain Joe and Abraham created the most magical experience on the sunset sail. They were friendly, funny, knowledgeable, and professional. I loved the little tips and information they gave us about the sites we were seeing, as well as Puerto Rico in general. There were only 5 passengers on the vessel, which created the best experience possible (as opposed to other sailings which are large and crowded). Would 100% recommend this!!!
Captain Joe & Maria Gave An Incredible Sail
David_E, Feb 2023
Captain Joe was wonderful and so was Maria his wife and CoCaptain. They shared wonderful info and history of Puerto Rico and have a very clean and well maintained 30’ sailboat. It was a wonderful experience complimented by extremely tasty sangrias!
Sheryl_K, Feb 2023
They overbooked by several people so unfortunately, even though we showed up on time, we did not get to sail. VERY disappointing. Can not recommend.
Response from Host, Feb 2023
Unfortunately, we make mistakes . . doesn't happen often. We manage a considerable volume of sales with limited resources, and we want to keep it that way. If you go to a Disney attraction this doesn't happens. We apologized to this customer and offer them a free sailing trip at another time. Apparently they couldn't take advantage of it
Great experience ! Fun and beautiful.
Linda_Y, Feb 2023
Captain Joe’s stories. The whole experience Met some nice people Weather was perfect. The service and care of our safety was excellent. Drinks were great! We laughed a lot
One of the highlights of our trip!
Meredith_C, Feb 2023
This was SO much fun, and truly such a special experience! I recommend it highly. This was the real deal - not a touristy party boat. We enjoyed a gorgeous sunset sail with a very small group, and our captain was so fantastic. He really engaged our 11 year old son, gave a wonderful tour of the San Juan coast, and gave us some great restaurant tips along the way. A really memorable evening.
Amazing experience worth every penny and moment
Sean_M, Feb 2023
It was great to get the conversation around actual sailing in the area beyond just an historical inventory of the buildings around the bay. A true sailing experience complete with listing into the wind and running your fingers in the water.
Best Valentines Day ever!
Annie_S, Feb 2023
The best. So private so romantic. An amazing guide that was so welcoming. Couldn’t recommend this more!
Response from Host, Feb 2023
Celebrating your important events in live with us, make us very proud. Thanks
Don’t do it
Stephanie_F, Feb 2023
Choppy scary dangerous ride and they at us at the front of the boat. No life vest, nothing to hold on to. I would never recommend. $200 down the drain. Don’t expect snacks either just a scary ride
Response from Host, Feb 2023
This is a smooth sailing ride, it's an authentic sailing boat, no Disney not crowdy mass tourism. Many of our customers, who are afraid of the water and don't know to swim, read in our description where it says that this is an authentic sailing trip that goes side ways and that a drink can be spilled, and knew what to expect. 31,000 enjoyed this ride without any problems. Our sailboats are inspected by USCG and the PFD1 (LIFE VESTS) are for emergencies, not comfortable to be used to enjoy a sailing trip. People who seat in the front of the mast, they hold to the mast halyards with no problem.. We have had no accidents in 9 years. There's no money refund once you sail, that's why this customer got so mad, they were safe at all times, enjoyed their sailing and wanted their money back with a cheap excuse.
Rona_P, Feb 2023
Captain Ivan's Narration and great ability steering his craft. Only 4 passengers which made it all the sweeter.
Response from Host, Feb 2023
When there's 4 only, it become a little sportier, and people love it. We can sail up to 6, never crowdy! Never mass tourism
Better suited to 4 people not 6
Rosalie_P, Feb 2023
Booked this tour with another couple. Says the boat holds six, but it’s more suited to four. Four passengers sit on benches in the back and two people sit on a cushion on the front of the sailboat holding on to ropes when the boat leans. We were situated in front so separated from the people we were traveling with. Couldn’t hear anything the captain was saying back there and weren’t able to talk to our friends. We were disappointed.
Response from Host, Feb 2023
Yes, it is for 6 people who wants a sailing trip aboard an authentic racer cruiser sailing boat. This is NOT the typical mass production boat tour, we specified on all our marketing, we don't over sale it. We say that this is an authentic sailing trip, that goes side ways and spill drinks sometimes . . . . . 31,000 people sailed here and many rated it 5 stars. We do the unexpected to just sailing the right, who read descriptions and arrives to location responsibly, but still there is people who show up that shouldn't have left their cushioned reclinable chair and their tv . . Our sailboats are J30 racer cruisers, that goes faster, sideways and doesn't come with bucket leather seats, and that's exactly why these experience is the envy of other mass touristy boats. Seating in the front of the mast is where many ones love to sail, because is apart, it's vip and it's private . . . . and you won't hear the others chat.

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