Old San Juan Sunset Sail

A fun way to get a different view of San Juan and Viejo San Juan. We left the dock right on time and enjoyed rum punch, snacks and interesting historical information provided by the excellent sailors on board. Great views of the harbor and the sunset. Plenty of excellent photo opportunities. Highly recommend!

We had the BEST time on this sailboat cruise! My husband planned this excursion for one of several 50th birthday surprises that he made for me in March 2023. The sunset cruise exceeded our expectations. The rum punch flowed freely and they had wonderful appetizers / finger foods, which we were not expecting. We probably could have made a meal out of it and next time we'll know not to eat dinner ahead of time! The crew was super fun and they mixed and mingled with all of the passengers. My husband volunteered me for a fun little event they do by selecting one of the passengers to fire off a little mini-cannon near the fort, so that was a fun memory. We enjoyed our time talking with several of crew including Diego, Fernando and Captain Dan, as well as others that we can't remember their names, but all were friendly and awesome! We highly recommend this cruise!

Beautiful experience enhanced by music provided by one of the guides, Ezra Imaizumi. I have recommended this to friends and they subsequently lived it, too.

We went with people of all ages and everyone loved it! I could not recommend this more. We had drinks and snacks that were included. The ship is beautiful and the staff were all personable.

Wonderful sailing experience. Our captain, Hiram, was informative and entertaining. I highly recommend this tour. Tapas and open bar included!

Our group of friends (with some spouses & moms along too!) really enjoyed this sunset cruise! The old fashioned schooner was really nice, the crew was awesome, and the whole experience was very fun. We had a good variety of drinks (rum punch, wine, beer, vodka drinks, etc) and small snacks (cheese/meat/cracker trays & ceviche). Our captain was funny and shared some great history. The trip lasted 2 hours and it was smooth sailing the whole way — with gorgeous sunset views. Highly recommend!!

Absolutely amazing. Great service great drinks. Captain was very knowledgeable with a great sense of humor. Very relaxing and chill. Would highly recommend and would do it again

Staff was great and it was beautiful scenery. The rum punch is delicious and snacks were provided. Beautiful sunset and not too cold on the water.

Overall the sail was good. The crew were friendly, attentive and gave us a good overview of what we were seeing, the history of the area, etc. and we enjoyed interacting with the other guests on board. The boat is on the smaller side, not a lot of room to move around. We unfortunately were dealing with incoming bad weather, so the boat left early and we were back within an hour, instead of a 2 hour sail. We were still able to get to the tip of the peninsula to see the Castillo San Morello from the water, which was pretty cool, as we had spent a lot of time walking around inside it earlier in the day. But we had to turn around right after that as the water was very rough once you rounded the corner out to the ocean. We also enjoyed the young gentleman who played guitar and sang for us. A few things that could have been done better: our email said to be at the meeting point at 445 for a 530 sailing time. We thought that seemed a little early but, ever ones to be on time, we actually got there at 430. Good thing we did as we actually LEFT the dock at 445 (because of the incoming weather), but we did not receive any prior notification to the change to the sailing time - if we had not gotten there early, we would have missed the boat. While they said that they were leaving early to allow us to have the experience, to be honest, it felt like they were rushing us out on a short tour, so that they didn't have to rebook us or refund our money due to the sail being canceled due to bad weather, as their info shows. We did not receive a partial refund due to the cruise time being cut in half. The appetizers were just that - small turkey and cheese sandwich pinwheels and small pieces of toast with some meat/veggies on it; based on the description given I would have expected something a little more upgraded. They did provide water, rum punch, beer and wine as advertised. Due to the above issues (and I realize the weather played a large part in it) I felt this was somewhat overpriced; it would have been nice to receive a partial refund (for instance, the afternoon sail, which is advertised as 1.5 hours, is $99) or to be able to reschedule/get a refund if we desired. And pre-sail communication could have been better.

Wonderful cruise with a great crew. The crew did a great job. It was so fun to watch them work the sails. A special call out to Ezra with his great enlargement on the guitar and singing.

It was so special, safe and memorable. The crew was fun and added a lot of info for the trip. The beverages and treats were a plus, we were surprised they were included and were so good. Only wish it were a longer cruise. Loved it and would consider it again on another trip. So glad it was a option for us to share on our 61st Wedding Anniversary. Thank You to the crew ! Gerald and Sheri

Great staff and family friendly! Great views of old San Juan and El Morro from the water. We even got to see cruise ship leaving dock as we returned. The staff was engaging with guests, plenty of refreshments for adults and kids!

Very attentive and friendly crew and beautiful evening for a sail. It was cool seeing all of the cruise ships as well.

Cancel for weather condition 🥹 2 day maybe next’s time so sad 😭 you call 📞 to cancel and thanks for safety

Amazing little trip to see the fort of old San Juan. Got some great pictures. The staff are amazing!! Even got a little concert and knowledge of the city is great! Drinks and appetizers were spot on. They always made sure you were taken care of.

Must see experience that everyone should do.... great host, vibe, food and drinks... really great experience.

Our sunset tour around the Old San Juan area was beautiful! The guides were fun and educational. They made it a wonderful experience. The office staff was also very helpful as we needed to reschedule because our flight got in so late. Thanks everyone! Highly recommend!

I loved when Ezra sang and played the guitar. Everyone was so amazing. Diego was very attentive and answered all of our questions. I highly recommend this excursion if you are in San Juan. The historical information was amazing.

The evening sunset sail on 3/19/23 was wonderful. The crew was kind, funny, accommodating and full of great information of sites throughout the harbor. Highly recommend. Don’t forget to tip generously and enjoy?

We had a great time. Great crew, Oz, Kevin, Alan… all friendly and informative. We had a fun time sailing through the San Juan bay/harbor

This was the highlight of my trip! I highly recommend it--it includes an open bar with signature drinks and hors d'oeuvres. The captain and guides were very attentive, and we had good interpretation of historic sites. Ezra played/sang a couple tunes on guitar (one original composition), which was awesome. Really beautiful evening on a beautiful tall ship.

This was a great time. The crew is amazing. The drinks were excellent. Informative, fun, and relaxing.

Really wonderful and relaxing trip! We loved the crew and being able to kick back with great drinks and appetizers. Many thanks!

We had a great time on the Amazing Grace with Ezra, Fiona, Kevin & Danny! It was our kids (4 & 6) first time on a boat and the crew was super sweet to them — they had a blast. They got to blast the cannon, steer the ship and honk the horn! Defiantly memorable and I know they’ll be talking about it for a while. More importantly the drinks kept coming for the adults - rum punch sneaks up on you :) you also get a little bit of a history lesson. Great way to end our trip to PR. If you’re driving to the Old San Juan Marina make sure you allow plenty of time to find parking at peak time! We went on a Sunday. There was insane traffic to get into the area.

It was a great experience. The views of the bay and the old city are beautiful. The crew, was extremely attentive and kind. Ezra even sang and played the guitar for us which was fantastic.

The best sunset sail I’ve ever been!!! Ezra, John, and Dani did a great job even though they were short staff they managed to give the best trip… drinks and food was amazing I gotta say I have the best birthday

My friends and I had an amazing time! The staff onboard was amazing, especially Diego and Fiona! Was definitely a highlight of the trip!

This was a fantastic evening 10/10. Wonderful crew, lovely sail. I would do it every day if I could 💙 Thank you!!!!

Staff was friendly and respectful. We ended up boarding last, and appreciated the phone call (we were in the parking lot) to check and see where we were. They set up pillows at the back of the ship for us to sit on and we had a more private area for our group! We saw some dolphins and also learned some history. Food and drinks were great and we always had something in hand!

This was so relaxing! The views of the harbor and the fort were amazing and the crew was great! I would definitely recommend this trip.

So much fun! Diego and Ezra were funny and professional and took very good care of us. There were lots of other people staffing the boat but those were the guys who we interacted with most and I have an awful memory for names! Great drinks and snacks, good conversation with fellow passengers and, of course, the scenery can’t be beat. It was a wonderful way to end our visit to San Juan.

What a beautiful way to view OSJ from the sea! The crew onboard did everything possible to make us feel welcome and ensured a great time was had by all. They took exceptional care of us, were polite, professional, funny and friendly. We 100% recommend this gorgeous sunset cruise!

Perfect afternoon sail for unwinding. Beautiful sceneries and excellent crew. Highly recommended if you have some spare afternoon time.

Fun, relaxing, family friendly, and educational. The drinks flowed freely, but this was not a frat party. No one was too drunk. The snacks were light, but good. The mates were very helpful. The first mate was very knowledgeable and shared a lot of interesting information about San Juan. He spoke English like a mainlander and was easy to understand.

Crew was terrific! They made the whole experience fun. They had great energy and made sure everyone had a good time

We did a sunset cruise with Ezra, Jaime, Diego, and Captain Danny. It was fantastic. The drinks were free flowing, the snacks were great, and the vibes were immaculate. Highly recommend!

The crew’s sailing expertise was top notch. They were also friendly, knowledgeable & professional. There was a nice variety of drinks available and the crew was very attentive, so you never had to wait for a refill. The snacks were just right; first pita chips with ham, salami & cheese slices followed shortly by ceviche, crackers & crab. All were delicious. The views were fantastic & the salsa type music made the experience even better. You are seated for most of the time, unless you need to use the facilities located below deck. Sandals are fine to wear if you’re steady on your feet. You’re allowed to bring a bag/backpack, although it’s nice not having to worry about it going over or being in the way of the crew as they man the ropes or hoist the sails. A small crossbody bag would be best if one is needed. Having a light jacket is not necessary but rather a personal preference/weather temp dependent item. A parking lot is located directly across from where you depart and was only $5 when we went. This was a fabulous experience, be sure to include it on your itinerary! ⛵️

Was an absolutely wonderful experience! The entire crew - Diego, Fernando, Dan, Ezra - were so professional and friendly. The view of Old San Juan was gorgeous and is a must see for anyone visiting.

The crew were very knowledgeable and kept the drinks coming! It was a great way to end our trip to Puerto Rico. Beautiful views, learned something about the culture, and had great food and drinks. Highly recommend!

These guys were awesome!! They were extremely friendly, funny, and a blast to hang out with! They served us all the drinks and appetizers you could want and were super friendly. The tour went through the bay and went over to the fort for a spectacular view of the island. They gave a good history lesson and everyone had an amazing time! Thank you and we would definitely do it again!

From the moment we stepped on board this was a wonderful experience. The fun started immediately with rum punch and snacks as we sailed around the harbor. The music was great and the pauses for brief historical lectures were very informative. Being out on the water, the breeze, the sky, the clouds and the sunset – it was all enchanting! Many thanks to Diego, Fernando, Jan and captain Dan, our very competent, knowledgeable and attentive crew. Go ahead and book this trip. You will not be disappointed!

It was a fun trip, learned a lot of new fun facts about Puerto Rico. The crew was amazing, very attentive!

It's a beautiful tall ship, the views were spectacular, the drinks were delicious, and most of all the crew was fantastic! Fernando, Fiona, Danny & John, thank you so much for providing us with such a great experience. Fernando especially deserves a shout out for how entertaining he was. I would recommend this trip to anyone who likes ships and sunsets!

Just had a truly enjoyable time on the 2-hour sunset sail around the harbor near old San Juan and the forts. I (a charter boat captain myself, in the US Virgin Islands) was one of a group of 14 celebrating a birthday, so we were looking forward to some nice views and drinks on the water and were not disappointed. From our arrival, the crew was friendly, accommodating, and safety conscious. The 80'+ gaff-rigged schooner was clean, well maintained, and roomy for the number of guests aboard. Diego welcomed us and informed us about the safety features of the boat, and along with Ezra and Fernando attended to everyone with drinks, snacks, history of Puerto Rico and personal interaction. Captain Daniel navigated smoothly on a nice breezy day to provide us with some amazing views. The entire crew's level of service was excellent! It was a thoroughly satisfying way to have some cocktails, be on the water and see Old San Juan.

What an awesome cruise! The team was amazing, funny and very very kind! Beautiful sunset and the best way to end an evening. I highly recommend and would love to return on our next trip

A memorable trip with a friendly crew, a beautiful sunset, spectacular views, and more than a few cocktails. Highly recommend.

Wow what an amazing experience! The staff and captain were so knowledgeable and friendly. Really made our first sailing experience memorable. Highly recommend this excursion.

Probably one of our favorite activities we did in San Juan! Food and drinks better than expected. Crew was very friendly

Amazing sunset cruise in Old San Juan! The guides were knowledgeable and helpful and the sights were amazing!