Top San Juan Sailing Trips

The experience was amazing!! Not only is this a sunset cruise, it is also a historical/ sightseeing/ party/ celebration cruise. The team was very knowledgeable and accommodating. They tended to every need and ensured you got the most out of your experience.

Very knowledgeable leader. Very good instruction and led us to see turtles and large schools of fish.

it was so much fun the crew was the best they made our day and my daughter birthday special food and drinks were great to !! would def do it again when in san juan

10/10 the tour guides were amazing made me feel so comfortable

Wonderful experience on this sunset sailing trip. The captain was very personable and extremely knowledgeable about the history of Puerto Rico. Drinks were included and delicious. A relaxing and low key vibe. Just a really fun and amazing sailing experience. Would definitely do it again next time we are on the island.

Very Relaxing tour. Enjoyed the scenery

My parents and I chartered Jimbo’s sailboat out of San Juan for my 30th birthday, and it was easily one of the highlights of our trip to Puerto Rico!Our 3-hour charter ended up being about 3.5 hours, because Jimbo was in absolutely no rush to get us off the boat. He even offered us complimentary, completely optional sailing lessons. You could either sit back, relax, and enjoy the ride or get hands-on and learn how to sail. My stepdad especially loved the unexpected opportunity to learn how to steer and help sail the boat!We started in the bay and headed out toward the Atlantic, passing some incredible sights along the way, including the Governor’s Mansion, the red-door entrance into Old San Juan, Castillo San Felipe del Morro, Castillo San Cristóbal, the historic cemetery along the oceanfront, La Perla, and the Puerto Rican Capitol.Jimbo had a cooler full of ice ready for the food and drinks we brought onboard, let me control the Bluetooth radio with my own phone and playlist, and even had a bathroom below deck. We spent the afternoon with our feet in the water, soaking up the sun, enjoying drinks, listening to music, and taking turns helping with the sails and steering while Jimbo guided us the entire time.The 3 hours flew by, and honestly, I wish I had the option to book a longer charter! Jimbo was knowledgeable, laid-back, attentive, and made the entire experience feel personal rather than rushed or touristy.He also mentioned that he offers sunset and evening sails for anyone who wants to see Old San Juan lit up at night — which is definitely on my list for next time!If you’re visiting San Juan, I highly recommend booking with Jimbo. We had an amazing time and would absolutely do it again! ⛵️🌴☀️

I had a wonderful time, far exceeded my expectation

It was absolutely amazing ! So peaceful and calm. Very professional. Would absolutely recommend. Captain Rafael and Victor were the best !

What an amazing excursion!!! Ivan was so pleasant and informative. Ivan was so kind! Will book again.

Informative and pleasant sail around the harbour. Be sure to wear sunscreen l, there is no shade. Water is provided.

Experience was so good, definitely would recommend and would do it again. Vibe was awesome and people that was also there where very friendly. Crew gave a good tour and had knowledge and where funny. Definitely a must do.

Great experience seeing San Juan with Captains Joe and Maria. It was educational and beautiful seeing the dolphins while learning of the historic beauty of San Juan.

The sunset sail was a wonderful experience. We seen the city walls from the bay which is a completely different perspective everyone should enjoy. Light snacks and sangria was provided and the best sangria I have ever had! Thank you for the wonderful experience, highly recommend!

What an incredible adventure! Thank you, Captain Jimbo!You made my 7-year-old daughter, who was absolutely terrified at the thought of sailing, fall in love with it. At first, she was in tears, and I honestly never imagined she’d calm down, let alone be smiling and laughing while the boat was heeling over. By the end of the trip, she was having an absolute blast!Thank you for your patience, encouragement, and for creating such an unforgettable experience. We’ll definitely be back!

Sérgio and Robert were great. Very knowledgeable and funny.