Picture of Sailboat on Atlantic in Puerto Rico.  Sail Old San Juan.
Picture of sailboat in front of Fortaleza the governor mansion of Puerto Rico.
Picture of Beneteau sailboat sailing upwind in San Juan Bay, Puerto Rico.
Picture of Sailboat under El Morro in San Juan.
Picture of asymmetrical spinnaker on Chili Pepper, a Beneteau sailboat.
Picture of woman waving from sailboat in Old San Juan.
Sailboat Chili Pepper sailing in the St Thomas International Regatta

Sail Old San Juan  |  San Juan, Puerto Rico  |  787.340.7567

All Sails are with a U.S. Coast Guard licensed Captain.  Our Captain and Staff are Vaccinated for Covid 19.

Private Day Charters – $290

Daytime charters for private groups of up to 6 passengers.  Day sails from San Juan for up to 2 hours, additional hours on request ($95/hr).  An exciting group adventure on a performance racing boat.  Day Charters can be booked at 10 am and 2pm (other times may be requested).

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Spinnaker Adventure Sail – $490

The adventure sail is for couples or private groups that want a thrilling sailing experience.  Captain and deckhand unfurl the asymmetrical spinnaker in the trade winds of San Juan. This is when the boat reaches top speeds and guests experience sailing at its best.  Groups are limited to 4 passengers.  Adventure Sails can be booked at 10 am (other times may be requested) and are approximately 2.5 hours. Be prepared to get wet and hold on.

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Private Sunset Charters – $390

Sunset charters for private groups of up to 6 passengers.  For those who want the privacy of chartering their own boat at sunset.  Complimentary beverages are included.  Sunet sails depart at 5pm (other times may be requested).

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Sunset Sail – $75 per person

An evening sailing cruise around Old San Juan.  Captain sails under El Morro of Old San Juan in the early evening.  This can be the most pleasant time to sail, with gentle breeze and cooler temperature.   Complimentary beverages included, trips last approximately 2 hours.  Sunset Sails depart at 5pm (other times may be requested).


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Question : “What do we bring?”  Answer:  Hat and sunglasses for day sails, camera, comfortable clothes.  Boat shoes if you have them (no street shoes please).

Q: “Are drinks included?” A: Yes; water, beer, rum, and soft drinks. Spanish Cava or Rose for sunset sails.  Please make special requests if you have any.  Ask about the key to the Captains Cabinet for select offerings.

Q: “Are you licensed and insured?” A: Yes, all sails are with a US Coast Guard licensed captain and the vessel has commercial insurance.

Q: “Will I get seasick?” A: No, you shouldn’t.

Q: “Do you sail on the ocean?” A: Only if you request and the conditions permit.  Over 90% of our sails are on San Juan Bay where it is calm with minimal motion.

Q:”Are there age restrictions?” A: Toddlers are allowed but not recommended. Children under 12 must wear a lifejacket at all times.  There is a certain level of physical exertion necessary, so frail persons should consider.

Q:”Do I need to help?” A: No, unless you desire.  Guests are invited to help trim or steer the boat, but it is not required, and are invited to simply sit, relax and enjoy the scenery.

Q:”Can I bring music?”  A: Yes, please do, our stereo is bluetooth enabled and guests are invited to play their own tunes.

Q:”What if it rains?” A: Showers are common but generally last just a few minutes.  Sails are cancelled and fully refunded with no processing fee if severe weather exists or the captain determines that conditions are unsafe.

Q:”Do I need to reserve?” A: Yes, all of our sails are booked in advance.  Refunds are issued with 48 hour cancellation notice, subject to 5% processing fee.

Q:”Can I book a private sunset sail?” Yes. Occasionally couples are grouped together on a trip.  If you would like a private trip, please book a Private Sunset Sail.

Q:”How many passengers are allowed?” A:  A maximum number of six passengers. Standard occupancy is between two and four.

Q:”Do I need to book in advance?” A: Yes; if you already have a date in mind, the sooner the better. But last minute sails happen all the time, just call and ask.

Q:”How do I reserve the day and time?” A: On our online booking system. Please call or email if you have any questions, concerns, or special requests.

Q:”Are payments secure?” A: Yes, everything is booked through Stripe.

Getting here...

Location: San Juan Bay Marina The San Juan Bay Marina is located behind the Sizzler restaurant at the San Antonio Bridge.  It is a short walk from Condado and the Hilton Caribe. Taxi service is available from Old San Juan, a short ride, as is public transportation (the bus). The easiest way to get here is to ask the taxi service to go to the Sizzler restaurant. Often times the San Juan Bay Marina is confused with Club Nautico de San Juan, which is on the opposite side of the bridge. Please bring our cell number – 787.340.7567  Call if you have any questions or get lost.  We can arrange for taxi service.

What to expect

Expect a fast and fun sail through San Juan Bay.  During the daytime expect great wind and a lively adventure.  Sunset sails are generally calmer and more relaxed.  Dolphins, sea turtles, and manatees have all been seen on trips.  The impressive El Morro and beautiful Old San Juan, cruise ships, fishing boats, and more are to be expected.

“Sensational Sailing in San Juan”
Sailing on the Chili Pepper is a great way to see San Juan from the water. My wife and I had been wanting to do something unique on our most recent visit. We spent 2 hours on Saturday afternoon sailing in San Juan Bay. The Chili Pepper is a fast, responsive, and stable boat. Because we expressed an interest in learning to sail, Captain Sebastian gave a good overview and then let me take the helm. For those people simply wanting to be out on the water without doing any of the work, I believe he would have been happy with that, too. Overall the experience was memorable and very reasonably priced.

2 months ago

Sail Old San Juan
Winning Team 2023 - First Place CSA 2 Round the Rocks Race. Great job by all. ... See MoreSee Less
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Sail Old San Juan  787.340.7567

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