Day Sailing
Day Sailing
cockpit photo
cockpit photo

All Sails are with a U.S. Coast Guard licensed Captain.

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).

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.

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).

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).


Question : “What do we bring?”  Answer:  Hat and sunglasses for day sails, camera, comfortable clothes.

Q: “Are drinks included?” A: Yes, in moderation; water, beer, cuba libre, and soft drinks. Champagne for sunset sails.  Please make special requests if you have any.

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, we can play your ipod or other mobile music device.

Q:”What if it rains?” A: Showers are common but generally last just a few minutes.  Sails are cancelled and fully refunded if severe weather exists or the captain determines that conditions are unsafe.

Q:”Do I need to reserve?” A: Yes, you need to reserve for a minimum of one person in order to reserve a group time.  Refunds are issued with 48 hour cancellation notice.

Q:”If I reserve and don’t show up, will I get a refund?” A: No, unfortunately not. The opportunity for us to rebook another group is no longer there.

Q:”Can I book a private sail?” Yes. Occasionally couples are grouped together on a trip.  However, if you would like your sail to be guaranteed private, just ask.  We will do our best to accommodate you.

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, highly recommended. 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: Please call or email. All scheduling is separate from online payment.

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

Q:”Do I need a PayPal account to reserve?” A: No, PayPal accepts credit cards without an account.

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.

Sail Old San Juan  787.340.7567


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