Sailing Date and Time

can be requested by

Calling 939.905.7044

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Sunset Sail – $99 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).

Currently not available.

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Private Day Charters – $390/Boat

Daytime charters for private groups of up to 6 passengers. Day sails from San Juan for 2 hours, additional hours on request ($95/hr).  Sail through the historic Port of San Juan, down to El Morro.  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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Private Sunset Charters – $490/Boat

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.  Sunset Sail depart at 5pm (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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Have a question first? Please call us at 939.905.7044 or email us at
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All Sails are with a U.S. Coast Guard licensed Captain.

Reservations for sail old san juan, charter sailing in san juan bay, puerto rico.  Reserve day sails, sunset sails, private charters, instruction, lessons, spinnaker runs, and have fun during your stay in san juan, puerto rico.  Fun thing to do in San Juan, Puerto Rico.  Close to Marriott hotel, La Concha hotel, viejo san juan, cruise ships and cruise ship terminals.  Short bus or taxi ride away, or walk from condado.  Have fun sailing on a performance racing boat.  Chili pepper is a beneteau First Class 10 racing boat that has been converted for day sailing.  Really fast sailing here if that is what you are looking for.  All sails are with a United States Coast Guard licensed captain, but you are welcome to help steer the boat, trim the sails, and direct where in the bay or ocean to sail.  The winds in san juan are excellent in general, the tradewinds blow at a steady 10 to 20 knots during the season, only a small shower once in a while.  But they are fun when they come, and if you don’t mind getting wet if it does happen to briefly shower, then you will have a great time.  This could be one of the most fun things to do while in San Juan, Puerto Rico, so charter a sail today. –