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Sailing Puerto Rico Old San Juan Bay

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Sailing Puerto Rico Old San Juan Bay

Sailing Puerto Rico Old San Juan Bay

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

2015/2016 Season Starts Soon!… First Bookings on NOVEMBER 14!!!

San Juan Bay Marina
Ave Fernandez Juncos Stop 10
San Juan PR 00907-3181
United States


Sailing Puerto Rico San Juan city Bay

Sailing Puerto Rico Old San Juan Bay. The sailing season in the Caribbean generally takes place between November and May.  The summer is hot and prone to tropical storms. The winter is cooler and the trade winds are ideal.  Expect daytime winds to range between ten and twenty knots.
The waters of Puerto Rico are under U.S. governance, and the U.S. Coast Guard maintains a steady presence here.  There is a U.S. Coast Guard station in San Juan Bay.

Click the Details tab above for our website url link


S/V Chili Pepper is a customized 10 meter Beneteau originally built for racing.  While based out of St. Thomas, USVI,  S/V Uncle Sam (prior name) was raced successfully and gained a solid reputation for winning in Caribbean regattas.  In 2011, S/V Uncle Sam was converted into S/V Chili Pepper, the beautiful day sailing vessel she is today.

Custom work for racing included a Glenn Henderson designed racing keel that keeps her stable and points high upwind, and an expanded cockpit for accommodating additional crew.  Combined with an open transom, these features make her a fantastic day sailing vessel.  The large cockpit is ideal for seating passengers in comfort and the open transom is great for getting in touch with the beautiful tropical waters of the Caribbean.

This boat was built for going fast.  The thrill of sailing is inevitable as she points high yet remains stable and moves through the water with ease.  Quick and responsive, the crew is put in tune with the wind and ocean, the way sailing is meant to be.

As a daysailor the vessel can be single handed by the Captain.  But the crew is invited to give a hand or take the helm.  So sit back and relax, or join the fun and grind away on the winches at the Captain’s command.  Either way, sailing on Chili Pepper is a fun and exciting experience and a great way to get out on the waters of Puerto Rico.

New in 2014, Chili Pepper was converted from tiller to wheel steering.  A big 40 inch wheel is now used to steer the boat and gives it the modern look and feel of contemporary, top-of-the-line sportboats.  And… with the addition of a retractable bowsprit and furling asymmetrical spinnaker, Chili Pepper is back in top form and will keep up with modern racers.



All trips include drinks:

Beer, water, coca-cola, and sparkling wine for sunset sails.  Special requests are taken.

Gear includes:

  • Fresh water swim shower.
  • Stereo system.
  • IPod loaded with music (or bring your own).
  • Marine toilet.
  • Zodiac dinghy.
  • Fishing Pole and Boatline.
  • BBQ.
  • Cooler with ice for drinks.
  • Furling Asymmetrical Spinnaker (on request).
  • GoPro camera with remote for capturing action video and photos.
Country PR
State San Juan
City San Juan
Zip Code 00907
Website Link Visit Link Here
Phone 787-340-7567
Country Puerto Rico
City San Juan
distance: 4,656 Miles
Address PR-16 & Av. Manuel Fernández Juncos & PR-26, San Juan, San Juan 00907, Puerto Rico
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