We pride ourselves on maintenance.  Chili Pepper is kept in top sailing form year round and hauled out for maintenance on a yearly basis.  Safety is of utmost importance to us, and having a reliable boat is a major component of that.

New for 2021 Season:

+ Quantum 105% battened racing Jib.

+ Code 0

New for 2020 Season:

+ Fully battened Quantum Mainsail.

+ Cockpit Cushions from ABC Florida.

New for 2019 Season

+ New Mast, Standing Rigging, Running Rigging.


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.

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.

In 2017 hurricane Irma decided to remove the old rig and so it was replaced with a brand new, ultra light powder coated mast and boom from US Spars for the 2018-2019 season.  All new standing and running rigging reduced weight aloft even further and Chili Pepper is more stable and points higher than ever!



All trips include drinks:

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

Gear includes:

  • Fresh water swim shower.
  • Bluetooth enabled Stereo system.
  • Marine toilet.
  • Fishing Pole and Boatline.
  • Cooler with ice for drinks.
  • Furling Asymmetrical Spinnaker (on request).
  • GoPro camera with remote for capturing action video and photos.

Picture of Beneteau sailboat sailing upwind in San Juan Bay, Puerto Rico.
Picture of two guests relaxing in the cockpit of sailboat during a daysail.
Picture of asymmetrical spinnaker on Chili Pepper, a Beneteau sailboat.
Boat Cushions Seating
Picture of two sailboats racing.
Picture of racing sailboat.

1 month ago

Sail Old San Juan
In Frenchtown, St Thomas, working at Sail Frenchtown. Ready to sail back to San Juan after a long time off due to Covid. ... See MoreSee Less
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