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 2022 Season:

+ Electric Yacht motor installation.  Chili Pepper is pure green energy.

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 guests are 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!

Electric Propulsion – For the 2021-2022 Season Chili Pepper received a new Electric Yacht motor installation.  The old diesel was pulled out and replaced with a clean, quiet, highly efficient electric drive.  There is absolutely no noticeable noise while motoring.  The greatest feature is that the drive can generate electricity while sailing.  Not only does Chili Pepper not use any fossil fuels, she can actually produce power just by going sailing.


Regatta Sailing

Chili Pepper Wins at 2022 St Thomas International Regatta – Chili Pepper raced at the 2022 STIR as a CSA 3 competitor.  With a trained crew of 9 she placed 1st in the first four races which was enough to secure a first place overall.  The team’s success was due to bi-weekly training, practice races against a sparring partner J92, and an optimized modern sailplan that included a large squaretop racing main built by Somerset Sails.  Chili Pepper is a competitive boat even by modern racing standards.

If you are interested in learning please check out Sail Frenchtown our sailing program and school meant to introduce new sailors to the sport.  If you are interested in pursuing sailing, let us know and we will put you on our newsletter.  Whether as crew, passive learners, vacation sailors, future boat owners, or future Regatta sailors, let us know if and how you would like to get involved. Please check out our website in St Thomas:


And if you are interested in yacht ownership, please go to:


Chili Pepper going upwind at STIR 2022 with FOX in the background, a Botin TP52 and one of the world’s fastest monohulls.


Upwind Sailing on Chili Pepper
Upwind at the St Thomas International Regatta 2021.


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.

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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