A real sailboat for authentic sailing.


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 2023/24 Season:

+ North Sails 3di mainsail.  This is the highest performance mainsail available.

New for 2023 Season:

New Rig!  US Spars mast, standing and running rigging.

New for 2022 Season:

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

+ Powered by Lithium Iron Phosphate batteries for performance and safety.

New for 2021 Season:

+ Quantum 105% battened racing Jib.

+ Code 0


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.

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 Round the Rock Race at STIR 2023 – Chili Pepper wins the annual Round the Rocks Race at STIR in CSA 2, a race around the island of St John.  Flying a symmetrical spinnaker for the running leg of the race Chili Pepper took the lead for a solid win.

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.  For the race Chili Pepper used a modern sailplan that included a large squaretop racing main built by Somerset Sails.

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.


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.
Comments Box SVG iconsUsed for the like, share, comment, and reaction icons Load more
Logo of GoPro