Caribbean Connection, From the Bay to the Blue Ridge

Step Back in Island History on a Day Sail aboard s/v Pepper

“When we brought her back here, a lot of people remembered her,” said Kim Sammartano.“It was neat; a lot of people came up and said they were happy to see her back in Coral Bay,” said Lance Davies.

After cruising and entertaining guests at Maho Bay Campground on St. John’s north shore for more than a decade, the sloop Pepper is back to her original home in Coral Bay with new owners Kim Sammartano and Lance Davies at the helm.

The traditional island sloop was built by hand under a large tree next to Skinny Legs in 1998 and had returned to her home bay since. As soon as she was launched, Pepper’s original owners sailed her directly to the north shore, where she was moored off-shore of Maho Bay Camps and operated as a successful day charter until the campground closed last summer.

Pepper is now back home in Coral Bay where Sammartano and Davies offer both full day and sunset cruises, with gourmet food, delicious libations and the opportunity to appreciate a traditional island boat.

From its inception, the wooden sloop was designed to pay homage to the Caribbean’s rich boat building history. Her story begins back in the late 1990s when captain Lisa Nathan was running a day charter business at Maho Bay Campground with her Morgan 34 Perstare.

Yearning to trade in her fiberglass vessel for something that was more evocative of the rich history of Caribbean boat building, Nathan commissioned Jody Culbert, who himself had fallen in love with traditional island sloops via an acquaintance in Anguilla.

Culbert built the vessel by hand right outside of Skinny Legs using Spanish cedar planking and the lead off nearby wrecked boats for ballast. You won’t find a cubby or bunk down below, but there’s plenty of space in Pepper’s oversized open cockpit for up to six guests. And with her elongated boom and oversized sail area, the 23-foot Pepper can put many vessels in her wake even without all the bells and whistles found on most charter boats.

After she was completed in 1998, Nathan and her husband, who happened to be a bartender at Skinny Legs, launched Pepper from the beach the bar and sailed her over to the North Shore. Just about 15 years later, she’s now back home under the loving care of Sammartano and Davies, who bought her last year.

A transplant from Atlanta most recently, Sammartano worked at Maho Bay Campground for the beloved eco-camp’s final season, which is where she met Pepper’s former owners who were looking to retire.

Fred Renner and Renee Procter had bought Pepper from Nathan and Kevin Block. For years Fred and Renee enjoyed a robust business with Pepper, taking out Maho guests season after season. As the campground was closing last summer, Fred and Renee were hoping to retire and looking for the perfect buyer for Pepper.

Sammartano’s then-boyfriend, now husband, Lance Davies, made the move to St. John after visiting and getting bitten by the island bug himself. A former commercial photographer, Davies worked as a dive master at Caneel Bay Resort’s Patagon Dive Center before the couple bought Pepper.

Instead of running to jobs in the city, Davies’ and Sammartano’s days are now spent cruising out of Coral Bay with guests who get to enjoy the traditional lines and fine-tuned sailing of a traditional island sloop.

“For me the best part is being on the water,” said Davies. “I would do anything on the water.”

Sammartano, meanwhile, loves meeting guests from across the globe, she explained. “I really like talking to people from everywhere,” she said. “I’ve lived in a few different cities and the people who come here are really interesting. This island draws an awesome group of people.”

While Pepper’s transom sports a four-stroke outboard motor these days, Davies only uses it to get off the mooring and it’s basically the sole nod to post-industrial age technology on the boat.

Once safely out in the harbor, Pepper’s sails do all work and guests enjoy the serene beauty of island sailing, not much differently than they would have 100 years ago or more.

carib conn turtleAfter cruising along the ruggedly beautiful East End of St. John, guests enjoy a  snorkel stop. Davies’ years of both diving and photography experience means those snorkel trips are expertly guided with the added bonus of stunning underwater snapshots of what you just saw.

While Davies is leading the snorkel, Sammartano is busy topside putting out a gourmet and vegetarian-friendly spread. Snacks might include hummus made with Sammartano’s home-roasted sesame seeds, creamy tofu salad pita sandwiches and there is always plenty of fresh fruit and gourmet cheese and crackers.

To wash all that down, Sammartano also whips up the boat’s signature Pepper Punch; a refreshing concoction of natural guava and passion fruit juices mixed up with a combination of rums.

After a leisurely lunch and a cocktail or two, guests enjoy a cruise back into Coral Bay harbor where they arrive around 2 p.m. Full day cruises aboard Pepper run $95 per person with only a two person minimum, making the trip ideal for honeymooners or vacationing couples. The cost includes water, soft drinks, cocktails, Sammartano’s amazing lunch and the guided snorkel.

For a shorter excursion, book the two-hour sunset cocktail cruise. This trip runs from about 4 to 6 p.m. depending on the time of year and includes delicious hors d’oeuvres, fine wine pairings, beer and cocktails for the cost of $65.

Sammartano and Davies also keep Maho Bay Camp’s eco-conscious spirit alive by offering only reusable plastic cups, water bottles and plates.

For more information about Pepper or to book a charter, call (340) 771-7011 or check out

Written by: Jaime Elliott

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