The spicy little island sloop named Pepper was built In 1998 by Kevin Block and Jody Colbert in the village of Coral Bay on the Caribbean island of St. John. The smallest and most beautiful of the United States Virgin Islands, St. John, is 2/3 national park . With it’s lush green hillsides, steady trade winds, and abundant bays, the island has a long standing reputation as a nature lovers and sailors destination.

The brightly colored Pepper quickly became a lovely and familiar sight on the island’s windswept turquoise waters. She was designed in the fashion of seaworthy little boats that centuries of islanders used for inter-island travel, transporting cargo, and fishing. These boats are a rare site today but were quite common in days gone by.

For almost two decades the Pepper was part of a successful charter business out of Maho Bay eco camps on St. John’s north shore. Captain Fred and first mate Renee’s daily snorkel adventure and sunset sails were very popular. They called their charter guests to the shore with the sounding of a conch shell. Pepper’s current owner Rob Rogerson was a frequent guest on those trips. Rob, a south Florida native, fell in love with St. John on his first trip there in 2001. It became his custom to begin his vacations in paradise with a swim in the warm clear waters of Maho Bay to touch Pepper’s hull to make sure that he wasn’t dreaming. Rob’s love for the island grew with each of his trips to “Love City”, as the island is fondly known by locals and tourists.

In 2017 Rob learned that the Pepper was for sale. Owner Kim Sammartano who had met Fred and Renee when she worked at Maho Bay camps bought the Pepper from them when the camp closed in 2013. She moved the boat back to Coral Bay on the east end of the island and began running charters there but after a few years she lost her partner and decided to sell. The opportunity to follow his island dream was the chance of a lifetime and he could not say no.

Bursting with excitement and optimism, Rob and his girlfriend and first mate Michelle McConville quit their jobs in Florida and made the move to St. John in August of 2017 and took the position as caretakers of a vacation rental property in Coral Bay. They purchased Pepper with intent of reestablishing the charter business and began to settle into a happy island life in paradise. The dream was becoming a reality.

Three weeks later St. John was struck by Hurricane Irma. With winds in excess of 200mph the island was brutally ravaged and the homes that Rob and Michelle were caring for was destroyed. Pepper was driven to the bottom of the bay by the wind and waves and feared lost like so many other boats and homes in the path of the storm. Rob and Michelle were physically unharmed but emotionally devasted. Their dream, like the island, was turned upside down. They remained on island with friends and helped with clean up like the rest of the tight knit Love City community and at the urging of emergency relief workers they evacuated one week after the storm with a wave other heartbroken Irma refugees.

Rob could just not bear the thought of his sweet little boat becoming a coral reef so in November of 2017 when flights began running to the region again they returned to St. John to help in recovery efforts and see if salvage might be possible. They were amazed at the hard working and resilient islanders, many who had also endured the cruelties of hurricane Maria that struck on the heals of Irma. This served to strengthen their resolve to return. With the help of an excellent salvage crew and the US Coast Guard they saw the Pepper lifted from the bottom of the bay, stripped of gear, covered in barnacles and filled with mud but, salvageable nonetheless.

For the next 5 months they traveled back and forth to the island to help in the recovery and work on Pepper. Cleaning a boat that was halfway to becoming a reef is a difficult at best and Rob made it his labor of love. In June of 2018 with the help of many friends Pepper was towed to Tortola, hauled out of the water and secured for safe keeping during the heart of the storm season which everyone prays will be mild. Rob plans to finish restoration in the fall and he and Michelle hope to begin charters on the good ship Pepper in the 2018/2019 season. We invite you to visit the lovely island of St. John and its wonderful people and we hope that you will come sailing with us. You can follow the adventures of Pepper on social media and on this site.

Thank you for sailing to our site. We hope to see you onboard someday soon!