The story of Pepper

The spicy little traditional island sloop named Pepper was custom built In 1998 by Kevin Block and Jody Culbert in the village of Coral Bay on the Caribbean island of St. John. Inspired from lines taken off an old island boat Pepper is 23′ long with a 7″ beam, 3.5′ draft and a giant 12′ open cockpit. With her wood mast and boom she is a beauty. With her double reefing system and 1500lbs of ballast she is quite sea worthy too! Perfect for taking up to 6 guests and a crew of 2 on day sail charters.

The smallest and most beautiful of the United States Virgin Islands, St. John, is 2/3 national park. With its lush green hillsides, steady trade winds, and abundant bays, the island has a long-standing reputation as a nature lovers and sailors destination. Custom built in Coral Bay on St Joh’s east end, 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 sight today but were quite common in days gone by.

For almost two decades Pepper was a successful day sail charter business out of Maho Bay eco-camps on St. John’s north shore. Originally with builder Kevin Block and his wife Lisa. They sold Pepper to Captain Fred and first mate Renee whose daily snorkel adventure and sunset sails were very popular for over a decade. Fred and Renee called their charter guests to the shore with the sounding of a conch shell. They took them to amazing snorkeling spots only accessible by boat and later fed them a picnic of home made delicacies. On the sunset sails there were snacks and custom made rum drinks! They soon had a large following and Pepper was booked up alomost every day. Fred and Renee later wrote a book about their time on St John and sailing Pepper called “Between The Sheets” The book is full of fun and witty stories and is available on Amazon. Rob Rogerson was a frequent guest at Maho Bay Camp’s and loved being a guest on Fred and Renee’s trips. Rob, a south Florida native, fell in love with St. John on his first trip there in 2001. During his frequent trips there it became his custom to mark his arrival on island 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 St. John grew with each of his trips to “Love City”, as the island is fondly known by locals and tourists. When Maho Bay Camps closed for good in 2013 Fred and Renee decided it was time to retire. They sold Pepper to Kim and Lance who moved her back to Coral Bay where she was built and resumed charter business there.

In 2017 Rob learned from Fred and Renee that the Pepper was for sale and a job as caretakers of a vacation rental property working for a wonderful family was available. 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 Michelle quit their jobs in Florida and made the move to St. John in August of 2017 and took the caretakers position at a beautiful property in Coral Bay. The job came with a free apartment and a cool island cat named Slim. They purchased Pepper with the intent of reestablishing the charter business and began to settle into happy island life in paradise. Things were looking good and 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 were 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 devastated. Their dream, like the island, was turned upside down. They remained on the island with friends and helped with clean up like the rest of the tight-knit Love City community but at the urging of emergency relief workers they evacuated one week after the storm with a wave other heartbroken Irma refugees.

Back in Florida at the homes they owned and had planned to rent out Rob could not stop thinking about St John and Pepper. He could 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 Rob and Michelle returned to St. John to help in recovery efforts and see if salvage might be possible. Power to many parts of the island wasn’t restored until the the spring of 2018 and home restoration went on for years. They were amazed at the hardworking and resilient islanders, many who had also endured the cruelties of hurricane Maria that struck on the heels 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 after nearly 3 months underwater, stripped of gear, covered in barnacles and filled with mud but, salvageable nonetheless.

For the next 6 months, they traveled back and forth to the island to help their friends in hurricane recovery and work on Pepper. Cleaning a boat that was halfway to becoming a reef is difficult at best and Rob made it his labor of love .They kept her safely moored with lots of friendly eyes looking out for her until a boat yard opened up were she could be hauled out, evaluated, and hopefully restored.

In June of 2018 with the help of friends Colin and Leah, Pepper was towed to the nearest boatyard, Nanny Cay Marina in Tortola B.V.I., a two hour trip from St. John across the Sir Francis Drake Channel. She was hauled out of the water, cleaned up. and secured for safekeeping during the Tropical storm season which thankfully was quiet. The restoration of Pepper took from fall of 2018 until spring of 2019. Pepper was surveyed to determine the extent of repairs needed, then her hull was stripped down, prepped, and repainted by Virgin Islands Marine Refinishers. Her standing and running rigging were replaced and she received a new head sail. The main sail, although stained from being underwater was still in good condition and is the only onboard reminder of her ordeal. There was some rot on the boom and mast that was professionally repaired and the spars were varnished until they were gleaming! Rob and Michelle made half a dozen trips to Tortola to do what work they could and oversee the costly professional work that was being done.

Rob and Michelle traveled back to Tortola in the late spring of 2019 to take Pepper on a sea trial – her first time sailing for the first time in 2 years! Brian Duff of BVI Yacht sales who had done the rigging work and been a trusted advisor in Pepper’ restoration joined them for the trip. They had clear skies and ideal wind conditions. Heads turned to see the brightly colored traditional Caribbean sloop as they sailed on a lively beam reach across the Drake channel, around the the popular ” Indian’s ” dive spot and onward to Norman Island where they tied up in Privateer Bay and went ashore for lunch and a toast Pirates Bight restaurant. Pepper sailed like a dream that day and their hearts were full with happiness for having salvaged and restored her. Back at Nanny Cay Marina they hauled her out and covered her up to wait out the always active Caribbean hurricane season then went home to Florida to make plans for their return.

They planned to move back to St John that fall and resume following the dream. They rented an apartment in Coral Bay, bought a car, shipped belongings a second time and were ready and excited to make the permanent move back to paradise . Then disaster struck again. Rob had a serious back injury while competing in a running race and other serious health issues followed . With no certain timeline for healing, the dream was in serious jeopardy again! Rob could not bear the thought of selling Pepper after so much struggle and there wasn’t enough money to live on St John and not be working. After lots of thought and soul searching a new plan took shape. Give up the apartment on St John, sell their car and belongings, and ship the boat to Florida to run charters in Rob’s familiar home sailing grounds between Palm Beach and Jupiter. Rob could work on recovery and getting stronger while sailing Pepper on a limited basis and Michelle would go back to work at her previous job as a purchasing agent for an Aero space engine manufacturer. They would save money and sail together while planning to return to St. John when they had the right situation.

In February of 2020 Pepper was towed to a waiting freighter off the coast of Tortola and shipped to Florida. Rob had been working hard on recovery and getting stronger by the day. He and Michelle began sailing Pepper with friends in anticipation of running charters. Pepper passed her U.S. Coast Guard Charter boat inspection with flying colors and they were ready to start business but in a another dark twist of fate the Covid pandemic delayed their plans for almost a year. They took advantage of the unwanted delay by hauling the boat and doing numerous improvements and upgrades. In early 2021 they finally began running limited private charters. Pepper was a hit in the Palm beaches and quickly became a familiar and welcome sight in local waters. They ran snorkeling trips to the Breakers reef off Palm Beach island and the man made reef off Peanut island. Their ecology trips to Munyon Island at MacArthur State Park and sunset sails along the mansions of Palm Beach were very popular. Rob and Michelle regaled their guests stories of their adventures in the islands while serving them beer from St. John brewers. Things were going well and life was good but it wasn’t the perfect fit for Pepper. She was only visiting .

Rob had vowed to bring her home one day and in 2022 he found a way! Not yet ready to return, Rob got the idea to reach out to St. John friends Colin and Leah Hansen who had helped Rob and Michelle tow Pepper to Tortola for repairs in 2018. They own a very successful day-charter business on St. John called Flyaway Charters. Rob asked if they were interested in leasing Pepper and adding her to their charter fleet and they loved the idea! As life long sailors with a passion for history and traditional boats, Colin and Leah are a perfect fit to manage Pepper. They will keep the boat in top condition and Rob and Michelle will be able to sail her when they visit the island. In May of 2022, to the delight of U.S. Virgin island residents and Pepper fans everywhere, Pepper was shipped home to begin the next chapter of her story. We anticipate her being a very busy little boat in the 2022-2023 season. If you would like information or are interested in booking a trip please contact Colin and Leah at or at 1 (340) 514-9627 They look forward to having you aboard!

Many thanks to all who have followed and supported us on this journey!