Pepper – Story of an Island Sloop

Activities / Uncategorized / January 12, 2024

The vibrant traditional island sloop, aptly named Pepper, embarked on its seafaring journey in 1998, meticulously crafted by the skilled hands of Kevin Block and Jody Culbert in the charming village of Coral Bay on the Caribbean jewel, St. John. Infused with inspiration drawn from timeless island boat designs, Pepper stood at 23 feet in length, boasting a 7 foot beam, a 3.5-foot draft, and a spacious 12-foot open cockpit. Her elegance was further enhanced by a wooden mast and boom, while a double reefing system and 1500 pounds of ballast rendered her admirably seaworthy. Ideal for intimate day sail charters, Pepper could comfortably accommodate six guests and a crew of two.

St. John, the smallest and most picturesque of the United States Virgin Islands, unfolded its natural wonders with lush green hillsides, steadfast trade winds, and inviting bays. Custom-crafted in the heart of Coral Bay on the island’s east end, Pepper swiftly became a familiar and delightful sight on the turquoise waters. Designed in homage to the sturdy vessels that once traversed these waters for inter-island travel, cargo transport, and fishing, Pepper paid homage to a bygone era.

For almost two decades, Pepper thrived as a day sail charter business, anchored in the scenic Maho Bay eco-camps on St. John’s north shore. Originally under the ownership of Kevin Block and his wife Lisa, Pepper later found new stewards in Captain Fred and first mate Renee. Their snorkel adventures and sunset sails gained popularity, beckoning guests to the shore with the soulful call of a conch shell. With breathtaking snorkeling spots, delectable homemade picnics, and custom rum drinks on sunset sails, Fred and Renee carved a niche for Pepper, creating a devoted following.

Rob Rogerson, a frequent guest at Maho Bay Camps, fell under the spell of St. John during his initial visit in 2001. His love for the island grew with each subsequent trip, and he marked his arrivals with a ritualistic swim in Maho Bay’s clear waters, reaching out to touch Pepper’s hull to ensure the reality of his island dream. When Maho Bay Camps closed in 2013, Fred and Renee decided to retire, passing Pepper into the hands of Kim and Lance, who brought her back to Coral Bay to resume her charter business.

In 2017, a twist of fate led Rob to discover that Pepper was for sale, coinciding with a caretaker opportunity on St. John. Seizing the chance to live his island dream, Rob and his girlfriend, Michelle, relocated to St. John, taking over the caretaker role and setting the stage for Pepper’s revival. Their joy, however, was short-lived as Hurricane Irma ravaged St. John, submerging Pepper and turning their dream upside down. Undeterred, Rob and Michelle returned, salvaged Pepper after months underwater, and dedicated themselves to her restoration.

Over six months, they toiled to resurrect Pepper, showcasing resilience akin to the islanders rebuilding their homes. From the depths of adversity, Pepper emerged rejuvenated, her hull painted, rigging renewed, and sails proudly unfurled. Rob and Michelle, undeterred by setbacks, resumed their plans to run charters on St. John.

Yet, fate had another twist in store. Rob’s serious back injury and subsequent health issues disrupted their plans. Undeterred, they pivoted, relocating Pepper to Florida to run charters in familiar waters. Despite a delay caused by the pandemic, they utilized the time to enhance Pepper further. In 2021, they commenced private charters, introducing Pepper to the Palm Beaches with snorkeling trips and sunset sails, weaving tales of island adventures over St. John-brewed beer.

As the year unfolded, Rob envisioned a new chapter for Pepper. In 2022, he reached out to St. John friends, Colin and Leah Hansen, who operated the successful Flyaway Charters. The idea of leasing Pepper and incorporating her into their charter fleet resonated, marking a poignant homecoming for the seasoned sloop. In May of 2022, Pepper sailed back to the U.S. Virgin Islands, ready to embark on a bustling charter season under the capable management of Colin and Leah. Pepper’s odyssey, marked by resilience, restoration, and unwavering determination, continued to capture the hearts of island enthusiasts, promising a vibrant future for the spicy little sloop.


A Message from owner, Rob Rogerson

It was wonderful to have the fully restored Pepper back home on St. John! Locals got used to their favorite island sloop coming and going out of Coral Harbor. Pepper had her first charters and she won her class in Coral Bay Yacht Club’s Commodores cup Regatta and she was well on her way to becoming one of St. Johns favorite day-sail charters once more.
In 2024 Rob & Michelle have decided to look for the next “Pepper People” either as a partnership or to purchase the boat or the business. What a great opportunity for an enterprising young couple to make a career of continuing an island tradition that has its roots in centuries of Caribbean maritime history.

If interested contact:
Rob Rogerson
561 339-1350

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