Carrying on the Sailing Traditions of Coral Bay- S/V Pepper Returns to St. John

Carrying on the Sailing Traditions of Coral Bay- S/V Pepper Returns to St. John

The mystical maritime history of St. John has many layers. From ancient ships with inaugural arrivals of discovery on these shores to present day recreational chartering…Boats of all shapes, types and sizes are an integral part of both the history and the future of St. John. The history of ships in our harbors is diverse but each story is interwoven into the quilt of this beautiful island’s maritime heritage. And each era has a tale to tell. But today, I want to tell you a story about late 20th century classic sailing traditions and boat building of Coral Bay. And, specifically, a story of one little boat with a decades old story to tell that has just returned to her home on St. John.

Carrying on the Sailing Traditions of Coral Bay- S/V Pepper Returns to St. John 1
Steve Simonsen copyright 2008

Even the beginnings of this tiny, yet iconic, vessel reflects a time of simplicity and eccentricity in Coral Bay. In 1998, Sailing Vessel Pepper was custom built by Kevin Block and Jody Culbert in the yard and shop of the home Culbert was renting. Following a sweltering summer of boat building in his backyard, Culbert’s landlord returned to St. John from his summer travels and was unimpressed with the 23 foot unfinished sailboat on his property….

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The building of Pepper- Coral Bay, 1998

I reminded him that I had gotten his permission but he said that he had no idea of the scale of the project and told me I had to clear out of the shop in two weeks of the end of the month or whatever. Kevin and I went into overdrive to get the boat painter and the boot top and bottom primer on because that sort of work goes so much easier while the hull is still upside down. Kevin did the lions share of the paint work as I was busy in the shop pre-fabbing other components while I still had the use of a fully equipped cabinet shop.

Getting kicked out of the shop probably knocked a couple of months off the build duration. In the meantime, Carolyn Caldwell, who had one of the little studio/gallery art shops at Skinny Legs let me trailer the boat to the back of her shop and throw an extension cord into her shop for power. She was making big bucks selling watercolors of Island Sloops and was very supportive of our endeavors and Pepper became a living exhibit for the tourists.

The Skinny Legs guys soon realized what an attraction the project had for the tourists and locals alike and let up move up a ways to a better spot that just happened to let the now upright hull be seen from the bar. – Jody Culbert

And, thus, Pepper was born near Skinny Legs with her canary yellow painted hull, while onlookers and visitors reveled at the construction process, offering unsolicited tips and advisement accompanied by ice cold beers for the hard working builders.

“We should have been on commission with Skinny’s…” reveled Culbert.

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Pepper’s original mast- Coral Bay – 1998

This laid the foundation for what would be the newest wooden sailboat in an abundant fleet of classic vessels moored in Coral Bay. Constructed from a mixed bag of donated and locally acquired old growth yellow pine, Greenheart and Spanish Cedar, this sloop was built in the tradition of inter-island commerce vessels of yesteryear. These types of vessels drove the economy between the islands in the eighteen to nineteen hundreds.

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Sloops on the dock in Cruz Bay- 1958

Pepper went on to sail throughout the waters surrounding St. John with her beautiful wooden hull, mast and boom….In her heyday, she was stationed at Maho Bay and was the primary charter operation for the beloved camps of yesteryear. First, under the watchful eye of her boat builder, Kevin Block, and his wife Captain 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 almost every day. Fred and Renee later wrote a book about their time on St John and sailing Pepper called “Between The Sheets”SailPepper.com

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Between the Sheets is available on Amazon if you’re looking for a bit more of Pepper’s story!

In the glory days of sailing in Coral Bay, it wouldn’t be uncommon to look out to the harbor and spot a sloop, such as Pepper, a cow horn or a Venus ketch. It would be commonplace to happen upon a traditional boat such as these being constructed on the shores of the tiny village on St. John’s East End. But, today, that classic wooden boat tradition is “fleeting.”

According to Coral Bay Yacht Club Commodore, Leah Randall Hanson (co-owner of Flyaway Charters and a wooden boater herself), back in the early 2000s Coral Bay Yacht Club boasted regattas with some 40 boats and multiple classes with a swelling traditional class.

“Coral Bay has a rich maritime tradition dating back for centuries,” Leah told me. “In the late 1970’s and early 1980’s there was a huge community of boat builders and a strong community and culture tied into the traditional boats in Coral Bay.”

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Leah and her husband Colin, racing their own traditional sailing vessel, Buxom, a 1938 wooden gaff rigged ketch, in Foxy’s Wooden Boat Regatta 2017. (Photo credit: Sara O’Neill)

But, over time, some moved on…Others began to show wear. Many were still here until Hurricane Irma. She wiped out most that remained. And Pepper, although she narrowly survived the storms, was still somewhat of a casualty of the catastrophic events of 2017. You see, her current owners, Rob and Michelle Rogerson, were long time visitors to the Maho Bay Camps and jumped at the chance to own and charter the iconic yellow vessel that had donned so many beautiful memories on the water for them. In August of 2017, they abandoned their lives in Florida, moved to St. John and purchased Pepper with the intent of reestablishing the charter business. And they began to settle into happy island life in paradise.

Three weeks later….

On September 6, 2017, Hurricane Irma swept over the tiny island of St. John, devastating everything in her path with 200MPH plus gusts of wind, tornadoes and sustained gusts swifter than any shoreline in the United States had ever witnessed. Under her wrath, Pepper was driven to the bottom of the bay along with a multitude of other vessels. Boats, vessels of history in Coral Harbor, were crashed upon the shorelines, swept out to sea and driven to the bottom of the ocean.

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Post Irma boat wreckage- Photo- Priscilla Sherman

Pepper was feared to be lost, along with a multitude of the remaining classic sailing vessels in Coral Harbor and Hurricane Hole. And, after time spent cleaning up with the Love City Community after the storms, Rob and Michelle headed back to Florida to recoup all that was lost in their recent investment. But, as the months went by, Rob couldn’t get Pepper out of his mind. So, he returned to St. John to find her. With the help of an excellent salvage crew and the US Coast Guard, they eventually saw Pepper lifted from the bottom of the bay after nearly three months underwater, stripped of gear, covered in barnacles and filled with mud. But, salvageable nonetheless.

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Rob and Michelle did Pepper’s sea trial on August 16, 2017. Less than one month before Hurricane Irma

The little yellow sailboat that could would live on!

But, while she WAS floating, there was work to be done and, in 2018, with the help of Leah and her husband Colin, Pepper was towed to Nanny Cay to be hauled out in the marina there. Colin and Leah were not without loss in the aftermath of Irma…As they assisted with getting Pepper to safety, they were mourning the loss of their own classic wooden sailboat, Buxom. Colin had restored and rejuvenated his 1938 gaff rigged Tahiti ketch and Leah and Colin fell in love with each other and a life together on that beautiful boat. Only to discover her after Irma, split laterally into two pieces. The hull and the deck, one sunk and one floating, about 20 feet apart from one another.

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Aerial shot of Buxom.- Photo- Jim Mack/STJIslandBoy Photo

So of course, when Rob and Michelle called for a tow to Nanny Cay, although they don’t normally tow with their powerboats, Colin and Leah said yes. They jumped at the chance to assist a wooden boater in saving their classic wooden sailboat.

After nearly a year in the boatyard, Pepper would sail again in the spring of 2019. But, due to health problems, Rob and Michelle were unable to return to living on St. John. Being forced to abandon their dream, Rob couldn’t swallow the pill of also abandoning the boat he had sunk his heart and soul into. And so, Pepper was brought to Florida on a freighter from Tortola for Rob, Michelle and their friends and family to sail the seas near their home and the proper healthcare that Rob required.

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Pepper leaving the USVI via cargo ship in 2019

In a synchronistic turn of events, last month Pepper was shipped BACK to St. John where Leah and Colin anxiously awaited. You see, Flyaway Charters will now be managing this beautiful vessel as a part of their Coral Bay based fleet! Following the loss of Buxom, Leah and Colin acquired another classic sailboat, Breath, and have been working over the years to restore her. The new arrival to their fleet, Pepper, has sent a “breath” of fresh air into Leah and Colin. And this charter boat power couples’ vast knowledge of the maritime history of St. John paired with their background in rehabilitating and sailing traditional wooden vessels, makes them the perfect “parents” to be welcoming Pepper HOME to Coral Bay.

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She’s back on St. John!

While Rob and Michelle remain in Florida, they knew that Pepper needed to come home and are entrusting their beloved sloop into the caring and knowledgeable hands of Colin and Leah in order for her to charter once again on St. John.

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Colin and Leah will be back to sailing a traditional wooden sailing vessel!

“Getting back one of these traditional boats is a HUGE deal,” Leah said. “Pepper’s return to St. John is awe inspiring for those of us that remember her. This past Thanksgiving Regatta, we were grateful for our some 13 boats with no traditional class. But with Pepper’s return, we will finally have a traditional class again.”

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Pepper is right back where she belongs…At Skinny Legs 🙂

Pepper is currently back in her home waters of Coral Bay and, this weekend, her mast was raised for a third time in the Virgin Islands. Leah and Colin are hopeful that they will be chartering Pepper again before the end of the summer. She will once again be picking up guests filled with anticipation for a day of classic sailing. From the dock near Skinny Legs. Where her story began.

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The raising of the mast- A community effort.

13 thoughts on “Carrying on the Sailing Traditions of Coral Bay- S/V Pepper Returns to St. John”

  1. Great story!

    On another topic–what can you tell us about Gerda N and Calvin C Marsh, after whom the main island roads were recently renamed?


  2. I loved this story! My husband and I took several snorkeling trips on Pepper with Captain Fred and first mate Renee. We loved those trips (Fred & Renee are great) and I still have my Pepper T-shirt! Glad she’s back.

    • Dear Joyce,
      Loved the article about Pepper! We’re coming to St. John in May 2023 & would be interested in a charter on Pepper. Is there a way you could connect us?

  3. I remember watching Pepper get built outside Skinny Legs… Hard work and great attitude by Kevin – who was bartending at Skinny’s when he wasn’t building…

  4. Kevin (with Jody) was the builder but Lisa P was the original captain, usually with her baby Carissa in tow. Shout out to Lisa P!

  5. I had the pleasure of being on Pepper’s maiden voyage to Jost with Kevin, Lisa & their, then, young daughter & my partner, at that time, Jack Simmons. We owned the beautiful 58′ wooden ketch, Johanna, in Coral Bay & for many years chartered her as well. Pepper indeed started being built where also Jack’s workshop was in what was called then, “the pig farm”.

    Thanks for the memories!

  6. It is true Lisa was the captain. Lisa could sail circles around anyone else who tried their hand at the helm! Just so everyone is aware I never claimed to be the captain of Pepper nor did I have anything to do with the writing of this otherwise wonderful story of S/V Pepper. Cheers Kevin

  7. This is an amazing story. I personally know Rob and Michelle, and know they love having thier “Pepper” Back where she belongs!

  8. Hi Kevin, this is Jody Culbert! Good to see you chip in here. Can I get some full res Pepper photos from you of Pepper especially under construction?

    Jody 251-545-9029

  9. After Rob and Michelle were surprised to find the Pepper quite salvageable after the storm! Rob brought a few of his lifeguard and sailing buddies to the island from Florida to give his a hand with the repairs. We spent weeks scraping, scrubbing, sanding, varnishing and polishing brass. What a beautiful vessel. It was a joy to be a small part in bringing her back.

    OK, I’ll confess. It was no sacrifice to work on the floating vessel because it was always followed by a run to Maho Bay for a dive and a beer wherever the musicians were that evening. It was a good work pace I could have gotten used to!

    Eventually, Rob decided that much of the work would have to be done on dry dock, so once again had to wait his turn. We covered the Pepper, left a solar panel connected to the bilge pump and returned to Florida. It was a joy when later Rob and Michelle shipped the Pepper to Palm Beach. But the Pepper was really not appreciated here as she had been back home. This is the coast of high performance, with little pride for tradition.

    But now, this beautiful and now, pristine island sloop is back where she belongs! If the storm did anything to her, is give her character and show how resilient she actually is! Enjoy her, guys!

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