Out of work? Then of course the first thing you need to do is buy a 1920 Chesapeake buyboat that’s been in the Caribbean for 50 years. That’s the way Michael Whitehill saw it, anyway. Here Robert Blake Whitehill tells of brother’s noble but inexplicable quest to repatriate a beautiful old girl named Winnie Estelle.

by Robert Blake Whitehill
photographs by John Bildahl

In the August 2011 issue of this magazine, editor-at-large Wendy Mitman Clarke introduced readers to a diamond in the rough—Winnie Estelle. She had stumbled upon the beautifully restored 1920s-vintage Chesapeake Bay oyster buyboat while cruising in, of all places, Guatemala. Clarke was smitten upon meeting this gorgeous vessel, especially since it was so far from home. I didn’t know it yet, but this same boat was destined to become the center of an uproar in the Whitehill family as well.

Winnie Estelle’s journey through the tropics was long, beginning in the 1960s, when she was moved from the Chesapeake to the West Indies, and eventually ended up hauling lumber between Honduras and Belize. But after that her story took a sad turn toward neglect; she fell into disrepair and eventually ended up wrecked on a reef in Belize. It was there, in the mid-80s, that Captain Roberto Smith found her and, yes, fell in love. (Clearly, she has that effect on people.)Smith rebuilt her, refinished her and gave her new life as a snorkeling charterboat in Belize. He performed heroically with his checkbook and sweat equity to bring Winnie back from the brink of destruction. But finally, after nearly 20 years of chartering her and keeping her seaworthy, Smith came to a crossroads, realizing it was time surrender Winnie’s stewardship to a new captain.

Meanwhile, back north on the Chesapeake Bay, in Centreville Md., another man was at a crossroads. This time, the intersection felt like that mythological place where the hero haggles with the devil. Forced into retirement after 40 years of loyalty to the same company, Mike Whitehill, my brother, decided retirement should include a piece of maritime heritage to call his own. This is where madness can be contagious if you stand too close. As I’ve written in previous issues, the Whitehills have had some interesting misadventures on the Bay—like when we landed a seaplane on the Chester River, only to run aground on a sandbar [“Flight of the Buccaneer” December, 2005] or when another Whitehill, ahem, thought it good sport to cruise the Chesapeake in an open electric boat at the start of a hurricane [see “The Electric Slide,” November 2005]. Collectively, we still think buying a boat will improve our peace of mind. It’s plain we aren’t right in the noggin when it comes to boats.

After careful consideration, which lasted as long as a three-year-old can contemplate ice cream before digging in, Mike decided that with his career over, his finances in shambles and all aspects of his future happiness cast into doubt, a Chesapeake Bay oyster buyboat would be the perfect fix. In Mike’s view, there could not be a more perfect cruising vessel. Endowed with beauty, economy, range and a beamy shoal draft, a buyboat could handle all the Bay’s waters from deep to shallow. Wasn’t an elderly wooden boat just what the doctor ordered? I suggested to Mike that blow-drying his hair while frisking in a Jacuzzi might be cheaper and quicker. But he was deep in the boat-buying daydream; the point flew right over his head.

So the quest began in earnest, namely with a phone call to Dave Wright, Vice Commodore of the Southern Fleet of the Chesapeake Bay Buyboat Association. Wright is a matchmaker, a siren really, who loves nothing more than bringing wayward buyboats back to the Bay to snare hapless yachtsmen. He had some leads. 
 “Buyboat customers love their history, and the clean, utilitarian looks,” Wright told me, “and they usually want one that’s bigger than everybody else’s.” I watched with a mixture of delight and horror as my brother went a-courting with a bachelor’s zeal for a new maritime romance. The only problem: Mike is already married to the charming and good-tempered Patricia, and she was hankering for some serious remodeling on their house.

At Wright’s suggestion, Mike checked out several boats for sale within driving distance. My sister-in-law, with her new kitchen now at risk, stayed behind in the not-yet-remodeled house with smoke rising from her ears. Lucky for him, Mike came away from his look-sees disappointed. Either the boats needed far too much work to make up for years of neglect, or the owners wanted way too much money. And the one boat he seriously considered went to another buyer before he could even make an offer. That really set the hook in Mike’s mouth. He was mad to buy 
a buyboat.

Wright, the indefatigable yenta, sensed the timing was perfect for his last suggestion. There was another buyboat for sale, and she was in pretty good shape. But there were a couple of catches: she was in Guatemala, and her current price included a local charter business. Despite all the red flags, Mike called Captain Roberto Smith, and talks about the Winnie Estelle got off to a good start. Meanwhile Mike’s wife got some new hobbies of her own—like Googling Maryland divorce statutes and studying untraceable poisons.

Undaunted and liking what he’d heard from Captain Smith, Mike jumped on a plane to Guatemala to look Winnie over. I mentioned to my wife Mary that my brother was having plenty of fun with all the boat shopping, and I wanted to fly south to watch. It was unusually quiet at my place for a couple of hours. Mary drew my attention to State Department warnings about Guatemala’s healthy kidnapping industry. The look in her eye shook my confidence that she would cough up a decent ransom if need arose. With my own sanity now in question, I girded my loins and got on a plane. Mary sounded pleasantly surprised that my first call home from Rio Dulce did not include a dollar figure for my freedom.

Winnie Estelle was hauled out on a rail, and all eyes were on Rio Dulce marine surveyor Casey Brooks for his verdict. The news in his report was good. “Winnie Estelle has been almost totally rebuilt, he wrote. “Maintenance is an ongoing thing, with intensive commitment given to preserving this historic vessel. Roberto Smith has dedicated many good years to the Winnie Estelle, and has done a superhuman job.” 

This was all my brother needed to hear. Winnie Estelle’s price was refigured without the charter business, a deal was struck, hands were shaken, and funds were wired. Mike now owned a buyboat. Before he could bring Winnie home, there was just one “small” project to be completed, a refit that took several weeks as 23 planks were cut from the jungle and dried, and swapped out for Winnie’s few ailing timbers. The delay was hard on Mike, whose cash reserves were running low. There are, it turns out, many ways to be held hostage.

On May 5, 2012, with the refit completed, it was time to set out for U.S. waters. The ship’s complement included Mike and myself, plus former owners Roberto Smith and Veronica Raimbault, and delivery captain James Johnson, who had flown down from Centreville for the delivery. Imagine the gamut of emotions Winnie Estelle evoked that day; the final voyage aboard her for some, and the very first cruise for others. At San Pedro, Belize, a dew-eyed Raimbault parted company to return home. There, Richard Johnson, James’s son, joined ship.

My wife was worried about all the open water that our Gulf crossing would see. She was not reassured when I said that the old inflatable, our only lifesaving equipment, was named Patches. Patricia, meanwhile, was looking into the state of my brother’s life insurance. 

Since Mike reserved the wheelhouse bunk for himself, I was berthed below decks in the old oyster hold with Jim, Richard and Roberto. Those accommodations were Spartan. Oysters, it seems, do not require upholstery to be happy, but I am no oyster. I cracked my head, elbows, shins and backside at every turn down there. The doughty diesel was so loud that earplugs were useless, making life belowdecks an exercise in sleep deprivation worthy of Gitmo—which coincidentally lay just over the horizon. 

Just about the only original timber left in Winnie was her keel, which we babied with lower RPMs in the wringing quartering seas along the way. That only made a long trip longer, but her seams held steady from stem to stern. Winnie Estelle and crew survived the seven-day trip, and she made her first U.S. landing in 40 years at Stock Island, just east of Key West. That is where Captain Smith said his good-byes to Winnie and crew and flew back to Guatemala. 

Contractors, not pirates, swarmed aboard Winnie, but Mike felt it in the treasury all the same. Bringing the 92-year-old vessel into the 21st Century was only supposed to take a few days, but it took a full three weeks, much to Michael’s distress. Finally, on June 2,  Winnie was pointed north for the last leg of the trip to the Chesapeake. Going outside around Florida, and inside from there to the Chesapeake, we were treated to a lunar eclipse over Cape Canaveral and fascinating storms along the way. Ancient timbers, modern navionics and a green crew all performed well together. Sixteen days later, the homecoming queen graced the Chester River with her regal presence.

A Whitehill with a wooden boat is a terrible thing to behold. While the crew had survived the trip, the financial hemorrhage continued to run fast and green. Winnie Estelle’s overhaul in the summer of 2012 included a complete sanding to bare wood, reseaming with red lead and dolphinite, priming and two topcoats, and some touch-up joinery. Then came the sexy steam punk stuff from Port Townsend Foundry in Washington State: custom-made bronze castings for her mast’s gooseneck, belaying pins and her boom bail. Patches, the lifeboat, was replaced by Minnie Estelle, a custom-scaled 14-foot Crab Alley tender, whose raked lines were drawn up to complement those of the mother ship. 

In August of 2012, Winnie Estelle was formally welcomed home at the Chesapeake Bay Buyboat Association’s annual reunion in Crisfield, Md. The great grandchildren of the builder Noah T. Evans were on hand, and they, as much as anyone, marveled at Winnie’s enduring beauty. There were even some former crewmembers in attendance who had not walked her decks in decades. In the fall, Winnie Estelle traveled north to show off her restored beauty at the Sultana Project’s Downrigging Weekend in Chestertown, Md.

Under our breath, we liken Mike’s mission to the fevered madness displayed in the movie Fitzcarraldo—a tale of a man driven to reach a rubber plantation in Peru with a steamboat . . . a journey that included treacherous rapids and even dragging the boat over a mountain and across two rivers. But, madness aside, everyone agrees, the main thing is that Winnie Estelle is home again, no one was permanently maimed or kidnapped, and no one suffered divorce. There was just one casualty—at my house, all plans for a major boat purchase are on indefinite hold. 

Wisely, Mike is already considering the next phase of Winnie’s new life on the Chesapeake. Fitting her out for short charters would give her a commercial appeal to the next owner. Partnering with maritime conservationists would also secure her place in history, as well as her future. For the moment, though, my brother simply enjoys cruising the Bay aboard his wonderful new boat.  He is justifiably proud of Winnie Estelle, and his role in bringing her home. 

Robert Blake Whitehill is an Eastern Shore native, screenwriter and author of the Ben Blackshaw series of mystery novels set on the Chesapeake Bay. Deadrise is on sale now. The sequel, Nitro Express, will be published in the fall. 

[July 2013 issue]