St. Michaels Escape

Sharing crab claws and sunset views, a group of MarineMax customers savors this historic Maryland harbor.

Tucked unobtrusively into the eastern shore of Chesapeake Bay, St Michaels is a quaint town with a hushed sensibility – the kind of seaside community where sibilant waves are the most cherished resource besides freshly caught seafood.

And yet, this unassuming Maryland community has a compelling, magnetic allure, one that often seduces boaters from all the way across the steely waters of the bight. This past September, a collective of Sea Ray owners in the Baltimore area succumbed to temptation, traversed the Chesapeake for the annual MarineMax Getaway in St. Michaels, Maryland, and learned why the magic of this town requires yearly visits.


Fifty-eight boaters, most between 30 and 60, became acquainted with one of Maryland’s most cherished vacation spots.

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A convoy of about 20 cast off from Gunpowder Bay near Baltimore on Friday September 14, leaving a few mavericks and geographically-dispersed stragglers to join with the crowd at a later juncture. The initial group cruised southeast across the bay toward the mouth of the Chester River, meeting with fellow skipper Al Saxon on his 360 Sedan Bridge at the Rock Hall peninsula just before everybody navigated lithely through the Kent Narrows into the top of Eastern Bay. By midafternoon, roughly 30 boats and 60 people had eased into their reserved slips at St. Michaels Harbour Inn Marina & Spa and prepared for the ensuing festivities.

Al, outwardly exhibiting traveler’s high from the excursion on the Chesapeake, reveled in the day’s events. “For me, the highlight of the trip was that two and a half hours across the bay, because I love driving my boat. But my wife Vicki was most excited about all the social aspects.”

Little did Vicki know that an unprecedented soiree was about to set the tone for the entire weekend. The whole clan sensed something was up when they saw a pristine 380 Sundancer sitting placidly and uninhabited in one of the slips. The group had not noticed this boat until this moment, but there it was, spotless and perfect. Jennifer Keller, the MarineMax Getaway coordinator, unfurled a plush carpet in front of the boat, began to pass out champagne glasses and filled everybody in:

Rob and Kim Jerome were currently in route from their home in Annapolis to rendezvous with the group and take their newly purchased Sea Ray for an inaugural drive. Their local MarineMax salesman was driving them to St Michaels where their new baby awaited, along with this clandestinely planned and expertly executed surprise party.

When Rob and Kim arrived, they got the rock star treatment. “It was overwhelming in the best way possible. Anything I could have possibly wanted was taken care of,” recalled Rob. And then his excitement shifted rapidly to the new boat. “They showed me how to operate it, cleaned it and even filled my tank. The only thing left for me to do was take it for a ride and buy a bloody Mary.”

The celebratory atmosphere of the Jeromes’ reception dovetailed seamlessly into the group’s first event, a private wine tasting at St Michaels Winery, just a breezy walk from the marina. Inside the intimate, incandescent tasting room, where vintage wine casks act as table stems, all toasted to a successful east-to-west jaunt, congratulated the Jeromes yet again and enjoyed the company of new friends.

Al took this opportunity to talk shop with his fellow Sea Ray enthusiasts “I got to meet a lot of boaters that I haven’t met before. You generally tend to hang out with your own yacht club, and the nice thing about MarineMax is that the customer base is from all over, so I met a lot of nice people.”

Jim agreed wholeheartedly and noted the diverse, yet familial feel of the entire group. “Everyone was very unique and the people we met were anywhere from mid 30s to mid 60s,” Jim said. “But boaters are a common breed of people because everybody already has something in common – age isn’t really a discriminating factor.”

Any successful vacation requires a delicate balance of coordinated activities and leisurely downtime to schmooze, nap or explore. Jim Filipids, owner of a 340 Sundancer, raved about the coordination all the events, but his wife Robin appreciated the relaxed ambiance that permeated the entire trip: “I liked when we were able to sit on the pier and just informally get to know each other.”

Saturday was Robin’s kind of day. The lax itinerary was ideal for sleeping in, chatting with dock neighbors and casually discovering all of the little nuances and nooks of St Michaels. Some even used their free time to venture a mile north to the Chesapeake Bay Maritime Museum, where they learned about the region’s rich cultural history.

Many used this downtime to shop at a host of local stores offering seasonal tchotchkes, memorabilia and swimwear. In cozy proximity to these charming coastal shops, a sea-side restaurant succinctly announces the historic town’s culinary fortes on painted wooden signs suspended slightly below the building’s blue tin roof: “Oysters. Clams. Fish. Shrimp. Scallops.” All sound tempting, but one crucial item is missing from this list: crab.

But MarineMax was already on top of it. On Saturday night the group gathered compactly onto a water taxi, which shuttled everyone from the marina to the Crab Claw, an authentic crab shack that looks like a hybrid between a bucolic red barn and a boathouse. This is a beloved local haunt, and once inside, the MarineMax cadre bounded claws-first into steamed crabs and fried chicken.

“Crab is a big thing in Maryland,” explained Jay Vogel, the proud owner of a 15-year-old 330 Sundancer, “and the Crab Claw is always hopping at Maryland steamed crab. Its delicious stuff.”

Jim, a restaurant owner himself, did not hide his admiration for the execution of the dinner. “My wife enjoyed all the social parts of the trip, but for me, I liked the food,” he said with a laugh.

The next morning, each Sea Ray departed at its own clip. Though some lingered, a few football fans headed back early to catch the future Super Bowl champs play their second game of the season. All the slips were empty by day’s end, but what remained were a shared collection of indelible memories and the certainty that all would return to the enchanting coastal town soon. “It was one of the best boating experiences I have ever had,” said Jim. “Prior to leaving St Michaels I told MarineMax, ‘put us down for next year – I’m in.’”

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