St. Michaels, Maryland, a Sleepy Nautical Town off the Chesapeake, Is the Perfect Stealth Weekend Escape

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It’s about this time of the summer when my thoughts turn to two things: the notion of weekend escapes—and the time and hassle it so often takes to reach those escapes. With my thoughts bogged down between a too-long drive from Brooklyn up to the Cape or a white-knuckled, one-lane crawl to one Hampton or another, I elected to take the road less traveled and pointed myself due south—to St. Michaels, Maryland, on the Eastern Shore of the Chesapeake Bay. (And, yes, if we must: It has made all the difference.)

What I found there—some of which I vaguely remembered from a long-ago Spring Break sailing trip around the Chesapeake with some college friends, one of whom somehow convinced his parents to let us borrow their family’s very large sailboat, a decision I’m still flabbergasted by all these years later—amazed me: A quaint, historical, Ye Olde America small nautical town not overrun by pleasure-seekers? (Other pleasure-seekers, I mean: When counting throngs of tourists, one always excepts one’s own party.)

A fast car, in my experience, always helps: Whether or not it actually cuts down on driving time (because it’s, um, fast) or adds to it (because it’s fun) is almost immaterial. If you have access to a fast car, jump on it and step on it. In this case, I was graced with a brand-new Maserati Levante GTS—and while the Levante is nominally classified as an SUV and presents itself to the outside world with little of the flash of look-at-me supercars, it also goes from a standstill to 60 miles an hour in four seconds (courtesy of a V-8 engine made in a joint venture with Ferrari at Ferrari’s fabled Mugello, Italy HQ) and features both a stereo system that outperforms those of cars costing twice as much and the kind of soundproofing in the cabin that allows you to ride in virtual silence, should you choose that. In short, it’s a luxurious stealth supercar—the kind of vehicle you can hand over to valets without your mind immediately picturing them at the steering wheel trying to jump the nearest drawbridge.

A mere three hours and change after setting off, my wife and I eased ourselves through sleepy St. Michaels and handed the keys off to the valets at the Inn at Perry Cabins, originally built as the farm and estate of Samuel Hambleton, a Navy purser during the War of 1812. Nestled amidst its 26 acres of forest and shoreline along the Miles River are a series of later additions to the property, which has operated as a hotel since the mid-20th century—at one point in the late 80s and early 90s, it was owned and operated by Sir Bernard Ashley, the engineer/businessman husband of Laura Ashley, and while the property has since changed hands, the aesthetic and design notes have been more along the lines of refinements and advancements rather than retoolings. What’s been added: An array of green-clay Har-Tru courts along with professional instruction, an 18-hole Pete Dye-designed golf course, a spa, and the sort of cuisine that takes every advantage of its location—among many, many other amazements on the menus, you will likely not find better, fresher, better-prepared crab cakes anywhere in the world.

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