“Monkey bread. Wow.”
My partner glances up from his own breakfast menu, then smiles — half in amusement and half in annoyance — because he knows I will elaborate. Which of course I do.
“Growing up, we had monkey bread,” I explain. “I haven’t seen or thought of it since childhood and I’ve never seen it on a formal menu.”
We are at Stars in St. Michaels — The Inn at Perry Cabin’s fine-dining restaurant. The night before, we enjoyed an elegant, romantic dinner here in front of a roaring fireplace — savoring Eastern Shore and Southern specialties like Maryland crab cakes, oysters rockefeller, shrimp and grits, and Smith Island (nine-layer) cake. This morning we are back for breakfast — rather he is. I have come for the coffee and view of the Miles River. But the monkey bread is throwing me off. My excitement for menus is typically reserved for spa treatments — hydrating facials, cocooning body wraps and scrubs, signature massages — not food. And never breakfast.

“What exactly is monkey bread,” he’s taunting me now. But there’s no going back.
“It is Christmas morning deliciousness,” I reply. “My mother made it every year.” As did the White House. In the early 1980s, First Lady Nancy Reagan popularized the sticky, pull-apart cinnamon dough by making it a staple of the Reagan White House Christmas. But the pastry actually dates back a century earlier to 1880s Hungary, where it was known as arany galuska (“golden dumpling”). In immigrating to the U.S., Hungarians brought the dessert with them. The connection to my childhood makes perfect sense. My mother is of Hungarian descent.
“So, are you ordering it?”
“I am.” And like everything we discover during this romantic, weekend getaway, The Inn at Perry Cabin adds its own distinctive flair.

The hotel’s signature cocktail for example — Wedding Crashers — is a nod to the comedy, starring actors Vince Vaughn and Owen Wilson, that was filmed here (watch the opening scene). The cocktail offers an eye-catching, wedding-esque, layered look of gold (bottom) to purple (top) — a fusion of St. Germain, tonic water, black pepper, pea blossom, and tequila.
As for my much-anticipated breakfast monkey bread? It arrives — French toast inspired — in its own small cast-iron skillet alongside a gooey caramel sauce that our server ceremoniously drizzles over it.
Nautically Inspired
The hotel’s interior is just as decadent. Our water-facing suite — eternally nautical — features a white with pops of blue color palette. Art-style coffee table books tell the stories of the local watermen and surrounding Eastern Shore region, while black-and-white vintage photos — many of sailboats and oyster shucking — line the walls. Doors lead onto a spacious balcony perfect for morning coffee and watching the sunrise over the river; our bathroom features both a walk-in shower and freestanding tub (where I indulge), while the living room fireplace (now gas) preserves the ambience of the hotel’s storied past. Even the elevators come with porthole-like mirrors.

In season, of course (April to November), the Inn employs its own fleet of captained sailboats and yachts for guests to explore the river and estuaries leading to the Chesapeake Bay. The fleet includes the recently restored 1902 skipjack — one of the last remaining boats used to dredge the Chesapeake Bay for oysters. The boat was also used by author James Michener in the research of his bestselling novel, Chesapeake.
The Watermen and Maritime Museum
For a deeper understanding of St. Michaels’ connection to the water, spend time at the Chesapeake Bay Maritime Museum, located next door to the Inn (take the shortcut through the hedge row). Here, as my boat-captain partner pours over the boats and the town’s ship-building legacy — a tradition that continues today with the training of apprentices in the craft — I become mesmerized by the hard lives the watermen (and women) lived.

The 18 acres on which the museum buildings (including the historic 1879 Hooper Strait lighthouse) now sit once served as a thriving seafood-processing center. While clams and crabs were an integral part of the operation, oysters were the town’s mainstay: St. Michaels was first to introduce canned oysters to the world. Work days were long. While the men masterfully shoveled the oysters so that each shell landed neatly on its end, the women would stand for hours in tiny wooden boxes (an attempt to keep the mud off their floor-length skirts) — shucking out the plump oyster meat and discarding the shells.
As one longtime resident noted, “Dig 10 feet deep into the ground here and you’ll find hordes of oyster shells. The lighthouse and a few of the museum buildings are built entirely on them.”
Spa Time
Modern-day St. Michaels offers a much softer side. A walk along the town’s cobblestone sidewalks reveals upscale wine bars and restaurants, historic pubs serving elevated cuisine, specialty boutiques, and back at The Inn at Perry Cabin — a luxury spa. Full disclosure: I visited this spa years ago. My friend and the former spa director here, Shoshana Weinberg (you may also know her from The Spa at Four Seasons Hong Kong) invited me when opening the spa. It was she who christened the treatment rooms with names like violet, rose, verbena, and lavender, and named the spa at that time — Linden Spa — a nod to the rows of linden trees lining the entrance to the hotel.

Now, decades later, as I step into the relaxation area to await my treatment, I am surprised and touched to see her meticulously framed, herb-and-flower sketches still lining the walls. Plant medicine was — and still is — an integral part of this spa. Treatments incorporate fresh herbs and flowers grown in the hotel’s own kitchen and vegetable gardens as well as nearby Eastern Shore farms. But The Spa at Perry Cabin (as it’s now known) has recently added a water element.
During the pandemic, the Inn began offering a private dining experience in small, glass-like boat houses set by the water’s edge. Now, in the warmer months, spa treatments — like my 90-minute customized, lemongrass-and-ginger-oil massage with Jenna — can be delivered in one of the picturesque houses surrounded by foliage for privacy. Relax afterward on the great lawn (complete with fire pit and white Adirondack chairs) and watch the boats glide up and down the river before meandering back to the spa — past blooming flowers, peach and apple trees.
Other Must Dos

Beyond the spa, gardens, fine dining, and maritime museum, St. Michael’s — and The Inn at Perry Cabin — offer a number of other must dos, including bringing your pup along for the stay. The Inn is extremely pet friendly as evidenced by the welcoming boat-shaped water bowls in the lobby. Other must dos include:
Take a Guided History Tour
This lively and informative walking tour begins at The Inn at Perry Cabin (the concierge will happily arrange). Leading us through town, our zealous guide Jay regaled us with tales of drunken sailors and fooling the British (War of 1812), shared history of the Inn’s namesake and previous incarnations as a tobacco farm, race-horse academy, and Laura Ashley-owned hotel, and pointed out the must-have pizza in town (Ava’s), and most haunted dwelling (Kemp House).
Sail the Waters
Don’t leave St. Michaels without getting out on the water, be it for sailing lessons — The Inn at Perry Cabin boasts one of the region’s most celebrated sailing programs. Or for sailing leisure. Opt for a private day (or half-day) captained sail complete with lunch, sunset cocktails, and dinner.
Kiss on the Kissing Bridge

Walk across St. Michael’s famous kissing bridge. This sweet pedestrian bridge (where ducks nest in spring and couples pose for wedding pictures) was made famous in 1928 when the romantic melodrama, The First Kiss, starring Gary Cooper and Fay Wray (of King Kong fame) was filmed here. Reportedly lost in a Hollywood fire, the film never aired, further adding to its romantic allure.
Shop for the Unusual
Void of mass chain and box stores, St. Michaels is rife with eclectic boutiques. The gift shop at the Chesapeake Bay Maritime Museum is worth a visit for unusual nautical-themed home decor (I brought home an oyster-shell tree). Downtown’s Simpatico specializes in Italian items: limoncello, wines, and meats, ceramic dinnerware, and Murano glass. And don’t miss Guilford & Company, the only gemologist-owned jewelry and antique store on Maryland’s Eastern Shore. Owner Julie Moriarty specializes in antique and estate jewelry, featuring brands like Tiffany and Co., Cartier, and Bulgari.
Savor Maryland Crabs and Cakes

Definitely sample the famed crabs and (Smith Island) cakes. The Inn at Perry Cabin serves a number of crab recipes — crab cakes, crab dip (served Eastern Shore style with pretzel rolls), crab sammy (sandwich), crab benedict, and crab imperial omelets. All were created by “Mama” (as she’s affectionately referred to by members of the Inn at Perry Cabin’s culinary team) who has been with the hotel for almost 20 years, and makes every crab item based on her personal love for the Eastern Shore.
As for the Smith Island cake: “It’s our state dessert,” Miss Vicky, a server at The Inn at Perry Cabin, says. The cake originated on Smith Island, a remote island in the Chesapeake Bay, by the wives of watermen who sent it along on their husbands’ fishing expeditions. The original cake is 8-to-12 thin layers of yellow cake with fudge frosting. Recipes have been handed down through generations and today’s variations include red velvet, white, lemon, and coconut. Bring a piece home (it’s sold all over town), or order from The Smith Island Baking Company, which offers nationwide delivery in two days.
Venture Out to Tilghman Island
For a glimpse of real-life watermen still at work, venture out to Tilghman Island, just a 20-minute drive from St. Michaels. The three-mile-long, one-mile-wide island (population 850) is home to commercial fishermen, many descendants of the seafaring families who arrived there in the 1700s. “I fish every day; oyster every winter,” one local tells us. For best eats, head to Two If By Sea, a no-frills cafe known for its fresh-caught fish, crabs, and oysters. Insider tip (from our guide, Jay): try the crabbie eggs benedict: a concoction of poached eggs, crab imperial, old bay, and mozzarella.
Feature image courtesy of The Inn at Perry Cabin.