Girlfriend Getaway to St. Michaels, Maryland 11

Surprises Abound in this Sleepy, Shoreside Town

Girlfriend getaways come in many varieties. Some are late night and loud (see: New Orleans), some are spent under beach umbrellas sipping umbrella drinks (see: Cancun). But for a ladies weekend that’s more about slowing down and catching up, St. Michaels is the spot.

Located less than an hour from the Chesapeake Bay Bridge, where the land begins to crumble like a perfect piece of cornbread, St. Michaels is the perennial favorite among Maryland’s seaside towns. Established by Episcopalians, constructed by shipbuilders, revived by oystermen and remade by tourism, St. Michaels boasts as many layers as an Eastern Shore dessert. 

You won’t find two-for-one hermit crabs here. Instead, you’ll discover an oh-so-strollable main street brimming with eclectic shops and eateries, as well as world-class accommodations gilded with small-town charm.

There are a lot of choices for where to lay your head in St. Michaels: quaint lodges and bed-and-breakfasts abound. But for a dose of luxury, choose the Inn at Perry Cabin. There’s a reason Architectural Digest named this hotel the most beautiful in the Old Line State. Actually, there are probably a couple of hundred reasons, and you’re sure to notice them all as you wander the sprawling property. The inn’s premier restaurant, Stars, overlooks the Miles River and offers a sophisticated take on Eastern Shore favorites, including the ice cream (a beach-weekend staple), made in-house daily.

The inn’s very own Linden Spa is especially worth a visit. Named for the fragrant trees that line the drive outside, this lovely oasis offers the services you’d expect (hot stones, facials, a steam room) with extra touches you might not. For example, whenever possible, the spa uses locally grown botanicals, some cultivated in the same ZIP code. After an herbal massage, recharge in the handsome relaxation room or flower-rimmed infinity pool.

Once you’ve been fed and pampered, hit the town. Do not pass go, do not collect $200, do not visit St. Michaels and miss the Chesapeake Bay Maritime Museum. More of an experience than a collection of exhibitions, the museum covers a couple of blocks and will ensure that you go home with more than a glowing complexion; after your visit, you should be well-versed in Eastern Shore history too.

Also located on the museum’s campus is a home that once belonged to Frederick Douglass’ sister, who was a close confidant and co-conspirator of the abolitionist.

In town, you’ll find more shops and seafood than you’ll know what to do with. Galleries and antique stores are the stars of Talbot Street, but you’ll also find beachy boutiques and yoga centers. If your group is into trying something new, schedule an aerial yoga class at the Studio. Then reclaim your calories at the Carpenter Street Saloon, which offers a shuttle back to the inn for your afternoon nap.

Finish your day by the water or a crackling fire, indulging in some wine and a little girl talk. Chances are you’ll be planning your next trip to St. Michaels.  


Inn at Perry Cabin by Belmond

308 Watkins Lane, St. Michaels, MD 21663 | @innbyperrycabin

Your crew can charter a luxury yacht or enroll in the sailing academy and earn your skippers’ caps. Afterward, visit Linden Spa where they’re committed to the use of rare botanicals—some even grown on the Eastern Shore.


Stars (at Inn at Perry Cabin by Belmond)

308 Watkins Lane, St. Michaels, MD 21663 | @innbyperrycabin

If you wake up at the Inn at Perry Cabin, you won’t have far to go for a proper meal. Try the crab chowder at Stars and be forever changed. Dessert is ice cream or sorbet, made in-house daily. 


Chesapeake Bay Maritime Museum

213 N. Talbot St., St. Michaels, MD 21663 | @chesapeakemaritime

The Chesapeake Bay Maritime Museum is a St. Michaels can’t-miss. Its campus is spread across 18 acres where you can explore a working boatyard, climb aboard an oyster skipjack or snap your photo in front of the Hooper Strait Light. 


St. Michael’s Winery | 609 S. Talbot St., St. Michaels, MD 21663 | @st_michaels_winery

Eastern Shore Brewing | 605 S. Talbot St., St. Michaels, MD 21663 | @eastern_shore_brewing

Lyon Distilling Company | 605 S. Talbot St., St. Michaels, MD 21663 | @lyondistilling 

When it’s time for a drink, visit the southern end of town for a one-two-three (yes, three!) punch of the good stuff. St. Michaels Winery, Eastern Shore Brewing and Lyon Distilling Co. will surely have something for even the pickiest partier.


Hopkins Original Art Gallery

301 S. Talbot St., St. Michaels, MD 21663| @hopkinsoriginal

There are more antique shops in downtown St. Michaels than there are traffic lights and even more art galleries. You may have to split up to visit them all.