• Megan Winslett

Chesapeake Bay Escape

Updated: Jan 2


St. Michaels, Maryland is only an hour and half drive outside of Washington, DC, (click here for Washington, DC hotel recs) however almost immediately after exiting the beltway, you quickly leave the city lights behind. The drive to St. Michaels is a peaceful, easy trip through the beautiful, rural area of Maryland. Upon driving into this quaint, coastal town, it's clear this is a special place. The downtown is "Norman Rockwell-esque" with colonial-style shops and restaurants lining the streets. It was a particular treat driving through downtown during the Christmas season, as each storefront was donned with holiday lighting.

Downtown St. Michaels, MD

St. Michaels sits on the Chesapeake Bay on Maryland's Eastern Shore. During the summer, visitors can enjoy a variety of outdoor and coastal activities including motor-boating, sailing, paddleboarding and kayaking. My kids and I visited the Chesapeake Bay Maritime Museum where we learned about the area's long history in boat-building and other water-related activities. The Maritime Museum is set on a campus right on the harbor where we toured a lighthouse residence from the early 1900's, witnessed boat-builders working on nautical creations and toured the museum of old boats and other artifacts from the area's maritime past.

Boat building at the Maritime Museum

Boat-building at the Maritime Museum

Just a few minutes from town by car or even bike is Belmond's Inn at Perry Cabin. This historic hotel has a past dating back to the late 1800's, but like all Belmond properties, each historic room is outfitted with the most luxurious modern amenities. The Inn offers 80 nautically-inspired decorated rooms in neutral tones and dark hardwood. Each room is distinct, leading many return visitors requesting a particular room number. We stayed in a Junior Suite with sweeping views of the bay. Our room had 2 queen beds and also featured a lovely sitting area next to a gas fireplace. The bathroom was sizeable with an exposed closet, over-sized soaking bathtub and separate walk-in marble shower.

This beautiful, waterfront resort offers an array of activities and amenities for visitors. There are two restaurants onsite, Purser's Pub with lighter fare and the AAA 4-star awarded Stars serving breakfast, lunch and dinner overlooking the Chesapeake Bay. During their stay, guests can visit the Inn's spa, outdoor pool, arrange a tee time at a partner golf course and as of this spring, play tennis on the resort's newly installed on property tennis courts. Additionally, the Inn at Perry Cabin offers complimentary bikes, kayaks, stand-up paddleboards, bocce ball and croquet. Guests are also invited to arrange a charter from one of the Inn's 40' sailboats, 53' Hinkley or custom motor boats.

Waterfront view from Stars Restaurant

The Inn at Perry Cabin is an idyllic escape to a coastal haven. This property is ideal for a long weekend get-away for adults, an add-on to a trip to the Washington, DC (click here to see some of my favorite DC hotels) or Baltimore areas or a fun family excursion during the summer.


Megan Winslett Travel can enhance your stay by adding complimentary breakfast each morning in Stars Restaurant and a $100 hotel credit. Contact me for more information or book at your own convenience through my Virtuoso online booking hotel tool.


53 views0 comments

Recent Posts

See All