Having lived in the South for four summers now, by August I am weary from the landlock. While everyone else flocks to the 30A or Alabama beaches, my heart tips towards the Eastern Shore of my youth. So, a few weeks ago, I called up my bestie and told her to meet me in St. Michaels, Maryland.

 

“Where?” asked everyone from Williamson County with whom I shared my travel plans. I was surprised to hear how few people had ever heard of the place. For those who don’t know, St. Michaels is to Washington, D.C. what the Hamptons are to Manhattanites. I hadn’t been to St. Michaels in years, but the memory was well-rooted in me from a visit over a decade ago: The quaint, walkable red brick-front downtown filled with Mom n’ Pop shops, the rich history, the fresh seafood and, of course, the beautiful Chesapeake Bay. I couldn’t wait to go back.

 

Since I was wanting upscale ease, I booked two nights at the Inn at Perry Cabin, an historic five-star resort in the heart of St. Michaels, and flew direct from BNA to Baltimore in under ninety minutes. Truly, if you’re wanting an easy weekend getaway, limiting flight time to under two hours is essential.

 

My friend Lacy met me at the airport and we rented a car to drive the remaining hour and twenty minutes to St. Michaels. Neither of us love traveling over the Chesapeake Bay Bridge, which hovers 186 feet over the water, so when we were hit with a torrential downpour during our nearly four-mile journey across it, I began to lament not booking Perry Cabin’s “Skip the Bridge” package. Every Friday from May to October, guests of the Inn can depart from Edgewater, Maryland (just thirty minutes from BWI) aboard a 55’ Hinckley Yacht for a journey across the Chesapeake –complete with white glove service– and arrive at the dock of Perry Cabin without spending a moment in traffic.

Entering the grounds of the Inn at Perry Cabin is a grand experience. Set on twenty-six acres of green lawns and gardens, the long driveway eventually reveals a sprawling white mansion on the banks of the Miles River. The manor was originally built in 1815 by Naval officer Samuel Hambleton, who retired in St. Michaels after the war of 1812. The Inn has gone through many additions and renovations over the years, and today it is equipped with every modern convenience while still maintaining its Old World charm. The classic architecture and tasteful nautical decor make the Inn feel truly timeless and elegant, like a French manicure or a pair of diamond stud earrings.

 

The water views from seemingly every window of the Inn are breathtaking. As sunset approached, we joined the other guests near the dock where we enjoyed a glass of rosé as the sun slowly dipped behind the horizon. Although it’s the East coast, the Bay affords an opportunity to see a waterfront sunset and I made sure to soak up every yellow, pink and purple-hazed moment of it.

 

The following morning, we enjoyed a patio breakfast at STARS, the Inn’s award-winning farm-to-table restaurant. I had a crab omelet and lemon yogurt with house-made granola that I will be thinking about for years to come. Later, we bicycled into town to peruse some of the shops. Filled with books, local art and coastal-inspired clothing, the shops offer something for everyone. There are also two wineries and the oldest brewery on the Eastern Shore if you are feeling inclined to imbibe. We enjoyed an afternoon coffee at the new Wildset hotel that was so good it inspired us to come back in the evening for dinner at Ruse, their restaurant. And it did not disappoint.

 

The walkability of St. Michaels might just be my favorite feature. After dinner, we walked back to Perry Cabin (although free car service is available) where we retired to our suite after some time chatting with other guests around the waterfront fire pits. Turns out, we weren’t the only girl’s trip on the grounds that weekend. Other guests included couples and a few mother-daughter duos. We also met several canine travel companions as the resort is extremely pet-friendly. The Inn offers seventy-eight guest rooms, of which thirty-five are suites. We stayed in the Great Heron, which has a large balcony with water views, a sumptuous living room and quite possibly the deepest bath tub I have ever had the privilege of soaking in.

The Inn at Perry Cabin is so genuinely lovely and comfortable that even if you’re a Type A traveler, you would be hard-pressed to leave the grounds. Everything you could possibly want to see or do is available at the resort. On our second day, rather than venturing out, we chose to enjoy the amenities at the Inn’s luxurious spa. We pre-gamed it in the steam room before indulging in ninety-minute massages. Sometimes hotel spas leave you wanting, but Carol gave me one of the most satisfying deep-tissue massages I have ever had. I left that room feeling like I had been wrung out in the best way.

 

We then spent a few hours poolside where we were served shrimp cocktail, fresh crudité and hummus (and more wine, who are we kidding). We decided that if our significant others were present, and they did not want to be on the relaxation train with us, they could instead be golfing. The Inn boasts the eighteen-hole Links at Perry Cabin golf course designed by the legendary Pete Dye. The waterfront par-72 course stretches over 7,000 yards and offers a challenging yet rewarding experience for golfers of all skill levels. There are also tennis courts and a gym on site for those who want to sweat without the steam room.

 

The Inn proudly owns an esteemed fleet of seven vessels, including a 1902 Stanley Norman Skipjack, that guests can rent for private or group charters. That evening, we joined three other guests for a sunset sail aboard the Stargazer. Fresh fruit plates and champagne were provided for us in ice-packed coolers, but honestly, once we set sail, I completely forgot they were there.

We’ve all heard about the “Power of Vitamin Sea,” and evidence supports that being near water has enormous mood-boosting benefits thanks to the negative ions present in the air. As we drifted further from shore on the last night of our trip, I could finally feel myself begin to let go. There was chit-chat amongst the group as the engine guided us out to sea, but once our sails went up and we caught wind –there was nothing but reverent silence.

 

I was struck suddenly by the fact that everything around me felt timeless: the water, the presence of a treasured friend, my billowing white dress, even the Inn itself, behind me now as I looked back at it from the water as the sun began to set. I could be in any era and these things would all have a place, I thought. Like snapshots of Camelot, a moment in a Fitzgerald novel or the pages of Martha Stewart Living magazine, I realized I am part of something that has always been and will always be. This is why I travel.

 

Tomorrow, before heading back to our respective lives, Lacy and I will visit the nearby towns of Tilghman, Oxford and Easton on the way back to the airport. Easton is enjoying a sort of culinary renaissance at the moment, and we’re told the restaurants rival anything you would find in New York City. I’m looking forward to it. And to the burger waiting for me at the Inn’s Purser’s Pub when we get back to shore, which I hear is the best in town.

 

But first, please excuse me while I sail off into the sunset.