Days 52-54 Solomon’s Island, MD to St. Michael’s, MD

Saturday- Monday May 17-19, 2025

We woke up around 2am to find that power had been restored to the block. Thank goodness, we were roasting. We turned the air back on and slumbered back off to sleep. Below is the screen shot of the wicked storm that passed through and disturbed so many folks’ Friday night fun.

Due to the windy weather forecast, we changed our plans to stop in Oxford. Instead, we headed directly to St. Michael’s, MD.

Our first day (Saturday) was spent anchored in a serene, wind-sheltered bay, where we enjoyed pure relaxation. We basked in the afternoon sun, letting its warmth melt away the stress of the week.

Later, we set off on a leisurely dinghy ride, winding through narrow, picturesque channels. Elegant homes lined the shores, their manicured lawns a vibrant green against the golden light of early evening. Every turn felt like a scene from a storybook—tranquil and beautiful.

As twilight settled in, the soft hum of celebration drifted across the water—two weddings were happening nearby, filling the air with laughter, music, and the unmistakable buzz of love. What a delightful evening!

The next two days we spent in a marina so we could explore the town. Let me begin by saying that St. Michael’s, Maryland, is easily one of the most picturesque towns either of us have ever encountered. Nestled along the Chesapeake Bay, it exudes historic charm and timeless beauty. The homes—many of which date back to the early 1800s—are impeccably maintained, their weathered facades full of character and stories. Lush gardens bursting with colorful blooms that fill the air with sweet, fragrant scents.

The town itself offers a delightful mix of charm and sophistication. Quaint, independently owned shops line the main streets, each one full of unique treasures and local artisan goods. A diverse array of restaurants caters to every palate, while several nearby wineries and craft breweries provide the perfect spots to unwind and savor the flavors of the region.

We kicked off the day with a visit to the Motor Museum, home to a rotating collection of gleaming classic cars, vintage motorcycles, and nostalgic memorabilia that revved up Jeff’s inner gear head.

With a little unexpected downtime afterward, I dusted off an old pandemic-era skill and gave Jeff a haircut—surprisingly, it turned out pretty well! Not too shabby for my first attempt since the Covid days.

Later, we met up with two fellow Looper couples at a lively local hotspot called Roxy’s. The place was buzzing with energy—perfect for swapping stories over cocktails and soaking up the good vibes.

From there, Jeff and I wandered over to Limoncello, where we shared a delicious Italian dinner that hit all the right notes.

The next day, we explored the Chesapeake Maritime Museum, a beautifully curated space with the largest collection of traditional watermen boats in the entire bay. A real maritime treasure trove!

To top things off, we reconnected with Looper friends David and Evy for drinks and pizza. They were so impressed by Jeff’s new ‘do that David asked for one too—so out came the clippers again, and I added “Loop Hair Stylist” to my resume!