Sailing into Summer: Annapolis Charm + Small-Town Stays in June (Annapolis & Easton, MD)
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June was about slowing down just enough to soak it all in — waterfront strolls, crab feasts by the dock, and history layered with charm. It was less about hopping around and more about settling into places that invite you to stay a little longer, breathe a little deeper, and let the rhythm of the water guide your pace.
We started with Annapolis — Maryland’s capital with a coastal soul. From exploring its cobblestone streets to sailing the Chesapeake, Annapolis delivered on every front. I shared my go-to spots for fresh seafood, favorite hidden corners in downtown, and even a few ways to experience this sailor’s haven without blowing your budget.
Then came Easton — smaller, quieter, and full of surprises. Nestled on the Eastern Shore, it’s the kind of town that sneaks up on you with its galleries, farmers markets, and slower pace of life. I covered where to stay, where to eat, and how to make the most of a short visit to this underrated gem.
While May was about movement, June leaned into the joy of staying put — of digging deeper into a place and letting it unfold at its own pace. These stops reminded me that adventure doesn’t always mean going far. Sometimes it just means looking a little closer at what’s nearby.
Whether you’re planning a weekend escape or just daydreaming about your next getaway, I hope this month’s posts give you a taste of Maryland’s quieter side — where maritime history, good food, and small-town magic meet.
Here’s to anchoring in, exploring slower, and making the most of wherever you land this summer.
