Need a weekend reset? From waterfront wine tastings to rooftop tacos and coastal hiking trails, Annapolis and the Eastern Shore offer the perfect mix of small-town charm, boutique lodging, and easy outdoor adventure. Whether you’re sipping rosé at Great Frogs Winery or catching a summer show at the Annapolis Garden Theater, there’s something here for everyone—just a short drive from DC.
Highlights include:
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Stay at 1313 West, a boutique hotel with NYC Polo Bar-inspired vibes.
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Dine at the Choptank for rooftop views or SeaSalt for upscale seafood.
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Catch live music during Dinner Under the Stars or sip local brews at Forward Brewing.
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Unwind at the Chesapeake Bay Beach Club with dipping pools and fire pits.