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Exploring the Charm of St. Michaels Itinerary

Last updated: 2024 Jun 14

Historic Walks and Waterfront Dining

Morning

Start your day with a delightful breakfast at Gina's Cafe, known for its cozy atmosphere and delicious dishes. Afterward, immerse yourself in the history of St. Michaels with the Chesapeake Beach North Beach Historic Guided Walking Tour. Explore the charming streets and learn about the town's maritime heritage.

Afternoon

For lunch, savor the fresh seafood at The Crab Claw while enjoying views of the harbor. Afterward, take a relaxing Chesapeake Beach Guided Walking Tour of the Railway Trail and admire the scenic beauty of the area.

Evening

In the evening, dine at the iconic St. Michaels Crab & Steak House, a local favorite for its surf and turf. After dinner, take a leisurely stroll along the waterfront and enjoy the peaceful ambiance of St. Michaels.

Bedtime

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Chesapeake Beach North Beach Historic Guided Walking Tour
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Chesapeake Beach Guided Walking Tour of the Railway Trail
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Culinary Delights and Artisanal Tastings

Morning

Enjoy a delicious breakfast at Ava's Pizzeria & Wine Bar, known for its authentic Italian cuisine. After breakfast, take a Chesapeake Beach North Beach Scenic Guided Walking Tour to appreciate the natural beauty of the area.

Afternoon

For lunch, head to Bistro St. Michaels for a taste of local flavors in a charming setting. Afterward, visit Eastern Shore Brewing for a tour of the brewery and a tasting of their handcrafted beers.

Evening

Indulge in a fine dining experience at Perry Cabin by Belmond - Stars Restaurant by Chef Jose Andres, where you can enjoy innovative dishes in a luxurious setting. After dinner, relax at the Harbourtowne Golf Resort and Conference Center with a nightcap at the bar.

Bedtime

Find amazing hotels in St. Michaels, Maryland.

Chesapeake Beach North Beach Scenic Guided Walking Tour
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Outdoor Adventures and Sunset Views

Morning

Start your day with a hearty breakfast at Awful Arthur's Seafood Company, a local institution known for its seafood specialties. After breakfast, embark on an outdoor adventure with activities like kayaking or biking along the scenic trails.

Afternoon

For a late lunch, enjoy the waterfront views at Town Dock Restaurant and savor the taste of the Chesapeake Bay. Afterward, take a relaxing cruise on the water to unwind and take in the beauty of the surroundings.

Evening

End your trip with a memorable dinner at Carpenter Street Saloon, a historic restaurant with a cozy atmosphere. After dinner, head to Limoncello Italian Restaurant & Wine Bar for a nightcap and enjoy the sunset views from their terrace.

Bedtime

Find amazing hotels in St. Michaels, Maryland.