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Romantic Weekend in St. Michaels with Waterfront Dining Itinerary

Last updated: 2024 Jun 14

Waterfront Romance and Charming Strolls

Morning

Start your day with a delightful breakfast at Gourmet by the Bay, enjoying the serene waterfront views. Afterward, take a romantic stroll along the St. Michaels Boardwalk, admiring the boats and the beauty of the Chesapeake Bay.

Afternoon

For lunch, savor the flavors of the region at Town Dock Restaurant, known for its fresh seafood. Afterward, visit the Chesapeake Bay Maritime Museum to learn about the maritime history of the area and enjoy the interactive exhibits.

Evening

In the evening, have a magical waterfront dining experience at 208 Talbot, known for its intimate ambiance and exquisite cuisine. After dinner, take a romantic sunset cruise on the bay with Patriot Cruises.

Bedtime

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Boutique Shopping and Culinary Delights

Morning

Enjoy a leisurely morning at a cozy B&B, and then head to Artistic Insights for a unique shopping experience, featuring local art and handcrafted items. For a charming brunch, visit Ava's Pizzeria & Wine Bar and enjoy their delicious wood-fired pizzas.

Afternoon

Afterward, explore the quaint streets of St. Michaels and visit the boutiques and galleries. For a sweet treat, stop by Justine's Ice Cream Parlor for their homemade ice cream. In the afternoon, take a relaxing Winery Tour at St. Michaels Winery and enjoy the local vintages.

Evening

Conclude your romantic weekend with a memorable dinner at Miles River Yacht Club, known for its elegant waterfront setting and gourmet cuisine. After dinner, take a romantic evening walk along the St. Michaels Nature Trail, strolling hand in hand under the starlit sky.

Bedtime

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