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Culinary Delights and Coastal Charm: 5-Day St. Michaels, Maryland Escape Itinerary

Last updated: 2024 Jun 14

Historic Waterfront and Local Flavors

Morning

Start your St. Michaels journey with a delightful breakfast at Gina's Cafe, known for its cozy atmosphere and delicious morning fare. Afterward, take a leisurely stroll along the charming St. Michaels Historic District, admiring the well-preserved 19th-century homes and the iconic Chesapeake Bay Maritime Museum (CBMM).

Afternoon

For lunch, savor the fresh catch of the day at The Crab Claw, a local favorite with waterfront dining. Post-lunch, enjoy a relaxing Chesapeake Bay Sailing Cruise on a classic yacht, taking in the scenic beauty of the bay and its gentle breezes.

Evening

As the sun sets, head to Stars Restaurant - Rooftop Grill Room & Lounge at Perry Cabin by Belmond for a sophisticated dinner with panoramic views. Afterward, enjoy a nightcap at Carpenter Street Saloon, a historic haunt with a lively atmosphere and a wide selection of drinks.

Bedtime

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4.79
St. Michaels Historic District
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4.79
Carpenter Street Saloon
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Culinary Exploration and Maritime Heritage

Morning

Indulge in a hearty breakfast at Bistro St. Michaels, a cozy spot with a French flair. Afterward, immerse yourself in the maritime history of the region with a visit to the Chesapeake Bay Maritime Museum (CBMM), spending the morning exploring the exhibits and historic boats.

Afternoon

For lunch, enjoy the casual elegance of Limoncello Italian Restaurant & Wine Bar, where you can savor Italian cuisine and a fine selection of wines. Post-lunch, take a short drive to Oxford, Maryland, a quaint and picturesque town, for a relaxed afternoon of strolling and exploring its small shops and waterfront park.

Evening

Dine at Miles River Yacht Club Dining Room, an exclusive experience with a refined menu and a view of the serene waters. After dinner, take a serene Sunset Kayaking Tour on the Miles River, gliding through the calm waters as the sky turns golden.

Bedtime

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4.75
Oxford, Maryland
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Golf, Gourmet, and Local Brews

Morning

Enjoy a breakfast with a view at Harbourtowne Golf Resort and Conference Center, where you can fuel up for a morning of golf. Tee off at the Harbourtowne Golf Links, a scenic course with challenging holes and beautiful waterfront vistas.

Afternoon

After a round of golf, head to Ava's Pizzeria & Wine Bar for a relaxed lunch, where you can enjoy gourmet pizzas and a selection of fine wines. Post-lunch, visit Eastern Shore Brewing for a brewery tour and tasting, learning about the craft beer process and enjoying some local brews.

Evening

For dinner, experience the elegant ambiance and exceptional steaks at Theo's Steaks, Sides & Spirits. Afterward, take a leisurely St. Michaels Winery Tasting to sample some of the region's best wines, ending the day on a refined note.

Bedtime

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3.61
Eastern Shore Brewing
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3.61
St. Michaels Winery Tasting
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Coastal Cuisine and Laid-Back Luxury

Morning

Start your day with a sumptuous breakfast at Town Dock Restaurant, a local gem with a menu featuring fresh, seasonal ingredients. After breakfast, head out for a morning of St. Michaels Crab & Oyster Crawl, visiting local crab shacks and oyster bars to taste the best of the bay's bounty.

Afternoon

Enjoy a casual lunch at Rustico Restaurant & Wine Bar, where you can relax in a rustic setting and enjoy a menu of comfort foods and a selection of wines. Post-lunch, take a scenic drive to Tilghman Island, Maryland, a nearby island with a laid-back vibe and beautiful waterfront views.

Evening

Dine at Awful Arthur's Seafood Company, known for its casual atmosphere and fresh seafood dishes. After dinner, take a romantic Moonlit Cruise on the Chesapeake, enjoying the gentle evening breeze and the shimmering reflections on the water.

Bedtime

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2.84
St. Michaels Crab & Oyster Crawl
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Farewell to St. Michaels

Morning

Enjoy a final breakfast at Perry Cabin by Belmond - Stars Restaurant by Chef Jose Andres, savoring the culinary creations in a luxurious setting. After breakfast, take a St. Michaels Food Tour, revisiting some of your favorite spots and discovering new culinary delights in the heart of this charming town.

Afternoon

For a leisurely lunch, head to Foode [1132] in nearby Easton, Maryland, where you can enjoy farm-to-table cuisine in a relaxed and friendly atmosphere. Spend the rest of the afternoon exploring the historic streets and boutiques of Easton, soaking in the small-town charm.

Evening

Conclude your St. Michaels journey with a memorable dinner at Waterfowl Chesapeake [1133], a restaurant with a focus on local, sustainable ingredients and a serene waterfront setting. Raise a glass to the memories made as you enjoy your final evening on the Eastern Shore.

Bedtime

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