Discover St Michael’s Maryland for the perfect weekend getaway. Nestled along the picturesque banks of the Chesapeake Bay, St Michael’s, Maryland, is a charming town rich in history and natural beauty. A favorite getaway from Washington, D.C., and Baltimore, this idyllic destination offers visitors the chance to live well, thrive mindfully, and travel with purpose. Here’s why St Michael’s makes a perfect day or weekend trip.

St Michael’s is a quaint escape where history mingles with the serene beauty of the Chesapeake Bay.”

— LiveThriveTravel.com

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A Glimpse into History

Founded in the early 1660s, St Michael’s brims with historic charm. The town played a significant role during the War of 1812 and is often dubbed “The Town That Fooled the British” for its clever defensive strategies. Walking through the quaint streets, you’ll encounter beautifully preserved 18th and 19th-century architecture, offering a window into America’s past.

St. Michael’s Walking Tour Your

Historical Sites

• Chesapeake Bay Maritime Museum: A beautiful waterfront museum with exhibits on the history of the Chesapeake Bay and maritime traditions.
• St. Michael’s Museum at St. Mary’s Square: This charming museum provides a glimpse into the local history and culture of St. Michael’s.
• Hopkins Original Frame Shop and Gallery: Located in a historic building, this gallery showcases local art and crafts, giving you a taste of the local artistic heritage.
• 1879 Hooper Strait Lighthouse: Part of the Chesapeake Bay Maritime Museum, this screw-pile lighthouse offers great views and interesting exhibits about lighthouse history.
• Higgins House: A great example of mid-19th century homes, providing insight into the architectural styles and local history of that period.
• St. Michaels Historic District: Simply walking through the area reveals numerous historic homes, shops, and buildings that tell the story of this charming town.

An Italian Escape in St Michael’s

While exploring the historic streets, make sure to visit Simpatico, Italy’s Finest! Here, you’ll feel as though you’ve walked through a direct portal from St Michael’s to Italy. The owner, Bobbi Parlett, is exceptionally warm and accommodating, matched only by her knowledgeable staff. Simpatico offers an exquisite selection of Italian wines, foods, and gifts that transport you straight to the heart of Italy. It’s an experience not to be missed in this charming Maryland town. You’ll find many gift options to add to your mindful living collection.

Top-Rated Activities

• Chesapeake Bay Maritime Museum – Dive into the region’s rich maritime heritage with interactive exhibits and historic vessels.
• Sail Selina II – Enjoy a private sailing experience on an elegant, historic yacht.
• St. Michaels Winery – Indulge in a delightful wine tasting at this beloved local winery.
• Patriot Cruises – Take a guided tour of the scenic Miles River aboard a traditional tour boat.

Accommodations for a Luxe Retreat

When planning your St. Michael’s Maryland weekend getaway, treat yourself to the finest stay through these highly-rated accommodations available on *Expedia.

• Inn at Perry Cabin – Experience world-class luxury at this stunning waterfront hotel.
• The Wildset – A chic and modern inn that emphasizes comfort and elegance.
• St. Michaels Inn – Offering comfortable and convenient accommodations with a touch of quaint charm.

Dining Experiences to Savor

Treat your taste buds at these top-rated local eateries:

• Ava’s Pizzeria & Wine Bar: Perfect for a casual, yet delicious dining experience. Don’t miss their wood-fired pizzas and extensive wine list.
• Bistro St. Michaels: Enjoy innovative American cuisine with a focus on seasonal and local ingredients.
• 208 Talbot: A fine dining establishment with a sophisticated menu, ideal for a romantic evening out.
• San Miguels: “Mexican Food Restaurant, a cozy, family-owned gem nestled on the corner of Talbot Street & Railroad Ave. At San Miguels, we take pride in crafting our sauces and salsas fresh in-house every day, ensuring each dish is bursting with authentic flavors.” BTW, the best Blood Orange Rosemary Margaritas!

St Michael’s is not just a beautiful destination; it’s a place where you can embrace mindful living. Whether you’re sailing on serene waters, enjoying locally crafted wines, or simply wandering through historic streets, each moment spent here is a step towards a more fulfilling and purposeful travel experience.

Discover the fascinating history, immerse yourself in enriching activities, and savor the local flavors. St Michael’s, Maryland, invites you to live well, thrive mindfully, and travel with purpose.

The St. Michaels Visitor Center is a great starting point for learning more about the area’s history and getting information on what to see and do.