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Best Places To Visit in St. Michaels, Maryland

St. Michaels Port Aerial view

Table of Contents

Day 1: The Heart of St. Michaels

Morning: A Warm Welcome

As the sun gently rose over the horizon, painting the sky with hues of pink and orange, our family set out on an exciting journey to the charming town of St. Michaels, Maryland. With the car packed and excitement bubbling over, we hit the road, eager to explore the many places to visit in St. Michaels, Maryland.

Our first stop was the Inn at Perry Cabin, a luxurious waterfront resort known for its elegant accommodations and beautiful gardens. As we drove up, the historic charm of the inn immediately captivated us. The friendly staff welcomed us warmly, and we quickly settled into our cozy suite, complete with a stunning view of the Miles River.

Maritime Adventures

After a hearty breakfast at the inn’s picturesque dining room, we were ready to start our adventure. Our first destination was the Chesapeake Bay Maritime Museum, a must-see among places to visit in St. Michaels, Maryland. The museum’s sprawling 18-acre waterfront campus offers interactive exhibits that captivate both young and old.

We started our tour with the Hooper Strait Lighthouse, where the kids were thrilled to climb up and imagine themselves as lighthouse keepers. Next, we explored the Watermen’s Wharf, learning about the history of the Chesapeake Bay’s fishing industry through hands-on displays. The highlight was the historic boatyard, where craftsmen were restoring antique boats, and we marveled at the intricate work involved.

A Taste of Local Flavors: Ava’s Pizzeria & Wine Bar

For lunch, we headed to Ava’s Pizzeria & Wine Bar, a local favorite with over 1000 glowing reviews. The casual, family-friendly atmosphere was perfect for our first meal in town. We enjoyed a delicious wood-fired pizza, paired with a refreshing glass of homemade lemonade for the kids and a local craft beer for my husband and me. The fresh, locally sourced ingredients made every bite a delight.

Talbot Street

With full bellies and happy hearts, we took a leisurely stroll down Talbot Street, the main thoroughfare of St. Michaels. The charming shops and boutiques offered a variety of unique finds. The kids were particularly taken with Justine’s Ice Cream Parlor, where they indulged in towering cones of creamy goodness.

Sunset on the Water: Patriot Cruises

As the day wound down, we made our way to Patriot Cruises for a sunset tour of the Chesapeake Bay. The gentle rocking of the boat, combined with the stunning views of the sun setting over the water, made for a magical experience. The historical narration provided interesting insights into the area’s rich maritime heritage, adding an educational twist to the scenic beauty.

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Day 2: Adventure and Relaxation

St. Michaels Nature Trail

Refreshed from a good night’s sleep, we began our day with a hearty breakfast at the inn. We then headed out to explore the St. Michaels Nature Trail. The scenic trail winds through the town and along the waterfront, offering beautiful views and a chance to spot local wildlife. The kids enjoyed the adventure, while my husband and I appreciated the peaceful surroundings.

A Sail on the Selina II

Next, we embarked on a private sailing charter with Sail Selina II. This intimate experience aboard a historic yacht is a highlight among places to visit in St. Michaels, Maryland. We learned about the art of sailing, and the kids even got a chance to steer the boat. The serene environment of the Chesapeake Bay, combined with the gentle breeze and the sound of the waves, made this an unforgettable experience.

Lunch at The Crab Claw

For lunch, we headed to The Crab Claw, an iconic seafood restaurant with immense popularity. Situated right on the water, it offers a quintessential Maryland dining experience. We indulged in a feast of steamed crabs, crab cakes, and other seafood delights. The casual, outdoor seating provided a perfect setting to enjoy our meal while watching boats pass by.

Shopping and Relaxation

After lunch, we explored more of the local shops. Chesapeake Trading Company and Silver Linings were among our favorite stops, where we found unique nautical gifts and jewelry. We then returned to the inn for some relaxation. My husband and I took advantage of the spa services, while the kids enjoyed a swim in the pool.

Dining at Bistro St. Michaels

Dinner was a special affair at Bistro St. Michaels, a restaurant renowned for its elegant cuisine and excellent service. The sophisticated yet cozy atmosphere was perfect for a family dinner. We savored dishes like seafood gumbo and braised short ribs, ending the meal with delectable desserts.

Day 3: History and Farewell

A Step Back in Time

Our final day began with a visit to the St. Michaels Museum at St. Mary’s Square, where we delved into the town’s rich history. The guided walking tour took us through historic homes and landmarks, providing fascinating stories and insights into the past. The kids were particularly intrigued by the tale of Muskrat Mary, a local legend.

Lunch at Foxy’s Harbor Grille

For our final lunch in St. Michaels, we chose Foxy’s Harbor Grille, known for its vibrant atmosphere and delicious seafood. We enjoyed fish tacos, shrimp salad, and a famous crab pretzel. The casual, waterfront setting made it a perfect spot to unwind and reflect on our trip.

The Classic Motor Museum

With a few hours left before we had to leave, we visited The Classic Motor Museum, where we marveled at the collection of vintage cars. The kids were fascinated by the antique tractors and muscle cars, while my husband and I appreciated the beautifully restored classics.

A Bittersweet Goodbye

As the sun began to set, we packed up our car and prepared to say goodbye to St. Michaels. We took one last stroll along the waterfront, capturing a few final photos to remember our trip. The peacefulness of the town, combined with its rich history and welcoming community, left a lasting impression on us.

As we drove away, we reflected on our incredible journey and the many places to visit in St. Michaels, Maryland. From maritime adventures to delicious meals, our trip had been filled with memorable moments. We left with hearts full of joy and a promise to return to this charming town in the future.


St. Michaels, Maryland, offers an enchanting mix of history, nature, and culinary delights, making it an ideal destination for a family getaway. Whether you’re exploring the Chesapeake Bay Maritime Museum, sailing on the Selina II, or dining at The Crab Claw, there are countless places to visit in St. Michaels, Maryland, that will capture your heart and create lasting memories. Plan your trip today and discover the magic of this charming town for yourself!


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