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undefined Itinerary

Last updated: 2024 Jun 14

Morning

Start your day at the Chesapeake Bay Maritime Museum, which offers visitors a range of exhibits, displays, and interactive experiences. The museum is dedicated to preserving the maritime history of the Chesapeake Bay area and includes a collection of historic boats, a lighthouse, and exhibits on the oyster industry.

Afternoon

For lunch, head to Ava's Pizzeria & Wine Bar, which offers delicious wood-fired pizzas and a great selection of wine. Afterward, take a stroll through the charming streets of St. Michael's, which are lined with historic homes, charming shops, and galleries.

Evening

In the evening, take a sunset sail on a historic skipjack. These traditional sailing vessels were once used for oyster dredging and provide a unique and scenic way to experience the Chesapeake Bay.

Bedtime

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Morning

Start your day with a visit to the St. Michael's Winery, which produces a range of award-winning wines. Take a tour of the vineyard and winery and enjoy a tasting of their delicious wines.

Afternoon

For lunch, check out the Crab Claw Restaurant, which is a local favorite for its delicious seafood dishes and waterfront location. Afterward, head to the St. Michael's Museum, which is housed in a charming historic building and offers a glimpse into the town's past.

Evening

In the evening, take a ghost tour of St. Michael's. These tours are led by knowledgeable guides who will share spooky stories and legends about the town's haunted past.

Bedtime

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Morning

Start your day with a bike ride along the scenic Rails to Trails bike path, which runs through St. Michael's and offers beautiful views of the surrounding countryside.

Afternoon

For lunch, head to the Carpenter Street Saloon, which is a local institution known for its delicious burgers and friendly atmosphere. Afterward, take a kayak or paddleboard tour of the Chesapeake Bay, which offers a unique perspective on the area's natural beauty.

Evening

In the evening, head to the St. Michael's Art League, which showcases the work of local artists and offers classes and workshops for visitors.

Bedtime

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Morning

Start your day with a visit to the Tilghman Island, which is a charming fishing village located just a short drive from St. Michael's. Take a tour of the village's historic homes and enjoy a seafood lunch at one of the local restaurants.

Afternoon

After lunch, head to the Oxford-Bellevue Ferry, which is the oldest privately owned ferry in the United States and provides a scenic 10-minute ride across the Tred Avon River.

Evening

Finish your day with a sunset cocktail at the Inn at Perry Cabin, which is a luxurious waterfront hotel that has played host to many famous guests over the years.

Bedtime

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