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5 Days in Chesapeake: Adventure and Charm

Discover the beauty and history of Chesapeake on your next adventure.

22 April 2023

Chesapeake is a quaint and charming city located in Virginia, United States. It offers plenty of opportunities for tourists to explore its history, culture, and beauty. From museums and historic landmarks to parks and water activities, Chesapeake has something for everyone.

Travel plan

• Check into the Chesapeake Bay Beach Club Hotel, a luxurious waterfront property that offers stunning views of the bay.
• Take a four-hour sailing excursion with Captain Salem on the 48-foot schooner Woodwind, and learn about the history of Annapolis while enjoying some local wine and cheese.
• Pamper yourself at the hotel's Lavender Fields Spa, which offers a variety of treatments using natural and organic products.
• Grab dinner at the nearby Harris Crab House, where you can dine al fresco on fresh seafood and watch the sunset over Kent Island.
• End the night with a soak in the hotel's infinity pool and hot tub, which overlook the bay.

• Rent bikes from Breezy Point Marina and explore the Chesapeake Bay Environmental Center, a 500-acre nature preserve with miles of trails, birdwatching opportunities, and kayaking tours.
• Refuel with brunch at Bridges Restaurant, a waterfront eatery that serves classic American fare with an Asian twist.
• Visit the Chesapeake Bay Maritime Museum in St. Michaels, which showcases the area's rich maritime history through interactive exhibits and demonstrations.
• Enjoy an early dinner at the Crab Claw Restaurant, where you can feast on crabs, mussels, and clams while enjoying the view of the harbor.
• Catch a movie under the stars at the historic Avalon Theater in Easton, which hosts outdoor screenings during the summer months.

• Visit the Harriet Tubman Underground Railroad National Historic Park, which honors the life and legacy of the famous abolitionist and conductor of the Underground Railroad.
• Stop by the Maryland Wine Bar & Shop, which offers locally produced wines and craft beers, as well as live music and events.
• Have lunch at Mason's Redux, a farm-to-table restaurant that highlights the region's seasonal ingredients and flavors.
• Take a tour of the Blackwater National Wildlife Refuge, where you can spot bald eagles, ospreys, and other rare bird species.
• Relax with a cold brew at RAR Brewing, a popular taproom in Cambridge that serves a rotating selection of beers and hosts trivia and game nights.

• Start the day with a kayak tour of the Wye Island Natural Resources Management Area, which offers scenic views of the Wye River and abundant wildlife.
• Visit the Academy Art Museum in Easton, which houses an extensive collection of American and European art, as well as rotating exhibitions and programs.
• Have lunch at Bartlett Pear Inn, a cozy restaurant with a seasonal menu that showcases the chef's culinary expertise and creativity.
• Explore the Chesapeake Bay Environmental Arts Center in Stevensville, which showcases the work of local artists and hosts workshops and events.
• Dine at Knoxie's Table, a farm-to-fork restaurant that offers classic Southern dishes with a Chesapeake twist.

• Take a walking tour of historic Chestertown, a charming town that dates back to the colonial era and features numerous museums, galleries, and shops.
• Have lunch at Lemon Leaf Café, a cozy eatery that offers fresh salads, sandwiches, and soups made with local ingredients.
• Visit the haunted Radcliffe House, a historic mansion that is said to be one of the most haunted places in Maryland.
• Enjoy a farewell dinner at Doc's Riverside Grille, a waterside restaurant with stunning views of the Chester River and a menu that features fresh seafood and American classics.
• End the night with a ghost tour of Chestertown, where you can hear spooky tales and legends about the town's haunted past.