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Discover Chesapeake: A Fun-Filled 4-Day Adventure

Discover the beauty of Chesapeake, where history meets nature.

22 April 2023

Chesapeake is a delightful and scenic destination for travelers to the United States, offering a diverse array of activities and attractions. Visitors can explore the pristine natural beauty of the Chesapeake Bay or visit historic landmarks such as the Great Bridge Battlefield and Waterways Museum. Whether you enjoy outdoor adventures or cultural experiences, Chesapeake has something to offer everyone.

Travel plan

• Check in to the Aloft Chesapeake hotel, a funky hotel with a splash of modernity, with a stylish bar and lounge area.
• Head to the Chesapeake Central Library and explore their extensive collection of historical documents and artifacts, including exhibits on local history and the vibrant arts scene, and a cozy café to grab a quick bite.
• Drive down to the Chesapeake Arboretum, an enchanting oasis where you can stroll through 48 acres of gardens and trails, marveling at breathtaking scenery and learning about the local flora and fauna.
• Take a break and enjoy some authentic Italian cuisine at The Pizzeria, a family-owned restaurant where the pizza crusts are crispy and the tomato sauce is as fresh as the ceiling art!
• Visit the Great Bridge Battlefield and Waterways Park, an area where you can explore the battlefield that played a role in the Revolutionary War and experience some of Chesapeake's unique tidal wetlands habitats.

• Start the day with a hearty breakfast at Sunrise Breakfast, a no-frills diner that serves up classics like eggs, bacon, and pancakes as well as more unusual dishes like a gyro omelet.
• Take a kayaking adventure with Chesapeake Bay Company, which offers guided kayaking tours with stunning views of the Chesapeake Bay and plenty of opportunities for wildlife sightings.
• Take a break at Dismal Swamp Canal Trail, an 8.5-mile mostly flat and gravel trail that meanders through a dense natural habitat filled with all kinds of flora and fauna, perfect for a meditative nature walk or bike ride.
• Stop by Chesapeake City Park, featuring an 18-hole championship disc golf course and a Water Spray Park for kids and adults.
• Grab a bite to eat at The Butcher's Son, a local meat mecca with locally sourced animal products processed and aged on-site.

• Start your foodie day with a visit to Battlefield Farmers' Market. The market offers all sorts of fresh produce, seafood and meat, along with delicious baked goods and unique artisan food products.
• After a quick snack, visit Chesapeake Bay Distillery and taste their award-winning spirits made in small batches such as Deep Sea Vodka, Ghost Pepper-infused Vodka along with many more.
• Later in the day experience wine tasting and vineyard touring with Mermaid Winery. The winery offers a variety of wine-tasting flights, from their famous Mermaid Mead and fruit wines to the traditional grapes.
• Dine at Traditions Grill, a casual family atmosphere that serves some of the best hand-cut steaks, burgers, and seafood in town.
• End your night with a unique bar hop to Don Julio, a Mexican cantina with an extensive list of margaritas and tequilas as well as live music, followed by Bucketheads, a casual bar that offers an extensive list of cocktails and local beers.

• Arrive early for a late breakfast at The Egg Bistro, voted ‘Best Brunch' by Coastal Virginia magazine. This place offers a creative spin on the classic breakfast menu and lunches.
• Head to Greenbrier Mall, an indoor shopping paradise with over 100 stores, eateries, and service providers.
• Visit General Wolfe St Bazaar, a unique boutique-style store featuring medieval and fantasy products, plus a bevy of gift items and toys.
• End your stay by visiting Weeping Radish Farm and Brewery, where you can experience a farm tour, sip fresh beer brewed on-site, and learn about the history of this iconic establishment.
• Before departing, make a quick stop at Grilled Cheese Bistro for a cheesy goodness indulgence that you will remember for days!