Un-Wine'd in Chesapeake

Set Chesapeake as your affordable hub and go on a wine-filled adventure! Explore a winery for the ages, and then make-your-own at a unique new winery. Take time to shop among historic sites along the way. This is a getaway you won’t want to miss!

Day 1:

Dedicate this afternoon to history. First stop: Williamsburg Winery, Virginia’s largest winery with an annual production of some 60,000 cases. The 50+ acres of vineyards surrounding the winery offer a beautiful backdrop to the Old World-style village. Take it all in with a guided tour of the winery and tasting session. Keep the engraved tasting glass as a memento. If it's not too late, drive over to Merchants Square, an 18th-century style retail village with over 40 shops and restaurants located adjacent to Colonial Williamsburg. Back in Chesapeake, your dinner at Passion The Restaurant will prove to be food for the soul. Enticing culinary creations and more great wine will be the perfect end to your first day. Consider resting at the Residence InnHyatt Place or Delta Hotels.

Day 2:

Start your day with breakfast at the local favorite The Egg Bistro - a mom-and-pop diner with upscale bistro food. Head over to Mermaid Winery, Norfolk's first winery, located in the Ghent neighborhood. You can view the winemaking process from the tasting bar! Skip lunch and go straight for dessert. Swing by the Carolina Cupcakery (In VA!) where you really don't know what you'll get. No fear ... that's a good thing! The Cupcakery offers over 100 flavors, of which only eight to 12 will be offered on a given day. After, spend an afternoon of antiquing (aka "walking off dessert").

Day 3:

Enjoy breakfast at your hotel before checking out and heading to Smithfield. Incorporated in 1752, Smithfield became a town devoted to the art of curing world-famous Smithfield Ham. Begin your visit downtown at the Visitor Center, also home to the Arts Center @ 319, offering tourist information, a gallery/gift shop and the chance to chat with resident artists. Further down Main Street is the Isle of Wight Museum, with its overview of the county’s history and the world’s oldest ham. Spend some time in Historic Downtown Smithfield browsing the unique shops and art galleries, and be sure to stop at the Genuine Smithfield Ham Shop inside the Taste of Smithfield for yet another tasty souvenir.


Discover things to do, places to stay, and where to dine in Smithfield. 


Visit a Virginia winery with your friends and family to discover exceptional, award-winning wines…