Aromas
Meeting for coffee is a first date go-to, but you can make it memorable with a stop at this local community hub. Enjoy the twin stimulants of freshly crafted coffee and home-baked goods, and if things are going well, you’re perfectly placed for a stroll down Duke of Gloucester Street to keep the date going.
Williamsburg Winery
Show that special someone a fancy time with a wine tasting and tour at the Williamsburg Winery. A few sips are always advisable to smooth the way for an enjoyable first date, and acres of lovely grounds offer a charming setting to get acquainted. Stop for lunch or dinner at the Gabriel Archer Tavern onsite.
Charly’s Airport Restaurant
This lunchtime spot is as local as it gets, and it has made itself a mainstay with hearty sandwiches on homemade bread and fresh pies that are worth saving room for. The real showstopper is the view of the Williamsburg Airport Runway, where small general aviation aircraft take off and land on clear days.
DOG Street Pub Running Club
If you prefer to avoid the stilted small talk of the first date; try panting the whole time instead. The DOG Street Pub Running Club is casual, family and dog friendly and launches from the home base at the corner of Henry and Duke of Gloucester Streets. There’s plenty of socializing before and after, and the regulars are quite friendly.
dogstreetpub.com/running-club.html
Jamestown-Scotland Ferry
Take this free cruise across the James River and enjoy the view of shore from mid-river. Print some maps for a historical scavenger hunt on the Surry side. Find Bacon’s Castle, St. Luke’s Church, and Smith’s Fort Plantation. With some snacks and a playlist, it’s like a mini road trip: the perfect litmus test fora budding relationship.