7 Delicious Date Ideas in Williamsburg

1. Breakfast at illy Caffè

Upon entering 🔺illy Caffè, you’ll feel as though you’ve been instantly transported to Europe. A creative design aesthetic and bright, modern artwork fill the space, creating a vibrant, distinctive atmosphere.

The menu features an excellent selection of authentic Italian coffee, from lattes and cappuccinos to classic espresso. Pair a beverage with one of their delicious pastries, such as an almond croissant, or a cheese or apple Danish. They also serve mimosas, cocktails, wine, and local craft beers.

Enjoy breakfast at one of their indoor tables or sit outside to soak up the vibes of delightful Merchants Square. After breakfast, stroll around and check out the shops or explore Colonial Williamsburg’s Historic Area.

2. Create a Gourmet Picnic Basket at The Cheese Shop

At 🔺The Cheese Shop, located in Merchants Square, every corner reveals something special, including a mix of chocolates, Italian pasta, Black Truffle potato chips, and many local Virginia products.

Place an order for one of their legendary sandwiches at the deli (or order online ahead of time), then head to the cheese counter and build your own platter from their selection of over 200 cheeses. Complete your picnic basket with fresh-baked French bread and ask for the best wine pairing from their cellar downstairs.

Best places for a picnic? Find a spot on the beautiful grounds at Bassett Hall (home to John D. Rockefeller Jr. and his wife, Abby Aldrich Rockefeller, during the restoration of Colonial Williamsburg).

3. Brunch at DoG Street Pub

🔺DoG Street Pub—on Duke of Gloucester Street in the heart of Colonial Williamsburg—was once an 80-year-old bank. Chef David Everett transformed the building into a gastropub in 2012, serving simple yet outstanding food. Many of the original features of the bank were preserved during the renovation, including the marble floors and cupola skylight.

Try the Pub Fry Up, a traditional English breakfast plate with over-easy eggs, a seared pork banger, grilled ham, baked beans, hash browns, and buttery toast. Complete your brunch with a mimosa, Irish coffee, or Bloody Mary (made with their spicy house mix). With its blend of historic architecture and flavorful dishes, DoG Street Pub provides a homey setting for a special date. 

4. Dinner & Drinks ‘Downstairs at Fat Canary’

The owners of 🔺Fat Canary a bistro well-known for its upscale dining experience, expanded the business with ‘Downstairs at Fat Canary.’ This little hideaway has a vibrant industrial feel with beautiful unfinished beams, original flooring, intimate booths in the back, and a long, curved bar. Low lighting gives the space a warm ambiance, ideal for a date night with a casual-meets-sophisticated feel.

The menu includes small plates that are excellent for sharing, such as shrimp dumplings, crispy Rappahannock oysters, and hoisin barbecued pork ribs. They have an extensive selection of wines from their wine cellar to complete the meal.

5. Coffee & Treats from Mobjack Bay Coffee Roasters

🔺Mobjack Coffee Roasters & Petite Cafe, located in the Historic Cole Digges House in Yorktown, delights with both its inviting exterior and interior. They roast their coffee on-site, which smells amazing from the moment you enter the building. To the left of the front door, discover a cozy room housing their coffee bar, bakery case full of treats, and a wood-burning fireplace.

Their assortment of sweets includes macarons, scones, apple turnovers, and freshly baked cookies, and they also serve gourmet sandwiches if you’re craving a savory bite. Grab coffee and treats at the counter and sit outside at one of their many picnic tables. Or take them to go and walk down to Yorktown Beach, 0.3 miles away, and enjoy the water view. If it's a cold or rainy day, get a table in the upstairs dining room instead. 

6. Wine Tasting & Charcuterie at Gabriel Archer Tavern

At Gabriel Archer Tavern at the historic 🔺Williamsburg Winery, enjoy a quintessential romantic setting with a covered terrace overlooking the vineyard and a farm-to-table menu. Sample a selection of local Virginia cheeses and charcuterie, served with bread, assorted pickles, and jams, paired with a glass of wine or a flight of four 2-oz pours.

For the ultimate wine lover’s experience, extend the date and learn more about their wine-making process by reserving one of their tours and tastings. The stunning property – with its European-style cellar and idyllic woods and gardens – is worth savoring for as long as your itinerary allows. 

7. Small Plates & Dessert at The Hound's Tale

Take the dog lover in your life to 🔺The Hound’s Tale. From the moment you enter, a cozy, inviting atmosphere greets you, and whimsical décor like dog figurines, artwork, and playful signs fill the space. Seating options include the bar, individual tables, booths along the sidewall, and comfy couches and armchairs at the front.

Indulge in a selection of regional wine and beer, cocktails, small plates, entrees, and the most incredible desserts. Share a few of their delectable starters (crab dip, flatbread, and fried brussels to name a few) and finish off with an irresistible cookie skillet, the ultimate dessert for two. 

More Food & Drink in Williamsburg

Explore all the delicious dining options in the Williamsburg area, from stellar fine dining restaurants to award-winning breweries.