Get ready for a food-filled adventure in Williamsburg, Jamestown, and Yorktown!

Start your days with delicious pancakes, explore historic sites, and enjoy unique dining experiences at colonial taverns and local bistros. Top it all off with tastings at breweries, the Williamsburg Winery, and a distillery for a truly memorable trip! 🍷🍺🥞

Restaurants can vary in capacity, operating hours, and seasonal hours. To ensure a smooth and enjoyable experience for your group, it's best to reach out to the Visit Williamsburg sales team at sales@visitwilliamsburg.com. They can provide detailed information and assist with coordinating your group travel arrangements.

Day One: Spirited History

Morning

  • Gather your group and kick off the day with a hearty breakfast at Colonial Pancake House. Enjoy their famous pancakes and soak in the friendly, welcoming atmosphere. It's the perfect spot to fuel up and chat about the day's adventures.

Mid-Morning

  • Embark on a group exploration of Colonial Williamsburg. Wander through the charming streets together, visiting iconic sites like the Governor's Palace, Bruton Parish Church, and the Capitol. Share stories and take plenty of group photos to capture the memories.

  • Take a stroll down Duke of Gloucester Street, often referred to as "the most historic avenue in all America", to Merchants Square, an 18th-century style retail village. With over 40 shops and restaurants, it provides a charming setting for unique shopping and dining experiences.

Lunch

  • Stop by the Cheese Shop in Merchant Square for their renowned sandwiches, crafted with the highest quality meats, cheeses, and freshly baked bread. It's a delicious and satisfying stop that sandwich lovers won't want to miss. Remember to call ahead and place your order.

Afternoon

  • Wander back to Colonial Williamsburg and immerse yourself into history by visiting the trade shops. Learn about the various trades of this historical period and listen to interpreters share fascinating stories about their lives during this transformative time.

  • Colonial Williamsburg is always bustling with events, reenactments, and activities that bring history to life. From military drills to theatrical performances, there's always something exciting happening. Explore upcoming events.

Dinner

  • The historic taverns at Colonial Williamsburg offer a unique dining experience that transports you back to the 18th century. Each tavern is meticulously designed to reflect the colonial era, with authentic decor and traditional recipes updated for modern tastes. It’s history served on a plate! Work with the Visit Williamsburg Sales Team to coordinator your groups dining experience.

Night

  • End your day with a visit to Copper Fox Distillery, known for its innovative and award-winning spirits. Enjoy a tasting session with your group, sampling a variety of craft spirits in a fun and lively atmosphere.

Colonial Williamsburg 2
Governor's Palace | Colonial Williamsburg
Copper Fox Distillery Sunset
Copper Fox Distillery

Day Two: Archology & Ale

Morning

  • Start your day at 1607 Coffee Company, known for its exceptional coffee and cozy ambiance. This popular spot is perfect for enjoying morning conversations with friends over gourmet espresso drinks and freshly baked pastries. The friendly atmosphere will set a cheerful tone for the day ahead.

Mid-Morning

  • Dive into history together at the Jamestown Settlement. This living history museum offers an immersive experience where you can learn about the first permanent English settlement in America. Explore the recreated fort, ships, and Powhatan town, and enjoy interactive exhibits that make history come alive.

  • Continue your historical adventure with a visit to Historic Jamestowne. Explore the archaeological site and see the remains of the original 1607 James Fort. It's a fascinating place to learn about early American history and share discoveries with your group.

Lunch

  • Head to the Williamsburg Winery for lunch at The Gabriel Archer Tavern. This charming spot offers a menu filled with fresh, locally sourced ingredients. Enjoy a relaxing meal with your group, surrounded by the beautiful vineyard scenery.

Afternoon

  • Stick around Williamsburg Winery for a tour and tasting. Stroll through the beautiful vineyard, learn about the winemaking process, and sample some of their finest wines. It's a relaxing and educational experience that everyone will enjoy.

Dinner

  • Gather your group for a casual dining experience at La Tienda in Williamsburg. Located on Jamestown Road, it offers a taste of Spain with authentic tapas, made-to-order paella, and their famous house sangria. The inviting atmosphere and delicious cuisine make it a must-visit spot for anyone looking to enjoy the flavors of Spain.

Night

  • Cap off your day with a visit to Frothy Moon. Enjoy a wide variety of craft beers in a lively and fun atmosphere. It's the perfect spot to relax, chat, and toast to a fantastic day spent together in Williamsburg.

Gabriel Archer Tavern food
Gabriel Archer Tavern | Williamsburg Winery
Influencer - Aleah and Seth Meyers - Frothy Moon Brewhouse
Beer Garden | Frothy Moon Brewhouse

Day Three: Brunch & Battlefields

Morning

  • Start your day with a delicious southern-style breakfast at Southern Pancake & Waffle House, a cozy, family-owned restaurant. Gather your group and enjoy a hearty meal featuring fluffy pancakes and crispy waffles. Fuel up and share some laughs before your adventure begins.

Mid-Morning

  • Continue your historical journey at the Yorktown Battlefield, the site of the last major battle of the American Revolutionary War. Wander through the historic grounds together, imagining the pivotal moments that shaped the nation's history. It's a great opportunity for group photos and shared discoveries.

  • Historic Yorktown is a charming village that offers a glimpse into America's colonial past. Nestled in this picturesque setting, you'll find Mobjack Coffee Roasters where you can enjoy expertly roasted coffees, teas, and delicious baked goods. Right next door is Little York Confectionery a nostalgic candy shop offering ice cream, house-made chocolates, and a variety of sweets. Together, these spots provide a delightful blend of history and culinary treats, making Yorktown a must-visit destination.

Lunch

  • Enjoy a delightful lunch at Riverwalk Restaurant, nestled along the serene banks of the York River. With breathtaking waterfront views, this charming spot offers a diverse menu featuring fresh seafood, pasta dishes, steaks, and lunchtime favorites like salads, burgers, and sandwiches. The warm and inviting ambiance, combined with exceptional service, makes it the perfect place for a leisurely meal with your group.

Afternoon

  • Step back in time as you explore the American Revolution Museum at Yorktown. Engage with interactive exhibits and outdoor living history demonstrations that bring the Revolutionary War to life. It's an educational and entertaining experience that everyone in your group will enjoy.

  • Grab a quick coffee from The 1781 Café at the American Revolution Museum before heading back to Williamsburg. Operated by AromasWorld, the café features a coffee-centric menu with espresso drinks, fresh roasted coffee, fine teas, and fruit smoothies.

  • Take a fascinating tour of Whitley's Peanut Factory in Williamsburg, where you can learn about the process of making their famous "Home-Cooked" Virginia peanuts. During the tour, you'll see how these gourmet peanuts are hand-cooked and slowly roasted, ensuring the highest quality and flavor. You'll also have the opportunity to sample a variety of their delicious products, from classic salted peanuts to unique flavored varieties. The friendly staff and informative tour make it a fun and educational experience.

Dinner

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    Dinner at Casa Pearl combines the unique flavors of oysters and tacos in a lively, retro atmosphere, perfect for a memorable meal. Amber Ox Public House provides a modern twist on classic Southern fare, using regionally sourced ingredients to create eclectic and elevated dishes. For a more intimate setting, The Study at Amber Ox offers a refined, deco-inspired lounge where you can enjoy turn-of-the-century cocktails, hors d'oeuvres, and desserts.

     

Night

  • End your day with a visit to the Virginia Beer Company. Enjoy a wide variety of craft beers in a fun and vibrant setting. It's the perfect spot to relax, chat, and toast to a trip well spent exploring the historic triangle together.

Mobjack Bay Coffee Couple
Mobjack Coffee | Yorktown
Yorktown Victory Monument - Sean Smith
Yorktown Victory Monument

More Itineraries

Itineraries

Day trips and itineraries for Colonial Williamsburg, Yorktown, and Jamestown Virginia