Williamsburg and Virginia’s Northern Neck

  • Bucolic landscapes and backroads
  • Colonial Williamsburg
  • Historic homes
  • Decorative arts
  • Revolutionary War history


April 21 - 27, 2024


  • Lodging in some of the South’s most unique inns, including two nights in the heart of Colonial Williamsburg and two nights on the Northern Neck at the acclaimed Hope and Glory Inn
  • Historical highlights and scenic drives
  • Stunning Colonial Williamsburg: America’s lightning rod for historic preservation
  • Lovely, quiet places in synch with the Chesapeake

Trip Description

Join Explore Up Close on an epic journey into the Old Dominion – Virginia! Our adventure will uncover some of the most-storied architecture in America, from across the centuries; and regions where the only roads are “backroads” (you know I can’t wait for that!). We’ll thrive on “the local” – food, drink, stories, and hospitality. And we’ll stay in some of the nicest boutique inns to be found anywhere. Is Virginia the South’s richest state for great stories? For preservation? For wine?! There’s one way to find out.

Virginia stands at the top of our rankings of fascinating southern states that have the punch to back up their amazing historical legacies, and this springtime trip will show off that “punch.”  We’ll spend an entire week exploring Virginia’s flatter, bucolic landscapes that spill east to the Chesapeake Bay then melt into it.  Our drive will take us through beautiful “Southside Virginia,” entering and departing the state with one overnight each direction.  We’ll spend two nights in the heart of Colonial Williamsburg and then two nights on the Northern Neck at the acclaimed Hope and Glory Inn.  The trip will feature historic homes and their stories, decorative arts, Revolutionary War history, and the Chesapeake way of life.


Sunday, April 21

We’ll depart from the western Carolinas this morning, heading for points north!

Enjoy our drive through the lovely North Carolina Piedmont, en route to the Berry Hill Resort, near South Boston, Virginia. Explore the beautiful grounds and lovely architecture. Berry Hill was built with fine craftsmanship by the enslaved people of the plantation of James Coles Bruce, a planter-politician. This house encompasses layers of important history and remains one of America’s outstanding examples of pure Greek Revival architecture. We’ll learn more about the people involved in this story on site!

Dinner and overnight at Berry Hill.

Monday, April 22

After breakfast and touring at Berry Hill, we’ll drive through “Southside Virginia” toward the Tidewater. Enjoy lunch en route; observe the change in landscape, as we drive onto the Yorktown Peninsula.

Our home for the next two nights will be the Williamsburg Lodge – just a block off of Duke of Gloucester Street (Colonial Williamsburg’s “main street”), and adjacent to both the Abby Aldrich Rockefeller Folk Art Museum, and the Dewitt Wallace Decorative Arts Museum.

Dinner and overnight, Colonial Williamsburg – America’s lightning rod for the historic preservation movement.

Tuesday, April 23

Today, we’ll enjoy the ultimate Williamsburg experience: We’ll tour some of the colonial city’s most important venues, like the Governor’s Palace and Virginia’s colonial Capitol Building. Also: Gardens, boutiques, taverns and cafés . . . and the delightful, world-class art museums.

We’ll enjoy a good old-fashioned tavern dinner this evening! Overnight, the Williamsburg Lodge.

Wednesday, April 24

Enjoy a local Williamsburg breakfast, then we’ll pack our lovely high-roofed van and explore the backroads of the Chesapeake. Our drive will take us from the Yorktown Peninsula to the Gloucester Peninsula . . . and eventually to the Northern Neck: the peninsula bordered by the Potomac River to the North; and by the Rappahannock River to the South.

Our home for our two-night stay on the Northern Neck will be the Hope and Glory Inn in Irvington, Virginia. It’s an award-winning inn, known for comfort, hospitality, great dining, and featuring owners who are “Chesapeake” through and through.

Dinner and overnight at the Hope and Glory Inn.

Thursday, April 25

It’s a day to explore the Northern Neck . . . by land and by water. Our driving tour will showcase places like Christ Church – one of Virginia’s most impressive historic churches, and Reedville – known for its “boatmen heritage” and nostalgic waterfront. We’ll complement those visits with local wine, and a Chesapeake cruise piloted by our Hope and Glory hosts.

Dinner and overnight, Virginia’s Northern Neck.

Friday, April 26

After saying farewell to our new friends, we’ll drive up the peninsula, eventually crossing the Rappahannock at Tappahannock, Virginia. (No doubt we can make up a clever ditty as we go to celebrate the crossing!) But first, we’ll “wende our way” through the bucolic landscape surrounding us . . . historic villages, farmstands, a timeless vibe.

After lunch, we’ll make our way into Virginia’s Piedmont, spending one last night in the Old Dominion.


Saturday, April 27

After an energizing breakfast . . . we make our way home. Say hello to our very own spring-clad Carolina countryside ( . . . not a bad way to end a great trip!).

Featured Experiences

Williamsburg Lodge

Iconic elegance and an exceptional culinary experience.
Representing the height of luxury in Historic Williamsburg, the iconic Williamsburg Inn has been reimagined to bring you the best of the old world and the new. The only Forbes Travel Guide Five-Star rated resort in the Historic Triangle. Staying true to its impressive Regency style, culinary options have been elevated to suit today’s evolved tastes.

Hope and Glory Inn

This romantic bed and breakfast was once an elite boarding school in 1890, and it has since graduated into a stylish hotel in Irvington within Virginia’s Northern Neck peninsula.

Come for the luxurious accommodations and stay for the unparalleled experiences that you can’t find anywhere else. Enjoy a variety of shabby-chic rooms and cottages, a dog-friendly micro-vineyard, a top-rated restaurant, scenic boat cruises, and so much more at this one-of-a-kind Virginia winery resort. It’s no surprise that we’ve gained significant acclaim from the media as well as numerous five-star reviews.

The Danville Bee Hotel

With its buzzworthy backstory and unique urban boutique style, The Bee is set for a headline-making hotel debut in Danville, Virginia’s bustling River District. The 47-room newcomer is located in what was once home to the city’s iconic broadsheet, The Danville Register & Bee, now freshly reimagined as a warm and welcoming home base for business travelers and Virginia vacationers.

What's Included

  • Comfortable high-roofed van transportation
  • Accommodation for 6 nights
  • Breakfast, 5 lunches, and 4 dinners
  • All activities / admissions per the itinerary
  • Guide and concierge service throughout the trip

Trip Price

$4,283 / person (double occupancy; single supplement, $1,025)

What's Not Included

Price does not include other meals, alcohol, or trip insurance (recommended).

..well-planned, from interesting and fun excursions planned each day, to comfortable lodging and transportation. Our trip leaders, Chumley and Khal, were impressive with their knowledge of each area we explored and gracious in their planning of every aspect of our trips.

Trip insurance safeguards your travel investment, your belongings, and most importantly, you. Though trip insurance is optional, we strongly encourage travelers to purchase trip insurance in the event you have to cancel or leave a trip for any reason. Please note, all trip participants should wait for confirmation from Explore Up Close that the trip has the minimum sign-up required to be a “go” before purchasing travel insurance. Please confirm with Explore Up Close before making any additional travel arrangements.

Once you have received confirmation from Explore Up Close, we recommend contacting a travel insurance provider directly to request a quote and compare pricing and features. You can find other providers that may fit your needs at www.insuremytrip.com, or we can gladly connect you with our travel agent.

This trip departs from Greenville / Spartanburg, South Carolina and Asheville, North Carolina. If you live elsewhere, please contact us to discuss travel arrangements, and we will look forward to assisting you!

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