Mountains to Coastal Virginia

This immersive multi-day journey through Virginia showcases the perfect blend of history, culture, scenic beauty, and local flavor. Beginning in the charming city of Staunton, travelers will experience vibrant arts, walkable downtown streets, and rich presidential history, then explore the living heritage of the Shenandoah Valley. The tour continues to Nelson County, where breathtaking Blue Ridge Mountain views meet craft beverages and relaxing resort experiences. In Richmond, guests dive into America’s past with guided tours of historic landmarks and lively neighborhoods, followed by hands-on activities and free time to explore. The experience concludes in Chesapeake, where coastal charm, Revolutionary War history, and waterfront dining create a memorable finale. This itinerary offers a well-rounded Virginia experience filled with storytelling, hands-on activities, and unforgettable scenery.

Day 1: Staunton

Staunton is the kind of town where you can discover magic hiding in plain sight. Its friendly blend of small-town charm and vibrant culture invites you to stroll red brick sidewalks, admire striking Victorian historic architecture, and experience a sense of unexpected delight around every corner.

Wander through independently owned downtown boutiques and cafes, and uncover details you didn’t even know you were searching for. Experience world-class music festivals and intimate theatre performances that feel more like discoveries than events.

Sip your way through inventive breweries, savor locally sourced and thoughtfully crafted cuisine, and escape into the natural beauty of nearby Shenandoah National Park.

Hotel Check-in

Dinner: The Depot Grill  

Show: American Shakespeare Center's Blackfriars Playhouse
The American Shakespeare Center (ASC) brings to life an authentic repertory theatre experience, performing Shakespeare’s timeless works alongside modern classics and bold new adaptations. Don’t just watch theatre—immerse yourself in it. As you take your seat, actors fill the Playhouse with live music, performing popular songs from our time, just as they would have in Shakespeare’s day.

Day 2: Staunton

Breakfast on Own at the Hotel

Woodrow Wilson Presidential Library & Museum - 90 minutes
Step into the life and times of one of America's most influential presidents. Immerse yourself in the World War I trench exhibit, take a peek at Wilson’s Pierce-Arrow limousine, walk the halls in the house where he was born and learn more about what makes Wilson a consequential and controversial president.

Guided Downtown Staunton Tour (walking or step-on) - 1 hour
You will enjoy a unique, customized tour of beautiful Staunton, Virginia, its wonderful architecture and attractions led by an experienced guide who knows its history… and its stories.

Lunch - On own in downtown - 2 hours
Explore downtown on your own. Self guided scavenger hunt. Shopping. Dining

Frontier Culture Museum
The Frontier Culture Museum is the biggest open-air living history museum in the Shenandoah Valley, as well as one of the top tourist destinations in Virginia. Costumed historical interpreters show the life and customs of the indigenous Native American tribes in Virginia, the arrival of the German, English and Irish settlers along the Great Wagon Road, and the painful journey of the enslaved Africans to the first permanent British colony in North America. Visitors may also interact with a blacksmith at an Irish Forge, woodworkers, tailors, and yarn spinners, and learn how the early settlers of America cooked and worked the land.

Depart for Nelson County 

Day 3: Nelson County

Nestled in Virginia’s Blue Ridge Mountains, Nelson County offers a perfect blend of scenic beauty and local flavor. From breathtaking views along the Blue Ridge Parkway to tastings on the renowned Nelson 151 Trail, visitors can explore wineries, breweries, and outdoor adventures all in one place. It’s a laid-back destination where nature, craft, and community come together. 

Happy Hour & Tour at Devils Backbone Basecamp Brewpub - 90 minutes

Hotel Check-in & Dinner on own at: Wintergreen Resort
Wintergreen Resort is a premier 11,000-acre, four-season mountain resort located in the Blue Ridge Mountains of Virginia.  Known for skiing, snowboarding, and the state’s largest snow tubing park in winter, it offers golf, tennis, hiking, and water activities at Lake Monocan during warmer months.

Day 4: Nelson County

Breakfast at Belties
Escape the ordinary and enjoy the extraordinary. At Belties, we offer more than just hand-crafted coffee and 18-layer scratch biscuits—we offer an experience. With our farmhouse cafe, views of the Blue Ridge Mountains, and the peaceful presence of our Belted Galloway cows grazing nearby, every visit is a chance to slow down, savor unforgettable flavors, and enjoy the simple pleasures of country hospitality.

Blueridge Tunnel Tour Guided Walking Tour - 2 hours
The Blue Ridge Tunnel in Afton, Virginia, offers a 2.25-mile (one-way) walking trail through a historic 4,273-foot railroad tunnel built in the 1850s.

Brunch at Hazy Mountain Vineyards & Brewery - 90 minutes
A Family-Owned Winery Producing From Estate Vineyards In the Blue Ridge Mountains of Virginia

Walton Mountain Museum
The Walton’s Mountain Museum showcases the television show of the 1960s, “The Waltons”. Earl Hamner, Jr., creator of The Walton’s, grew up in Schuyler and many of the scripts were based on life as a boy in Schuyler, VA. The museum displays replicas of rooms on the TV show, such as John-Boy’s Bedroom, Ike Godsey’s Store, the kitchen and living room. A 30-minute video featuring Earl Hamner, Jr. and the stars of “The Waltons”, hundreds of photographs and pieces of memorabilia, and a gift shop are in the museum.

Virginia Distillery Co.
Discover the art of American Single Malt—book a tour and tasting to explore our craft, history, and award-winning whisky firsthand.

Depart for Richmond

Hotel Check-In - Dinner on own at the hotel

Candle Making - 2 hours
We come to you! Enjoy this group candle making experience without leaving the hotel. 

Day 5: Richmond

Breakfast - included at the hotel

Historic Richmond Tour - 3 hours
Meet your step-on guide and journey through Richmond’s historic neighborhoods, rich with stories of the past. Your tour includes a stop at the Virginia State Capitol, designed by Thomas Jefferson and the oldest continuously operating state capitol in the country.

Lunch & Shopping - 2 hours
Enjoy free time and lunch on your own in Carytown, Richmond’s iconic “Mile of Style.” With more than 30 locally owned restaurants to choose from, there’s something for every taste. There will be plenty of time to browse the district’s eclectic mix of boutiques, specialty shops, and one-of-a-kind finds.

Historic St. John’s Church - 1 hour
Step back in time at historic St. John’s Church, where your group will experience a full-scale reenactment of Patrick Henry’s famous “Give me liberty, or give me death!” speech. Performed in the very place it was delivered, this immersive program brings the Revolutionary era to life with costumed interpreters, dramatic storytelling, and audience engagement.

Depart for Chesapeake

Hotel Check-in

Dinner on own at Summit Pointe - 2 hours

Day 6: Chesapeake

Breakfast is included at the hotel.

Historical Village-Guided Walking Tour - 90 minutes
Explore Chesapeake, VA's rich history through this curated walking tour focusing on Revolutionary War sites and local heritage. Key options include guided tours of the Great Bridge Battlefield & Waterways Museum and self-guided options exploring African-American heritage or city-wide historical sites.

Chesapeake Planetarium
While comfortably seated under a 30-foot dome, enjoy unforgettable journeys through space!

Lunch - Lockside Bar & Grill
There is no better place than lunch with a view! Lockside is located in the heart of Great Bridge, Chesapeake right on the water. Our warm and inviting atmosphere for casual fine dining will make you feel at home without all the work of preparing your favorite seafood & steak dishes. Lockside, supports sour local fishermen with purchasing local seafood and fresh produce from local farmers.

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