Colonial cobblestones, Appalachian trails, riverside hamlets, and salty sea breeze—Virginia is for lovers… of adventure, history, and beauty.
Day 1: Alexandria – Where the Past Lives On
Wander the cobblestone streets of Old Town Alexandria Dine along the Potomac River at historic waterfront restaurants Shop boutiques on King Street Visit Gadsby’s Tavern Museum and Carlyle House
🛏️ Stay: The Alexandrian or Morrison House
🍽️ Eat: Virtue Feed & Grain
🚶♀️ Vibe: Colonial elegance meets modern charm
Day 2: Arlington & Mount Vernon – National Legacy
Pay your respects at Arlington National Cemetery Tour George Washington’s Mount Vernon Estate Walk the Mount Vernon Trail along the Potomac Optional: Evening trip across the river to D.C. monuments by moonlight
🛏️ Stay: Mount Vernon Inn or Hyatt Arlington
🍽️ Eat: Mount Vernon Inn Restaurant (colonial fare!)
Day 3: Fredericksburg – Civil War & Colonial Roots
Explore Fredericksburg & Spotsylvania National Military Park Stroll historic Downtown Fredericksburg for antiques & coffee Visit James Monroe Museum and Kenmore Plantation Paddle on the Rappahannock River or sip wine at Potomac Point Winery
🛏️ Stay: Richard Johnston Inn or The Kenmore Inn
🍽️ Eat: Foode or Brock’s Riverside Grill
Day 4: Richmond – The Soul of the South
Tour Virginia Museum of Fine Arts and American Civil War Museum Bike the Capital Trail along the James River Explore trendy neighborhoods like Scott’s Addition and Carytown Craft brews + history = heaven
🛏️ Stay: Quirk Hotel or Linden Row Inn
🍽️ Eat: L’Opossum (quirky & upscale) or Mama J’s Kitchen (soul food heaven)
Day 5: Charlottesville – Jefferson’s Virginia
Tour Monticello, Jefferson’s iconic estate Stroll the Historic Downtown Mall Sip your way through the Monticello Wine Trail Hike Saunders-Monticello Trail or enjoy skyline views
🛏️ Stay: Clifton Inn or Oakhurst Inn
🍷 Wine Tip: Try King Family, Jefferson Vineyards, or Pippin Hill
🍽️ Eat: The Alley Light or C&O
Day 6: Shenandoah National Park – Skyline Drive Dreaming
Drive Skyline Drive for breathtaking views Hike Dark Hollow Falls, Stony Man, or Old Rag Look for wildlife: deer, black bears, and hawks Stay in a rustic lodge or camp under the stars
🛏️ Stay: Skyland Lodge or Big Meadows Lodge
🥾 Hiker Tip: Bring layers, water, and your camera
Day 7: Harrisonburg – Heart of the Valley
Visit Explore More Discovery Museum (great for kids) Tour White Oak Lavender Farm Sample craft beer at Brothers Craft Brewing Enjoy a peaceful evening in the Shenandoah Valley
🛏️ Stay: Joshua Wilton House or By the Side of the Road Inn
🍽️ Eat: Local Chop & Grill House
Day 8: Staunton – Small Town with Big Culture
Explore Woodrow Wilson Presidential Library Visit the American Shakespeare Center’s Blackfriars Playhouse Dine and shop in the beautifully preserved downtown Tour Frontier Culture Museum
🛏️ Stay: The Blackburn Inn
🍽️ Eat: Zynodoa (Southern farm-to-table)
Day 9: Lexington – Civil War & Horse Country
Visit VMI, Washington and Lee University, and Lee Chapel Tour Virginia Horse Center Stroll downtown Lexington’s red brick sidewalks Explore Natural Bridge State Park nearby
🛏️ Stay: The Georges (boutique inn)
🍽️ Eat: Southern Inn or Bistro on Main
Day 10: Roanoke – Star City Adventure
Hike or drive to the Roanoke Star on Mill Mountain Visit the Taubman Museum of Art Sample Southern eats in the Grandin Village Ride the Blue Ridge Parkway for amazing vistas
🛏️ Stay: Hotel Roanoke or The Liberty Trust
🍽️ Eat: Lucky or Alexander’s
Day 11: Floyd & Blue Ridge Highlands – Appalachian Soul
Explore the Blue Ridge Music Center and catch a porch jam Browse Floyd Country Store – live music & old-time dancing Hike Buffalo Mountain Natural Area Preserve Visit Chateau Morrisette Winery with a mountain view
🛏️ Stay: Hotel Floyd or a cozy cabin
🎻 Vibe: Artsy, musical, and mountain-chic
Day 12: Abingdon & Damascus – Trail Towns & Theater
Walk or bike the Virginia Creeper Trail Attend a show at the Barter Theatre, America’s oldest Shop and eat your way through quaint Abingdon Explore nearby Grayson Highlands for wild ponies
🛏️ Stay: The Martha Washington Inn
🍽️ Eat: 128 Pecan or The Tavern
Day 13: Williamsburg – Step Back in Time
Explore Colonial Williamsburg and costumed interpreters Tour Jamestown Settlement and Historic Yorktown Ride a carriage, fire a musket, spin wool! Optional: Family thrills at Busch Gardens nearby
🛏️ Stay: Williamsburg Inn or a colonial guesthouse
🍽️ Eat: The Fat Canary or King’s Arms Tavern
Day 14: Virginia Beach – Atlantic Coast Finale
Sink your toes in the sand at Virginia Beach Oceanfront Explore First Landing State Park and Cape Henry Lighthouse Stroll the Virginia Beach Boardwalk Visit the Virginia Aquarium & Marine Science Center
🛏️ Stay: The Cavalier or Oceanfront Hotel
🍽️ Eat: Waterman’s Surfside Grille or Tautog’s
🌅 Vibe: Beachside relaxation, great seafood, sunny farewell
🎒 Traveler Tips:
🗺️ Start north in Alexandria and loop clockwise for smooth flow 🧳 Pack for layers: mountains can be chilly, coastal humid 🥾 Bring hiking boots, wine-tasting clothes, and comfy shoes 🏕️ Mix stays: B&Bs, historic inns, cabins, and beach hotels 🎟️ Book colonial or theater experiences in advance 🐎 Best for all: families, history lovers, hikers, wine fans, romantic getaways, or RVers
Hagan Happenstance 