Virginia
5
Day Itinerary •
USA
Five days in Virginia lets you explore the full extraordinary breadth of the Old Dominion, from the mountain grandeur of Shenandoah National Park and Skyline Drive to the remarkable colonial heritage of Williamsburg, the extraordinary Chesapeake Bay coast and the magnificent Appalachian highlands of southwest Virginia. This route covers the complete Virginia experience. The extraordinary Luray Caverns and Skyline Drive, Thomas Jefferson's Monticello and the Blue Ridge Parkway, the magnificent Colonial Williamsburg and Natural Bridge, the extraordinary Virginia Beach and Chincoteague wild ponies and the remarkable Appalachian Trail.
Best Time To Visit
April to June or September to November
Getting There
Fly into Dulles (IAD), Richmond (RIC) or Norfolk (ORF)
Getting Around
Rental car essential throughout Virginia
Budget Per Day
Approx $120 to $200 per person per day
Difficulity
Easy to moderate, some Shenandoah and Appalachian hiking
DAY 1
SHENANDOAH NATIONAL PARK
MORNING
LURAY CAVERNS AND THE SHENANDOAH VALLEY
Luray Caverns is the most extraordinary cave system in the eastern United States, its extraordinary formations of stalactites, stalagmites and flowstone in chambers up to 10 stories high and the remarkable Stalacpipe Organ, the world's largest musical instrument spanning 3.5 acres of cavern, giving the finest cave experience on the East Coast. The Shenandoah Valley town of Luray with its extraordinary Hawksbill Creek and the nearby Shenandoah River are unmissable. Entry approx $30. Drive: 1.5 hr drive
MIDDAY
SKYLINE DRIVE, THE MOST EXTRAORDINARY MOUNTAIN DRIVE IN THE EAST
Skyline Drive runs the entire 105-mile length of Shenandoah National Park along the Blue Ridge crest, its extraordinary succession of 75 overlooks giving continuous panoramic views of the Shenandoah Valley to the west and the Virginia piedmont to the east. The Stony Man Overlook, Thorofare Mountain and Big Meadows at mile 51 are unmissable. Entry $35 per vehicle covers the entire park. Drive: 45 min drive
AFTERNOON
DARK HOLLOW FALLS AND APPALACHIAN TRAIL RIDGELINE
Dark Hollow Falls is the most extraordinary short hike in Shenandoah, its extraordinary 70-foot cascade on a 1.4-mile round trip through old-growth hemlock forest. The Appalachian Trail along the Shenandoah ridgeline gives the most extraordinary ridge walking in Virginia. Hawksbill Summit at 4,051 feet, the highest point in the park, gives the finest 360-degree view on a 2.9-mile round trip. Both free with park entry.
💎 HIDDEN GEM
The extraordinary Bearfence Mountain scramble in Shenandoah at mile 56.4 is the finest hidden hike in the park, its extraordinary 1-mile rock scramble loop giving a 360-degree summit view of the Shenandoah Valley entirely unknown to most visitors who stay on the main trails. Free with park entry.
🍽 WHERE TO EAT
Breakfast: The Mimslyn Inn, Luray The finest breakfast in Luray since 1931. Extraordinary local Virginia eggs and strong coffee. | Lunch: Big Meadows Lodge, Shenandoah Outstanding park lodge lunch. Extraordinary local Virginia produce with Skyline Drive views. | Dinner: Gathering Grounds, Luray The finest restaurant in Luray. Extraordinary local Shenandoah Valley produce and craft beer.
DAY 2
CHARLOTTESVILLE AND BLUE RIDGE
MORNING
MONTICELLO AND THOMAS JEFFERSON'S VIRGINIA
Monticello is the most extraordinary historic house in Virginia, Jefferson's extraordinary Palladian villa above Charlottesville where he designed every detail of the house, gardens and plantation from his swivel chair to the alcove bed. The extraordinary restored slave quarters, the mulberry grove and Jefferson's vegetable garden of 330 varieties give the most complete plantation experience in Virginia. The UVA Rotunda on the Lawn is a 15-minute drive away and free. Monticello approx $32. Drive: 1.5 hr drive
MIDDAY
CHARLOTTESVILLE WINE COUNTRY AND THE BLUE RIDGE PARKWAY
The Charlottesville wine region produces the finest Viognier and Cabernet Franc in America, its extraordinary concentration of 40-plus wineries on the Monticello Wine Trail including King Family Vineyards, Barboursville Vineyards and Trump Winery giving the finest wine tasting experience in the South. The Blue Ridge Parkway south of Waynesboro gives the extraordinary continuation of Skyline Drive with magnificent overlooks of the Virginia piedmont. Tastings approx $15 to $25. Drive: 20 min drive
AFTERNOON
NATURAL BRIDGE AND LEXINGTON VMI
Natural Bridge is one of the Seven Natural Wonders of the World, its extraordinary 215-foot limestone arch spanning Cedar Creek in the Shenandoah Valley giving the finest natural arch experience in Virginia. The Virginia Military Institute in Lexington, the finest military college campus in the South, and the remarkable Stonewall Jackson House give the most extraordinary Civil War heritage in the Shenandoah Valley. Natural Bridge entry approx $20, VMI museum free.
💎 HIDDEN GEM
The extraordinary Ash Lawn-Highland near Charlottesville is the finest hidden presidential home in Virginia, its extraordinary working farm estate of President James Monroe giving the most intimate and least crowded presidential home experience in the state. Entry approx $14. Far less visited than Monticello just down the road.
🍽 WHERE TO EAT
Breakfast: Bluegrass Grill, Charlottesville The finest breakfast in Charlottesville. Extraordinary local Virginia eggs and strong coffee. | Lunch: The Local, Charlottesville Outstanding local Virginia farm-to-table lunch near the University. Extraordinary produce. | Dinner: The Inn at Little Washington The most celebrated restaurant in Virginia. Extraordinary local ingredients. Book months ahead.
DAY 3
COLONIAL VIRGINIA
MORNING
COLONIAL WILLIAMSBURG, THE MOST EXTRAORDINARY LIVING HISTORY IN AMERICA
Colonial Williamsburg is the most extraordinary living history experience in America, its extraordinary 301-acre reconstruction of Virginia's 18th-century colonial capital with costumed tradespeople, the magnificent Governor's Palace, the Capitol and the Raleigh Tavern giving the finest American colonial experience in the country. The extraordinary evening programs and the Colonial Williamsburg Trades give the most authentic daytime experience. Entry approx $45. Drive: 2 hr drive
MIDDAY
YORKTOWN BATTLEFIELD AND THE END OF THE REVOLUTION
Yorktown National Battlefield is the most extraordinary Revolutionary War site in Virginia, its extraordinary earthworks where General Cornwallis surrendered to Washington and Rochambeau in October 1781 ending the American Revolution giving the most important battlefield in American history. The extraordinary Yorktown Victory Monument and the reconstructed French fleet gun batteries are unmissable. The Colonial National Historical Parkway drive between Williamsburg and Yorktown is extraordinary. Entry free. Drive: 30 min drive
AFTERNOON
JAMESTOWN SETTLEMENT AND THE FIRST ENGLISH COLONY
Jamestown Settlement is the most extraordinary colonial heritage site in Virginia, its extraordinary recreation of the 1607 James Fort, the Powhatan village and the three replica ships that carried the first permanent English settlers to America giving the finest insight into the founding of English America. The original Jamestown archaeological site on Jamestown Island nearby gives the most extraordinary access to the actual 1607 fort foundations still being excavated. Settlement entry approx $18.
💎 HIDDEN GEM
The extraordinary College of William and Mary campus in Williamsburg is the second oldest university in America, its extraordinary 1695 Wren Building the oldest surviving college building in North America and the campus itself giving the finest historic college architecture in Virginia. Free to walk. The most extraordinary hidden gem in Williamsburg.
🍽 WHERE TO EAT
Breakfast: The Cheese Shop, Williamsburg The finest breakfast sandwich in Williamsburg since 1971. Extraordinary local Virginia cheese. | Lunch: Shields Tavern, Colonial Williamsburg The most extraordinary colonial lunch in America. Extraordinary 18th-century Virginia cuisine. | Dinner: Blue Talon Bistro, Williamsburg The finest restaurant in Williamsburg. Extraordinary local Virginia produce and outstanding wine.
DAY 4
CHESAPEAKE COAST
MORNING
CHINCOTEAGUE NATIONAL WILDLIFE REFUGE AND WILD PONIES
Chincoteague National Wildlife Refuge on Assateague Island is the most extraordinary wildlife experience in Virginia, its extraordinary herd of wild Chincoteague ponies descended from shipwrecked Spanish horses roaming the barrier island salt marshes in a landscape of extraordinary coastal beauty. The extraordinary annual Pony Swim in late July when the herd crosses the channel to Chincoteague Island is the most extraordinary free event in Virginia. Wildlife Loop drive free. Drive: 2.5 hr drive
MIDDAY
ASSATEAGUE ISLAND NATIONAL SEASHORE
Assateague Island National Seashore is the most extraordinary barrier island in Virginia, its extraordinary 37-mile undeveloped Atlantic beach with wild ponies grazing on the dunes, loggerhead sea turtles nesting in summer and the most extraordinary migratory bird stopover on the East Coast Atlantic Flyway. The Tom's Cove Hook at the Virginia end of Assateague gives the finest beach and pony encounter. Entry $25 per vehicle. Drive: 30 min drive
AFTERNOON
VIRGINIA BEACH BOARDWALK AND CAPE HENRY
Virginia Beach is the most extraordinary resort city on the Virginia coast, its extraordinary 3-mile oceanfront boardwalk, the remarkable Cape Henry Lighthouse at the entrance to Chesapeake Bay and the extraordinary First Landing State Park giving the finest coastal experience in the state. Cape Henry is where the English colonists first landed in Virginia in April 1607 before sailing up to Jamestown. First Landing State Park gives the finest coastal forest. Park entry $7.
💎 HIDDEN GEM
The extraordinary Chincoteague ponies on the Assateague beach at dawn before any other visitors arrive is the most extraordinary wildlife experience in Virginia, the ponies grazing on the dunes in extraordinary proximity with the Atlantic Ocean as backdrop. Free. Arrive by 6am for the finest encounter of the day.
🍽 WHERE TO EAT
Breakfast: Bill's Seafood, Chincoteague The finest seafood breakfast on Chincoteague Island. Extraordinary local crab cakes and strong coffee. | Lunch: AJ's on the Creek, Chincoteague Outstanding local Chincoteague oysters and clam chowder. The finest waterfront lunch on the island. | Dinner: Catch 31, Virginia Beach The finest seafood restaurant on the Virginia Beach boardwalk. Extraordinary local Atlantic seafood.
DAY 5
RICHMOND
MORNING
RICHMOND SCOTT'S ADDITION CRAFT BREWERY DISTRICT
Richmond's Scott's Addition neighborhood is the most extraordinary craft brewery district in Virginia, its extraordinary concentration of over 15 breweries, cideries and distilleries in former industrial warehouses giving the finest craft spirits experience in the state. The Veil Brewing Company, Ardent Craft Ales and Triple Crossing Brewing are the finest in the district. The extraordinary Diamond District redevelopment surrounding Scott's Addition is transforming Richmond's north side. Most tastings free. Drive: 2.5 hr drive
MIDDAY
VIRGINIA MUSEUM OF FINE ARTS AND THE FAN DISTRICT
The Virginia Museum of Fine Arts is the most extraordinary free art museum in the South, its extraordinary collection of 50,000 works including the finest collection of Faberge imperial eggs outside Russia, a remarkable Art Nouveau collection and the most extraordinary African art collection in the Southeast giving the finest single free museum in Virginia. The Fan District of Victorian rowhouses surrounding the museum is the finest neighborhood in Richmond. VMFA free. Drive: 20 min walk
AFTERNOON
BELLE ISLE AND THE JAMES RIVER RAPIDS
Belle Isle in the James River is the most extraordinary urban wilderness in Virginia, its extraordinary 54-acre island of Civil War ironworks ruins, granite outcrops and James River rapids accessible by a pedestrian suspension bridge giving the finest free outdoor experience in Richmond. The extraordinary Class III and IV rapids of the James River through downtown Richmond are the most extraordinary urban whitewater in America. The Brown's Island outdoor concert venue is extraordinary. Both free.
💎 HIDDEN GEM
The extraordinary Hollywood Cemetery in Richmond is the finest historic cemetery in Virginia, its extraordinary hilltop setting above the James River containing the graves of Presidents Monroe and Tyler, Confederate President Jefferson Davis and 18,000 Confederate soldiers in the most extraordinary Victorian garden cemetery in the South. Free. Open daily.
🍽 WHERE TO EAT
Breakfast: Brenner Pass, Richmond The finest breakfast in Richmond. Extraordinary Alpine-inspired local Virginia produce. | Lunch: Perly's, Richmond The most legendary Jewish deli in Richmond. Extraordinary local Virginia ingredients since 1947. | Dinner: The Roosevelt, Richmond The finest farm-to-table restaurant in Richmond. Extraordinary local Virginia produce and craft cocktails.
Where To Stay
Luray and Charlottesville, Nights 1 to 2 Mimslyn Inn or Quirk Hotel Charlottesville. Approx $120 to $240. Williamsburg and VA Beach, Nights 3 to 4 Williamsburg Inn or Hilton Virginia Beach. Approx $140 to $280. Richmond, Night 5 The Graduate Richmond or Quirk Hotel Richmond. Approx $120 to $200 per night.
Top Tips
1. Skyline Drive in October for peak fall color is the most extraordinary drive in the eastern United States.
2. Book Monticello timed entry at monticello.org at least 2 weeks ahead. The garden tour is extraordinary.
3. Chincoteague Pony Swim in late July is the most extraordinary free wildlife event in Virginia. Arrive early.
4. Colonial Williamsburg evening candlelight programs are the finest and least crowded experience in the park.
5. Virginia Museum of Fine Arts in Richmond is the finest free art museum in the South. The Faberge eggs are extraordinary.
6. The Inn at Little Washington is the only two-Michelin-star restaurant in Virginia. Book months ahead.
Total Budget
$120 to $200/day