24 days in Virginia Itinerary

24 days in Virginia Itinerary

Created using Inspirock Virginia holiday builder

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Route & dates

24 days in Virginia Itinerary

Start: Boston
Fly:  4​h 15​min
1
Virginia Beach
— 8 nights
Drive:  2​h 30​min
2
Chincoteague Island
— 2 nights
Drive:  3​h
3
Williamsburg
— 3 nights
Train:  1​h
4
Richmond
— 2 nights
Drive:  2​h 30​min
5
Millboro
— 1 night
Drive:  2​h
6
Shenandoah National Park
— 2 nights
Drive:  1​h 15​min
7
Luray
— 2 nights
Drive:  2​h
8
Alexandria
— 3 nights
Fly:  3​h 15​min
End: Boston

8
nights
Virginia Beach

Virginia Beach ©
Holding a record for the longest pleasure beach in the world, Virginia Beach showcases 35 miles of coastline and maintains a longstanding reputation as a family-friendly vacation destination.
Satisfy your inner culture vulture at Wright Brothers National Memorial and Virginia Aquarium & Marine Science Center. Brock Environmental Center - Chesapeake Bay Foundation and Cape Henry Lighthouse will appeal to history buffs. Explore the numerous day-trip ideas around Virginia Beach: Jockey's Ridge State Park (in Nags Head), Weyanoke Bird and Wildflower Sanctuary (in Norfolk) and Eastern Shore of Virginia National Wildlife Refuge (in Cape Charles). The adventure continues: kick back and relax at Virginia Beach, take in the exciting artwork at The Bird Store - The Outer Banks Wildlife Gallery, take a leisurely stroll along Virginia Beach Boardwalk, and browse for treasures at Skipjack Nautical Wares & Marine Art Gallery.

To see photos, ratings, reviews, and tourist information, read Virginia Beach trip planner .

Boston to Virginia Beach is an approximately 4.5-hour flight. You can also drive; or take a bus. Plan for a bit warmer temperatures traveling from Boston in October, with highs in Virginia Beach at 74°F and lows at 56°F. Cap off your sightseeing on the 20th (Sun) early enough to go by car to Chincoteague Island.

Things to do in Virginia Beach

Parks Wildlife Nature

Side Trips

Kill Devil Hills, Jockey's Ridge State Park, Skipjack Nautical Wares & Marine Art Gallery, Eastern Shore of Virginia National Wildlife Refuge, Weyanoke Bird and Wildflower Sanctuary
Highlights from your plan
Virginia Beach ©
Virginia Beach
Wright Brothers National Memorial ©
Wright Brothers National Memorial
Jockey's Ridge State Park ©
Jockey's Ridge State Park

2
nights
Chincoteague Island

Chincoteague Island ©
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Start off your visit on the 21st (Mon): explore the landscape on two wheels at Bike Depot, get a new perspective on things with Boat Tours & Water Sports, and then get outside with Donald J. Leonard. Get ready for a full day of sightseeing on the next day: stop by Wine Cheese & More, let the kids burn off some steam at Chincoteague Veteran's Memorial Park, and then explore the wealth of natural beauty at Chincoteague National Wildlife Refuge.

To see traveler tips, reviews, photos, and tourist information, read Chincoteague Island trip tool .

Drive from Virginia Beach to Chincoteague Island in 2.5 hours. Alternatively, you can take a bus; or take a bus. In October, daily temperatures in Chincoteague Island can reach 71°F, while at night they dip to 54°F. Wrap up your sightseeing on the 22nd (Tue) early enough to drive to Williamsburg.

Things to do in Chincoteague Island

Parks Wildlife Outdoors
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Nature & Wildlife Tours
Chincoteague Veteran's Memorial Park ©

3
nights
Williamsburg

Williamsburg ©
Founded in 1632 as a fortified settlement on the high ground between two rivers, Williamsburg served as a colonial capital of Virginia for over 80 years.
Do some cultural sightseeing at Colonial Williamsburg and Bruton Parish Episcopal Church. Popular historic sites such as Historic Jamestowne and George Wythe House are in your itinerary. Next up on the itinerary: steep yourself in history at Jamestown Settlement, explore the striking landscape of Colonial National Historical Park, stroll around Tyndall's Point Park, and look for gifts at Yankee Candle Company.

For photos, other places to visit, more things to do, and other tourist information, read Williamsburg online trip builder .

Traveling by car from Chincoteague Island to Williamsburg takes 3 hours. Alternatively, you can take a bus. In October, daily temperatures in Williamsburg can reach 75°F, while at night they dip to 55°F. Finish your sightseeing early on the 25th (Fri) to allow enough time to take a train to Richmond.

Things to do in Williamsburg

Historic Sites Museums Parks

Side Trips

Tyndall's Point Park, Colonial Parkway
Highlights from your plan
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne
Jamestown Settlement ©
Jamestown Settlement

2
nights
Richmond

Richmond ©
The capital city of Virginia, Richmond has diverse architecture, a large collection of monuments, and world-class museums that reveal the city's important role in American history.
Start off your visit on the 26th (Sat): wander the streets of Carytown, explore the world behind art at Virginia Museum of Fine Arts, then stroll the grounds of Hollywood Cemetery, and finally take in the exciting artwork at Shockoe Bottom Clay. On the 27th (Sun), you'll have a packed day of sightseeing: immerse yourself in nature at Pocahontas State Park, look for gifts at For the Love of Chocolate, then get engrossed in the history at White House of the Confederacy, and finally find something for the whole family at Kings Dominion.

For where to stay, more things to do, ratings, and other tourist information, you can read our Richmond visit planner .

Traveling by train from Williamsburg to Richmond takes an hour. Alternatively, you can drive. In October, daily temperatures in Richmond can reach 73°F, while at night they dip to 51°F. Finish up your sightseeing early on the 27th (Sun) so you can travel to Millboro.

Things to do in Richmond

Museums Shopping Historic Sites

Side Trips

Kings Dominion, Pocahontas State Park
Highlights from your plan
Virginia Museum of Fine Arts ©
Virginia Museum of Fine Arts
Hollywood Cemetery ©
Hollywood Cemetery
White House of the Confederacy ©
White House of the Confederacy

1
night
Millboro

Millboro ©
You've now added Shenandoah Valley to your itinerary. Kick off your visit on the 28th (Mon): contemplate the waterfront views at Goshen Pass and then admire the verdant scenery at Shenandoah Valley.

For traveler tips, ratings, photos, and tourist information, go to the Millboro travel route planner.

You can drive from Richmond to Millboro in 2.5 hours. Traveling from Richmond in October, expect Millboro to be slightly colder, temps between 59°F and 45°F. Wrap up your sightseeing by early afternoon on the 28th (Mon) to allow time for travel to Shenandoah National Park.

Things to do in Millboro

Nature Parks Wildlife

Side Trips

Shenandoah Valley, Goshen Pass
Highlights from your plan
Shenandoah Valley ©
Shenandoah Valley
Goshen Pass ©
Goshen Pass

2
nights
Shenandoah National Park

Shenandoah National Park ©
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
You've added Pinnacles, Overall Run Falls, Rose River Falls, and other attractions to your itinerary. Kick off your visit on the 26th (Sat): hike along Mary's Rock Summit Trail, head outdoors with Shenandoah River Adventures, admire the sheer force of Rose River Falls, then admire the sheer force of Overall Run Falls, then take in the awesome beauty at Pinnacles, and finally cruise along Skyline Drive. On the 27th (Sun), you'll have a packed day of sightseeing: take your sightseeing to a higher altitude at Hawksbill Mountain, then take in the dramatic scenery at Dark Hollow Falls, and then take in the awesome beauty at Bearfence Mountain.

For maps, where to stay, traveler tips, and other tourist information, go to the Shenandoah National Park day trip planner .

Traveling by car from Millboro to Shenandoah National Park takes 2 hours. When traveling from Millboro in October, plan for somewhat warmer days and about the same nights in Shenandoah National Park: temperatures range from 71°F by day to 49°F at night. Cap off your sightseeing on the 27th (Sun) early enough to go by car to Luray.

Things to do in Shenandoah National Park

Parks Nature Outdoors

Side Trip

Finders Keepers
Highlights from your plan
Old Rag Mountain Hike ©
Old Rag Mountain Hike
Skyline Drive ©
Skyline Drive
Mary's Rock Summit Trail ©
Mary's Rock Summit Trail

2
nights
Luray

Luray ©
Nestled in the heart of the valley formed by the Shenandoah River, Luray draws visitors with a vast underground cavern system adorned with stalactites, stalagmites, and mirrored pools.
Start off your visit on the 31st (Thu): hike along Kennedy Peak Hike, then take in breathtaking views at Luray Caverns, and then hike along Luray Hawksbill Greenway. Get ready for a full day of sightseeing on the 1st (Fri): trek along Stony Man Mountain Overlook, then kick your exploration up a notch at some of the top local zipline courses and adventure parks, then take an in-depth tour of The Car and Carriage Caravan Museum, and finally examine the collection at Luray Valley Museum.

To find where to stay, maps, traveler tips, and tourist information, you can read our Luray vacation builder tool .

You can drive from Shenandoah National Park to Luray in 1.5 hours. In October in Luray, expect temperatures between 70°F during the day and 48°F at night. Finish up your sightseeing early on the 1st (Fri) so you can go by car to Alexandria.

Things to do in Luray

Parks Outdoors Trails
Highlights from your plan
Luray Caverns ©
Luray Caverns
Stony Man Mountain Overlook ©
Stony Man Mountain Overlook
Zipline

3
nights
Alexandria

Alexandria ©
Just a few metro stops away from the bustle of Washington D.C., Alexandria provides a respite from the fast-paced capital.
Escape the urban bustle at Great Falls Park and Hidden Oaks Nature Center. Your inner history buff will appreciate Old Town and The Tomb of the Unknown Soldier. Step out of Alexandria with an excursion to Steven F. Udvar-Hazy Center in Chantilly--about 42 minutes away. The adventure continues: explore the different monuments and memorials at Arlington National Cemetery, test your problem-solving skills at popular escape rooms, and admire the landmark architecture of George Washington's Mount Vernon.

For reviews, maps, other places to visit, and more tourist information, refer to the Alexandria day trip app .

Traveling by car from Luray to Alexandria takes 2 hours. Alternatively, you can do a combination of car and train; or do a combination of taxi and bus. Traveling from Luray in November, Alexandria is a bit warmer at night with lows of 42°F. Wrap up your sightseeing on the 4th (Mon) to allow time to travel back home.

Things to do in Alexandria

Historic Sites Parks Nature

Side Trips

Arlington, Steven F. Udvar-Hazy Center, Hidden Oaks Nature Center, Great Falls Park, George Washington's Mount Vernon
Highlights from your plan
Old Town ©
Old Town
Arlington National Cemetery ©
Arlington National Cemetery
Steven F. Udvar-Hazy Center ©
Steven F. Udvar-Hazy Center

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