57 days in Virginia Itinerary

57 days in Virginia Itinerary

Created using Inspirock Virginia sightseeing planner

Plan created by another user. Make it yours
1
Chincoteague Island
— 5 nights
2
Virginia Beach
— 6 nights
3
Williamsburg
— 7 nights
4
Charlottesville
— 6 nights
5
Lexington
— 6 nights
6
Damascus
— 2 nights
7
Shenandoah National Park
— 6 nights
8
Luray
— 6 nights
9
Winchester
— 6 nights
10
Alexandria
— 6 nights

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5
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.
You'll find plenty of places to visit near Chincoteague Island: Onancock (Ker Place & Hopkins & Bros. Store). There's still lots to do: explore the striking landscape of Chincoteague National Wildlife Refuge, head outdoors with Donald J. Leonard, identify plant and animal life at Wildlife Areas, and go for a walk through Chincoteague Island Waterman's Memorial.

To find photos, reviews, and other tourist information, use the Chincoteague Island day trip planning app.

Montreal, Canada to Chincoteague Island is an approximately 8.5-hour combination of flight, bus, and taxi. You can also fly; or drive. In October, Chincoteague Island is a bit warmer than Montreal - with highs of 25°C and lows of 14°C. Wrap up your sightseeing on the 17th (Thu) to allow time to drive to Virginia Beach.

Things to do in Chincoteague Island

Parks · Wildlife · Outdoors · Museums

Side Trips

Highlights from your trip
©
Nature / Wildlife Tour
Nature & Wildlife Tours
5.0
©
Gift & Specialty Shop
MamerSass
5.0

6
nights
Virginia Beach

Virginia Beach ©

The Resort City

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.
Venture out of the city with trips to Norfolk (Weyanoke Bird and Wildflower Sanctuary & Skystar Wheel), Old Point Comfort Lighthouse (in Hampton) and Chesapeake Bay Bridge-Tunnel (in Cape Charles). There's much more to do: take in the waterfront at Virginia Beach Boardwalk, enjoy the sand and surf at Virginia Beach, sample the fine beverages at Tarnished Truth Distilling Company, and take an in-depth tour of Military Aviation Museum.

To find photos, traveler tips, and tourist information, go to the Virginia Beach trip planner.

Drive from Chincoteague Island to Virginia Beach in 2.5 hours. Alternatively, you can take a bus; or take a bus. October in Virginia Beach sees daily highs of 27°C and lows of 15°C at night. Finish your sightseeing early on the 23rd (Wed) to allow enough time to drive to Williamsburg.

Things to do in Virginia Beach

Parks · Museums · Outdoors · Nature

Side Trips

Highlights from your trip
©
Pier / Boardwalk
Virginia Beach Boardwalk
4.5
©
Military Museum
Military Aviation Museum
4.8

7
nights
Williamsburg

Williamsburg ©

Colonial Capital

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.
You'll find plenty of places to visit near Williamsburg: Richmond (Bill Bojangles Robinson Monument, Virginia Museum of Fine Arts, &more), Newport News (The Mariners' Museum & Park & The Noland Trail) and Smithfield (St. Luke's Historic Church & Museum & Windsor Castle Park). There's much more to do: steep yourself in history at Colonial Williamsburg, take in the history at Yorktown Battlefield, get engrossed in the history at Historic Jamestowne, and take in the architecture and atmosphere at Bruton Parish Episcopal Church.

To find photos, maps, traveler tips, and other tourist information, go to the Williamsburg tour itinerary planning website.

Drive from Virginia Beach to Williamsburg in 1.5 hours. Alternatively, you can take a bus; or take a bus. Expect a daytime high around 28°C in October, and nighttime lows around 15°C. Finish your sightseeing early on the 30th (Wed) to allow enough time to drive to Charlottesville.

Things to do in Williamsburg

Historic Sites · Museums · Parks · Theme Parks

Side Trips

Highlights from your trip
©
Historic Site
Historic Jamestowne
4.7

6
nights
Charlottesville

Charlottesville ©

Hoo-Ville

Situated at the foothills of the Blue Ridge Mountains, Charlottesville is perhaps best known as the home of three of the United States' founding fathers, including Thomas Jefferson.
You'll find plenty of places to visit near Charlottesville: The Quarry Gardens (in Schuyler), James Madison's Montpelier (in Montpelier Station) and Bold Rock Hard Cider (in Nellysford). And it doesn't end there: take in nature's colorful creations at Monticello, contemplate the long history of Frontier Culture Museum, head outdoors with Cavalier Sporting Clays, and relax in the rural setting at Open Gate Farm.

To find ratings, maps, photos, and tourist information, refer to the Charlottesville itinerary planner.

Drive from Williamsburg to Charlottesville in 2.5 hours. Alternatively, you can take a bus. Plan for little chillier nights when traveling from Williamsburg in October since evenings lows in Charlottesville dip to 11°C. Finish your sightseeing early on the 5th (Tue) so you can drive to Lexington.

Things to do in Charlottesville

Parks · Outdoors · Historic Sites · Breweries & Distilleries

Side Trips

Highlights from your trip
©
Must see
Monticello
4.7
©
World heritage site
University of Virginia
4.5

6
nights
Lexington

Lexington ©
Home to two prestigious educational institutions, Lexington was founded in 1778.
Explore the numerous day-trip ideas around Lexington: Lynchburg (Blackwater Creek Trail, Room Escape Games, &more), National D-Day Memorial (in Bedford) and Roanoke (Beer Tastings & Tours & Mill Mountain Star & Park). There's still lots to do: deepen your understanding at Virginia Military Institute, experience rural life at Hudson Heritage Farms, take in the exciting artwork at Earth, Fire, & Spirit Pottery, and take an in-depth tour of Brownsburg Museum.

To see where to stay, more things to do, reviews, and other tourist information, refer to the Lexington trip planner.

Traveling by car from Charlottesville to Lexington takes 1.5 hours. Alternatively, you can do a combination of train and taxi. Expect a bit cooler weather when traveling from Charlottesville in November: highs in Lexington hover around 10°C, while lows dip to 0°C. Finish up your sightseeing early on the 11th (Mon) so you can travel to Damascus.

Things to do in Lexington

Parks · Historic Sites · Wildlife · Museums

Side Trips

Highlights from your trip
©
Educational Site
Virginia Military Institute
4.8
©
Geologic Formation
Natural Bridge State Park
4.3

2
nights
Damascus

Damascus ©
Damascus is a town in Washington County, Virginia, United States. Kick off your visit on the 12th (Tue): trek along Virginia Creeper National Recreation Trail, admire the majestic nature at Grayson Highlands State Park, and then trek along Appalachian Trail. On your second day here, explore the striking landscape at The Channels Natural Area Preserve and then take an in-depth tour of The Birthplace of Country Music Museum.

For reviews, ratings, and more tourist information, read Damascus road trip planner.

Traveling by car from Lexington to Damascus takes 3 hours. While traveling from Lexington, expect a bit warmer days and about the same nights in Damascus, ranging from highs of 16°C to lows of 3°C. Finish up your sightseeing early on the 13th (Wed) so you can travel to Shenandoah National Park.

Things to do in Damascus

Parks · Trails · Outdoors · Nature

Side Trips

Highlights from your trip

6
nights
Shenandoah National Park

Shenandoah National Park ©
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
Get out of town with these interesting Shenandoah National Park side-trips: Grand Caverns (in Grottoes), SoLace Studios Fine Handcrafts (in Elkton) and Brix and Columns Vineyards (in McGaheysville). Next up on the itinerary: tour the pleasant surroundings at Skyline Drive, head outdoors with Shenandoah River Adventures, take in the awesome beauty at Pinnacles, and work some fitness into your day at Limberlost Trail.

For where to stay, maps, and more tourist information, read Shenandoah National Park trip itinerary builder.

Traveling by car from Damascus to Shenandoah National Park takes 4.5 hours. Alternatively, you can do a combination of car and flight. In November in Shenandoah National Park, expect temperatures between 17°C during the day and 3°C at night. Cap off your sightseeing on the 19th (Tue) early enough to go by car to Luray.

Things to do in Shenandoah National Park

Parks · Outdoors · Nature · Trails

Side Trips

Highlights from your trip
©
Scenic Drive
Skyline Drive
4.7
©
Hiking Trail
Limberlost Trail
4.8

6
nights
Luray

Luray ©

Cabin Capital of Virginia

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.
Venture out of the city with trips to Culpeper (Museum of Culpeper History & Moving Meadows Farm), Shenandoah Valley Cultural Heritage Museum at The Edinburg Mill (in Edinburg) and Front Royal (Blue Ridge Hospice Thrift Shop & Buzzard Rock North). And it doesn't end there: explore the stunning scenery at Luray Caverns, tour the pleasant surroundings at Whiteoak Canyon Falls, take in nature's colorful creations at Birdsong Pleasure Garden, and trek along Kennedy Peak Hike.

For more things to do, ratings, other places to visit, and tourist information, read our Luray online journey builder.

Traveling by car from Shenandoah National Park to Luray takes 1.5 hours. In November, daily temperatures in Luray can reach 16°C, while at night they dip to 1°C. Finish your sightseeing early on the 25th (Mon) to allow enough time to drive to Winchester.

Things to do in Luray

Parks · Outdoors · Trails · Museums

Side Trips

Highlights from your trip
©
Canyon
Luray Caverns
4.6

6
nights
Winchester

Winchester ©
Winchester is an independent city located in the northwestern portion of the Commonwealth of Virginia. Get out of town with these interesting Winchester side-trips: Bluemont (Raven Rocks & Wild Hare Hard Cider), Cascade Falls (in Pembroke) and Leesburg (Ida Lee Park, Audubon Naturalist Society Rust Nature Sanctuary, &more). The adventure continues: get a taste of life in the country at Rocking S Ranch, stroll through The Washington & Old Dominion Trail, admire the majestic nature at Sky Meadows State Park, and walk around Glenwood Park.

For traveler tips, more things to do, photos, and more tourist information, read our Winchester trip maker site.

Getting from Luray to Winchester by car takes about 1.5 hours. Expect a daytime high around 14°C in November, and nighttime lows around 1°C. Cap off your sightseeing on the 1st (Sun) early enough to go by car to Alexandria.

Things to do in Winchester

Parks · Outdoors · Trails · Nature

Side Trips

Highlights from your trip
©
Must see
Rocking S Ranch
4.9
©
Waterfall
Cascade Falls
4.9

6
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.
Explore the numerous day-trip ideas around Alexandria: National Museum of the Marine Corps (in Triangle), Quantico National Cemetery (in Quantico) and Aslin Brewery (in Herndon). There's lots more to do: steep yourself in history at Arlington National Cemetery, explore the activities along Great Falls Park, take a leisurely stroll along Old Town Waterfront, and see the interesting displays at Steven F. Udvar-Hazy Center.

To see traveler tips, more things to do, reviews, and tourist information, you can read our Alexandria online tour planner.

You can drive from Winchester to Alexandria in 2 hours. Other options are to do a combination of taxi, train, and subway; or do a combination of taxi and bus. Traveling from Winchester in December, Alexandria is a bit warmer at night with lows of 3°C. Wrap up your sightseeing on the 7th (Sat) early enough to travel back home.

Things to do in Alexandria

Historic Sites · Parks · Museums · Nature

Side Trips

Highlights from your trip

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