14 days in Virginia & Portland Itinerary

14 days in Virginia & Portland Itinerary

Created using Inspirock United States sightseeing planner

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Route & dates

Start: Portland
+2
Fly + Bus + Taxi:  9 h 15 min
1
Luray
— 1 night
Drive:  1 h 30 min
2
Charlottesville
— 1 night
Drive:  2 h 15 min
3
Williamsburg
— 3 nights
Drive:  1 h 15 min
4
Virginia Beach
— 2 nights
Drive:  2 h 30 min
5
Chincoteague Island
— 1 night
Drive:  3 h 45 min
6
Arlington
— 2 nights
Subway + Fly:  7 h
7
Portland
— 3 nights
End: Portland

1
night
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.
Kick off your visit on the 25th (Thu): sample the fine beverages at Copper Fox Distillery, then take a memorable drive along Skyline Drive, and then take in breathtaking views at Luray Caverns.

To see photos, other places to visit, traveler tips, and more tourist information, use the Luray trip itinerary maker tool.

Portland to Luray is an approximately 9.5- hour combination of flight, bus, and taxi. You can also do a combination of flight and car; or drive. Due to the time zone difference, you'll lose 3 hours traveling from Portland to Luray. Traveling from Portland in July, Luray is somewhat warmer at night with lows of 66°F. Wrap up your sightseeing on the 25th (Thu) early enough to drive to Charlottesville.

Things to do in Luray

Parks Nature Outdoors

Side Trips

Copper Fox Distillery, Skyline Drive
Find places to stay Jul 24 — 25:
Highlights from your plan
Luray Caverns ©
Luray Caverns
Skyline Drive ©
Skyline Drive
Copper Fox Distillery ©
Copper Fox Distillery

1
night
Charlottesville

Charlottesville ©
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.
On the 26th (Fri), steep yourself in history at James Monroe's Highland, admire the natural beauty at Monticello, then relax in the rural setting at Carter Mountain Orchard, and finally admire the striking features of University of Virginia.

To see more things to do, photos, ratings, and more tourist information, read Charlottesville trip itinerary app.

Drive from Luray to Charlottesville in 1.5 hours. Expect a daytime high around 88°F in July, and nighttime lows around 68°F. Wrap up your sightseeing on the 26th (Fri) to allow time to drive to Williamsburg.

Things to do in Charlottesville

Historic Sites Parks
Find places to stay Jul 25 — 26:
Highlights from your plan
Monticello ©
Monticello
Carter Mountain Orchard ©
Carter Mountain Orchard
University of Virginia ©
University of Virginia

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.
Go for a jaunt from Williamsburg to Richmond to see Virginia Museum of Fine Arts about 1h 05 min away. There's much more to do: make a splash at Busch Gardens Williamsburg, steep yourself in history at Historic Jamestowne, gain insight at College of William & Mary, and take in the architecture and atmosphere at Bruton Parish Episcopal Church.

For reviews, traveler tips, ratings, and other tourist information, use the Williamsburg visit planner.

Traveling by car from Charlottesville to Williamsburg takes 2.5 hours. Alternatively, you can take a bus. In July, daytime highs in Williamsburg are 91°F, while nighttime lows are 73°F. Cap off your sightseeing on the 29th (Mon) early enough to go by car to Virginia Beach.

Things to do in Williamsburg

Historic Sites Museums Theme Parks

Side Trip

Virginia Museum of Fine Arts
Find places to stay Jul 26 — 29:
Highlights from your plan
Busch Gardens Williamsburg ©
Busch Gardens Williamsburg
Colonial Williamsburg ©
Colonial Williamsburg
Historic Jamestowne ©
Historic Jamestowne

2
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.
Start off your visit on the 30th (Tue): get up close and personal with brilliant marine life at Virginia Aquarium & Marine Science Center, enjoy the sand and surf at Virginia Beach, and then take in the waterfront at Virginia Beach Boardwalk. Here are some ideas for day two: stroll through Sandbridge Beach, then brush up on your military savvy at Military Aviation Museum, and then sample the fine beverages at Tarnished Truth Distilling Company.

For ratings, other places to visit, more things to do, and other tourist information, you can read our Virginia Beach trip itinerary app.

Drive from Williamsburg to Virginia Beach in 1.5 hours. Alternatively, you can take a bus; or take a bus. In July, plan for daily highs up to 89°F, and evening lows to 73°F. Finish your sightseeing early on the 31st (Wed) so you can drive to Chincoteague Island.

Things to do in Virginia Beach

Parks Beaches Outdoors
Find places to stay Jul 29 — 31:
Highlights from your plan
Virginia Beach Boardwalk ©
Virginia Beach Boardwalk
Virginia Beach ©
Virginia Beach
Virginia Aquarium & Marine Science Center ©
Virginia Aquarium & Marine Science Center

1
night
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 1st (Thu): visit a coastal fixture at Assateague Lighthouse, explore the wealth of natural beauty at Chincoteague National Wildlife Refuge, and then take in the exciting artwork at Tryfan Gallery.

For reviews, maps, traveler tips, and other tourist information, read our Chincoteague Island trip itinerary builder website.

You can drive from Virginia Beach to Chincoteague Island in 2.5 hours. Alternatively, you can take a bus; or take a bus. In July, daytime highs in Chincoteague Island are 86°F, while nighttime lows are 72°F. Wrap up your sightseeing on the 1st (Thu) to allow time to drive to Arlington.

Things to do in Chincoteague Island

Parks Nature Wildlife

Side Trip

Assateague Lighthouse
Find places to stay Jul 31 — Aug 1:
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Chincoteague National Wildlife Refuge
Assateague Lighthouse ©
Assateague Lighthouse
Tryfan Gallery ©
Tryfan Gallery

2
nights
Arlington

Arlington ©
Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.
On the 2nd (Fri), get to know the fascinating history of The Tomb of the Unknown Soldier, then steep yourself in history at Arlington National Cemetery, then make a trip to John F. Kennedy Grave Site, and finally see the interesting displays at Steven F. Udvar-Hazy Center. Get ready for a full day of sightseeing on the 3rd (Sat): learn about all things military at National Museum of the Marine Corps, admire the striking features of George Washington's Mount Vernon, and then take a stroll through Old Town.

To see where to stay, maps, other places to visit, and other tourist information, go to the Arlington trip itinerary builder app.

Drive from Chincoteague Island to Arlington in 4 hours. Alternatively, you can do a combination of bus, taxi, flight, and subway; or do a combination of taxi, bus, and subway. In August, daytime highs in Arlington are 87°F, while nighttime lows are 71°F. Wrap up your sightseeing on the 3rd (Sat) to allow time to travel to Portland.

Things to do in Arlington

Historic Sites Museums Neighborhoods

Side Trips

National Museum of the Marine Corps, Steven F. Udvar-Hazy Center, Old Town, George Washington's Mount Vernon
Find places to stay Aug 1 — 3:
Highlights from your plan
The Tomb of the Unknown Soldier ©
The Tomb of the Unknown Soldier
Arlington National Cemetery ©
Arlington National Cemetery
Steven F. Udvar-Hazy Center ©
Steven F. Udvar-Hazy Center

3
nights
Portland

A big city with a small-town feel, Portland is home to the country's biggest rose test garden, perched on a hill overlooking downtown.
When in Portland, make a side trip to see Multnomah Falls in Bridal Veil, approximately Bridal Veil away. And it doesn't end there: admire the natural beauty at International Rose Test Garden, look for gifts at Powell's City of Books, walk around South Park Blocks, and indulge your senses at some of the top wineries in the area.

For photos, where to stay, more things to do, and other tourist information, go to the Portland planner.

You can do a combination of subway and flight from Arlington to Portland in 7 hours. Alternatively, you can do a combination of subway, bus, and flight; or drive. Due to the time zone difference, you'll gain 3 hours traveling from Arlington to Portland. Plan for little chillier nights when traveling from Arlington in August since evenings lows in Portland dip to 60°F. Cap off your sightseeing on the 6th (Tue) early enough to travel back home.

Things to do in Portland

Parks Nature Tours

Side Trips

Multnomah Falls, Columbia River Gorge National Scenic Area
Find places to stay Aug 3 — 6:
Highlights from your plan
Wine Tours & Tastings
International Rose Test Garden ©
International Rose Test Garden
Columbia River Gorge National Scenic Area ©
Columbia River Gorge National Scenic Area

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