15 days in Boston, Virginia & District of Columbia Itinerary

15 days in Boston, Virginia & District of Columbia Itinerary

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Route & dates

15 days in Boston, Virginia & District of Columbia Itinerary

Start: Portland
Fly:  8​h 15​min
1
Boston
— 2 nights
+2
Fly + bus + taxi:  7​h 15​min
2
Chincoteague Island
— 1 night
Drive:  3​h
3
Williamsburg
— 3 nights
Drive:  2​h 15​min
4
Charlottesville
— 1 night
Drive:  1​h 30​min
5
Luray
— 1 night
Drive:  2​h
6
Washington DC
— 3 nights
Drive:  15​min
7
Arlington
— 1 night
Fly:  7​h
End: Portland

2
nights
Boston

Boston ©
Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
You'll explore and learn at Museum of Fine Arts and The House of the Seven Gables. Popular historic sites such as Freedom Trail and Old North Church & Historic Site are in your itinerary. You'll find plenty of places to visit near Boston: Hampton Beach State Park (in Hampton) and Dolphin & Whale Watching (in Gloucester). There's still lots to do: admire all the interesting features of Fenway Park and browse the exhibits of New England Holocaust Memorial.

To see ratings, where to stay, reviews, and other tourist information, use the Boston trip itinerary builder tool .

Portland to Boston is an approximately 8.5-hour flight. You can also drive; or take a train. The time zone difference when traveling from Portland to Boston is 3 hours. Traveling from Portland in July, you can expect nighttime temperatures to be a bit warmer in Boston, with lows of 67°F. Finish your sightseeing early on the 25th (Thu) to allow enough time to travel to Chincoteague Island.

Things to do in Boston

Outdoors Museums Historic Sites

Side Trips

Hampton Beach State Park, The House of the Seven Gables, Dolphin & Whale Watching
Highlights from your plan
The House of the Seven Gables ©
The House of the Seven Gables
Dolphin & Whale Watching
Hampton Beach State Park ©
Hampton Beach State Park

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.
Kick off your visit on the 26th (Fri): identify plant and animal life at Chincoteague National Wildlife Refuge. On the next day, surround yourself with nature on a nature and wildlife tour, visit a coastal fixture at Assateague Lighthouse, then get engrossed in the history at Museum of Chincoteague, and finally look for gifts at Wine Cheese & More.

To see ratings, reviews, more things to do, and tourist information, refer to the Chincoteague Island trip app .

Traveling by combination of flight, bus, and taxi from Boston to Chincoteague Island takes 7.5 hours. Alternatively, you can drive; or do a combination of train and bus. July in Chincoteague Island sees daily highs of 86°F and lows of 72°F at night. Finish up your sightseeing early on the 27th (Sat) so you can go by car to Williamsburg.

Things to do in Chincoteague Island

Wildlife Nature Parks

Side Trip

Assateague Lighthouse
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Nature & Wildlife Tours
Museum of Chincoteague ©
Museum of Chincoteague

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.
You'll explore the less-touristy side of things at Water Country USA and Bruton Parish Episcopal Church. Satisfy your inner culture vulture at Colonial Williamsburg and Abby Aldrich Rockefeller Folk Art Museum. Take a break from Williamsburg with a short trip to The Mariners' Museum & Park in Newport News, about 38 minutes away. Next up on the itinerary: witness the site of a historic battle at Yorktown Battlefield, steep yourself in history at American Revolution Museum at Yorktown, and admire the masterpieces at DeWitt Wallace Decorative Arts Museum.

To see where to stay, photos, ratings, and other tourist information, go to the Williamsburg route planning website .

Getting from Chincoteague Island to Williamsburg by car takes about 3 hours. Other options: take a bus. In July in Williamsburg, expect temperatures between 91°F during the day and 73°F at night. Finish your sightseeing early on the 30th (Tue) to allow enough time to drive to Charlottesville.

Things to do in Williamsburg

Museums Historic Sites Theme Parks

Side Trips

Yorktown, The Mariners' Museum & Park
Highlights from your plan
Water Country USA ©
Water Country USA
American Revolution Museum at Yorktown ©
Yorktown Battlefield ©
Yorktown Battlefield

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.
Start off your visit on the 31st (Wed): get engrossed in the history at Thomas Jefferson's Monticello, then contemplate the long history of James Monroe's Highland, then admire the landmark architecture of University of Virginia, and finally steep yourself in history at The Glass Palette - Interactive Glass Art Studio.

To find where to stay, maps, photos, and other tourist information, read our Charlottesville tour planner.

Traveling by car from Williamsburg to Charlottesville takes 2.5 hours. Alternatively, you can take a bus. Plan for a bit cooler nights when traveling from Williamsburg in July since evenings lows in Charlottesville dip to 68°F. Finish up your sightseeing early on the 31st (Wed) so you can go by car to Luray.

Things to do in Charlottesville

Historic Sites Parks
Highlights from your plan
James Monroe's Highland ©
James Monroe's Highland
University of Virginia ©
University of Virginia

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.
Start off your visit on the 1st (Thu): take an in-depth tour of The Car and Carriage Caravan Museum, then hike along Kennedy Peak Hike, and then hike along Stony Man Mountain Hike.

To find more things to do, other places to visit, ratings, and other tourist information, go to the Luray trip itinerary app .

Traveling by car from Charlottesville to Luray takes 1.5 hours. Alternatively, you can do a combination of bus and car. In July, daily temperatures in Luray can reach 86°F, while at night they dip to 66°F. Finish your sightseeing early on the 1st (Thu) to allow enough time to drive to Washington DC.

Things to do in Luray

Outdoors Trails Parks
Highlights from your plan
Stony Man Mountain Hike ©
Stony Man Mountain Hike
The Car and Carriage Caravan Museum ©

3
nights
Washington DC

Washington DC ©
The capital of the United States, the District of Columbia contains the lion's share of the country's most treasured monuments, memorials, and public museums.
Get some cultural insight at Harpers Ferry National Historical Park and National Gallery of Art. You'll explore and learn at National Air and Space Museum and National Portrait Gallery. Take a break from Washington DC with a short trip to National Museum of the Marine Corps in Triangle, about 56 minutes away. There's lots more to do: learn more about the world around you at Smithsonian National Museum of Natural History, take an in-depth tour of United States Holocaust Memorial Museum, and appreciate the history behind Vietnam Veterans Memorial.

For traveler tips, more things to do, reviews, and tourist information, go to the Washington DC holiday maker tool .

You can drive from Luray to Washington DC in 2 hours. Alternatively, you can do a combination of taxi and bus; or take a bus. Traveling from Luray in August, plan for a bit warmer nights in Washington DC, with lows around 71°F. Finish up your sightseeing early on the 4th (Sun) so you can go by car to Arlington.

Things to do in Washington DC

Museums Historic Sites Nature

Side Trips

Harpers Ferry National Historical Park, National Museum of the Marine Corps
Highlights from your plan
National Air and Space Museum ©
National Air and Space Museum
National Museum of the Marine Corps ©

1
night
Arlington

Arlington ©
Located just across the Potomac River from Washington, D.C., the county of Arlington blends big city and sprawling suburban environments.
Start off your visit on the 5th (Mon): get to know the fascinating history of Tomb of the Unknowns, then take a stroll through Old Town, then take in the exciting artwork at Torpedo Factory Art Center, and finally explore the different monuments and memorials at Arlington National Cemetery.

To see more things to do, where to stay, other places to visit, and more tourist information, refer to the Arlington trip website .

Arlington is just a short distance from Washington DC. In August, daytime highs in Arlington are 87°F, while nighttime lows are 71°F. Finish your sightseeing early on the 5th (Mon) so you can travel back home.

Things to do in Arlington

Historic Sites Neighborhoods Museums

Side Trip

Alexandria
Highlights from your plan
The Tomb of the Unknown Soldier ©
The Tomb of the Unknown Soldier
Old Town ©
Old Town
Torpedo Factory Art Center ©
Torpedo Factory Art Center

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