14 days in United States Itinerary

14 days in United States Itinerary

Created using Inspirock United States holiday planner

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Route & dates

14 days in United States Itinerary

Start: Toronto
Ferry + Fly:  4​h
1
Boston
— 4 nights
Fly:  3​h
2
Washington DC
— 2 nights
Fly:  3​h 15​min
3
Virginia Beach
— 5 nights
Fly:  4​h 15​min
4
Chicago
— 2 nights
Fly + Ferry:  4​h 30​min
End: Toronto

4
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.
Take a break from the city and head to Perkins Cove and Ogunquit Beach. Cape Neddick Nubble Lighthouse and Plimoth Plantation are good opportunities to explore the local culture. Explore Boston's surroundings by going to When Pigs Fly Company Store (in Kittery) and Strawbery Banke Museum (in Portsmouth). There's much more to do: get to know the fascinating history of Freedom Trail, hunt for treasures at Quincy Market, and buy something for everyone on your list at Faneuil Hall Marketplace.

To find where to stay, more things to do, maps, and other tourist information, you can read our Boston trip itinerary planner.

Toronto, Canada to Boston is an approximately 4-hour combination of flight and bus. You can also do a combination of bus and flight; or drive. In August, daytime highs in Boston are 32°C, while nighttime lows are 21°C. Finish your sightseeing early on the 9th (Thu) to allow enough time to travel to Washington DC.

Things to do in Boston

Parks Historic Sites Museums

Side Trips

Ogunquit, Nubble Lighthouse, Plimoth Plantation, Strawbery Banke Museum, When Pigs Fly Company Store
Highlights from your plan
Plimoth Plantation ©
Plimoth Plantation
Ogunquit Beach ©
Ogunquit Beach
Nubble Lighthouse ©
Nubble Lighthouse

2
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.
Start off your visit on the 10th (Fri): see the interesting displays at National Air and Space Museum, learn more about the world around you at Smithsonian National Museum of Natural History, and then pause for some photo ops at Washington Monument. Get ready for a full day of sightseeing on the next day: admire the masterpieces at National Gallery of Art and then explore the world behind art at National Portrait Gallery.

Plan my trip to Washington DC with suggested itineraries provided by Inspirock.

You can do a combination of bus and flight from Boston to Washington DC in 3 hours. Other options are to do a combination of train and flight; or drive. Prepare for a bit warmer weather when traveling from Boston in August: high temperatures in Washington DC hover around 36°C and lows are around 25°C. Finish up your sightseeing early on the 11th (Sat) so you can travel to Virginia Beach.

Things to do in Washington DC

Museums
Highlights from your plan
National Air and Space Museum ©
National Air and Space Museum
National Portrait Gallery ©
National Portrait Gallery
National Gallery of Art ©
National Gallery of Art

5
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.
Virginia Aquarium & Marine Science Center and Virginia Beach Surf & Rescue Museum will appeal to museum buffs. Visiting Jockey's Ridge State Park and Virginia Beach will get you outdoors. Get out of town with these interesting Virginia Beach side-trips: Yorktown Battlefield (in Yorktown), Life on a Sandbar (in Nags Head) and Corolla (Nature & Wildlife Tours & Currituck Beach Lighthouse and Museum). There's much more to do: steep yourself in history at Governor's Palace, pause for some serene contemplation at Bruton Parish Episcopal Church, and pick up a one of a kind souvenir at Virginia Beach Antique Mall.

To see photos, where to stay, ratings, and other tourist information, use the Virginia Beach holiday planner .

Traveling by combination of flight and taxi from Washington DC to Virginia Beach takes 3.5 hours. Alternatively, you can drive; or do a combination of train and tram. In August, plan for daily highs up to 35°C, and evening lows to 25°C. Cap off your sightseeing on the 16th (Thu) early enough to travel to Chicago.

Things to do in Virginia Beach

Parks Historic Sites Outdoors

Side Trips

Williamsburg, Nags Head, Corolla, Yorktown Battlefield
Highlights from your plan
Virginia Beach ©
Virginia Beach
Governor's Palace ©
Governor's Palace
Nature & Wildlife Tours

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
On the 16th (Thu), relax in the rural setting at Garwood Orchards. Here are some ideas for day two: stroll through Millennium Park and then admire the majestic nature at Indiana Dunes State Park.

Ask Inspirock to suggest an itinerary and make planning a trip to Chicago fast, fun, and easy.

Traveling by combination of taxi and flight from Virginia Beach to Chicago takes 4.5 hours. Alternatively, you can drive; or do a combination of tram and train. The time zone changes from Eastern Standard Time to Central Standard Time, which is usually a -1 hour difference. In August, daytime highs in Chicago are 33°C, while nighttime lows are 22°C. Wrap up your sightseeing on the 18th (Sat) to allow time to travel back home.

Things to do in Chicago

Parks Nature

Side Trips

Indiana Dunes State Park, Garwood Orchards, Warren Dunes State Park
Highlights from your plan
Indiana Dunes State Park ©
Indiana Dunes State Park
Warren Dunes State Park ©
Warren Dunes State Park
Millennium Park ©
Millennium Park

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