11 days in United States Itinerary

11 days in United States Itinerary

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Route & dates

11 days in United States Itinerary

Toronto
Fly + bus:  4​h
Boston
— 2 nights
bus + Fly:  3​h 15​min
New York City
— 4 nights
bus + Fly:  4​h 45​min
Chicago
— 2 nights
Fly:  6​h 45​min
Portland
— 2 nights
Fly:  8​h 15​min
Toronto

2
days
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.
Kick off your visit on the 17th (Sun): explore the world behind art at Museum of Fine Arts and then stop by Brookline Booksmith. Get ready for a full day of sightseeing on the next day: look for gifts at Harvard Book Store, take a stroll through Newbury Street, make a trip to Louisburg Square, then wander the streets of North End, and finally browse the different shops at Faneuil Hall Marketplace.

For maps, where to stay, more things to do, and other tourist information, you can read our Boston road trip planning website .

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 June, daily temperatures in Boston can reach 28°C, while at night they dip to 18°C. Wrap up your sightseeing by early afternoon on the 19th (Tue) to allow enough time to travel to New York City.

Things to do in Boston

#Shopping, #Neighborhoods, #Parks

Side Trips

Harvard Book Store, Nantasket Beach, Brookline Booksmith
Highlights from your plan
Brookline Booksmith ©
Brookline Booksmith
Museum of Fine Arts ©
Museum of Fine Arts
Nantasket Beach ©
Nantasket Beach

4
days
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Fifth Avenue and Statue of Liberty National Monument are good opportunities to explore the local culture. The adventure continues: make a trip to Times Square, stroll through Central Park, see the interesting displays at 9/11 Memorial, and explore the world behind art at The Metropolitan Museum of Art.

For where to stay, photos, traveler tips, and more tourist information, you can read our New York City trip planner.

Do a combination of bus and flight from Boston to New York City in 3.5 hours. Alternatively, you can drive; or take a bus. In June, plan for daily highs up to 31°C, and evening lows to 21°C. On the 23rd (Sat), wrap the sightseeing up by early afternoon so you can travel to Chicago.

Things to do in New York City

#Parks, #Museums, #Neighborhoods
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
Times Square ©
Times Square
9/11 Memorial ©
9/11 Memorial

1
day
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Start off your visit on the 24th (Sun): get to know the fascinating history of Millennium Park, then explore the world behind art at The Art Institute of Chicago, and then shop like a local with The Magnificent Mile.

To find traveler tips, maps, other places to visit, and tourist information, you can read our Chicago travel route planning tool .

You can do a combination of bus and flight from New York City to Chicago in 5 hours. Other options are to do a combination of train and flight; or drive. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. In June, daily temperatures in Chicago can reach 32°C, while at night they dip to 20°C. Finish your sightseeing early on the 25th (Mon) to allow enough time to travel to Portland.

Things to do in Chicago

#Shopping, #Neighborhoods, #Museums
Highlights from your plan
The Magnificent Mile ©
The Magnificent Mile
The Art Institute of Chicago ©
The Art Institute of Chicago
Millennium Park ©
Millennium Park

2
days
Portland

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.
Kick off your visit on the 25th (Mon): admire the natural beauty at Portland Japanese Garden and then stop by Powell's City of Books. Get ready for a full day of sightseeing on the next day: admire the verdant scenery at Sokol Blosser Winery, do a tasting at Carlton Winemakers Studio, and then stop by Penner-Ash Wine Cellars.

For more things to do, ratings, and other tourist information, go to the Portland day trip planner .

Getting from Chicago to Portland by flight takes about 7 hours. Other options: do a combination of train and flight; or drive. Traveling from Chicago to Portland, you'll gain 2 hours due to the time zone difference. Expect slightly colder evenings in Portland when traveling from Chicago in June, with lows around 15°C. On the 27th (Wed), wrap the sightseeing up by early afternoon so you can travel back home.

Things to do in Portland

#Wineries, #Parks, #Shopping

Side Trips

Sokol Blosser Winery, Carlton Winemakers Studio, Penner-Ash Wine Cellars
Highlights from your plan
Carlton Winemakers Studio ©
Carlton Winemakers Studio
Powell's City of Books ©
Powell's City of Books
Sokol Blosser Winery ©
Sokol Blosser Winery

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