23 days in East Coast of USA, Philadelphia & Chicago Itinerary

23 days in East Coast of USA, Philadelphia & Chicago Itinerary

Created using Inspirock United States tour itinerary planner

Make it your trip
Fly
1
Washington DC
— 3 nights
Train
2
Philadelphia
— 2 nights
Train
3
New York City
— 4 nights
Fly
4
Boston
— 3 nights
Drive
5
New Haven
— 3 nights
Fly
6
Chicago
— 3 nights
Fly
7
Miami
— 3 nights
Fly

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Washington DC

— 3 nights
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.
Satisfy your inner culture vulture at National Air and Space Museum and Washington National Cathedral. There's still lots to do: admire the masterpieces at National Gallery of Art, get engrossed in the history at United States Holocaust Memorial Museum, get to know the fascinating history of The Tomb of the Unknown Soldier, and ponder the world of politics at White House.

Use Inspirock's suggestions to plan your Washington DC trip and find the best activities and attractions for your vacation.

Rome, Italy to Washington DC is an approximately 12-hour flight. The time zone difference moving from Central European Standard Time to Eastern Standard Time is minus 6 hours. October in Washington DC sees daily highs of 25°C and lows of 14°C at night. Finish up your sightseeing early on the 17th (Sun) so you can catch the train to Philadelphia.

Things to do in Washington DC

Museums · Zoos & Aquariums · Historic Sites · Parks

Side Trip

Philadelphia

— 2 nights

The City of Brotherly Love

Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S. democracy, as it was once the meeting place for the country's Founding Fathers.
Start off your visit on the 18th (Mon): explore the world behind art at Rodin Museum, then explore the world behind art at Barnes Foundation, then get engrossed in the history at Eastern State Penitentiary, and finally get a sense of history and politics at Independence Hall. Get ready for a full day of sightseeing on the next day: admire the local landmark of Longwood Gardens, then admire the masterpieces at Philadelphia Museum of Art, and then appreciate the history behind Liberty Bell Center.

To find traveler tips, reviews, and tourist information, you can read our Philadelphia online sightseeing planner.

Take a train from Washington DC to Philadelphia in 2.5 hours. Alternatively, you can drive; or take a bus. October in Philadelphia sees daily highs of 24°C and lows of 13°C at night. Finish your sightseeing early on the 19th (Tue) so you can take a train to New York City.

Things to do in Philadelphia

Museums · Parks · Historic Sites

Side Trip

New York City

— 4 nights

Big Apple

Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
Satisfy your inner culture vulture at The Metropolitan Museum of Art and American Museum of Natural History. There's lots more to do: go for a walk through Central Park, explore the world behind art at The Museum of Modern Art (MoMA), appreciate the history behind Statue of Liberty National Monument, and pause for some serene contemplation at St. Paul's Chapel.

To see other places to visit, maps, and other tourist information, go to the New York City vacation maker site.

You can take a train from Philadelphia to New York City in 1.5 hours. Alternatively, you can drive; or take a bus. In October, daily temperatures in New York City can reach 24°C, while at night they dip to 16°C. Cap off your sightseeing on the 23rd (Sat) early enough to catch the flight to Boston.

Things to do in New York City

Museums · Historic Sites · Parks · Neighborhoods

Boston

— 3 nights

Beantown

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.
Louisa May Alcott's Orchard House and Peabody Essex Museum are good opportunities to explore the local culture. Next up on the itinerary: get lost in a book at John F. Kennedy Presidential Museum & Library, explore the world behind art at Museum of Fine Arts, stroll the grounds of Mount Auburn Cemetery, and browse the exhibits of New England Holocaust Memorial.

For other places to visit, maps, more things to do, and other tourist information, go to the Boston travel route planning site.

You can fly from New York City to Boston in 2.5 hours. Alternatively, you can drive; or take a train. Expect little chillier temperatures when traveling from New York City in October; daily highs in Boston reach 20°C and lows reach 11°C. Wrap up your sightseeing on the 26th (Tue) to allow time to drive to New Haven.

Things to do in Boston

Museums · Historic Sites · Parks

Side Trips

New Haven

— 3 nights
New Haven, in the U.S. state of Connecticut, is the principal municipality in Greater New Haven, which had a total population of 862,477 in 2010. On the 27th (Wed), steep yourself in history at The Mark Twain House & Museum and then look and learn at Mystic Seaport Museum. Here are some ideas for day two: see the interesting displays at The Submarine Force Museum, steep yourself in history at Olde Mistick Village, and then stroll through Gillette Castle State Park.

To see traveler tips, more things to do, other places to visit, and tourist information, you can read our New Haven trip maker app.

Traveling by car from Boston to New Haven takes 2.5 hours. Alternatively, you can take a train; or take a bus. In October in New Haven, expect temperatures between 22°C during the day and 10°C at night. Wrap up your sightseeing by early afternoon on the 29th (Fri) to allow enough time to fly to Chicago.

Things to do in New Haven

Museums · Historic Sites · Childrens Museums · Shopping

Side Trips

Chicago

— 3 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 30th (Sat): walk around Millennium Park, pause for some photo ops at Cloud Gate, admire the masterpieces at The Art Institute of Chicago, then see where the action happens at Wrigley Field, and finally take in the spiritual surroundings of Fourth Presbyterian Church. On the next day, get curious at Museum of Science and Industry, then get a new perspective on nature at Field Museum, and then don't miss a visit to Buckingham Fountain.

To find other places to visit and more tourist information, read our Chicago driving holiday planning app.

Traveling by flight from New Haven to Chicago takes 3.5 hours. Alternatively, you can drive; or do a combination of train and bus. You'll gain 1 hour traveling from New Haven to Chicago due to the time zone difference. In October, plan for daily highs up to 21°C, and evening lows to 11°C. On the 1st (Mon), wrap the sightseeing up by early afternoon so you can fly to Miami.

Things to do in Chicago

Museums · Childrens Museums · Parks · Historic Sites

Miami

— 3 nights

Magic City

Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
On the 2nd (Tue), see the interesting displays at Vizcaya Museum and Gardens, then enjoy some diversion at Lock & Load Miami, then take a stroll through Lincoln Road, and finally shop like a local with Britto Central. Get ready for a full day of sightseeing on the 3rd (Wed): don't miss a visit to Ocean Drive, then appreciate the extensive heritage of Art Deco Historic District, and then kick back and relax at South Beach.

To see other places to visit, photos, and more tourist information, refer to the Miami day trip website.

Traveling by flight from Chicago to Miami takes 5 hours. Alternatively, you can drive; or do a combination of bus and subway. Traveling from Chicago to Miami, you'll lose 1 hour due to the time zone difference. Plan for much hotter temperatures traveling from Chicago in November, with highs in Miami at 32°C and lows at 24°C. Wrap up your sightseeing by early afternoon on the 4th (Thu) to allow enough time to fly back home.

Things to do in Miami

Neighborhoods · Shopping · Historic Sites · Parks

Side Trip