35 days in United States Itinerary

35 days in United States Itinerary

Created using Inspirock United States trip maker

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Route & dates

35 days in United States Itinerary

Start: New York City
1
New York City
— 5 nights
Drive:  4​h
2
Boston
— 5 nights
Drive:  12​h 30​min
3
Detroit
— 1 night
Drive:  4​h 45​min
4
Chicago
— 5 nights
bus + shuttle:  33​h
5
Key West
— 4 nights
Drive:  2​h 30​min
6
Key Largo
— 2 nights
Drive:  1​h 30​min
7
Miami Beach
— 1 night
Drive:  4​h
8
Orlando
— 5 nights
Drive:  14​h
9
Washington DC
— 5 nights
Drive:  4​h 15​min
End: New York City


Learn more about your trip

5
nights
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.
New York City is known for museums, nightlife, shopping, historic sites, and parks. Your plan includes some of its best attractions: stroll around Central Park, explore the world behind art at The Metropolitan Museum of Art, pause for some photo ops at Statue of Liberty National Monument, and get great views at Top of the Rock.

Plan my New York City trip by asking Inpirock to come up with tips and suggestions.

Use the Route module to see travel options from your home to New York City. October in New York City sees daily highs of 70°F and lows of 57°F at night. Wrap up your sightseeing on the 6th (Sun) early enough to travel to Boston.

Things to do in New York City

Museums Parks Historic Sites
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

5
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.
Change things up with these side-trips from Boston: The Breakers (in Newport), Plymouth Rock (in Plymouth) and Marginal Way Walkway (in Ogunquit). Next up on the itinerary: admire the masterpieces at Museum of Fine Arts, explore the different monuments and memorials at Granary Burying Ground, get lost in a book at John F. Kennedy Presidential Museum & Library, and appreciate the extensive heritage of Freedom Trail.

To find ratings, maps, where to stay, and other tourist information, use the Boston journey planner .

You can do a combination of bus and flight from New York City to Boston in 3 hours. Other options are to fly; or drive. Traveling from New York City in October, expect Boston to be a bit cooler, temps between 64°F and 50°F. You'll have a few hours on the 11th (Fri) to wrap things up before traveling to Detroit.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Marginal Way Walkway, The Breakers, Plymouth Rock
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden

1
night
Detroit

Detroit ©
Founded in 1701 by a French explorer and adventurer, Detroit exerted a profound impact on the world for most of the 20th century.
Start off your visit on the 12th (Sat): see the interesting displays at Greenfield Village, then see the interesting displays at The Henry Ford, then explore the world behind art at Detroit Institute of Arts, and finally take a leisurely stroll along Detroit RiverFront.

For other places to visit, ratings, traveler tips, and other tourist information, go to the Detroit road trip planning app .

Traveling by flight from Boston to Detroit takes 5 hours. Alternatively, you can do a combination of bus and flight; or drive. In October, daytime highs in Detroit are 63°F, while nighttime lows are 48°F. Wrap up your sightseeing on the 12th (Sat) to allow time to travel to Chicago.

Things to do in Detroit

Museums

Side Trip

Dearborn
Highlights from your plan
Detroit Institute of Arts ©
Detroit Institute of Arts
The Henry Ford ©
The Henry Ford
Greenfield Village ©
Greenfield Village

5
nights
Chicago

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, historic sites, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, admire the landmark architecture of Skydeck Chicago - Willis Tower, engage your brain at Museum of Science and Industry, and admire all the interesting features of Millennium Park.

To find where to stay, ratings, traveler tips, and more tourist information, read Chicago trip tool .

Fly from Detroit to Chicago in 4 hours. Alternatively, you can do a combination of bus and flight; or drive. The time zone difference when traveling from Detroit to Chicago is minus 1 hour. Expect a daytime high around 65°F in October, and nighttime lows around 49°F. Wrap up your sightseeing by early afternoon on the 17th (Thu) to allow enough time to travel to Key West.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trip

Ernest Hemingway Birthplace
Highlights from your plan
Walking tours
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

4
nights
Key West

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Take a break from Key West with a short trip to Bahia Honda State Park in Big Pine Key, about 50 minutes away. Spend the 21st (Mon) exploring nature at Dry Tortugas National Park. There's lots more to do: see the interesting displays at The Ernest Hemingway Home and Museum, see majestic marine mammals with a dolphin and whale watching tour, take in the waterfront at Mallory Square, and take a memorable tour with Tours.

For more things to do, other places to visit, where to stay, and tourist information, refer to the Key West driving holiday website .

You can fly from Chicago to Key West in 6 hours. Alternatively, you can drive; or do a combination of bus and shuttle. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In October, Key West is warmer than Chicago - with highs of 86°F and lows of 77°F. Finish your sightseeing early on the 22nd (Tue) so you can drive to Key Largo.

Things to do in Key West

Parks Outdoors Nature

Side Trip

Bahia Honda State Park
Highlights from your plan
Dolphin & Whale Watching
The Ernest Hemingway Home and Museum ©

2
nights
Key Largo

Key Largo ©
The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.
Start off your visit on the 23rd (Wed): discover the deep blue sea with a scuba or snorkeling tour, cast your line with a fishing tour, and then identify plant and animal life at Florida Keys Wild Bird Rehabilitation Center. Get ready for a full day of sightseeing on the 24th (Thu): admire the majestic nature at John Pennekamp Coral Reef State Park, explore the gorgeous colors at Spiegel Grove, and then explore the landscape on two wheels at Key Largo Chamber of Commerce and Florida Keys Visitor Center.

Planning Key Largo trip won't be overwheling when you use's Insprock itinerary maker.

Traveling by car from Key West to Key Largo takes 2.5 hours. Alternatively, you can take a bus. Expect a daytime high around 85°F in October, and nighttime lows around 73°F. Wrap up your sightseeing on the 24th (Thu) to allow time to drive to Miami Beach.

Things to do in Key Largo

Wildlife Parks Outdoors

Side Trip

Fishing Charters & Tours
Highlights from your plan
Spiegel Grove ©
Spiegel Grove
Fishing Charters & Tours

1
night
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Kick off your visit on the 25th (Fri): take in the waterfront at Miami Beach Boardwalk, buy something for everyone on your list at Lincoln Road, then admire the landmark architecture of Art Deco Historic District, and finally enjoy the sand and surf at South Beach.

To find where to stay, more things to do, other places to visit, and more tourist information, refer to the Miami Beach holiday builder .

Drive from Key Largo to Miami Beach in 1.5 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 87°F, and evening lows to 74°F. Finish your sightseeing early on the 25th (Fri) to allow enough time to travel to Orlando.

Things to do in Miami Beach

Neighborhoods Historic Sites Parks
Highlights from your plan
Lincoln Road ©
Lincoln Road
Art Deco Historic District ©
Art Deco Historic District
South Beach ©
South Beach

5
nights
Orlando

Orlando ©
For most people, any mention of Orlando immediately conjures up images of sprawling theme parks filled with characters plucked right out of popular animated movies.
Orlando is known for theme parks, nightlife, fun & games, shopping, and museums. Your plan includes some of its best attractions: find something for the whole family at Universal's Islands of Adventure, admire the natural beauty at Harry P. Leu Gardens, discover the magic at Walt Disney World Resort, and explore the world behind art at Charles Hosmer Morse Museum of American Art.

For other places to visit, maps, traveler tips, and more tourist information, you can read our Orlando trip site .

Traveling by flight from Miami Beach to Orlando takes 3.5 hours. Alternatively, you can drive; or do a combination of bus and flight. Traveling from Miami Beach in October, Orlando is slightly colder at night with lows of 69°F. Wrap up your sightseeing on the 30th (Wed) to allow time to travel to Washington DC.

Things to do in Orlando

Theme Parks Parks Fun & Games

Side Trip

Charles Hosmer Morse Museum of American Art
Highlights from your plan
Magic Kingdom Park ©
Magic Kingdom Park
Universal's Islands of Adventure ©
Universal's Islands of Adventure
Walt Disney World Resort ©
Walt Disney World Resort

5
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.
Explore the numerous day-trip ideas around Washington DC: Gettysburg (Victorian Photography Studio & Gettysburg National Military Park). There's much more to do: examine the collection at National Air and Space Museum, admire the masterpieces at National Gallery of Art, ponder the world of politics at United States Capitol, and get a new perspective on nature at Smithsonian National Museum of Natural History.

To find ratings, maps, where to stay, and more tourist information, refer to the Washington DC trip itinerary planner.

Getting from Orlando to Washington DC by flight takes about 4.5 hours. Other options: do a combination of flight and train; or drive. Traveling from Orlando in October, expect Washington DC to be slightly colder, temps between 71°F and 54°F. Cap off your sightseeing on the 4th (Mon) early enough to travel back home.

Things to do in Washington DC

Museums Parks Historic Sites

Side Trips

Gettysburg, The Tomb of the Unknown Soldier
Highlights from your plan
Gettysburg National Military Park ©
National Air and Space Museum ©
National Air and Space Museum
National Gallery of Art ©
National Gallery of Art

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