14 days in United States Itinerary

14 days in United States Itinerary

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Route & dates

14 days in United States Itinerary

Start: Newark
train:  30​min
1
New York City
— 2 nights
Fly:  6​h
2
Orlando
— 1 day
Fly:  4​h
3
Miami
— 1 night
Drive:  2​h 30​min
4
Marathon
— 1 night
Drive:  30​min
5
Big Pine Key
— 1 night
bus:  45​min
6
Key West
— 2 nights
Fly:  5​h 45​min
7
Chicago
— 1 night
Fly:  3​h 45​min
8
Washington DC
— 2 nights
Fly:  3​h
9
Boston
— 2 nights
Fly:  3​h
End: Newark


Learn more about your trip

2
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.
Appreciate the collections at The Metropolitan Museum of Art and New York Public Library. Your cultural itinerary includes sights like Fifth Avenue and 9/11 Memorial. The adventure continues: don't miss a visit to Times Square, go for a walk through Central Park, get a new perspective on nature at American Museum of Natural History, and enjoy breathtaking views from Empire State Building.

To see traveler tips, photos, ratings, and tourist information, go to the New York City online attractions planner .

Newark to New York City is an approximately half hour car ride. You can also take a train; or take a bus. May in New York City sees daily highs of 69°F and lows of 55°F at night. Finish up your sightseeing early on the 14th (Tue) so you can travel to Orlando.

Things to do in New York City

Museums Parks Neighborhoods
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
9/11 Memorial ©
9/11 Memorial
American Museum of Natural History ©
American Museum of Natural History

1
day
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.
Kick off your visit on the 15th (Wed): get in on the family fun at Discovery Cove.

For traveler tips, where to stay, photos, and other tourist information, read our Orlando trip itinerary planner.

Traveling by flight from New York City to Orlando takes 6 hours. Alternatively, you can do a combination of bus and flight; or drive. In May, Orlando is somewhat warmer than New York City - with highs of 88°F and lows of 69°F. Wrap up your sightseeing on the 15th (Wed) early enough to drive to Miami.

Things to do in Orlando

Parks Beaches Theme Parks
Highlights from your plan
Discovery Cove ©
Discovery Cove

1
night
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
Kick off your visit on the 16th (Thu): kick back and relax at South Beach, wander the streets of Lincoln Road, and then tour the water at your own pace with Mark the Shark.

For photos, other places to visit, where to stay, and tourist information, go to the Miami trip itinerary tool .

Drive from Orlando to Miami in 4 hours. Alternatively, you can take a bus; or take a train. May in Miami sees daily highs of 87°F and lows of 74°F at night. Finish up your sightseeing early on the 16th (Thu) so you can go by car to Marathon.

Things to do in Miami

Outdoors Tours Parks

Side Trip

Miami Beach
Highlights from your plan
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road

1
night
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Start off your visit on the 17th (Fri): look for all kinds of wild species at Crane Point Museum & Nature Center, identify plant and animal life at The Turtle Hospital, then identify plant and animal life at Pigeon Key Foundation, and finally enjoy the sand and surf at Sombrero Beach.

To see maps, where to stay, and tourist information, read Marathon online trip itinerary planner .

Drive from Miami to Marathon in 2.5 hours. Alternatively, you can take a bus; or do a combination of tram, flight, and bus. In May, plan for daily highs up to 88°F, and evening lows to 77°F. Finish your sightseeing early on the 17th (Fri) to allow enough time to take a bus to Big Pine Key.

Things to do in Marathon

Parks Wildlife Beaches
Highlights from your plan
Sombrero Beach ©
Sombrero Beach
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center
The Turtle Hospital ©
The Turtle Hospital

1
night
Big Pine Key

Big Pine Key ©
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. On the 18th (Sat), take in the exciting artwork at Artists in Paradise Gallery, then identify plant and animal life at National Key Deer Refuge, and then immerse yourself in nature at Bahia Honda State Park.

Plan a Big Pine Key trip in moments using our itinerary builder.

Big Pine Key is just a stone's throw from Marathon. May in Big Pine Key sees daily highs of 88°F and lows of 77°F at night. Finish your sightseeing early on the 18th (Sat) to allow enough time to take a bus to Key West.

Things to do in Big Pine Key

Parks Nature Beaches
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge
Artists in Paradise Gallery ©
Artists in Paradise Gallery

2
nights
Key West

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.
Start off your visit on the 19th (Sun): identify plant and animal life at Key West Butterfly & Nature Conservatory, take in the exciting artwork at Key West Pottery, then view the masterpieces at Alan S. Maltz Gallery, and finally choose your vessel at Fun In The Sun Key West. On the next day, see the interesting displays at The Ernest Hemingway Home and Museum, then admire the majestic nature at Fort Zachary Taylor, then take in the exciting artwork at 7 Artists & Friends, and finally fly like a bird with a parasailing or paragliding tour.

For where to stay, reviews, other places to visit, and more tourist information, read our Key West trip itinerary planning site .

You can take a bus from Big Pine Key to Key West in an hour. Alternatively, you can drive. In May in Key West, expect temperatures between 85°F during the day and 77°F at night. Wrap up your sightseeing on the 20th (Mon) to allow time to travel to Chicago.

Things to do in Key West

Outdoors Museums Tours
Highlights from your plan
Alan S. Maltz Gallery ©
Alan S. Maltz Gallery
The Ernest Hemingway Home and Museum ©

1
night
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 21st (Tue): admire the masterpieces at The Art Institute of Chicago, admire all the interesting features of Millennium Park, and then get a taste of the local shopping with The Magnificent Mile.

To see other places to visit, ratings, reviews, and more tourist information, use the Chicago trip itinerary builder .

You can fly from Key West to Chicago in 6 hours. Alternatively, you can drive; or do a combination of shuttle and bus. The time zone difference moving from Eastern Standard Time to Central Standard Time is minus 1 hour. When traveling from Key West in May, plan for little chillier days in Chicago, with highs around 71°F, while nights are colder with lows around 52°F. Finish your sightseeing early on the 21st (Tue) so you can travel to Washington DC.

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
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.
On the 22nd (Wed), explore the world behind art at National Gallery of Art, examine the collection at National Air and Space Museum, and then contemplate the waterfront views at Tidal Basin. Get ready for a full day of sightseeing on the 23rd (Thu): get engrossed in the history at United States Holocaust Memorial Museum, get a new perspective on nature at Smithsonian National Museum of Natural History, then examine the collection at The National Archives Museum, and finally explore the world behind art at National Portrait Gallery.

To see ratings, photos, other places to visit, and other tourist information, use the Washington DC trip itinerary builder website .

You can fly from Chicago to Washington DC in 4 hours. Alternatively, you can do a combination of flight and train; or drive. The time zone difference when traveling from Chicago to Washington DC is 1 hour. Traveling from Chicago in May, plan for somewhat warmer nights in Washington DC, with lows around 58°F. Wrap up your sightseeing on the 23rd (Thu) early enough to travel to Boston.

Things to do in Washington DC

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

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.
On the 24th (Fri), take in the spiritual surroundings of Trinity Church, then don't miss a visit to Newbury Street, then explore the world behind art at Museum of Fine Arts, and finally browse the different shops at Faneuil Hall Marketplace. Here are some ideas for day two: steep yourself in history at Orchard House, then immerse yourself in nature at Walden Pond State Reservation, then stroll the grounds of Mount Auburn Cemetery, and finally stop by Brookline Booksmith.

To find ratings, where to stay, photos, and more tourist information, read Boston trip maker site .

Getting from Washington DC to Boston by combination of flight and bus takes about 3 hours. Other options: do a combination of train, flight, and bus; or drive. Prepare for slightly colder weather when traveling from Washington DC in May: high temperatures in Boston hover around 67°F and lows are around 50°F. Finish your sightseeing early on the 25th (Sat) to allow enough time to travel back home.

Things to do in Boston

Historic Sites Museums Shopping

Side Trips

Concord, Brookline Booksmith, Mount Auburn Cemetery
Highlights from your plan
Louisa May Alcott's Orchard House ©
Louisa May Alcott's Orchard House
Museum of Fine Arts ©
Museum of Fine Arts
Mount Auburn Cemetery ©
Mount Auburn Cemetery

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