16 days in United States Itinerary

16 days in United States Itinerary

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Route & dates

16 days in United States Itinerary

Start: Chicago
Fly:  5​h
1
Orlando
— 2 nights
Fly:  3​h 30​min
2
Miami
— 2 nights
Fly:  4​h 30​min
3
Washington DC
— 2 nights
Fly:  3​h 30​min
4
New York City
— 3 nights
bus + Fly:  3​h
5
Boston
— 3 nights
Fly:  5​h 45​min
6
Miami Beach
— 2 nights
Fly:  5​h 45​min
End: Chicago

2
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.
Your day-by-day itinerary now includes Walt Disney World Resort. Kick off your visit on the 6th (Mon): make an unforgettable trip to Walt Disney World Resort.

To find photos, other places to visit, more things to do, and more tourist information, you can read our Orlando attractions planner.

Chicago to Orlando is an approximately 5-hour flight. You can also drive; or take a bus. The time zone difference when traveling from Chicago to Orlando is 1 hour. Plan for a bit warmer temperatures traveling from Chicago in May, with highs in Orlando at 88°F and lows at 69°F. On the 8th (Wed), you'll travel to Miami.

Things to do in Orlando

Theme Parks
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort

2
nights
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.
On the 10th (Fri), you'll have a packed day of sightseeing: get a taste of the local shopping with Aventura Mall.

To find ratings, reviews, where to stay, and other tourist information, refer to the Miami trip planner .

Traveling by flight from Orlando to Miami takes 3.5 hours. Alternatively, you can drive; or do a combination of flight and train. In May, daytime highs in Miami are 87°F, while nighttime lows are 74°F. Wrap up your sightseeing by early afternoon on the 10th (Fri) to allow enough time to travel to Washington DC.

Things to do in Miami

Shopping

Side Trip

Aventura Mall
Highlights from your plan
Aventura Mall ©
Aventura Mall

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.
Kick off your visit on the 11th (Sat): learn more about the world around you at Smithsonian National Museum of Natural History, examine the collection at United States Holocaust Memorial Museum, then pause for some photo ops at Vietnam Veterans Memorial, then appreciate the history behind Korean War Veterans Memorial, and finally appreciate the history behind Jefferson Memorial. Get ready for a full day of sightseeing on the next day: get engrossed in the history at Newseum, pause for some photo ops at National World War II Memorial, and then stroll the grounds of Arlington National Cemetery.

To see ratings, where to stay, more things to do, and other tourist information, refer to the Washington DC travel itinerary planner.

You can fly from Miami to Washington DC in 4.5 hours. Alternatively, you can do a combination of flight and train; or drive. In May, Washington DC is a bit cooler than Miami - with highs of 76°F and lows of 58°F. Wrap up your sightseeing on the 12th (Sun) to allow time to travel to New York City.

Things to do in Washington DC

Museums Historic Sites

Side Trip

Arlington National Cemetery
Highlights from your plan

3
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.
Escape the urban bustle at Ocean Grove Beach and Edgar Felix Memorial Bikeway. Head to Woodbury Common Premium Outlets and Hudson Beach Glassfor some retail therapy. You'll find plenty of places to visit near New York City: Kittatinny Valley State Park (in Newton), Scranberry Coop Antiques (in Andover) and Brid's Closet (in Cornwall on Hudson). It doesn't end there: hunt for treasures at Chelsea Market and cruise along Hawk's Nest Highway.

For where to stay, other places to visit, more things to do, and other tourist information, refer to the New York City trip website .

Traveling by flight from Washington DC to New York City takes 3.5 hours. Alternatively, you can take a train; or drive. While traveling from Washington DC, expect slightly colder days and about the same nights in New York City, ranging from highs of 69°F to lows of 55°F. Finish your sightseeing early on the 15th (Wed) so you can travel to Boston.

Things to do in New York City

Parks Shopping Outdoors

Side Trips

Kittatinny Valley State Park, Ocean Grove Beach, Scranberry Coop Antiques, Edgar Felix Memorial Bikeway, Hudson Beach Glass
Highlights from your plan
Ocean Grove Beach ©
Ocean Grove Beach
Woodbury Common Premium Outlets ©
Woodbury Common Premium Outlets
Chelsea Market ©
Chelsea Market

3
nights
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.
Escape the urban bustle at Dolphin & Whale Watching and Hampton Beach State Park. Shop till you drop at Faneuil Hall Marketplace and Maynard Outdoor Store. Step out of Boston to go to North Hampton and see North Hampton State Beach, which is approximately 1h 30 min away. And it doesn't end there: take a stroll through North End, admire the natural beauty at Boston Public Garden, hunt for treasures at Quincy Market, and tour the pleasant surroundings at Boston Common.

To see traveler tips, where to stay, ratings, and tourist information, read Boston itinerary tool .

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 May, plan for slightly colder nights in Boston, with lows around 50°F. Wrap up your sightseeing on the 18th (Sat) to allow time to travel back home.

Things to do in Boston

Outdoors Parks Beaches

Side Trips

Hampton Beach State Park, Dolphin & Whale Watching, Maynard Outdoor Store, North Hampton State Beach
Highlights from your plan
Dolphin & Whale Watching
Hampton Beach State Park ©
Hampton Beach State Park
North End ©
North End

2
nights
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.
Your day-by-day itinerary now includes South Beach. On the 19th (Sun), enjoy the sand and surf at South Beach, tour the pleasant surroundings at Collins Park, stroll through Haulover Beach Park, then get a taste of the local shopping with Bal Harbour Shops, and finally view the masterpieces at Britto Central. On your second day here, take in nature's colorful creations at Butterfly World and then see some colorful creatures with a scuba or snorkeling tour.

For ratings, more things to do, where to stay, and other tourist information, you can read our Miami Beach trip itinerary planning website .

Getting from Boston to Miami Beach by flight takes about 6 hours. Other options: do a combination of flight and bus; or drive. When traveling from Boston in May, plan for a bit warmer days in Miami Beach, with highs around 87°F, while nights are much hotter with lows around 74°F. Wrap up your sightseeing by early afternoon on the 21st (Tue) to allow time for travel back home.

Things to do in Miami Beach

Outdoors Parks Beaches

Side Trips

Bal Harbour, Butterfly World, Scuba & Snorkeling
Highlights from your plan
Haulover Beach Park ©
Haulover Beach Park
Butterfly World ©
Butterfly World
Scuba & Snorkeling

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