21 days in United States Itinerary

21 days in United States Itinerary

Created using Inspirock United States trip planner

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Route & dates

21 days in United States Itinerary

Start: New York City
1
New York City
— 4 nights
Drive:  2​h 30​min
2
Montauk
— 1 night
Drive:  1​h 45​min
3
Greenport
— 1 night
Drive:  30​min
4
Orient
— Few hours
Drive:  45​min
5
New London
— Few hours
Drive:  1​h 15​min
6
Newport
— 2 nights
Drive:  1​h 45​min
7
Hyannis Port
— Few hours
Drive:  2​h 30​min
8
Nantucket
— 4 nights
Drive:  2​h 30​min
9
Hyannis Port
— Few hours
Drive:  30​min
10
Sandwich
— 1 night
bus:  1​h
11
Boston
— 3 nights
Drive:  2​h 30​min
12
Stockbridge
— 1 night
Drive:  1​h 30​min
13
Hyde Park
— 2 nights
Drive:  2​h
14
New York City
— 1 night
End: New York City

4
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.
Museum-lovers will appreciate The Metropolitan Museum of Art and American Museum of Natural History. Do some cultural sightseeing at 9/11 Memorial and New York Public Library. Next up on the itinerary: admire all the interesting features of Central Park, explore the world behind art at The Museum of Modern Art (MoMA), steep yourself in history at Theodore Roosevelt Birthplace National Historic Site, and admire the striking features of New York City Hall.

For photos, maps, more things to do, and more tourist information, read our New York City day trip planner .

If you are flying in from Netherlands, the closest major airports are La Guardia Airport, Newark Liberty International Airport and John F Kennedy International Airport. Expect a daytime high around 24°C in May, and nighttime lows around 15°C. Wrap up your sightseeing by early afternoon on the 5th (Sun) to allow enough time to drive to Montauk.

Things to do in New York City

Museums Historic Sites Parks
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 ©

1
night
Montauk

Montauk is a census-designated place (CDP) that includes the hamlet with the same name located in the town of East Hampton in Suffolk County, New York, on the eastern end of the South Shore of Long Island. Start off your visit on the 5th (Sun): make a trip to Gosman's Restaurant.

To see other places to visit, traveler tips, reviews, and other tourist information, go to the Montauk trip planning app .

You can drive from New York City to Montauk in 2.5 hours. Alternatively, you can take a bus; or take a train. Traveling from New York City in May, expect slightly colder with lows of 11°C in Montauk. Wrap up your sightseeing on the 6th (Mon) to allow time to drive to Greenport.

Things to do in Montauk

Tours Wildlife Outdoors

Side Trip

Guild Hall
Highlights from your plan
Fishing Charters & Tours
Guild Hall ©
Guild Hall
Gosman's Restaurant ©
Gosman's Restaurant

1
night
Greenport

Greenport
To see other places to visit and more tourist information, read our Greenport online trip builder .

Traveling by car from Montauk to Greenport takes 2 hours. In May, daytime highs in Greenport are 20°C, while nighttime lows are 13°C. On the 7th (Tue), you're off toOrient.

Things to do in Greenport

Parks Outdoors Tours

few
hours
Orient

Orient
Orient is a hamlet and census-designated place (CDP) in Suffolk County, Long Island, New York, United States. For other places to visit, photos, and other tourist information, you can read our Orient trip website .

Orient is very close to Greenport. In May, daily temperatures in Orient can reach 20°C, while at night they dip to 13°C. You'll set off for New London on the 7th (Tue).

Things to do in Orient

Parks Beaches Nature

few
hours
New London

New London ©
New London is a seaport city and a port of entry on the northeast coast of the United States. To find other places to visit, traveler tips, maps, and tourist information, refer to the New London trip planner .

Drive from Orient to New London in 1.5 hours. In May, daytime highs in New London are 21°C, while nighttime lows are 10°C. Finish your sightseeing early on the 7th (Tue) to allow enough time to drive to Newport.

Things to do in New London

Museums

Side Trip

Mystic Seaport Museum
Highlights from your plan
Mystic Seaport Museum ©
Mystic Seaport Museum

2
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Start off your visit on the 7th (Tue): contemplate the long history of Colony House.

For more things to do, traveler tips, photos, and more tourist information, go to the Newport itinerary maker website .

Traveling by car from New London to Newport takes 1.5 hours. In May in Newport, expect temperatures between 21°C during the day and 11°C at night. Cap off your sightseeing on the 9th (Thu) early enough to go by car to Hyannis Port.

Things to do in Newport

Historic Sites Outdoors Museums
Highlights from your plan
Ocean Drive Historic District ©
Ocean Drive Historic District
Thames Glass ©
Thames Glass
The Breakers ©
The Breakers

few
hours
Hyannis Port

Hyannis Port
To see where to stay, reviews, photos, and more tourist information, refer to the Hyannis Port day trip planner.

You can drive from Newport to Hyannis Port in 2 hours. In May, daily temperatures in Hyannis Port can reach 21°C, while at night they dip to 11°C. You'll set off for Nantucket on the 9th (Thu).

Things to do in Hyannis Port

Tours Adventure Outdoors

4
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Get some cultural insight at Whaling Museum and Unitarian Universalist Meeting House Nantucket. Deepen your sense of the past at sights like Great Point Light and Oldest House (Jethro Coffin House). And it doesn't end there: take an in-depth tour of Egan Maritime's Nantucket Shipwreck & Lifesaving Museum, contemplate the long history of Wauwinet, kick back and relax at Surfside Beach, and make a trip to Brant Point Lighthouse.

For traveler tips, maps, reviews, and tourist information, use the Nantucket trip website .

You can drive from Hyannis Port to Nantucket in 2.5 hours. In May, daytime highs in Nantucket are 19°C, while nighttime lows are 11°C. Finish up your sightseeing early on the 13th (Mon) so you can go by car to Hyannis Port.

Things to do in Nantucket

Parks Beaches Outdoors
Highlights from your plan
Jetties Beach ©
Jetties Beach
Whaling Museum ©
Whaling Museum

few
hours
Hyannis Port

Hyannis Port ©
Start off your visit on the 13th (Mon): steep yourself in history at Kennedy Compound, then examine the collection at Toad Hall Classic Sports Car Museum, and then get lost in a book at Osterville Village Library.

To find other places to visit, reviews, more things to do, and other tourist information, refer to the Hyannis Port road trip planning app .

Drive from Nantucket to Hyannis Port in 2.5 hours. Wrap up your sightseeing on the 13th (Mon) to allow time to drive to Sandwich.

Things to do in Hyannis Port

Historic Sites Museums

Side Trip

Osterville Village Library
Highlights from your plan
Toad Hall Classic Sports Car Museum ©
Osterville Village Library ©
Osterville Village Library

1
night
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Kick off your visit on the 13th (Mon): make a trip to Mayflower II and then appreciate the history behind Plymouth Rock.

To see ratings, maps, photos, and other tourist information, go to the Sandwich road trip planning tool .

Sandwich is just a stone's throw from Hyannis Port. In May, daily temperatures in Sandwich can reach 21°C, while at night they dip to 9°C. You'll have a few hours on the 14th (Tue) to wrap things up before traveling to Boston.

Things to do in Sandwich

Historic Sites Museums Shopping

Side Trip

Plymouth
Highlights from your plan
Plymouth Rock ©
Plymouth Rock

3
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.
Deepen your sense of the past at sights like Marginal Way Walkway and Louisa May Alcott's Orchard House. Get some cultural insight at Museum of Fine Arts and Peabody Essex Museum. There's lots more to do: explore the different monuments and memorials at Mount Auburn Cemetery, contemplate the long history of The Paul Revere House, admire all the interesting features of Fenway Park, and appreciate the extensive heritage of Freedom Trail.

To find photos, where to stay, more things to do, and tourist information, read our Boston road trip planner .

Traveling by bus from Sandwich to Boston takes an hour. Alternatively, you can drive. In May in Boston, expect temperatures between 22°C during the day and 11°C at night. Finish your sightseeing early on the 17th (Fri) to allow enough time to drive to Stockbridge.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Louisa May Alcott's Orchard House, Peabody Essex Museum, Marginal Way Walkway, Mount Auburn Cemetery
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Museum of Fine Arts ©
Museum of Fine Arts
Louisa May Alcott's Orchard House ©
Louisa May Alcott's Orchard House

1
night
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Kick off your visit on the 18th (Sat): get a taste of the local shopping with Schantz Galleries, take in the spiritual surroundings of National Shrine of the Divine Mercy, and then explore the world behind art at Norman Rockwell Museum.

For ratings, traveler tips, photos, and other tourist information, refer to the Stockbridge online driving holiday planner .

You can drive from Boston to Stockbridge in 2.5 hours. Alternatively, you can take a bus; or take a train. Traveling from Boston in May, plan for a bit cooler nights in Stockbridge, with lows around 8°C. Cap off your sightseeing on the 18th (Sat) early enough to go by car to Hyde Park.

Things to do in Stockbridge

Museums Historic Sites Shopping
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
Schantz Galleries ©
Schantz Galleries
National Shrine of the Divine Mercy ©

2
nights
Hyde Park

Hyde Park ©
Hyde Park is a town in Dutchess County, New York, bordering the Hudson River north of Poughkeepsie. On the 18th (Sat), take in the exciting artwork at Albert Shahinian Fine Art. Here are some ideas for day two: steep yourself in history at Vanderbilt Mansion National Historic Site, contemplate the long history of Home of Franklin D. Roosevelt, and then steep yourself in history at Franklin D. Roosevelt Presidential Library and Museum.

For where to stay, reviews, and tourist information, refer to the Hyde Park journey planner .

Getting from Stockbridge to Hyde Park by car takes about 1.5 hours. Other options: take a train; or do a combination of bus and train. In May in Hyde Park, expect temperatures between 26°C during the day and 11°C at night. Finish your sightseeing early on the 20th (Mon) to allow enough time to drive to New York City.

Things to do in Hyde Park

Historic Sites Museums Shopping

Side Trips

Poughkeepsie, Albert Shahinian Fine Art
Highlights from your plan

1
night
New York City

New York City ©
To find reviews, traveler tips, photos, and tourist information, you can read our New York City trip maker tool .

You can drive from Hyde Park to New York City in 2 hours. Other options are to take a train; or take a bus. Traveling from Hyde Park in May, New York City is a bit warmer at night with lows of 15°C. Finish up your sightseeing early on the 21st (Tue) so you can travel back home.

Things to do in New York City

Museums Historic Sites
Highlights from your plan
Frick Collection ©
Frick Collection

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