21 days in United States Itinerary

21 days in United States Itinerary

Created using Inspirock United States trip itinerary builder

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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 15​min
2
Southampton
— 1 night
Drive:  45​min
3
Orient
— 1 night
Drive:  2​h 30​min
4
Newport
— 2 nights
Drive:  1​h 45​min
5
Hyannis Port
— Few hours
Drive:  2​h 30​min
6
Nantucket
— 4 nights
Drive:  1​h 30​min
7
Sandwich
— 1 night
bus:  1​h
8
Boston
— 3 nights
Drive:  2​h 30​min
9
Stockbridge
— 1 night
Drive:  1​h 30​min
10
Hyde Park
— 2 nights
Drive:  2​h
11
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.
Satisfy your inner culture vulture at The Metropolitan Museum of Art and American Museum of Natural History. Deepen your sense of the past at sights like 9/11 Memorial and Ellis Island. Next up on the itinerary: go for a walk through Central Park, pause for some serene contemplation at St. Patrick's Cathedral, wander the streets of Times Square, and examine the collection at New York Public Library.

For maps, ratings, more things to do, and tourist information, you can read our New York City journey maker tool .

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. In May, daily temperatures in New York City can reach 24°C, while at night they dip to 15°C. Cap off your sightseeing on the 5th (Sun) early enough to travel to Southampton.

Things to do in New York City

Museums Parks Historic Sites
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
Southampton

Southampton
To see other places to visit, ratings, maps, and other tourist information, read Southampton travel planner.

You can drive from New York City to Southampton in 2 hours. Expect a bit cooler weather when traveling from New York City in May: highs in Southampton hover around 20°C, while lows dip to 13°C. On the 6th (Mon), you're off toOrient.

Things to do in Southampton

Outdoors Parks Beaches

1
night
Orient

Orient ©
Orient is a hamlet and census-designated place (CDP) in Suffolk County, Long Island, New York, United States. On the 6th (Mon), admire the masterpieces at Oysterponds Historical Society, then look for gifts at The Candy Man, then explore and take pictures at Lavender By The Bay, and finally enjoy the sand and surf at Orient Beach State Park.

To find traveler tips, photos, maps, and more tourist information, read our Orient trip planner.

Getting from Southampton to Orient by car takes about an hour. In May, daily temperatures in Orient can reach 20°C, while at night they dip to 13°C. You will leave for Newport on the 7th (Tue).

Things to do in Orient

Beaches Nature Outdoors

Side Trip

Lavender By The Bay
Highlights from your plan
Oysterponds Historical Society ©
Oysterponds Historical Society
Lavender By The Bay ©
Lavender By The Bay
The Candy Man ©
The Candy Man

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): see the interesting displays at The Breakers.

For where to stay, reviews, maps, and more tourist information, you can read our Newport travel route planner .

Traveling by car from Orient to Newport takes 2.5 hours. May in Newport sees daily highs of 21°C and lows of 11°C at night. Wrap up your sightseeing on the 9th (Thu) early enough to drive to Hyannis Port.

Things to do in Newport

Historic Sites Outdoors Trails
Highlights from your plan
Ocean Drive Historic District ©
Ocean Drive Historic District
The Breakers ©
The Breakers
The Elms ©
The Elms

few
hours
Hyannis Port

Hyannis Port ©
On the 9th (Thu), learn about all things military at Cape Cod Maritime Museum, then see the interesting displays at Toad Hall Classic Sports Car Museum, and then don't miss a visit to Kennedy Compound.

For photos, ratings, where to stay, and tourist information, read our Hyannis Port day trip planning app .

Traveling by car from Newport to Hyannis Port takes 2 hours. Expect a daytime high around 21°C in May, and nighttime lows around 11°C. Cap off your sightseeing on the 9th (Thu) early enough to go by car to Nantucket.

Things to do in Hyannis Port

Museums Historic Sites
Highlights from your plan
Toad Hall Classic Sports Car Museum ©
Cape Cod Maritime Museum ©
Cape Cod Maritime Museum

4
nights
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Your cultural itinerary includes sights like Whaling Museum and Wauwinet. Popular historic sites such as Great Point Light and Brant Point Lighthouse are in your itinerary. There's lots more to do: take in the architecture and atmosphere at Unitarian Universalist Meeting House Nantucket, kick back and relax at Jetties Beach, visit a coastal fixture at Sankaty Head Lighthouse, and brush up on your knowledge of spirits at Cisco Brewers.

To find traveler tips, reviews, maps, and other tourist information, go to the Nantucket trip planner .

Getting from Hyannis Port to Nantucket by car takes about 2.5 hours. May in Nantucket sees daily highs of 19°C and lows of 11°C at night. Finish your sightseeing early on the 13th (Mon) to allow enough time to travel to Sandwich.

Things to do in Nantucket

Historic Sites Beaches Outdoors
Highlights from your plan
Sankaty Head Lighthouse ©
Sankaty Head Lighthouse
Whaling Museum ©
Whaling Museum

1
night
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Start off your visit on the 13th (Mon): see the interesting displays at Heritage Museums & Gardens, take an in-depth tour of Plimoth Plantation, then steep yourself in history at Mayflower II, and finally appreciate the history behind Plymouth Rock. On the next day, explore and take pictures at Coonamessett Farm, then admire the masterpieces at Highfield Hall & Gardens, and then get curious at Sandwich Glass Museum.

For where to stay, photos, more things to do, and tourist information, read our Sandwich trip builder .

Traveling by combination of ferry and taxi from Nantucket to Sandwich takes 1.5 hours. Alternatively, you can do a combination of ferry and bus. In May, daytime highs in Sandwich are 21°C, while nighttime lows are 9°C. Wrap up your sightseeing by early afternoon on the 14th (Tue) to allow time for the bus ride to Boston.

Things to do in Sandwich

Museums Historic Sites Childrens Museums

Side Trips

Plymouth, Falmouth
Highlights from your plan
Plimoth Plantation ©
Plimoth Plantation
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Sandwich Glass Museum ©
Sandwich Glass Museum

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.
Museum-lovers will get to explore Museum of Fine Arts and Otis House. Satisfy your inner culture vulture at Mount Auburn Cemetery and Trinity Church. The adventure continues: get engrossed in the history at John F. Kennedy Presidential Museum & Library, steep yourself in history at The Paul Revere House, stroll the grounds of Granary Burying Ground, and explore and take pictures at Fenway Park.

For photos, other places to visit, maps, and more tourist information, refer to the Boston road trip site .

You can take a bus from Sandwich to Boston in an hour. Alternatively, you can drive. In May, daytime highs in Boston are 22°C, while nighttime lows are 11°C. You'll have a few hours on the 17th (Fri) to wrap things up before traveling to Stockbridge.

Things to do in Boston

Museums Historic Sites

Side Trip

Mount Auburn Cemetery
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Mount Auburn Cemetery ©
Mount Auburn Cemetery

1
night
Stockbridge

Stockbridge ©
Stockbridge is a town in Berkshire County in western Massachusetts, United States. Kick off your visit on the 17th (Fri): explore the world behind art at Norman Rockwell Museum and then take in the spiritual surroundings of National Shrine of the Divine Mercy.

Plan my day in Stockbridge using traveler tips and tourist information provided by Inspirock.

Getting from Boston to Stockbridge by car takes about 2.5 hours. Other options: take a bus; or take a train. Traveling from Boston in May, expect slightly colder with lows of 8°C in Stockbridge. Finish your sightseeing early on the 18th (Sat) to allow enough time to drive to Hyde Park.

Things to do in Stockbridge

Museums Historic Sites
Highlights from your plan
Norman Rockwell Museum ©
Norman Rockwell Museum
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), steep yourself in history at Vanderbilt Mansion National Historic Site, then steep yourself in history at Home of Franklin D. Roosevelt, and then get your bearings at Franklin D. Roosevelt Presidential Library and Museum. On the next day, contemplate the long history of Val-Kill Cottage, then explore the world behind art at Storm King Art Center, and then take in the exciting artwork at DM Weil Gallery.

For photos, ratings, more things to do, and tourist information, refer to the Hyde Park road trip planning app .

Drive from Stockbridge to Hyde Park in 1.5 hours. Alternatively, you can 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) so you can drive to New York City.

Things to do in Hyde Park

Historic Sites Museums Parks

Side Trips

Storm King Art Center, DM Weil Gallery
Highlights from your plan
DM Weil Gallery ©
DM Weil Gallery
Storm King Art Center ©
Storm King Art Center

1
night
New York City

New York City ©
On the 20th (Mon), take in the spiritual surroundings of Cathedral Church of Saint John the Divine, then pause for some photo ops at Statue of Liberty National Monument, then take in the spiritual surroundings of Trinity Church, and finally enjoy breathtaking views from Empire State Building. Here are some ideas for day two: explore the world behind art at Cooper Hewitt, Smithsonian Design Museum, then admire the masterpieces at Frick Collection, and then admire the landmark architecture of Federal Hall.

For reviews, photos, other places to visit, and other tourist information, you can read our New York City road trip planning website .

Drive from Hyde Park to New York City in 2 hours. Alternatively, you can take a train; or take a bus. Expect somewhat warmer evenings in New York City when traveling from Hyde Park in May, with lows around 15°C. Finish up your sightseeing early on the 21st (Tue) so you can travel back home.

Things to do in New York City

Historic Sites Museums
Highlights from your plan
Empire State Building ©
Empire State Building
Frick Collection ©
Frick Collection
Statue of Liberty National Monument ©

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