38 days in United States Itinerary

38 days in United States Itinerary

Created using Inspirock United States trip planner

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Route & dates

38 days in United States Itinerary

Start: Amsterdam
Fly:  9​h 30​min
1
Boston
— 5 nights
Fly + Drive:  4​h
2
Fire Island
— 1 night
Drive + Fly:  5​h 30​min
3
Orlando
— 5 nights
Fly + Drive:  6​h 30​min
4
Shelter Island
— 1 day
Drive:  2​h 45​min
5
Montauk
— 5 nights
Drive:  2​h 30​min
6
New York City
— 6 nights
Fly:  3​h 15​min
7
Washington DC
— 6 nights
Fly:  3​h 45​min
8
Chicago
— 6 nights
Fly:  11​h
End: Amsterdam

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.
Step off the beaten path and head to Dolphin & Whale Watching and The Breakers. Satisfy your inner culture vulture at Marginal Way Walkway and Boston Tea Party Ships & Museum. You'll find plenty of places to visit near Boston: Ogunquit Beach (in Ogunquit), Provincetown (Cortile Gallery & Sea Space Marine Discovery Center) and Tributary Brewing (in Kittery). The adventure continues: take a stroll through North End, pause for some serene contemplation at St. Mary's Catholic Church, look for all kinds of wild species at Swasey Parkway, and stroll through Cliff Walk.

To see other places to visit, where to stay, ratings, and tourist information, go to the Boston road trip site .

Amsterdam, The Netherlands to Boston is an approximately 9.5-hour flight. You can also do a combination of train and flight. The time zone difference moving from Central European Time to Eastern Standard Time is minus 6 hours. May in Boston sees daily highs of 22°C and lows of 11°C at night. Finish up your sightseeing early on the 3rd (Mon) so you can travel to Fire Island.

Things to do in Boston

Parks Outdoors Museums

Side Trips

Provincetown, Newport, Ogunquit, Swasey Parkway, Hampton Beach State Park
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
The Breakers ©
The Breakers
Hampton Beach State Park ©
Hampton Beach State Park

1
night
Fire Island

Fire Island ©
Fire Island is the large center island of the outer barrier islands parallel to the south shore of Long Island, New York. Kick off your visit on the 4th (Tue): stroll through Kismet Beach and then go for a stroll along the water at Sailors Haven Visitor Center.

For traveler tips, more things to do, and other tourist information, use the Fire Island tour itinerary planning site .

The Route module can help you plan travel from Boston to Fire Island. In June, daily temperatures in Fire Island can reach 30°C, while at night they dip to 19°C. Wrap up your sightseeing on the 4th (Tue) early enough to travel to Orlando.

Things to do in Fire Island

Parks Outdoors Beaches
Highlights from your plan
Sailors Haven Visitor Center ©
Sailors Haven Visitor Center

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.
You'll get in some beach time at Beach at Daytona Beach and Ormond Beach. Explore hidden gems such as Scuba & Snorkeling and Cocoa Beach. Explore Orlando's surroundings by going to Alpaca Magic USA (in Homosassa), Ellie Schiller Homosassa Springs Wildlife State Park (in Homosassa Springs) and Hightower Beach Park (in Satellite Beach). The adventure continues: enjoy the sea views from Ponce de Leon Inlet Lighthouse & Museum, take a stroll through International Drive, test your team's savvy at popular escape rooms, and make an unforgettable trip to Disney's Typhoon Lagoon Water Park.

To find out how to plan a trip to Orlando, use our trip itinerary maker.

The Route module can help you plan travel from Fire Island to Orlando. Traveling from Fire Island in June, things will get somewhat warmer in Orlando: highs are around 38°C and lows about 26°C. Finish your sightseeing early on the 10th (Mon) so you can travel to Shelter Island.

Things to do in Orlando

Parks Outdoors Beaches

Side Trips

Alpaca Magic USA, Beach at Daytona Beach, Hightower Beach Park, Scuba & Snorkeling, Ellie Schiller Homosassa Springs Wildlife State Park
Highlights from your plan
Ormond Beach ©
Ormond Beach
Beach at Daytona Beach ©
Beach at Daytona Beach

1
day
Shelter Island

Shelter Island ©
Shelter Island is a hamlet and census-designated place (CDP) within the Town of Shelter Island in Suffolk County, New York, United States. On the 11th (Tue), steep yourself in history at Shelter Island Historical Society and then look for all kinds of wild species at Mashomack Preserve.

Ask Inspirock to suggest an itinerary and make planning a trip to Shelter Island fast, fun, and easy.

Use the Route module to find suitable travel options from Orlando to Shelter Island. Expect a bit cooler temperatures when traveling from Orlando in June; daily highs in Shelter Island reach 26°C and lows reach 18°C. On the 11th (Tue), wrap the sightseeing up by early afternoon so you can travel to Montauk.

Things to do in Shelter Island

Wildlife Parks Historic Sites
Highlights from your plan
Mashomack Preserve ©
Mashomack Preserve
Shelter Island Historical Society ©
Shelter Island Historical Society

5
nights
Montauk

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. Step off the beaten path and head to Elizabeth A. Morton National Wildlife Refuge and Trustom Pond National Wildlife Refuge. Your cultural itinerary includes sights like Guild Hall and Coffee Pot Cellars Tasting Room. Explore the numerous day-trip ideas around Montauk: Roger W. Wheeler State Beach (in Narragansett), Quogue Wildlife Refuge (in Quogue) and Home Sweet Home Museum (in East Hampton). There's lots more to do: kick back and relax at Ponquogue Beach, take a stroll through Main Beach, stroll through Cooper's Beach, and do a tasting at The Old Field Vineyards.

For photos, reviews, other places to visit, and more tourist information, you can read our Montauk trip itinerary planner .

Traveling by car from Shelter Island to Montauk takes 1.5 hours. In June, daily temperatures in Montauk can reach 27°C, while at night they dip to 18°C. Finish up your sightseeing early on the 16th (Sun) so you can go by car to New York City.

Things to do in Montauk

Parks Outdoors Beaches

Side Trips

East Hampton, Southampton, Southold, Ponquogue Beach, Elizabeth A. Morton National Wildlife Refuge
Highlights from your plan
Ponquogue Beach ©
Ponquogue Beach
South Fork Natural History Museum ©
South Fork Natural History Museum

6
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. Satisfy your inner culture vulture at Times Square and New York Public Library. Take a break from New York City with a short trip to Edwin B. Forsythe National Wildlife Refuge in Oceanville, about 1h 55 min away. Next up on the itinerary: appreciate the history behind 9/11 Memorial, take in the pleasant sights at The High Line, admire the landmark architecture of Empire State Building, and explore and take pictures at Central Park.

For where to stay, maps, ratings, and more tourist information, go to the New York City trip planning site .

You can drive from Montauk to New York City in 2.5 hours. Other options are to take a bus; or take a train. When traveling from Montauk in June, plan for a bit warmer days and about the same nights in New York City: temperatures range from 31°C by day to 21°C at night. Wrap up your sightseeing on the 22nd (Sat) early enough to travel to Washington DC.

Things to do in New York City

Museums Parks Historic Sites

Side Trip

Edwin B. Forsythe National Wildlife Refuge
Highlights from your plan
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
New York Public Library ©
New York Public Library
Frick Collection ©
Frick Collection

6
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.
Discover out-of-the-way places like Gettysburg National Military Park Museum & Visitor Center and Smithsonian National Museum of Natural History. Your cultural itinerary includes sights like Gettysburg National Military Park and United States Holocaust Memorial Museum. You'll find plenty of places to visit near Washington DC: Adkins Arboretum (in Ridgely), Blackwater National Wildlife Refuge (in Cambridge) and Layton's Chance Vineyard and Winery (in Vienna). Next up on the itinerary: see the interesting displays at National Air and Space Museum, appreciate the history behind Vietnam Veterans Memorial, get engrossed in the history at Newseum, and admire the landmark architecture of George Washington's Mount Vernon.

To see reviews, photos, traveler tips, and more tourist information, you can read our Washington DC online itinerary builder .

Getting from New York City to Washington DC by flight takes about 3.5 hours. Other options: take a train; or drive. Traveling from New York City in June, expect nights in Washington DC to be about the same, around 24°C, while days are somewhat warmer, around 35°C. Cap off your sightseeing on the 28th (Fri) early enough to travel to Chicago.

Things to do in Washington DC

Museums Parks Wildlife

Side Trips

Gettysburg, Steven F. Udvar-Hazy Center, Blackwater National Wildlife Refuge, Freedom Museum, Betterton Beach
Highlights from your plan

6
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Eschew the tourist crowds and head to Jasper-Pulaski Fish and Wildlife Area and Cowles Bog. The Art Institute of Chicago and The Field Museum are good opportunities to explore the local culture. Change things up with these side-trips from Chicago: St. Julian Winery-Union Pier (in Union Pier), Whirlpool Compass Fountain (in Saint Joseph) and Carpenter Creek Cellars (in Remington). Next up on the itinerary: look for all kinds of wild species at Sarett Nature Center, do a tasting at Butler Winery, tour the pleasant surroundings at Hawthorn Hollow - Nature Sanctuary and Arboretum, and relax in the rural setting at Matt's Produce.

To see traveler tips, reviews, where to stay, and tourist information, you can read our Chicago vacation planning site .

Traveling by flight from Washington DC to Chicago takes 4 hours. Alternatively, you can do a combination of train and flight; or drive. The time zone difference when traveling from Washington DC to Chicago is minus 1 hour. In June, Chicago is slightly colder than Washington DC - with highs of 32°C and lows of 20°C. Wrap up your sightseeing by early afternoon on the 4th (Thu) to allow enough time to travel back home.

Things to do in Chicago

Parks Wildlife Trails

Side Trips

Chesterton, Hawthorn Hollow - Nature Sanctuary and Arboretum, Volo Bog State Natural Area, Whirlpool Compass Fountain, Jasper-Pulaski Fish and Wildlife Area
Highlights from your plan
Jasper-Pulaski Fish and Wildlife Area ©
The Art Institute of Chicago ©
The Art Institute of Chicago
Field Museum ©
Field Museum

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