15 days in East Coast of USA & Chicago Itinerary

15 days in East Coast of USA & Chicago Itinerary

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Route & dates

15 days in East Coast of USA & Chicago Itinerary

Start: Kingston
Drive:  6​h 30​min
1
New York City
— 3 nights
Fly:  3​h 30​min
2
Washington DC
— 2 nights
Fly:  3​h 45​min
3
Chicago
— 1 night
Fly:  4​h
4
Myrtle Beach
— 2 nights
Drive:  2​h 15​min
5
Charleston
— 1 night
Drive:  2​h 15​min
6
Savannah
— 2 nights
Drive:  1​h
7
Hilton Head
— 1 night
Fly + bus:  6​h 15​min
8
Marathon
— 2 nights
shuttle + Fly:  10​h
End: Kingston

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.
New York City is known for museums, nightlife, historic sites, parks, and shopping. Your plan includes some of its best attractions: go for a walk through Central Park, explore the world behind art at The Metropolitan Museum of Art, take in panoramic vistas at Empire State Building, and pause for some photo ops at 9/11 Memorial.

To see traveler tips, other places to visit, maps, and other tourist information, read New York City online driving holiday planner .

Kingston, Canada to New York City is an approximately 6.5-hour combination of car, bus, and flight. You can also drive; or do a combination of train, flight, and bus. Plan for a bit warmer nights when traveling from Kingston in May since evenings lows in New York City dip to 15°C. Wrap up your sightseeing by early afternoon on the 10th (Thu) to allow time for travel to Washington DC.

Things to do in New York City

Parks Museums Historic Sites
Highlights from your plan
Central Park ©
Central Park
Empire State Building ©
Empire State Building
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art

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 11th (Fri), examine the collection at United States Holocaust Memorial Museum, explore the different monuments and memorials at Arlington National Cemetery, then pause for some photo ops at Vietnam Veterans Memorial, and finally appreciate the history behind Korean War Veterans Memorial. Get ready for a full day of sightseeing on the 12th (Sat): appreciate the history behind National World War II Memorial, then pause for some photo ops at Jefferson Memorial, and then learn more about the world around you at Smithsonian National Museum of Natural History.

To see photos, reviews, other places to visit, and tourist information, you can read our Washington DC vacation builder website .

You can fly from New York City to Washington DC in 3.5 hours. Alternatively, you can take a train; or drive. Expect somewhat warmer weather when traveling from New York City in May: highs in Washington DC hover around 29°C, while lows dip to 17°C. Finish your sightseeing early on the 12th (Sat) so you can travel to Chicago.

Things to do in Washington DC

Museums Historic Sites

Side Trip

Arlington National Cemetery
Highlights from your plan
Arlington National Cemetery ©
Arlington National Cemetery
Korean War Veterans Memorial ©
Korean War Veterans Memorial

1
night
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Kick off your visit on the 13th (Sun): take in panoramic vistas at Skydeck Chicago - Willis Tower and then admire the masterpieces at The Art Institute of Chicago.

To find reviews, more things to do, other places to visit, and other tourist information, go to the Chicago road trip planning site .

Getting from Washington DC to Chicago by flight takes about 4 hours. Other options: drive; or take a train. The time zone difference when traveling from Washington DC to Chicago is minus 1 hour. Prepare for slightly colder weather when traveling from Washington DC in May: high temperatures in Chicago hover around 26°C and lows are around 13°C. On the 13th (Sun), wrap the sightseeing up by early afternoon so you can travel to Myrtle Beach.

Things to do in Chicago

Museums
Highlights from your plan
The Art Institute of Chicago ©
The Art Institute of Chicago
Skydeck Chicago - Willis Tower ©
Skydeck Chicago - Willis Tower

2
nights
Myrtle Beach

Myrtle Beach ©
Myrtle Beach is a coastal city on the east coast of the United States in Horry County, South Carolina. On the 14th (Mon), admire nature's wide array of creatures at Ripley's Aquarium of Myrtle Beach, wander the streets of Broadway at the Beach, and then enjoy breathtaking views from Myrtle Beach SkyWheel.

To find other places to visit, more things to do, maps, and tourist information, you can read our Myrtle Beach trip maker app .

Traveling by flight from Chicago to Myrtle Beach takes 4 hours. Alternatively, you can drive; or take a bus. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In May, Myrtle Beach is a bit warmer than Chicago - with highs of 30°C and lows of 20°C. Wrap up your sightseeing on the 15th (Tue) early enough to drive to Charleston.

Things to do in Myrtle Beach

Zoos & Aquariums Parks Shopping
Highlights from your plan
Ripley's Aquarium of Myrtle Beach ©
Ripley's Aquarium of Myrtle Beach
Broadway at the Beach ©
Broadway at the Beach
Myrtle Beach SkyWheel ©
Myrtle Beach SkyWheel

1
night
Charleston

Many visitors describe their Charleston holiday as a warm embrace by an old, dear friend--who lived about 200 years ago.
Start off your visit on the 15th (Tue): don't miss a visit to Riley Waterfront Park and then get the lay of the land with Walking tours. On the next day, get up close to creatures of the deep with a dolphin and whale watching tour and then take in the views from Arthur Ravenel Jr. Bridge.

For traveler tips, maps, and other tourist information, go to the Charleston travel planner .

You can drive from Myrtle Beach to Charleston in 2.5 hours. Alternatively, you can take a bus. In May, daytime highs in Charleston are 32°C, while nighttime lows are 21°C. Finish your sightseeing early on the 16th (Wed) so you can drive to Savannah.

Things to do in Charleston

Tours Wildlife Outdoors
Highlights from your plan
Walking tours
Dolphin & Whale Watching
Joe Riley Waterfront Park ©
Joe Riley Waterfront Park

2
nights
Savannah

Savannah ©
Georgia's oldest city, Savannah displays its colonial history proudly on every corner.
Kick off your visit on the 17th (Thu): appreciate the extensive heritage of Fort Pulaski National Monument, explore the different monuments and memorials at Bonaventure Cemetery, stroll through Forsyth Park, then stroll the grounds of Colonial Park Cemetery, and finally admire the landmark architecture of Historic Savannah Theatre.

You can plan Savannah trip in no time by asking Inspirock to help create your itinerary.

Getting from Charleston to Savannah by car takes about 2.5 hours. Other options: take a bus; or take a train. In May, daily temperatures in Savannah can reach 33°C, while at night they dip to 20°C. Finish up your sightseeing early on the 18th (Fri) so you can go by car to Hilton Head.

Things to do in Savannah

Historic Sites Nightlife Parks

Side Trip

Fort Pulaski National Monument
Highlights from your plan
Bonaventure Cemetery ©
Bonaventure Cemetery
Forsyth Park ©
Forsyth Park
Fort Pulaski National Monument ©
Fort Pulaski National Monument

1
night
Hilton Head

A Hilton Head vacation may be heaven for a golfer, but the area also offers all kinds of other options for sports fans.
Start off your visit on the 18th (Fri): relax and rejuvenate at some of the top local wellness centers, enjoy the sand and surf at Coligny Beach, and then see majestic marine mammals with a dolphin and whale watching tour.

For maps, reviews, traveler tips, and other tourist information, read our Hilton Head route planner.

You can drive from Savannah to Hilton Head in an hour. Another option is to take a bus. May in Hilton Head sees daily highs of 32°C and lows of 22°C at night. Cap off your sightseeing on the 19th (Sat) early enough to travel to Marathon.

Things to do in Hilton Head

Outdoors Beaches Parks
Highlights from your plan
Dolphin & Whale Watching
Coligny Beach ©
Coligny Beach
Spas & Wellness

2
nights
Marathon

A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Kick off your visit on the 19th (Sat): take in the views from Seven Mile Bridge. Get ready for a full day of sightseeing on the next day: look for all kinds of wild species at Dolphin Research Center and then see what you can catch with a fishing tour.

To see maps, other places to visit, where to stay, and more tourist information, use the Marathon trip planner .

Traveling by combination of taxi, flight, and shuttle from Hilton Head to Marathon takes 6.5 hours. Alternatively, you can do a combination of taxi, flight, and bus; or drive. Plan for somewhat warmer temperatures traveling from Hilton Head in May, with highs in Marathon at 36°C and lows at 29°C. Wrap up your sightseeing by early afternoon on the 21st (Mon) to allow enough time to travel back home.

Things to do in Marathon

Wildlife Parks Tours

Side Trip

Fishing Charters & Tours
Highlights from your plan
Fishing Charters & Tours
The Turtle Hospital ©
The Turtle Hospital
Dolphin Research Center ©
Dolphin Research Center

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