30 days in United States Itinerary

30 days in United States Itinerary

Created using Inspirock United States trip planner

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Route & dates

30 days in United States Itinerary

Start: Los Angeles
Fly:  7​h 15​min
1
Chicago
— 2 nights
Fly + Bus:  4​h 45​min
2
New York City
— 14 nights
Drive:  5​h 15​min
3
Chincoteague Island
— 1 night
Drive:  3​h
4
Williamsburg
— 2 nights
Drive:  2​h 15​min
5
Charlottesville
— 2 nights
Drive:  3​h
6
Floyd
— 2 nights
Drive:  3​h 15​min
7
Shenandoah National Park
— 2 nights
Drive:  1​h 15​min
8
Luray
— 3 nights
Bus + Fly:  9​h
End: Los Angeles

2
nights
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 25th (Tue): admire the majestic nature at Indiana Dunes State Park and then look for all kinds of wild species at Cowles Bog. Get ready for a full day of sightseeing on the 26th (Wed): contemplate the waterfront views at Lake Michigan and then kick back and relax at Whihala Beach Co Park.

To find reviews, more things to do, photos, and more tourist information, read our Chicago trip maker website .

Los Angeles to Chicago is an approximately 7.5-hour flight. You can also do a combination of bus and flight; or drive. Due to the time zone difference, you'll lose 2 hours traveling from Los Angeles to Chicago. In June, daytime highs in Chicago are 32°C, while nighttime lows are 20°C. Finish your sightseeing early on the 26th (Wed) so you can travel to New York City.

Things to do in Chicago

Parks Outdoors Nature

Side Trips

Chesterton, Whihala Beach, Lake Michigan
Highlights from your plan
Indiana Dunes State Park ©
Indiana Dunes State Park
Whihala Beach ©
Whihala Beach
Cowles Bog ©
Cowles Bog

14
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.
Take a break from the city and head to Cupsogue Beach County Park and Fire Island National Seashore. Visit Meschutt Beach and Bay Head Beach for some beach relaxation. Explore New York City's surroundings by going to Woodbury Common Premium Outlets (in Central Valley), The Amazing Olive (in Port Jefferson) and Poughkeepsie (Walkway Over the Hudson State Historic Park & Adams Fairacre Farms). The adventure continues: take a stroll through Fifth Avenue, make a trip to The Metropolitan Museum of Art, steep yourself in history at Home of Franklin D. Roosevelt, and kick back and relax at Manasquan Beach.

To find maps, photos, traveler tips, and other tourist information, refer to the New York City route builder .

Traveling by combination of flight and bus from Chicago to New York City takes 5 hours. Alternatively, you can fly; or drive. Traveling from Chicago to New York City, you'll lose 1 hour due to the time zone difference. In June in New York City, expect temperatures between 31°C during the day and 21°C at night. Finish your sightseeing early on the 10th (Wed) to allow enough time to drive to Chincoteague Island.

Things to do in New York City

Parks Outdoors Beaches

Side Trips

Milford, Poughkeepsie, Hyde Park, DM Weil Gallery, Pocono Environmental Education Center
Highlights from your plan
9/11 Memorial ©
9/11 Memorial
Home of Franklin D. Roosevelt ©
Home of Franklin D. Roosevelt

1
night
Chincoteague Island

Chincoteague Island ©
Famous for a wild breed of horses--Chincoteague Ponies--Chincoteague Island embraces the mystery of some of North America’s oldest inhabitants.
Kick off your visit on the 11th (Thu): look for all kinds of wild species at Chincoteague National Wildlife Refuge. Keep things going the next day: examine the collection at Delmarva Discovery Center, see the interesting displays at Chincoteague Bay Field Station, then stroll through Bike Depot, and finally stop by Sundial Books.

To see photos, where to stay, maps, and more tourist information, refer to the Chincoteague Island trip itinerary builder tool .

You can drive from New York City to Chincoteague Island in 5.5 hours. Alternatively, you can do a combination of train, flight, and taxi; or do a combination of train and bus. In July in Chincoteague Island, expect temperatures between 35°C during the day and 26°C at night. Wrap up your sightseeing on the 12th (Fri) to allow time to drive to Williamsburg.

Things to do in Chincoteague Island

Parks Nature Wildlife

Side Trips

Chincoteague Bay Field Station, Delmarva Discovery Center
Highlights from your plan
Chincoteague National Wildlife Refuge ©
Delmarva Discovery Center ©
Delmarva Discovery Center
Chincoteague Bay Field Station ©
Chincoteague Bay Field Station

2
nights
Williamsburg

Williamsburg ©
Founded in 1632 as a fortified settlement on the high ground between two rivers, Williamsburg served as a colonial capital of Virginia for over 80 years.
On the 13th (Sat), stroll through Yorktown Beach, browse the different shops at Williamsburg Antique Mall, then take an in-depth tour of Historic Jamestowne, and finally do a tasting at Silver Hand Meadery. Get ready for a full day of sightseeing on the 14th (Sun): do a tasting at Saude Creek Vineyards, take in the spiritual surroundings of Historic Christ Church, and then learn about winemaking at The Dog and Oyster Vineyard.

For where to stay, other places to visit, traveler tips, and more tourist information, refer to the Williamsburg itinerary planner .

Getting from Chincoteague Island to Williamsburg by car takes about 3 hours. Other options: take a bus. In July in Williamsburg, expect temperatures between 38°C during the day and 26°C at night. Finish your sightseeing early on the 14th (Sun) so you can drive to Charlottesville.

Things to do in Williamsburg

Wineries Beaches Parks

Side Trips

Irvington, Yorktown Beach, Saude Creek Vineyards
Highlights from your plan
Saude Creek Vineyards ©
Saude Creek Vineyards
Historic Jamestowne ©
Historic Jamestowne
Historic Christ Church ©
Historic Christ Church

2
nights
Charlottesville

Charlottesville ©
Situated at the foothills of the Blue Ridge Mountains, Charlottesville is perhaps best known as the home of three of the United States' founding fathers, including Thomas Jefferson.
Start off your visit on the 15th (Mon): do a tasting at Hill Top Berry Farm & Winery, see the interesting displays at Walton's Mountain Museum, then contemplate the long history of Mulberry Row, and finally stop by C'ville Arts. Keep things going the next day: learn about winemaking at Keswick Vineyards, steep yourself in history at Civil War Medical Museum, then steep yourself in history at Michie Tavern ca. 1784, and finally gain insight at The Glass Palette - Interactive Glass Art Studio.

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

Getting from Williamsburg to Charlottesville by car takes about 2.5 hours. Other options: take a bus; or do a combination of train and bus. Plan for slightly colder nights when traveling from Williamsburg in July since evenings lows in Charlottesville dip to 23°C. Finish your sightseeing early on the 16th (Tue) to allow enough time to travel to Floyd.

Things to do in Charlottesville

Historic Sites Museums Wineries

Side Trips

Hill Top Berry Farm & Winery, The Exchange Hotel Civil War Medical Museum, Walton's Mountain Museum, Keswick Vineyards
Highlights from your plan
Mulberry Row ©
Mulberry Row
Walton's Mountain Museum ©
Walton's Mountain Museum

2
nights
Floyd

Floyd ©
Floyd is a town in Floyd County, Virginia, United States. Kick off your visit on the 17th (Wed): contemplate the long history of Mabry Mill, then examine the collection at The Mount Airy Visitors Center, then see the interesting displays at The Andy Griffith Museum, and finally get a taste of the local shopping with Bell Gallery and Garden. Keep things going the next day: identify plant and animal life at Rocky Knob Recreational Area, then stop by Floyd Country Store, then view the masterpieces at Troika Contemporary Crafts, and finally learn about winemaking at Whitebarrel Winery.

To see reviews, more things to do, where to stay, and tourist information, you can read our Floyd holiday builder app .

Traveling by car from Charlottesville to Floyd takes 3 hours. Traveling from Charlottesville in July, expect Floyd to be a bit cooler, temps between 33°C and 19°C. Cap off your sightseeing on the 18th (Thu) early enough to travel to Shenandoah National Park.

Things to do in Floyd

Museums Shopping Parks

Side Trips

Mount Airy, Mabry Mill, Whitebarrel Winery
Highlights from your plan
The Andy Griffith Museum ©
The Andy Griffith Museum
Mabry Mill ©
Mabry Mill
Whitebarrel Winery ©
Whitebarrel Winery

2
nights
Shenandoah National Park

Shenandoah National Park ©
Shenandoah National Park showcases a particularly scenic section of Virginia's Blue Ridge Mountains.
Start off your visit on the 19th (Fri): do a tasting at Stinson Vineyards, then take in the dramatic natural features at Natural Chimneys Park and Campground, and then view the masterpieces at Black Bear Art Studio. Here are some ideas for day two: stop by SoLace Studios Fine Handcrafts, then get outside with Shenandoah River Adventures, then explore the different monuments and memorials at Dean Cemetery, and finally do a tasting at Moss Vineyards.

To see traveler tips, maps, reviews, and other tourist information, read Shenandoah National Park driving holiday planner .

Traveling by car from Floyd to Shenandoah National Park takes 3 hours. Expect a bit warmer evenings in Shenandoah National Park when traveling from Floyd in July, with lows around 23°C. Wrap up your sightseeing on the 20th (Sat) early enough to drive to Luray.

Things to do in Shenandoah National Park

Outdoors Wineries Nature

Side Trips

SoLace Studios Fine Handcrafts, Natural Chimneys Park and Campground, Black Bear Art Studio, Stinson Vineyards, Moss Vineyards
Highlights from your plan
Stinson Vineyards ©
Stinson Vineyards
Moss Vineyards ©
Moss Vineyards
Natural Chimneys Park and Campground ©

3
nights
Luray

Luray ©
Nestled in the heart of the valley formed by the Shenandoah River, Luray draws visitors with a vast underground cavern system adorned with stalactites, stalagmites, and mirrored pools.
Start off your visit on the 21st (Sun): look for gifts at R.H. Ballard Shop & Gallery, learn about winemaking at Desert Rose Ranch & Winery, then learn about winemaking at Rappahannock Cellars, and finally do a tasting at Little Washington Winery. Keep things going the next day: sample the fine beverages at River Hill Wine & Spirits, then take in the history at New Market State Historical Park, then steep yourself in history at Belle Grove Plantation, and finally see the interesting displays at Dinosaur Land.

To find other places to visit, maps, and tourist information, read Luray trip planner.

Traveling by car from Shenandoah National Park to Luray takes 1.5 hours. In July, daytime highs in Luray are 35°C, while nighttime lows are 22°C. Wrap up your sightseeing by early afternoon on the 23rd (Tue) to allow time for travel back home.

Things to do in Luray

Wineries Historic Sites Parks

Side Trips

Washington, Rappahannock Cellars, Dinosaur Land, Belle Grove Plantation, Desert Rose Ranch & Winery
Highlights from your plan
Desert Rose Ranch & Winery ©
Desert Rose Ranch & Winery
Dinosaur Land ©
Dinosaur Land
Rappahannock Cellars ©
Rappahannock Cellars

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