39 days in United States Itinerary

39 days in United States Itinerary

Created using Inspirock United States tour planner

Make it your trip
Fly
1
Key West
— 4 nights
Fly
2
Orlando
— 4 nights
Drive
3
Amelia Island
— 2 nights
Drive
4
Savannah
— 2 nights
Drive
5
Charleston
— 4 nights
Drive
6
Asheville
— 4 nights
Fly
7
Washington DC
— 4 nights
Train
8
Philadelphia
— 2 nights
Train
9
New York City
— 5 nights
Fly
10
North Conway
— 2 nights
Fly
11
Chicago
— 4 nights
Fly
12
Nashville
— 1 night
Fly

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Key West

— 4 nights

Conch Republic

Located just 140 km (90 mi) from Cuba, Key West is an island only about 6.4 km (4 mi) long and 1.6 km (1 mi) wide.
Key West is known for wildlife, adventure, and museums. Your plan includes some of its best attractions: examine the collection at The Ernest Hemingway Home and Museum, get engrossed in the history at Key West Firehouse Museum, take in nature's colorful creations at Audubon House & Tropical Gardens, and browse the exhibits of Truman Little White House.

To find traveler tips, reviews, more things to do, and more tourist information, go to the Key West road trip app.

Atlanta to Key West is an approximately 3.5-hour flight. You can also drive; or take a bus. Traveling from Atlanta in May, plan for somewhat warmer nights in Key West, with lows around 77°F. Wrap up your sightseeing on the 5th (Wed) early enough to fly to Orlando.

Things to do in Key West

Museums · Historic Sites · Parks · Outdoors

Orlando

— 4 nights

Theme Park Capital of the World

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.
Have a day of magic on the 6th (Thu) at Walt Disney World Resort. Have a day of magic on the 8th (Sat) at Magic Kingdom Park. The adventure continues: find something for the whole family at Universal's Islands of Adventure.

For where to stay, other places to visit, photos, and other tourist information, read Orlando trip builder tool.

Fly from Key West to Orlando in 3 hours. Alternatively, you can drive; or take a bus. Traveling from Key West in May, expect a bit cooler with lows of 69°F in Orlando. Finish your sightseeing early on the 9th (Sun) so you can drive to Amelia Island.

Things to do in Orlando

Theme Parks

Amelia Island

— 2 nights
The southernmost Sea Island off the coast of Florida, Amelia Island takes its name from Princess Amelia of England.
Kick off your visit on the 10th (Mon): indulge in some personalized pampering at Amelia Massage Associates, then immerse yourself in nature at Fort Clinch State Park, then brush up on your knowledge of spirits at Marlin & Barrel Distillery, and finally steep yourself in history at Amelia Island Historic District. Here are some ideas for day two: explore the different monuments and memorials at Bosque Bello Cemetery, then enjoy the sand and surf at Seaside Park, then learn more about the world around you at Cumberland Island National Seashore Museum, and finally see what you can catch with Fish Amelia Island.

To see maps, where to stay, traveler tips, and more tourist information, read our Amelia Island trip tool.

You can drive from Orlando to Amelia Island in 3 hours. Other options are to do a combination of train and taxi; or do a combination of bus and taxi. In May, daytime highs in Amelia Island are 84°F, while nighttime lows are 68°F. Wrap up your sightseeing on the 11th (Tue) to allow time to drive to Savannah.

Things to do in Amelia Island

Historic Sites · Outdoors · Wildlife · Tours

Side Trip

Savannah

— 2 nights

The Hostess City of the South

Georgia's oldest city, Savannah displays its colonial history proudly on every corner.
Start off your visit on the 12th (Wed): examine the collection at American Prohibition Museum, take a stroll through Savannah Historic District, admire the striking features of Mickve Israel Temple, then take in the spiritual surroundings of Cathedral of St. John the Baptist, then brush up on your military savvy at Webb Military Museum, and finally walk around Forsyth Park. Get ready for a full day of sightseeing on the next day: stop by The Point, then see the interesting displays at Pat Conroy Literary Center, then settle in for a delightful tour with a horse-drawn carriage tour, and finally brush up on your knowledge of spirits at Ghost Coast Distillery.

To see ratings, photos, reviews, and tourist information, refer to the Savannah holiday tool.

Drive from Amelia Island to Savannah in 2.5 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of taxi and train. May in Savannah sees daily highs of 83°F and lows of 64°F at night. Finish your sightseeing early on the 13th (Thu) so you can drive to Charleston.

Things to do in Savannah

Historic Sites · Neighborhoods · Museums · Shopping

Side Trip

Charleston

— 4 nights
Many visitors describe their Charleston holiday as a warm embrace by an old, dear friend--who lived about 200 years ago.
Charleston is known for parks, historic sites, and shopping. Your plan includes some of its best attractions: capture your vacation like a pro with an inspiring photography tour, contemplate the long history of Fort Sumter National Monument, explore the galleries of Warren Lasch Conservation Center - H.L. Hunley Submarine, and take an in-depth tour of Nathaniel Russell House.

To find where to stay, more things to do, ratings, and more tourist information, read our Charleston online driving holiday planner.

You can drive from Savannah to Charleston in 2.5 hours. Another option is to take a bus. In May, daytime highs in Charleston are 81°F, while nighttime lows are 64°F. Finish up your sightseeing early on the 17th (Mon) so you can go by car to Asheville.

Things to do in Charleston

Historic Sites · Parks · Museums · Tours

Side Trip

Asheville

— 4 nights

Land of the Sky

Asheville nestles between two major mountain ranges in the scenic western section of North Carolina.
Get out of town with these interesting Asheville side-trips: Ole Smoky Tennessee Moonshine (in Pigeon Forge), Tennessee Legend Distillery - Newport Hwy (in Sevierville) and Gatlinburg (Tennessee Homemade Wines, Ole Smoky Whiskey Barrelhouse, &more). Next up on the itinerary: get a dose of the wild on Tumblestone Tours and Transportation, admire all the interesting features of Newfound Gap Road, pause for some photo ops at Rockefeller Memorial, and let your taste buds guide you at a local gastronomic tour.

For ratings, photos, and tourist information, you can read our Asheville journey planner.

You can drive from Charleston to Asheville in 4.5 hours. Other options are to do a combination of flight and bus; or take a bus. Traveling from Charleston in May, things will get little chillier in Asheville: highs are around 75°F and lows about 53°F. Wrap up your sightseeing on the 21st (Fri) early enough to fly to Washington DC.

Things to do in Asheville

Outdoors · Tours · Breweries & Distilleries · Scenic Drive

Side Trips

Washington DC

— 4 nights
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.
Washington DC is known for museums, historic sites, and nightlife. Your plan includes some of its best attractions: admire the masterpieces at National Gallery of Art, get engrossed in the history at United States Holocaust Memorial Museum, appreciate the history behind Vietnam Veterans Memorial, and examine the collection at National Air and Space Museum.

To find reviews, maps, where to stay, and other tourist information, use the Washington DC route planner.

Getting from Asheville to Washington DC by flight takes about 3 hours. Other options: drive; or do a combination of bus and train. In May, plan for daily highs up to 76°F, and evening lows to 58°F. Wrap up your sightseeing on the 25th (Tue) to allow time to take a train to Philadelphia.

Things to do in Washington DC

Museums · Zoos & Aquariums · Parks

Philadelphia

— 2 nights

The City of Brotherly Love

Steeped in cultural and historical heritage, Philadelphia is known as the birthplace of U.S. democracy, as it was once the meeting place for the country's Founding Fathers.
On the 26th (Wed), take in the architecture and design of University of Pennsylvania, sample some tasty brews at Philly Brew Tours, then take a stroll through Society Hill, and finally tour the pleasant surroundings at Franklin Square. Get ready for a full day of sightseeing on the 27th (Thu): ponder the design of Longwood Gardens, admire the masterpieces at Brandywine River Museum of Art, and then take a stroll through Boathouse Row.

For reviews, other places to visit, where to stay, and tourist information, use the Philadelphia trip planner.

Getting from Washington DC to Philadelphia by train takes about 2.5 hours. Other options: drive; or take a bus. In May, daytime highs in Philadelphia are 74°F, while nighttime lows are 56°F. Finish your sightseeing early on the 27th (Thu) to allow enough time to take a train to New York City.

Things to do in Philadelphia

Parks · Breweries & Distilleries · Tours · Museums

Side Trips

New York City

— 5 nights

Big Apple

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, and shopping. Your plan includes some of its best attractions: don't miss a visit to Central Park, admire the striking features of Grand Central Terminal, explore the galleries of The Metropolitan Museum of Art, and go for a walk through The High Line.

To find out how to plan a trip to New York City, use our trip itinerary maker.

Traveling by train from Philadelphia to New York City takes 1.5 hours. Alternatively, you can drive; or take a bus. Traveling from Philadelphia in May, expect nights in New York City to be about the same, around 55°F, while days are slightly colder, around 69°F. Cap off your sightseeing on the 1st (Tue) early enough to catch the flight to North Conway.

Things to do in New York City

Museums · Parks · Neighborhoods · Shopping

North Conway

— 2 nights
North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
Start off your visit on the 2nd (Wed): explore the striking landscape at Black Cap Hiking Trail, then indulge your thirst for a good beer at Tuckerman Brewing Company, and then learn about winemaking at Sap House Meadery. Get ready for a full day of sightseeing on the next day: admire the sheer force of Crawford Notch State Park, then get interesting insight from Bretton Woods Canopy Tour, and then admire the sheer force of Glen Ellis Falls.

For traveler tips, maps, and tourist information, read our North Conway trip planner.

Fly from New York City to North Conway in 3 hours. Alternatively, you can drive; or do a combination of train and bus. In June, North Conway is little chillier than New York City - with highs of 75°F and lows of 58°F. Cap off your sightseeing on the 3rd (Thu) early enough to catch the flight to Chicago.

Things to do in North Conway

Nature · Parks · Outdoors · Wildlife

Side Trips

Chicago

— 4 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Change things up with these side-trips from Chicago: SaltTreeYoga (in Ottawa) and Whiskey Acres Distilling Co. (in DeKalb). There's lots more to do: explore the world behind art at The Art Institute of Chicago, admire the landmark architecture of Rockefeller Memorial Chapel, get to know the resident critters at Lincoln Park Zoo, and walk around Millennium Park.

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

Traveling by flight from North Conway to Chicago takes 4 hours. Alternatively, you can drive; or take a bus. The time zone difference when traveling from North Conway to Chicago is minus 1 hour. Traveling from North Conway in June, you will find days in Chicago are somewhat warmer (81°F), and nights are about the same (63°F). Finish up your sightseeing early on the 7th (Mon) so you can catch the flight to Nashville.

Things to do in Chicago

Parks · Museums · Zoos & Aquariums · Shopping

Side Trips

Nashville

— 1 night

Music City U.S.A.

Known as the capital of country music, the thriving city of Nashville combines old-world southern charm with a progressive urban flair.
Kick off your visit on the 8th (Tue): wander the streets of Downtown Nashville, see a show at Grand Ole Opry, and then get engrossed in the history at The Johnny Cash Museum & Cafe.

To find where to stay, other places to visit, traveler tips, and more tourist information, use the Nashville online itinerary planner.

Getting from Chicago to Nashville by flight takes about 3 hours. Other options: drive; or take a bus. Expect somewhat warmer weather when traveling from Chicago in June: highs in Nashville hover around 88°F, while lows dip to 67°F. Wrap up your sightseeing on the 8th (Tue) to allow time to fly back home.

Things to do in Nashville

Neighborhoods · Museums · Nightlife

United States travel guide

4.5
Specialty Museums · Beaches · Historic Sites
More than the country of car-packed streets seen in TV shows and movies, the United States of America is a complex and diverse home to over 300 million people living in a wide range of landscapes and climates. From its big-city skyscrapers to its sprawling natural parks, the country's ''melting pot'' combines many ethnic groups that share a strong sense of national identity despite their cultural differences. A country of road trips and big blue skies, the United States harbors orderly cities filled with restaurants, parks, museums, and innumerable sightseeing opportunities, as well as pristine natural areas perfect for a holiday in the great outdoors. To see as much as you can of this diverse land quickly, drive over some of the more than 6 million km (4 million mi) of highways leading through deserts, mountain peaks, fertile fields, and giant urban centers.

New Hampshire travel guide

4.6
Scenic Drive · Geologic Formations · Ski Areas
The Granite State
One of the country's smallest and least populous states, New Hampshire's wealth of recreational offerings make it a popular vacation destination. Its many pristine natural areas attract skiers, snowmobilers, hikers, and mountaineers from around the world. Named after a county in England, New Hampshire was the first of the North American colonies to establish a government independent of Great Britain's authority. Though New Hampshire's official nickname refers to its extensive granite formations and quarries, the state's license plates carry the motto "Live Free or Die," reflecting the sense of independence prized by the famously terse natives. Find out why America's artists continue to find inspiration in New Hampshire by taking a trip to its quaint villages and sightseeing in the area's old colonial towns.

Illinois travel guide

4.4
Observation Decks · Parks · Art Museums
The Prairie State
The most populous state in the country's Midwest region, Illinois features a diverse landscape that includes both the enormous urban sprawl of Chicago and flat central plains, devoted almost entirely to farmland. With a great selection of things to do, Chicago is the state's centerpiece, featuring world-famous architecture and renowned museums. Farther away from this giant urban center, you can explore historical landmarks dedicated to local heroes Abraham Lincoln and Ernest Hemingway. The state also includes a prehistoric Native American site, one of only 20 World Heritage Sites in the United States, a unique feature well-worth adding to your itinerary.