57 days in United States Itinerary

57 days in United States Itinerary

Created using Inspirock United States itinerary planner

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Route & dates

57 days in United States Itinerary

Start: Winnipeg
Fly:  5 h 30 min
1
Chicago
— 5 nights
Fly:  4 h
2
Boston
— 3 nights
Fly + Bus:  3 h 15 min
3
New York City
— 6 nights
Drive:  15 min
4
Brooklyn
— 2 nights
Fly:  4 h 15 min
5
Savannah
— 2 nights
Drive:  1 h 45 min
6
Saint Simons Island
— 2 nights
Drive:  3 h 45 min
7
Orlando
— 2 nights
Fly:  4 h
8
Miami
— 2 nights
Drive:  2 h 30 min
9
Marathon
— 2 nights
Bus:  1 h 15 min
10
Key West
— 2 nights
Fly:  5 h 45 min
11
Columbus
— 2 nights
Drive:  1 h 15 min
12
LaGrange
— 2 nights
Drive + Fly:  4 h 15 min
13
Nashville
— 2 nights
Bus + Fly:  4 h
14
New Orleans
— 5 nights
Fly:  3 h 45 min
15
Austin
— 4 nights
Drive:  1 h 30 min
16
San Antonio
— 5 nights
Fly:  4 h 15 min
17
Colorado Springs
— 1 night
Fly:  3 h 15 min
18
Aspen
— 3 nights
Fly + Drive:  9 h
19
Anchorage
— 2 nights
Drive + Fly:  11 h 45 min
End: Winnipeg

5
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, historic sites, nightlife, zoos & aquariums, and childrens museums. Your plan includes some of its best attractions: admire the masterpieces at The Art Institute of Chicago, admire nature's wide array of creatures at Lincoln Park Zoo, explore and take pictures at Wrigley Field, and take in panoramic vistas at Skydeck Chicago - Willis Tower.

To see ratings, maps, and more tourist information, read Chicago sightseeing planning app .

Winnipeg, Canada to Chicago is an approximately 5.5-hour flight. You can also do a combination of flight and bus; or drive. Plan for a bit warmer temperatures traveling from Winnipeg in April, with highs in Chicago at 17°C and lows at 5°C. Cap off your sightseeing on the 6th (Sat) early enough to travel to Boston.

Things to do in Chicago

Museums Parks Childrens Museums

Side Trip

Frank Lloyd Wright Home and Studio
Highlights from your plan
Fox in a Box Chicago ©
Fox in a Box Chicago
The Art Institute of Chicago ©
The Art Institute of Chicago
Museum of Science and Industry ©
Museum of Science and Industry

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.
Boston is known for historic sites, museums, parks, shopping, and nightlife. Your plan includes some of its best attractions: explore the world behind art at Museum of Fine Arts, look for gifts at Brookline Booksmith, let the kids burn off some steam at Christopher Columbus Waterfront Park, and get curious at Museum of Science.

To see where to stay, more things to do, other places to visit, and other tourist information, you can read our Boston trip planner .

You can do a combination of flight and bus from Chicago to Boston in 4 hours. Alternatively, you can do a combination of flight, taxi, and bus; or drive. You'll lose 1 hour traveling from Chicago to Boston due to the time zone difference. Expect a daytime high around 15°C in April, and nighttime lows around 5°C. Finish up your sightseeing early on the 9th (Tue) so you can travel to New York City.

Things to do in Boston

Museums Historic Sites Childrens Museums

Side Trips

Brookline Booksmith, Mount Auburn Cemetery
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Fenway Park ©
Fenway Park
Mount Auburn Cemetery ©
Mount Auburn Cemetery

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.
New York City is known for museums, nightlife, shopping, historic sites, and parks. Your plan includes some of its best attractions: take in the pleasant sights at Central Park, get a new perspective on nature at American Museum of Natural History, enjoy breathtaking views from Top of the Rock, and admire the landmark architecture of Empire State Building.

To find photos, traveler tips, other places to visit, and more tourist information, refer to the New York City trip builder site .

Do a combination of bus and flight from Boston to New York City in 3.5 hours. Alternatively, you can do a combination of bus and flight; or drive. April in New York City sees daily highs of 19°C and lows of 8°C at night. Finish your sightseeing early on the 15th (Mon) so you can drive to Brooklyn.

Things to do in New York City

Museums Parks 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
Brooklyn

Brooklyn ©
Though it may be less popular or touristy than its big brother Manhattan, Brooklyn boasts of one of the largest and hippest art districts in the United States.
On the 16th (Tue), meet the residents at Bronx Zoo and then take in nature's colorful creations at Brooklyn Botanic Garden. Get ready for a full day of sightseeing on the 17th (Wed): contemplate in the serene atmosphere at Brooklyn Tabernacle and then admire all the interesting features of Yankee Stadium.

To see where to stay, photos, traveler tips, and tourist information, read our Brooklyn road trip website .

Brooklyn is very close to New York City. In April, daily temperatures in Brooklyn can reach 19°C, while at night they dip to 8°C. Wrap up your sightseeing on the 17th (Wed) to allow time to travel to Savannah.

Things to do in Brooklyn

Parks Zoos & Aquariums Historic Sites

Side Trip

Bronx
Highlights from your plan
Brooklyn Botanic Garden ©
Brooklyn Botanic Garden
Bronx Zoo ©
Bronx Zoo
Yankee Stadium ©
Yankee Stadium

2
nights
Savannah

Savannah ©
Georgia's oldest city, Savannah displays its colonial history proudly on every corner.
Start off your visit on the 18th (Thu): contemplate in the serene atmosphere at Mickve Israel Temple, get thoroughly spooked out with a ghost and vampire tour, then stroll through Forsyth Park, then explore the different monuments and memorials at Bonaventure Cemetery, and finally take a stroll through Savannah Historic District. On the 19th (Fri), you'll have a packed day of sightseeing: admire the landmark architecture of Historic Savannah Theatre, contemplate in the serene atmosphere at Cathedral of St. John the Baptist, brush up on your military savvy at Webb Military Museum, then take in the spiritual surroundings of Second African Baptist Church, and finally don't miss a visit to River Street Savannah.

For maps, where to stay, more things to do, and tourist information, you can read our Savannah itinerary maker app .

Getting from Brooklyn to Savannah by combination of train and flight takes about 4.5 hours. Other options: do a combination of subway, bus, and flight; or drive. Prepare for a bit warmer weather when traveling from Brooklyn in April: high temperatures in Savannah hover around 29°C and lows are around 16°C. Cap off your sightseeing on the 19th (Fri) early enough to go by car to Saint Simons Island.

Things to do in Savannah

Historic Sites Tours Shopping
Highlights from your plan
Webb Military Museum ©
Webb Military Museum
Savannah Historic District ©
Savannah Historic District
Cathedral of St. John the Baptist
Cathedral of St. John the Baptist

2
nights
Saint Simons Island

Saint Simons Island ©
St. On the 20th (Sat), contemplate the long history of Fort Frederica National Monument, then enjoy the sand and surf at East Beach, then examine the collection at St. Simons Lighthouse Museum, and finally identify plant and animal life at Georgia Sea Turtle Center. On the 21st (Sun), you'll have a packed day of sightseeing: take a stroll through Jekyll Island Historic District, tour the pleasant surroundings at Driftwood Beach, take in nature's colorful creations at Wesley Memorial & Gardens, then take in the spiritual surroundings of Christ Church, and finally don't miss a visit to Tree Spirits of St. Simons Island.

To see photos, where to stay, ratings, and other tourist information, refer to the Saint Simons Island route builder tool .

Traveling by car from Savannah to Saint Simons Island takes 2 hours. Alternatively, you can do a combination of bus and taxi. In April, daytime highs in Saint Simons Island are 28°C, while nighttime lows are 19°C. Finish your sightseeing early on the 21st (Sun) to allow enough time to drive to Orlando.

Things to do in Saint Simons Island

Parks Beaches Outdoors

Side Trip

Jekyll Island
Highlights from your plan
Driftwood Beach ©
Driftwood Beach
Christ Church ©
Christ Church
Fort Frederica National Monument ©
Fort Frederica National Monument

2
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.
On the 22nd (Mon), get in on the family fun at Walt Disney World Resort. On your second day here, get in on the family fun at Universal Orlando Resort.

To see other places to visit, more things to do, traveler tips, and more tourist information, go to the Orlando online visit planner .

Drive from Saint Simons Island to Orlando in 4 hours. Alternatively, you can do a combination of taxi and bus; or do a combination of taxi, bus, and train. Traveling from Saint Simons Island in April, expect nights in Orlando to be about the same, around 21°C, while days are a bit warmer, around 34°C. Wrap up your sightseeing on the 23rd (Tue) to allow time to drive to Miami.

Things to do in Orlando

Theme Parks
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort

2
nights
Miami

Miami ©
Florida’s mecca of fun in the sun, the lively tropical metropolis of Miami is one of the world’s top vacation spots.
On the 24th (Wed), see the interesting displays at Vizcaya Museum and Gardens, explore and take pictures at American Airlines Arena, and then don't miss a visit to Bayside Marketplace. Get ready for a full day of sightseeing on the 25th (Thu): wander the streets of Lincoln Road, stroll through South Beach, and then get to know the fascinating history of Art Deco Historic District.

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

You can drive from Orlando to Miami in 4 hours. Alternatively, you can take a bus; or take a train. Traveling from Orlando in April, you can expect nighttime temperatures to be somewhat warmer in Miami, with lows of 25°C. Finish up your sightseeing early on the 25th (Thu) so you can go by car to Marathon.

Things to do in Miami

Shopping Parks Neighborhoods

Side Trip

Miami Beach
Highlights from your plan
Lincoln Road ©
Lincoln Road
Vizcaya Museum and Gardens ©
Vizcaya Museum and Gardens
Art Deco Historic District ©
Art Deco Historic District

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 26th (Fri): look for all kinds of wild species at Dolphin Research Center, then sample the tasty concoctions at Islamorada Beer Company Brewery and Tasting Room, and then take a tour by water with Boat Tours & Water Sports. On the 27th (Sat), you'll have a packed day of sightseeing: kick back and relax at Sombrero Beach, then look for all kinds of wild species at The Turtle Hospital, and then enjoy the sand and surf at Bahia Honda State Park.

To find where to stay, reviews, other places to visit, and other tourist information, read Marathon driving holiday planner .

Getting from Miami to Marathon by car takes about 2.5 hours. Other options: take a bus; or do a combination of tram, flight, and bus. April in Marathon sees daily highs of 35°C and lows of 28°C at night. Finish up your sightseeing early on the 27th (Sat) so you can catcht the bus to Key West.

Things to do in Marathon

Parks Outdoors Wildlife

Side Trips

Islamorada, Bahia Honda State Park
Highlights from your plan
Fishing Charters & Tours
Bahia Honda State Park ©
Bahia Honda State Park
Sombrero Beach ©
Sombrero Beach

2
nights
Key West

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.
Start off your visit on the 28th (Sun): look for all kinds of wild species at Key West Butterfly & Nature Conservatory, then see the interesting displays at The Ernest Hemingway Home and Museum, then make a trip to Duval Street, and finally don't miss a visit to Mallory Square. On the 29th (Mon), you'll have a packed day of sightseeing: glide through the air with a parasailing or paragliding tour.

To find more things to do, reviews, where to stay, and tourist information, refer to the Key West trip itinerary maker app .

Take a bus from Marathon to Key West in 1.5 hours. Alternatively, you can drive. In April, daily temperatures in Key West can reach 33°C, while at night they dip to 27°C. Wrap up your sightseeing by early afternoon on the 29th (Mon) to allow enough time to travel to Columbus.

Things to do in Key West

Adventure Tours Outdoors
Highlights from your plan
Parasailing & Paragliding
The Ernest Hemingway Home and Museum ©
The Ernest Hemingway Home and Museum
Key West Butterfly & Nature Conservatory ©

2
nights
Columbus

Columbus ©
Columbus is a city in the U.S. Start off your visit on the 30th (Tue): take an in-depth tour of National Civil War Naval Museum, then learn about all things military at National Infantry Museum and Soldier Center, then appreciate the history behind Kadie the Cow of Columbus, and finally don't miss a visit to Toomer's Corner. Keep things going the next day: admire the majestic nature at Providence Canyon State Outdoor Recreation Area and then appreciate the extensive heritage of Columbus Riverwalk.

For reviews, ratings, maps, and tourist information, read our Columbus vacation app .

You can fly from Key West to Columbus in 6 hours. Alternatively, you can do a combination of flight and bus; or drive. Plan for little chillier temperatures traveling from Key West in April, with highs in Columbus at 29°C and lows at 15°C. Finish up your sightseeing early on the 1st (Wed) so you can travel to LaGrange.

Things to do in Columbus

Parks Nature Museums

Side Trips

Toomer's Corner, Providence Canyon State Outdoor Recreation Area
Highlights from your plan
National Civil War Naval Museum ©
National Civil War Naval Museum
Kadie the Cow of Columbus ©
Kadie the Cow of Columbus

2
nights
LaGrange

LaGrange ©
LaGrange is a city and the county seat of Troup County, Georgia, United States. Kick off your visit on the 2nd (Thu): identify plant and animal life at Callaway Gardens and then identify plant and animal life at Wild Animal Safari. Get ready for a full day of sightseeing on the 3rd (Fri): contemplate the long history of Hills & Dales Estate, make a trip to Historic Downtown Senoia, and then steep yourself in history at Little White House.

For traveler tips, other places to visit, more things to do, and other tourist information, go to the LaGrange trip itinerary maker app .

Traveling by car from Columbus to LaGrange takes an hour. In May in LaGrange, expect temperatures between 32°C during the day and 17°C at night. Wrap up your sightseeing on the 3rd (Fri) to allow time to travel to Nashville.

Things to do in LaGrange

Parks Wildlife Historic Sites

Side Trips

Pine Mountain, Little White House, Senoia Welcome Center
Highlights from your plan
Hills & Dales Estate ©
Hills & Dales Estate
Little White House ©
Little White House
Senoia Welcome Center ©
Senoia Welcome Center

2
nights
Nashville

Nashville ©
Known as the capital of country music, the thriving city of Nashville combines old-world southern charm with a progressive urban flair.
On the 4th (Sat), see a show at Grand Ole Opry, admire the natural beauty at Gaylord Opryland Resort Gardens, then test your problem-solving skills at popular escape rooms, and finally see the interesting displays at The Johnny Cash Museum & Cafe. Keep things going the next day: see the interesting displays at Country Music Hall of Fame and Museum, then explore the galleries of Lotz House Museum, then see the interesting displays at RCA Studio B, and finally learn the secrets of beer at a beer tour and tasting.

For ratings, more things to do, where to stay, and other tourist information, read our Nashville trip website .

The Route module can help you plan travel from LaGrange to Nashville. You'll gain 1 hour traveling from LaGrange to Nashville due to the time zone difference. In May, daily temperatures in Nashville can reach 31°C, while at night they dip to 17°C. Finish your sightseeing early on the 5th (Sun) so you can travel to New Orleans.

Things to do in Nashville

Museums Tours Parks

Side Trip

Lotz House Museum
Highlights from your plan
Lotz House Museum ©
Lotz House Museum
Room Escape Games
Beer Tastings & Tours

5
nights
New Orleans

New Orleans ©
Known for its Creole cuisine, rich musical tradition, and nearby swamps and plantations, New Orleans is one of the nation's oldest cities.
New Orleans is known for historic sites, museums, nightlife, shopping, and parks. Your plan includes some of its best attractions: brush up on your military savvy at The National WWII Museum, appreciate the extensive heritage of Jackson Square, take a stroll through Garden District, and meet the residents at Audubon Aquarium of the Americas.

To see more things to do, ratings, and tourist information, go to the New Orleans trip maker tool .

Getting from Nashville to New Orleans by flight takes about 4 hours. Other options: drive; or do a combination of bus and train. When traveling from Nashville in May, plan for little chillier days and somewhat warmer nights in New Orleans: temperatures range from 24°C by day to 24°C at night. Cap off your sightseeing on the 10th (Fri) early enough to travel to Austin.

Things to do in New Orleans

Parks Museums Historic Sites
Highlights from your plan
New Orleans City Park ©
New Orleans City Park
The National WWII Museum ©
The National WWII Museum
Garden District ©
Garden District

4
nights
Austin

Austin ©
Despite its laid-back college vibe, Austin is an influential center for politics, technology, film, and music.
Austin is known for museums, nightlife, fun & games, nature, and parks. Your plan includes some of its best attractions: hike along Lady Bird Lake Hike-and-Bike Trail, take in the exciting artwork at Harry Ransom Center, get a sense of history and politics at Texas State Capitol, and admire the striking features of The Driskill.

To see traveler tips, other places to visit, and more tourist information, refer to the Austin day trip app .

Traveling by flight from New Orleans to Austin takes 4 hours. Alternatively, you can drive; or take a bus. When traveling from New Orleans in May, plan for somewhat warmer days and a bit cooler nights in Austin: temperatures range from 34°C by day to 21°C at night. Finish up your sightseeing early on the 14th (Tue) so you can go by car to San Antonio.

Things to do in Austin

Parks Outdoors Museums
Highlights from your plan
The Escape Game Austin ©
The Escape Game Austin
Lady Bird Johnson Wildflower Center ©
Lady Bird Johnson Wildflower Center
Texas State Capitol ©
Texas State Capitol

5
nights
San Antonio

San Antonio ©
As the state’s second largest city, San Antonio embodies Texas’ rich cultural heritage while maintaining the Old West charm of an oil town.
Go for a jaunt from San Antonio to Fredericksburg to see National Museum of the Pacific War about 1h 25 min away. Pack the 18th (Sat) with family-friendly diversions at SeaWorld San Antonio. The adventure continues: contemplate the long history of The Alamo, admire the architecture and history at Mission San Jose, shop like a local with The San Antonio River Walk, and admire the natural beauty at San Antonio Botanical Garden.

For traveler tips, ratings, other places to visit, and more tourist information, refer to the San Antonio trip planner .

You can drive from Austin to San Antonio in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 36°C in May, and nighttime lows around 22°C. Finish your sightseeing early on the 19th (Sun) so you can travel to Colorado Springs.

Things to do in San Antonio

Theme Parks Museums Parks

Side Trip

National Museum of the Pacific War
Highlights from your plan
National Museum of the Pacific War ©
National Museum of the Pacific War
The San Antonio River Walk ©
The San Antonio River Walk
The Alamo ©
The Alamo

1
night
Colorado Springs

Colorado Springs ©
Stunning Garden of the Gods Park scenery, blue skies and the glory of Pikes Peak-America’s Mountain have attracted visitors to Colorado Springs for more than a century.
On the 19th (Sun), admire nature's wide array of creatures at Cheyenne Mountain Zoo and then get your game on at Battlefield Colorado.

To plan Colorado Springs vacation without wasting time, ask Inspirock to design an itinerary.

You can fly from San Antonio to Colorado Springs in 4.5 hours. Alternatively, you can do a combination of flight and shuttle; or drive. Due to the time zone difference, you'll gain 1 hour traveling from San Antonio to Colorado Springs. Traveling from San Antonio in May, you will find days in Colorado Springs are slightly colder (23°C), and nights are much colder (6°C). Finish your sightseeing early on the 20th (Mon) so you can travel to Aspen.

Things to do in Colorado Springs

Parks Zoos & Aquariums Fun & Games
Highlights from your plan
Battlefield Colorado ©
Battlefield Colorado
Garden of the Gods ©
Garden of the Gods
Cheyenne Mountain Zoo ©
Cheyenne Mountain Zoo

3
nights
Aspen

Aspen ©
Known as a ski resort town, Aspen's history goes back to its roots as a silver-mining village tucked away in an isolated valley of the Rocky Mountains.
Venture out of the city with trips to Vail Mountain Resort (in Vail), Thermal Spas (in Glenwood Springs) and Vail Valley Escape Room (in Avon). There's still lots to do: stroll through Aspen Snowmass, appreciate the history behind The John Denver Sanctuary, and browse the collection at Pitkin County Library.

For more things to do, photos, ratings, and other tourist information, read Aspen online trip itinerary planner .

Traveling by flight from Colorado Springs to Aspen takes 3.5 hours. Alternatively, you can drive; or do a combination of shuttle and flight. Expect a bit cooler temperatures when traveling from Colorado Springs in May; daily highs in Aspen reach 19°C and lows reach 1°C. Finish your sightseeing early on the 23rd (Thu) so you can travel to Anchorage.

Things to do in Aspen

Parks Winter Sports Outdoors

Side Trips

Thermal Spas, Vail Mountain Resort, Aspen Snowmass, Vail Valley Escape Room
Highlights from your plan
Aspen Snowmass ©
Aspen Snowmass
Thermal Spas
The John Denver Sanctuary
The John Denver Sanctuary

2
nights
Anchorage

Anchorage ©
Home to nearly half of Alaska's population, the port city of Anchorage covers a staggering area of over 4,900 sq km (1,900 sq mi) surrounded by mountains.
Kick off your visit on the 24th (Fri): examine the collection at Anchorage Museum at Rasmuson Center, tour the pleasant surroundings at Alaska Zoo, and then trek along Virgin Creek Falls Trail. Get ready for a full day of sightseeing on the next day: delve into the lush surroundings at Chugach National Forest and then appreciate the extensive heritage of Tony Knowles Coastal Trail.

Plan a trip to Anchorage easily and quickly by telling Inspirock to suggest an itinerary.

Do a combination of flight and car from Aspen to Anchorage in 9 hours. Alternatively, you can do a combination of shuttle, flight, and car; or drive. The time zone difference when traveling from Aspen to Anchorage is minus 2 hours. Plan for a bit warmer nights when traveling from Aspen in May since evenings lows in Anchorage dip to 6°C. Wrap up your sightseeing by early afternoon on the 26th (Sun) to allow enough time to travel back home.

Things to do in Anchorage

Parks Trails Outdoors

Side Trip

Chugach National Forest
Highlights from your plan
Alaska Zoo ©
Alaska Zoo
Tony Knowles Coastal Trail ©
Tony Knowles Coastal Trail
Anchorage Museum at Rasmuson Center ©
Anchorage Museum at Rasmuson Center

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