22 days in United States Itinerary

22 days in United States Itinerary

Created using Inspirock United States itinerary planner

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Route & dates

22 days in United States Itinerary

Start: Cape Town
Fly + Drive:  28​h
1
Jacksonville
— 4 nights
Drive:  2​h 45​min
2
Orlando
— 5 nights
Fly:  6​h
3
New York City
— 3 nights
bus + Fly:  4​h 45​min
4
Chicago
— 2 nights
Fly:  6​h 15​min
5
San Francisco
— 3 nights
Fly + bus:  8​h 45​min
6
New York City
— 2 nights
bus + Fly:  21​h 45​min
End: Cape Town


Learn more about your trip

4
nights
Jacksonville

Jacksonville ©
The sprawling city of Jacksonville is not only Florida's most populous city, but also the largest city by land area in the continental United States.
Kids will appreciate attractions like St. Augustine Beach and St. Augustine Wild Reserve. Step out of the city life by going to Fort Clinch State Park and St. Augustine Alligator Farm Zoological Park. Change things up with these side-trips from Jacksonville: St. Augustine (St. Augustine Lighthouse & Maritime Museum, Inc., St. Augustine Distillery, & more) and Marlin & Barrel Distillery (in Fernandina Beach). There's more to do: test your problem-solving skills at popular escape rooms and indulge your thirst for a good beer at Aardwolf Brewing Company.

To see other places to visit, maps, where to stay, and other tourist information, use the Jacksonville trip itinerary tool .

Cape Town, South Africa to Jacksonville is an approximately 28-hour flight. Traveling from Cape Town to Jacksonville, you'll gain 7 hours due to the time zone difference. Traveling from Cape Town in October, expect Jacksonville to be a bit warmer, temps between 32°C and 19°C. Wrap up your sightseeing on the 6th (Sun) early enough to drive to Orlando.

Things to do in Jacksonville

Parks Wildlife Breweries & Distilleries

Side Trips

St. Augustine, Amelia Island
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
Fort Clinch State Park ©
Fort Clinch State Park

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.
Your day-by-day itinerary now includes Disney's Typhoon Lagoon Water Park as well as Epcot. You'll visit kid-friendly attractions like Walt Disney World Resort and Universal Orlando Resort.

To find where to stay, traveler tips, reviews, and more tourist information, you can read our Orlando trip maker .

Traveling by car from Jacksonville to Orlando takes 3 hours. Alternatively, you can take a train; or take a bus. Expect somewhat warmer evenings in Orlando when traveling from Jacksonville in October, with lows around 24°C. On the 11th (Fri), you'll travel to New York City.

Things to do in Orlando

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

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.
Start off your visit on the 12th (Sat): meet the residents at Central Park Zoo and then take in the pleasant sights at Central Park. On your second day here, admire the landmark architecture of Empire State Building, meet the residents at Bronx Zoo, and then race across the water with a speed boat tour.

For maps, other places to visit, reviews, and more tourist information, you can read our New York City trip planner .

Getting from Orlando to New York City by flight takes about 6 hours. Other options: do a combination of flight and bus; or drive. Traveling from Orlando in October, expect New York City to be little chillier, temps between 24°C and 16°C. On the 14th (Mon), wrap the sightseeing up by early afternoon so you can travel to Chicago.

Things to do in New York City

Parks Zoos & Aquariums Outdoors

Side Trip

Bronx Zoo
Highlights from your plan
Central Park ©
Central Park
Statue of Liberty National Monument ©
Bronx Zoo ©
Bronx Zoo

2
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Here are some ideas for day two: get curious at Museum of Science and Industry, then explore the world behind art at The Art Institute of Chicago, and then admire the landmark architecture of Skydeck Chicago - Willis Tower.

To find traveler tips, where to stay, ratings, and tourist information, read Chicago travel route tool .

You can do a combination of bus and flight from New York City to Chicago in 5 hours. Other options are to fly; or drive. The time zone difference moving from Eastern Standard Time (EST) to Central Standard Time (CST) is minus 1 hour. Plan for a bit cooler temperatures traveling from New York City in October, with highs in Chicago at 21°C and lows at 11°C. Wrap up your sightseeing on the 16th (Wed) to allow time to travel to San Francisco.

Things to do in Chicago

Museums Parks Childrens Museums
Highlights from your plan
Museum of Science and Industry ©
Museum of Science and Industry
Lincoln Park Zoo ©
Lincoln Park Zoo
The Art Institute of Chicago ©
The Art Institute of Chicago

3
nights
San Francisco

San Francisco ©
San Francisco is a top holiday destination featuring scenic beauty and great ethnic and cultural diversity.
Kick off your visit on the 17th (Thu): see the interesting displays at Cable Car Museum, then get curious at Exploratorium, and then explore and take pictures at Alcatraz Island. Get ready for a full day of sightseeing on the 18th (Fri): kick back and relax at China Beach, kick back and relax at Marshall’s Beach, then snap pictures at Golden Gate Bridge, and finally make a trip to Lombard Street.

For photos, ratings, other places to visit, and more tourist information, read our San Francisco itinerary planner.

You can fly from Chicago to San Francisco in 6.5 hours. Other options are to do a combination of flight and train; or drive. You'll gain 2 hours traveling from Chicago to San Francisco due to the time zone difference. Traveling from Chicago in October, expect San Francisco to be a bit warmer, temps between 26°C and 15°C. Cap off your sightseeing on the 19th (Sat) early enough to travel to New York City.

Things to do in San Francisco

Parks Outdoors Beaches
Highlights from your plan
Alcatraz Island ©
Alcatraz Island
Exploratorium ©
Exploratorium
Marshall’s Beach ©
Marshall’s Beach

2
nights
New York City

New York City ©
Kick off your visit on the 19th (Sat): get some thrills on the water with a speed boat tour and then meet the residents at Bronx Zoo. On the next day, admire nature's wide array of creatures at Central Park Zoo and then make a trip to Central Park.

For other places to visit, where to stay, traveler tips, and tourist information, use the New York City trip planner .

Do a combination of flight and bus from San Francisco to New York City in 9 hours. Alternatively, you can fly; or drive. The time zone difference moving from Pacific Standard Time (PST) to Eastern Standard Time (EST) is 3 hours. Finish up your sightseeing early on the 21st (Mon) so you can travel back home.

Things to do in New York City

Parks Zoos & Aquariums Outdoors

Side Trips

Bronx Zoo, Joel L. Lefkowitz Park at West Meadow Beach
Highlights from your plan
Central Park ©
Central Park
Bronx Zoo ©
Bronx Zoo
Central Park Zoo ©
Central Park Zoo

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