19 days in United States Itinerary

19 days in United States Itinerary

Created using Inspirock United States travel route maker

Make it your trip
Fly
1
Chicago
— 3 nights
Fly
2
Orlando
— 4 nights
Fly
3
New York City
— 5 nights
Drive
4
Provincetown
— 2 nights
Drive
5
Sandwich
— 1 night
Drive
6
Salem
— 3 nights
Drive to General Edward Lawrence Logan International Airport, Fly to Ben Gurion International Airport

S M T W T F S
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Chicago

— 3 nights

Windy City

A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Chicago is known for museums, parks, and nightlife. Your plan includes some of its best attractions: explore the world behind art at The Art Institute of Chicago, get up close and personal with brilliant marine life at Shedd Aquarium, ponder the design of Buckingham Fountain, and stroll around Millennium Park.

To find traveler tips, photos, and other tourist information, read our Chicago driving holiday planning app.

Tel Aviv, Israel to Chicago is an approximately 15.5-hour flight. You'll gain 8 hours traveling from Tel Aviv to Chicago due to the time zone difference. Expect a bit cooler weather when traveling from Tel Aviv in October: highs in Chicago hover around 21°C, while lows dip to 11°C. Finish your sightseeing early on the 13th (Wed) so you can travel to Orlando.

Things to do in Chicago

Museums · Parks · Childrens Museums · Zoos & Aquariums

Side Trip

Find places to stay Oct 10 — 13:

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.
Pack the 14th (Thu) with family-friendly diversions at Universal's Islands of Adventure. Pack the 17th (Sun) with family-friendly diversions at Universal Orlando Resort. There's still lots to do: get in on the family fun at Walt Disney World Resort and discover the magic at Magic Kingdom Park.

For where to stay, reviews, more things to do, and tourist information, refer to the Orlando online holiday planner.

Fly from Chicago to Orlando in 5.5 hours. Alternatively, you can drive; or take a bus. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Orlando. Prepare for a bit warmer weather when traveling from Chicago in October: high temperatures in Orlando hover around 34°C and lows are around 24°C. Finish your sightseeing early on the 17th (Sun) to allow enough time to travel to New York City.

Things to do in Orlando

Find places to stay Oct 13 — 17:

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: tour the pleasant surroundings at Central Park, don't miss a visit to Empire State Building, admire the landmark architecture of Grand Central Terminal, and enjoy breathtaking views from Top of the Rock.

To see traveler tips, maps, and more tourist information, you can read our New York City trip itinerary planning site.

Traveling by flight from Orlando to New York City takes 6 hours. Alternatively, you can drive; or take a bus. Plan for little chillier temperatures traveling from Orlando in October, with highs in New York City at 24°C and lows at 16°C. Wrap up your sightseeing on the 22nd (Fri) early enough to drive to Provincetown.

Things to do in New York City

Find places to stay Oct 17 — 22:

Provincetown

— 2 nights

Birthplace of American Liberty

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Start off your visit on the 23rd (Sat): get your bearings at Salt Pond Visitor Center, get engrossed in the history at Atwood Museum, and then kick back and relax at Chatham Lighthouse Beach. Get ready for a full day of sightseeing on the 24th (Sun): appreciate the history behind Pilgrim Monument & Provincetown Museum and then kick back and relax at Cape Cod National Seashore.

For reviews, photos, maps, and other tourist information, read Provincetown trip planning tool.

Traveling by car from New York City to Provincetown takes 5.5 hours. Alternatively, you can fly; or do a combination of train and ferry. In October, Provincetown is a bit cooler than New York City - with highs of 20°C and lows of 11°C. Finish up your sightseeing early on the 24th (Sun) so you can go by car to Sandwich.

Things to do in Provincetown

Beaches · Parks · Outdoors · Museums

Side Trips

Find places to stay Oct 22 — 24:

Sandwich

— 1 night
Sandwich is a town in Barnstable County, Massachusetts, United States. On the 25th (Mon), get curious at Sandwich Glass Museum, then don't miss a visit to Old King's Hwy, then relax in the rural setting at Coonamessett Farm, and finally explore the landscape on two wheels at Shining Sea Bikeway.

To find where to stay, other places to visit, maps, and more tourist information, go to the Sandwich road trip app.

You can drive from Provincetown to Sandwich in 1.5 hours. Another option is to take a bus. In October in Sandwich, expect temperatures between 20°C during the day and 9°C at night. Cap off your sightseeing on the 25th (Mon) early enough to go by car to Salem.

Things to do in Sandwich

Parks · Outdoors · Trails · Childrens Museums

Side Trip

Find places to stay Oct 24 — 25:

Salem

— 3 nights

Witch City

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Kick off your visit on the 26th (Tue): steep yourself in history at The House of the Seven Gables, go for a stroll along the water at Pickering Wharf, then gain some tasty knowledge on Salem Food Tours, and finally stop by Crow Haven Corner. Get ready for a full day of sightseeing on the 27th (Wed): steep yourself in history at Ropes Mansion, get engrossed in the history at Gallows Hill Museum/Theatre, contemplate the long history of The Old Manse, then browse the exhibits of Louisa May Alcott's Orchard House, and finally take in the views from Minuteman National Park - Old North Bridge.

To find ratings, other places to visit, photos, and tourist information, read our Salem online road trip planner.

Drive from Sandwich to Salem in 2 hours. Alternatively, you can take a bus; or do a combination of bus and train. In October, daytime highs in Salem are 20°C, while nighttime lows are 8°C. Finish your sightseeing early on the 28th (Thu) so you can travel back home.

Things to do in Salem

Historic Sites · Museums · Breweries & Distilleries · Wineries

Side Trip

Find places to stay Oct 25 — 28:

United States travel guide

4.5
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.