14 days in Florida, Chicago & New York City Itinerary

14 days in Florida, Chicago & New York City Itinerary

Created using Inspirock United States tour builder

Plan created by another user.Make it yours

Route & dates

1
St. Augustine
— 1 night
2
Orlando
— 3 nights
3
Fort Lauderdale
— 1 night
4
Key West
— 2 nights
5
Chicago
— 3 nights
6
New York City
— 3 nights

1
night
St. Augustine

St. Augustine ©
St. Start off your visit on the 11th (Sun): look for all kinds of wild species at St. Augustine Alligator Farm Zoological Park. Keep things going the next day: take an in-depth tour of St. Augustine Pirate & Treasure Museum, browse the exhibits of St. Augustine Lighthouse & Maritime Museum, Inc., thenenjoy the sand and surf at St. Augustine Beach, and finally sample the fine beverages at St. Augustine Distillery.

For where to stay, other places to visit, traveler tips, and other tourist information, refer to the St. Augustine trip builder website.

San Juan, Puerto Rico to St. Augustine is an approximately 7.5-hour flight. Due to the time zone difference, you'll gain 1 hour traveling from San Juan to St. Augustine. Traveling from San Juan in October, expect St. Augustine to be a bit cooler, temps between °C and °C. Wrap up your sightseeing on the 12th (Mon) to allow time to drive to Orlando.

Things to do in St. Augustine

Parks Museums Wildlife
Highlights from your plan
St. Augustine Beach ©
St. Augustine Beach
St. Augustine Pirate & Treasure Museum ©
St. Augustine Pirate & Treasure Museum
St. Augustine Alligator Farm Zoological Park ©

3
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.
You'll visit kid-friendly attractions like Disney's Typhoon Lagoon Water Park and World of Disney. Eschew the tourist crowds and head to Boat Tours & Water Sports and Disney Springs. The adventure continues: make an unforgettable trip to Walt Disney World Resort, take in a show at Happily Ever After Fireworks, get some fabulous bargains at Orlando Vineland Premium Outlets, and cool off at Disney’s Blizzard Beach Water Park.

To find reviews, other places to visit, traveler tips, and more tourist information, read our Orlando day trip website.

Getting from St. Augustine to Orlando by car takes about 2 hours. Other options: take a bus. In October, daily temperatures in Orlando can reach °C, while at night they dip to °C. Finish your sightseeing early on the 15th (Thu) so you can drive to Fort Lauderdale.

Things to do in Orlando

Theme Parks Shopping Tours

Side Trip

Boat Tours & Water Sports
Highlights from your plan
World of Disney ©
World of Disney
Boat Tours & Water Sports
Disney's Typhoon Lagoon Water Park ©
Disney's Typhoon Lagoon Water Park

1
night
Fort Lauderdale

Fort Lauderdale ©
Known as the "Venice of America" because of its extensive network of navigable waterways, Fort Lauderdale welcomes over 10 million annual visitors, most of them attracted by the city's popular beaches and marinas.
On the 16th (Fri), buy something for everyone on your list at Sawgrass Mills and then kick back and relax at Fort Lauderdale Beach.

Start your trip to Fort Lauderdale by creating a personalized itinerary on Inspirock.

Drive from Orlando to Fort Lauderdale in 4 hours. Alternatively, you can fly; or take a bus. Expect a bit warmer evenings in Fort Lauderdale when traveling from Orlando in October, with lows around °C. Cap off your sightseeing on the 16th (Fri) early enough to travel to Key West.

Things to do in Fort Lauderdale

Beaches Outdoors Parks

Side Trip

Sawgrass Mills
Highlights from your plan
Fort Lauderdale Beach ©
Fort Lauderdale Beach
Sawgrass Mills ©
Sawgrass Mills

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.
On the 17th (Sat), immerse yourself in nature at Fort Zachary Taylor, identify plant and animal life at Key West Butterfly & Nature Conservatory, and then see some colorful creatures with a scuba or snorkeling tour. Keep things going the next day: explore the galleries of Truman Little White House, thenexamine the collection at Mel Fisher Maritime Heritage Museum, and then kick back and relax at Bahia Honda State Park.

For traveler tips, other places to visit, where to stay, and more tourist information, go to the Key West trip itinerary planner.

Traveling by flight from Fort Lauderdale to Key West takes 3.5 hours. Alternatively, you can drive; or take a bus. In October, daily temperatures in Key West can reach °C, while at night they dip to °C. Cap off your sightseeing on the 18th (Sun) early enough to travel to Chicago.

Things to do in Key West

Outdoors Parks Beaches

Side Trip

Bahia Honda State Park
Highlights from your plan
Scuba & Snorkeling
Fort Zachary Taylor ©
Fort Zachary Taylor
Bahia Honda State Park ©
Bahia Honda State Park

3
nights
Chicago

Chicago ©
A huge and vibrant city, Chicago is home to top-notch theaters, shops, museums, galleries, and restaurants.
Step off the beaten path and head to Lakefront Trail and Field Museum. Family-friendly places like Boat Tours & Water Sports and Lake Michigan will thrill your kids. There's lots more to do: explore the world behind art at The Art Institute of Chicago, appreciate the history behind Cloud Gate, get curious at Museum of Science and Industry, and appreciate the extensive heritage of Chicago Riverwalk.

To find traveler tips, photos, reviews, and more tourist information, refer to the Chicago trip itinerary planning website.

Traveling by flight from Key West to Chicago takes 6 hours. Alternatively, you can drive; or do a combination of shuttle and bus. The time zone difference when traveling from Key West to Chicago is minus 1 hour. Traveling from Key West in October, expect Chicago to be much colder, temps between °C and °C. Finish your sightseeing early on the 21st (Wed) so you can travel to New York City.

Things to do in Chicago

Museums Childrens Museums Tours

Side Trip

Lake Michigan
Highlights from your plan
Museum of Science and Industry ©
Museum of Science and Industry
Lakefront Trail ©
Lakefront Trail
Field Museum ©
Field Museum

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.
Bring the kids along to Central Park and The Metropolitan Museum of Art. You'll explore and learn at New York Public Library and 9/11 Memorial. There's much more to do: see the interesting displays at Ground Zero Museum Workshop, walk around World Trade Center's Liberty Park, take a memorable tour with Tours, and admire the landmark architecture of The Oculus.

For reviews, traveler tips, maps, and more tourist information, read our New York City day trip planning site.

Getting from Chicago to New York City by flight takes about 5 hours. Other options: drive; or take a bus. The time zone difference moving from Central Standard Time to Eastern Standard Time is 1 hour. Traveling from Chicago in October, plan for somewhat warmer nights in New York City, with lows around °C. Wrap up your sightseeing on the 24th (Sat) early enough to travel back home.

Things to do in New York City

Museums Parks Neighborhoods
Highlights from your plan
Central Park ©
Central Park
The Metropolitan Museum of Art ©
The Metropolitan Museum of Art
New York Public Library ©
New York Public Library

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