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

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Route & dates

Start: San Juan, Puerto Rico
Fly + Drive:  5 h
1
St. Augustine
— 1 night
Drive:  2 h
2
Orlando
— 3 nights
Fly:  3 h 30 min
3
Fort Lauderdale
— 1 night
Fly:  3 h 15 min
4
Key West
— 2 nights
Fly:  5 h 45 min
5
Chicago
— 3 nights
Fly + Bus:  4 h 45 min
6
New York City
— 3 nights
+2
Subway + Train + Fly:  7 h
End: San Juan, Puerto Rico

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., then enjoy the sand and surf at St. Augustine Beach, and finally sample the fine beverages at St. Augustine Distillery.

To find other places to visit, reviews, photos, and other tourist information, refer to the St. Augustine trip builder website.

San Juan, Puerto Rico to St. Augustine is an approximately 5- hour combination of flight and car. You can also do a combination of flight and bus. 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 31°C and 22°C. Wrap up your sightseeing on the 12th (Mon) to allow time to drive to Orlando.

Things to do in St. Augustine

Parks Museums Beaches
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 Springs and Boat Tours & Water Sports. Eschew the tourist crowds and head to Disney's Typhoon Lagoon Water Park and Orlando Vineland Premium Outlets. There's lots more to do: make an unforgettable trip to Disney’s Blizzard Beach Water Park, add some entertainment to your itinerary with Happily Ever After Fireworks, look for gifts at World of Disney, and get in on the family fun at Walt Disney World Resort.

To find photos, traveler tips, maps, and more tourist information, you can read our Orlando trip itinerary planner.

Traveling by car from St. Augustine to Orlando takes 2 hours. Alternatively, you can take a bus. Expect a daytime high around 34°C in October, and nighttime lows around 24°C. Finish your sightseeing early on the 15th (Thu) so you can travel to Fort Lauderdale.

Things to do in Orlando

Theme Parks Shopping Tours

Side Trip

Boat Tours & Water Sports
Highlights from your plan
Disney Springs ©
Disney Springs
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.

Fly from Orlando to Fort Lauderdale in 3.5 hours. Alternatively, you can drive; or take a bus. Expect a bit warmer evenings in Fort Lauderdale when traveling from Orlando in October, with lows around 28°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

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, then examine the collection at Mel Fisher Maritime Heritage Museum, and then kick back and relax at Bahia Honda State Park.

To find traveler tips, more things to do, photos, 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 do a combination of train and flight; or drive. In October, daily temperatures in Key West can reach 35°C, while at night they dip to 29°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
Fort Zachary Taylor ©
Fort Zachary Taylor
Bahia Honda State Park ©
Bahia Honda State Park
Key West Butterfly & Nature Conservatory ©
Key West Butterfly & Nature Conservatory

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 Museum of Science and Industry. Escape the urban bustle at Boat Tours & Water Sports and Lake Michigan. Next up on the itinerary: get a new perspective on nature at Field Museum, indulge in some culinary diversions at a local gastronomic tour, explore the world behind art at The Art Institute of Chicago, and pause for some photo ops at Cloud Gate.

To find where to stay, photos, traveler tips, and tourist information, use the Chicago tour builder app.

Traveling by flight from Key West to Chicago takes 6 hours. Alternatively, you can drive; or do a combination of shuttle and bus. You'll gain 1 hour traveling from Key West to Chicago due to the time zone difference. Expect cooler temperatures when traveling from Key West in October; daily highs in Chicago reach 21°C and lows reach 11°C. Finish up 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
Lakefront Trail ©
Lakefront Trail
Museum of Science and Industry ©
Museum of Science and Industry
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 New York Public Library. You'll explore and learn at The Metropolitan Museum of Art and Ground Zero Museum Workshop. There's lots more to do: take a stroll through Greenwich Village, walk around World Trade Center's Liberty Park, take in the views from Brooklyn Bridge, and appreciate the history behind 9/11 Memorial.

To find reviews, traveler tips, maps, and other tourist information, read our New York City trip itinerary builder tool.

Traveling by combination of flight and bus from Chicago to New York City takes 5 hours. Alternatively, you can fly; or drive. Traveling from Chicago to New York City, you'll lose 1 hour due to the time zone difference. Expect a bit warmer evenings in New York City when traveling from Chicago in October, with lows around 16°C. Finish your sightseeing early on the 24th (Sat) to allow enough time 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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