15 days in Florida Itinerary

15 days in Florida Itinerary

Created using Inspirock Florida planner

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Route & dates

15 days in Florida Itinerary

Start: Chicago
Fly:  5​h 45​min
1
Key West
— 4 nights
Fly:  2​h 30​min
2
Miami
— 4 nights
Fly:  3​h 15​min
3
Orlando
— 6 nights
Fly:  5​h
End: Chicago

4
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.
Attractions like Key West Butterfly & Nature Conservatory and National Key Deer Refuge make great kid-friendly stops. Go for a jaunt from Key West to Big Pine Key to see Bahia Honda State Park about 48 minutes away. Spend the 27th (Wed) exploring nature at Dry Tortugas National Park. There's still lots to do: examine the collection at The Ernest Hemingway Home and Museum, explore the different monuments and memorials at Key West Cemetery, make a trip to Duval Street, and pause for some photo ops at Florida Keys Historical Military Memorial.

Find out how to plan Key West trip without stress by asking Inspirock to help create an itinerary.

Chicago to Key West is an approximately 6-hour flight. You can also drive; or do a combination of bus and shuttle. Due to the time zone difference, you'll lose 1 hour traveling from Chicago to Key West. Plan for much warmer temperatures traveling from Chicago in November, with highs in Key West at 81°F and lows at 73°F. Finish your sightseeing early on the 27th (Wed) to allow enough time to travel to Miami.

Things to do in Key West

Parks Nature Wildlife

Side Trip

Big Pine Key
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
National Key Deer Refuge ©
National Key Deer Refuge

4
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.
Bring the kids along to South Beach and Island Dolphin Care. You'll find plenty of places to visit near Miami: Everglades National Park (Osceola panthers & Shark Valley Visitor Center) and Florida Keys Wild Bird Rehabilitation Center (in Tavernier). And it doesn't end there: wander the streets of Lincoln Road, examine the collection at Vizcaya Museum and Gardens, have fun at Lock & Load Miami, and appreciate the extensive heritage of Art Deco Historic District.

For ratings, more things to do, maps, and tourist information, refer to the Miami trip planner .

Traveling by flight from Key West to Miami takes 2.5 hours. Alternatively, you can do a combination of flight and bus; or drive. In November, daytime highs in Miami are 82°F, while nighttime lows are 70°F. Wrap up your sightseeing on the 1st (Sun) early enough to travel to Orlando.

Things to do in Miami

Parks Museums Outdoors

Side Trips

Miami Beach, Everglades National Park, Key Largo
Highlights from your plan
Island Dolphin Care ©
Island Dolphin Care
South Beach ©
South Beach
Miami Children's Museum ©
Miami Children's Museum

6
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.
Attractions like Walt Disney World Resort and Universal's Islands of Adventure make great kid-friendly stops. There's much more to do: find something for the whole family at Universal Orlando Resort, discover the magic at Disney's Hollywood Studios, laugh and play at Discovery Cove, and make a splash at Disney's Typhoon Lagoon Water Park.

To see other places to visit, traveler tips, reviews, and other tourist information, refer to the Orlando trip itinerary planning app .

You can fly from Miami to Orlando in 3.5 hours. Other options are to drive; or do a combination of train and flight. Traveling from Miami in December, expect a bit cooler with lows of 59°F in Orlando. Wrap up your sightseeing on the 7th (Sat) to allow time to travel back home.

Things to do in Orlando

Theme Parks Parks Beaches

Side Trip

Winter Park
Highlights from your plan
Walt Disney World Resort ©
Walt Disney World Resort
Universal Orlando Resort ©
Universal Orlando Resort
Universal's Islands of Adventure ©
Universal's Islands of Adventure

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