5 days in Florida Itinerary

5 days in Florida Itinerary

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Route & dates

5 days in Florida Itinerary

Start: Chicago
Fly + shuttle:  5​h 30​min
1
DeLand
— Few hours
shuttle + Fly:  4​h 15​min
2
Key West
— 2 nights
bus:  45​min
3
Big Pine Key
— 1 night
Drive:  3​h
4
Miami Beach
— 1 night
Fly:  5​h 45​min
End: Chicago

few
hours
DeLand

DeLand ©
DeLand is a city in the U.S. To see where to stay, maps, more things to do, and tourist information, you can read our DeLand visit planner .

Chicago to DeLand is an approximately 5.5-hour combination of flight and shuttle. You can also do a combination of flight and bus; or drive. You'll lose 1 hour traveling from Chicago to DeLand due to the time zone difference. In December, DeLand is much hotter than Chicago - with highs of 75°F and lows of 57°F. Finish your sightseeing early on the 26th (Wed) so you can travel to Key West.

Things to do in DeLand

Historic Sites
Highlights from your plan
Stetson Mansion ©
Stetson Mansion

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.
Start off your visit on the 27th (Thu): admire the majestic nature at Fort Zachary Taylor, then see the interesting displays at The Ernest Hemingway Home and Museum, then identify plant and animal life at Key West Butterfly & Nature Conservatory, and finally look for gifts at De La Gallery. Get ready for a full day of sightseeing on the next day: see the interesting displays at Mel Fisher Maritime Heritage Museum, admire the natural beauty at Audubon House & Tropical Gardens, then get engrossed in the history at Truman Little White House, then pause for some serene contemplation at Saint Mary Star of the Sea, and finally stroll the grounds of Key West Cemetery.

To see more things to do, photos, reviews, and tourist information, refer to the Key West trip itinerary website .

You can do a combination of shuttle and flight from DeLand to Key West in 4.5 hours. Alternatively, you can do a combination of train and flight; or drive. Plan for somewhat warmer nights when traveling from DeLand in December since evenings lows in Key West dip to 71°F. Finish your sightseeing early on the 28th (Fri) so you can drive to Big Pine Key.

Things to do in Key West

Historic Sites Museums Parks
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Fort Zachary Taylor ©
Fort Zachary Taylor

1
night
Big Pine Key

Big Pine Key ©
Big Pine Key is a census-designated place and unincorporated community in Monroe County, Florida, United States, on an island of the same name in the Florida Keys. Kick off your visit on the 29th (Sat): identify plant and animal life at Crane Point Museum & Nature Center, enjoy the sand and surf at Sombrero Beach, and then immerse yourself in nature at Bahia Honda State Park.

To see reviews, ratings, traveler tips, and other tourist information, use the Big Pine Key day trip planner .

Drive from Key West to Big Pine Key in an hour. Alternatively, you can take a bus. In December, daily temperatures in Big Pine Key can reach 80°F, while at night they dip to 71°F. Cap off your sightseeing on the 29th (Sat) early enough to go by car to Miami Beach.

Things to do in Big Pine Key

Parks Outdoors Beaches

Side Trip

Marathon
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
Sombrero Beach ©
Sombrero Beach
Crane Point Museum & Nature Center ©
Crane Point Museum & Nature Center

1
night
Miami Beach

Miami Beach ©
Separated by water from the neighboring city of Miami, Miami Beach sits on a barrier island between Biscayne Bay and the Atlantic Ocean.
Kick off your visit on the 30th (Sun): stroll through South Beach, appreciate the extensive heritage of Art Deco Historic District, then wander the streets of Lincoln Road, and finally get a taste of the local shopping with Collins Avenue.

To find where to stay, other places to visit, ratings, and other tourist information, use the Miami Beach day trip app .

Traveling by car from Big Pine Key to Miami Beach takes 3 hours. Alternatively, you can do a combination of bus, flight, and tram; or do a combination of shuttle and bus. Expect a daytime high around 81°F in December, and nighttime lows around 68°F. Wrap up your sightseeing on the 30th (Sun) early enough to travel back home.

Things to do in Miami Beach

Neighborhoods Shopping Parks
Highlights from your plan
South Beach ©
South Beach
Lincoln Road ©
Lincoln Road
Art Deco Historic District ©
Art Deco Historic District

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