7 days in Florida Keys Itinerary
7 days in Florida Keys Itinerary
Created using Inspirock Florida Keys sightseeing planner
Start: Chicago
Fly
1
Key Largo
— 1 night
Drive
2
Marathon
— 2 nights
Drive
3
Key West
— 3 nights
Fly
End: Chicago
Fri, Dec 25 - Thu, Dec 31
Edit
S | M | T | W | T | F | S |
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20
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21
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22
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23
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24
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25
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26
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27
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28
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29
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30
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31
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1
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2
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See full calendar
1
night
1
night

Diving Capital of the World
The northernmost island of the Florida Keys, Key Largo provides stunning scenery, a number of watersports opportunities, and plenty of areas to relax on vacation.On the 25th (Fri), get up close and personal with brilliant marine life at Island Dolphin Care and then pause for some serene contemplation at Key Largo Baptist Church. Keep things going the next day: see the vivid underwater world at Spiegel Grove, look for all kinds of wild species at Florida Keys Wild Bird Rehabilitation Center, then take a memorable tour with Tours, and finally relax and rejuvenate at Island Flow Yoga.
To see photos, more things to do, and other tourist information, you can read our Key Largo trip builder app.
Chicago to Key Largo is an approximately 7.5-hour flight. You can also drive; or do a combination of bus and shuttle. The time zone changes from Central Standard Time to Eastern Standard Time, which is usually a 1 hour difference. In December, Key Largo is much warmer than Chicago - with highs of 79°F and lows of 66°F. Wrap up your sightseeing on the 26th (Sat) early enough to drive to Marathon.
Things to do in Key Largo
Side Trip
Highlights from your trip
2
nights
2
nights

Heart of the Florida Keys
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.On the 27th (Sun), take in the architecture and atmosphere at San Pablo Catholic Church, then examine the collection at Crane Point Museum & Nature Center, then tour the pleasant surroundings at Sombrero Beach, and finally soothe aching muscles at some of the top local wellness centers. Here are some ideas for day two: take a memorable tour with Tours, then look for all kinds of wild species at The Turtle Hospital, and then enjoy the sand and surf at Bahia Honda State Park.
To see ratings, more things to do, and other tourist information, go to the Marathon trip itinerary maker.
Traveling by car from Key Largo to Marathon takes 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 80°F in December, and nighttime lows around 71°F. Cap off your sightseeing on the 28th (Mon) early enough to go by car to Key West.
Things to do in Marathon
Side Trip
Highlights from your trip
3
nights
3
nights

Conch Republic
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.Kids will appreciate attractions like Key West Butterfly & Nature Conservatory and Duval Street. Next up on the itinerary: examine the collection at The Ernest Hemingway Home and Museum, get up close and personal with brilliant marine life at Key West Aquarium, contemplate the long history of Truman Little White House, and admire the natural beauty at Audubon House & Tropical Gardens.
To find other places to visit, maps, photos, and more tourist information, read Key West tour planner.
You can drive from Marathon to Key West in 1.5 hours. Another option is to take a bus. In December, daytime highs in Key West are 79°F, while nighttime lows are 71°F. Finish your sightseeing early on the 31st (Thu) to allow enough time to travel back home.
Things to do in Key West
Highlights from your trip
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Florida Keys travel guide
An archipelago of about 1,700 islands extending in a gentle arc south and southwest of Florida's mainland, the Florida Keys divide the Atlantic from the Gulf of Mexico. Many visitors on vacation come to scuba dive in the coral reefs, fossilized and exposed as sea levels declined over thousands of years. In addition to being one of the world's top diving and fishing spots, the Keys feature hundreds of shops, restaurants, bars, and various tourist attractions, most of them crowded all year long with visitors on vacation. To soak up the Keys' atmosphere and discover writer Ernest Hemingway's former haunts, drive from one island to the other all the way to Key West, located just 140 km (90 mi) from Cuba.