9 days in Florida Keys Itinerary

9 days in Florida Keys Itinerary

Created using Inspirock Florida Keys route builder

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Route & dates

9 days in Florida Keys Itinerary

Start: Chicago
Fly:  6​h 15​min
1
Big Pine Key
— 2 nights
bus:  45​min
2
Key West
— 6 nights
Fly:  5​h 45​min
End: Chicago

2
nights
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. On the 23rd (Sat), kick back and relax at Sombrero Beach, then look for all kinds of wild species at The Turtle Hospital, and then enjoy the sand and surf at Bahia Honda State Park. On the 24th (Sun), you'll have a packed day of sightseeing: take in the views from Seven Mile Bridge, identify plant and animal life at Crane Point Museum & Nature Center, then view the masterpieces at Shady Palm Art Gallery & Photography, and finally look for all kinds of wild species at National Key Deer Refuge.

For where to stay, other places to visit, maps, and tourist information, read our Big Pine Key tour builder site .

Chicago to Big Pine Key is an approximately 6.5-hour flight. You can also do a combination of flight and shuttle; or drive. You'll lose 1 hour traveling from Chicago to Big Pine Key due to the time zone difference. Prepare for much hotter weather when traveling from Chicago in November: high temperatures in Big Pine Key hover around 82°F and lows are around 72°F. Finish your sightseeing early on the 24th (Sun) so you can take a bus to Key West.

Things to do in Big Pine Key

Parks Wildlife Outdoors

Side Trip

Marathon
Find places to stay Nov 22 — 24:
Highlights from your plan
Bahia Honda State Park ©
Bahia Honda State Park
The Turtle Hospital ©
The Turtle Hospital
National Key Deer Refuge ©
National Key Deer Refuge

6
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.
Spend the 28th (Thu) exploring nature at Dry Tortugas National Park. The adventure continues: see the interesting displays at The Ernest Hemingway Home and Museum, take a leisurely stroll along Mallory Square, identify plant and animal life at Key West Butterfly & Nature Conservatory, and take a tour by water with Boat Tours & Water Sports.

To see photos, where to stay, other places to visit, and tourist information, go to the Key West trip builder tool .

Take a bus from Big Pine Key to Key West in an hour. Alternatively, you can drive. November in Key West sees daily highs of 81°F and lows of 73°F at night. Finish your sightseeing early on the 30th (Sat) to allow enough time to travel back home.

Things to do in Key West

Outdoors Parks Tours
Find places to stay Nov 24 — 30:
Highlights from your plan
The Ernest Hemingway Home and Museum ©
Mallory Square ©
Mallory Square

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