7 days in Florida Keys Itinerary

7 days in Florida Keys Itinerary

Created using Inspirock Florida Keys vacation builder

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Route & dates

7 days in Florida Keys Itinerary

Start: Chicago
Fly + bus:  7​h 45​min
1
Marathon
— 3 nights
bus:  1​h 15​min
2
Key West
— 3 nights
Fly:  5​h 45​min
End: Chicago

3
nights
Marathon

Marathon ©
A tiny city just 16 km (10 mi) long, Marathon is spread across several islands in the middle of the Florida Keys.
Get outdoors at Florida Keys Wild Bird Rehabilitation Center and Bahia Honda State Park. You'll explore the less-touristy side of things at Dolphin Research Center and Sunset Park Beach. Change things up with these side-trips from Marathon: Islamorada (Michelle Nicole Lowe Art Gallery & Scuba & Snorkeling). There's still lots to do: enjoy the sand and surf at Anne's Beach, tour the pleasant surroundings at Calusa Beach, and snap pictures at Old Seven Mile Bridge.

To see photos, more things to do, traveler tips, and other tourist information, read Marathon driving holiday planner .

Chicago to Marathon is an approximately 8-hour combination of flight and bus. You can also do a combination of flight and shuttle; or drive. You'll lose 1 hour traveling from Chicago to Marathon due to the time zone difference. Traveling from Chicago in December, things will get much warmer in Marathon: highs are around 80°F and lows about 71°F. Wrap up your sightseeing on the 25th (Tue) early enough to take a bus to Key West.

Things to do in Marathon

Parks Outdoors Beaches

Side Trips

Islamorada, Big Pine Key, Florida Keys Wild Bird Rehabilitation Center, Sunset Park Beach
Highlights from your plan
Dolphin Research Center ©
Dolphin Research Center
Scuba & Snorkeling

3
nights
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.
You'll get in some beach time at Fort Zachary Taylor and Smathers Beach. Escape the urban bustle at Kayaking & Canoeing and Stand-Up Paddleboarding. There's still lots to do: enjoy the sea views from Key West Lighthouse and Keeper's Quarters Museum, brush up on your military savvy at U.S. Coast Guard Cutter Ingham Maritime Museum, identify plant and animal life at Key West Butterfly & Nature Conservatory, and explore and take pictures at Audubon House & Tropical Gardens.

For reviews, where to stay, ratings, and other tourist information, refer to the Key West trip itinerary maker app .

Take a bus from Marathon to Key West in 1.5 hours. Alternatively, you can drive. In December, plan for daily highs up to 79°F, and evening lows to 71°F. Finish up your sightseeing early on the 28th (Fri) so you can travel back home.

Things to do in Key West

Outdoors Adventure Tours
Highlights from your plan
Kayaking & Canoeing
Saint Mary Star of the Sea ©
Saint Mary Star of the Sea

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