Chicago to Key West

Day 9: Florida City FL to Key West FL

Day 9: Florida City FL to Key West FL

Postcard from Key West, Florida.

Florida City to the southernmost point in the continental United States was a straight 127 miles long line completing the 2073 miles driven since leaving Chicago 9 days ago and, given the sunny weather, switching to a convertible wasn’t a bad idea for this finale.

The Keys: long bridges connecting the islands, green and blue warm waters, briny smell coming from the ocean, palm trees everywhere, sandy beaches, roosters and chickens walking freely among locals and tourists.

Idyllic? Maybe. But I know I am a big-city person

Reminder: salads and greens for the next 2 weeks please.




Driving from Florida City to Key West Cheat Sheet

Accommodation in the Keys:

  • Kingsail Resort, 7050 Overseas Hwy, Marathon, FL 33050. One of the cheapest, affordable options on the Keys. The room are clean, the bed comfortable, parking easy, food options close by. All I needed.

Where to eat and what to see between Florida City FL and Key West FL

  • Southernmost Point Bar1327 Duval St, Key West, FL 33040. Nice bar on the beach with killing mojitos.
  • Southernmost Beach Café, 1405 Duval St, Key West, FL 33040 another nice bar right on the beach good for a cold beer or two.
  • Higgs Memorial Beach, Atlantic Blvd (at Reynolds St), Key West, FL 33040 a tiny, free city beach with incredibly blue, warm waters.
  • DJ’s Clam Shack, 629 Duval St, Key West, FL 33040 I’ve been to Miami twice. Twice I had a faboulous lobster rolls in this little place.
  • Seven Mile Bridge The longest of the bridges connecting the keys. You drive for 7 miles (doh!) with the ocean on both side of the road. Incredible.


Driving from Florida City to Key West FAQ

How many miles are from Florida City to Key West?

There are 125 miles from Florida City to Key West, 105 of which are on the Keys.

How long does it take to drive from Florida City to Key West?

To drive from Florida City to Key West takes about 2 and half hours. It took me probably 4 hours cause I stop for pictures and such a few times.

What’s the best thing about driving from Florida City to Key West?

The road itself and the views, hands down.

What are the major attractions along the way in a road trip from Florida City to Key West?

The major attractions on a road trip from Florida City to Key West are the Keys themselves: both the road and the bridges and the beaches, the water and the views. Driving on the Keys is a great experience.

What type of car is best to drive from Florida City to Key West?

A convertible! It got to be a convertible! There is no question about it. I did return my midsize in Miami and rented a Mustang convertible. Driving roof down on these roads is an incredible feeling


My itinerary on a road trip from Chicago to Key West



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