Florida Keys Road Trip

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Roadtripping in the Florida Keys

Updated 05.22.2020:  I don’t often take press trips, but I couldn’t resist this Florida Keys road trip. Sponsored by The Florida Keys & Key West, the Prime Time in Paradise itinerary had a little bit of everything on a jaunt through the Florida Keys.

Boomer adventure was certainly a running theme! Check out my Florida Keys Road Trip itinerary to plan your next trip.

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I’ll be adding more great Florida Keys road tripping ideas, including tips from guest writers, because one trip to the Keys is never enough. Be sure to bookmark this page or subscribe to the Road Trip Newsletter to be the first to know!

Florida Keys road trip itinerary

After being picked up at the Miami airport, my drive through the Florida Keys officially began in Key Largo. Along the way, I fished out of Islamorado, kayaked at Big Pine Key and roamed the quaint streets of Key West. Don’t ask me how many pieces of key lime pie I ate because I’m not telling!

The Islander Resort, A Guy Harvey Outpost, was my two-night headquarters in Islamorada. And for two nights in Key West, I stayed at The Gates Hotel.

Boomer Fun in the Florida Keys

If you’re in a hurry, the drive from Miami to Key West takes about half a day. But why rush through the fun? I recommend taking your time, stopping for overnight stays at several of the keys. If you do, be sure to add these experiences to your itinerary.

Five Funky Things To Do in the Florida Keys

I had no idea that the Florida Keys had so many fun options for active boomers, but this trip to Florida completely changed my mind. I found Five Funky Things To Do in the Florida Keys that you’re going to love!

Fishing in the Keys: A Boomer Woman’s First Catch

When I arrived at Whale Harbor Marina in Islamorada, my misconceptions about offshore fishing were about to be turned on their head. Fishing in the Florida Keys shares the story about my experience. It was so much fun! And, yes, I caught the biggest fish!

Looking for a place to stay on a road trip in the Florida Keys? Start your Florida Keys hotel search with us.

Kayaking Big Pine Key

You don’t have to be an expert to enjoy a guided kayaking adventure at Big Pine Key, part of the Florida Keys National Marine Sanctuary. Paddling a kayak through thick mangrove forests is almost spooky. Guide, Bill Keogh, introduced us to a wildlife paradise in the Florida Keys, albeit a very humid one. Read more about my Big Pine Key kayaking tour.

If You Only Have One Day in Key West

How do you make the most of one day in Key West? Well, with a little energy and a ticket for the hop-on hop-off for Old Town Trolley, it can be done. Click on If You Only Have One Day in Key West to read about the highlights. My tips make for an excellent do-it-yourself Key West cruise excursion.


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