Florida Keys Road Trip

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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 fun Florida Keys itinerary.

Boomer adventure was certainly a running theme! I went deep sea fishing for the first time, kayaked through a mangrove swamp and enjoyed exploring Key West among many other adventures. Check out my Florida Keys Road Trip itinerary to plan your next trip to Florida.

Boomer Travel Tip

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 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.

When looking for a place to stay, I recommend starting your Florida Keys lodging search at Tripadvisor for the best pricing and location. But always check the reviews before booking!

Would you like to book Florida Keys activities ahead of time? I recommend starting with the tours and activities at Viator. Most include free cancellation.

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.

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