Florida Keys Road Trip

This article may contain referral links. Read our DISCLOSURE

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! 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.

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 researching lodging, I recommend starting your Florida Keys road trip search at HotelsCombined for the best pricing and location. But always check the reviews at TripAdvisor before booking.

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.

man feeding a tarpon fish in Islamorado Florida

Five Funky Things To Do in the Florida Keys

Are you looking for funky things to do in the Florida Keys? While there are plenty of fun activities in the Keys, some are more unique than others. On a Florida Keys road trip, as a guest of The Florida Keys and Key West, I expected to indulge in tasty seafood, treat myself to key […]

Read More >
Fishing in Islamorada with Capt. Skip Bradeen.

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

Fishing in the Florida Keys? This travel princess? Those were my thoughts when I learned a Florida Keys press visit would include a half-day fishing charter with Captain Skip Bradeen on the Blue Chip Too. When our group of travel writers arrived at Whale Harbor Marina in Islamorada, my misconceptions about offshore fishing were about […]

Read More >
Kayaking Big Pine Key

A Taste of Kayaking in the Florida Keys

Driving over a mile-long bridge that spans cerulean blue water—snorkeling with a multitude of color fish—tasting that first delicate bite of key lime pie—are these the scenes that come to mind when you think of a boomer road trip in the Florida Keys? Those were certainly the images that crowded my mind. And then the folks […]

Read More >
Discover butterflies and more on a day in Key West.

If You Only Have One Day in Key West

Our boomer travel readers love visiting Florida. And who can blame them? From spending a weekend on Amelia Island to fishing in the Florida Keys, there’s so much to do! If your Florida travel plans include “spend a day in Key West,” I might as well warn you—that’s not enough time. With a vibrant waterfront […]

Read More >
dry tortugas day trip to fort jefferson

Tips for a Dry Tortugas National Park Day Trip from Key West, Florida

Are you a boomer traveler who enjoys a national park adventure? What about a remote trip that includes sailing to an off-the-beaten-path national park in Florida? If so, you’re in luck. Guest contributor, Erika Nelson, is here to share her tips for a Dry Tortugas day trip. It’s the perfect addition to a Florida Keys […]

Read More >
Florida keys

Breaking for Spring in the Florida Keys

Does a visit to the Flordia Keys sound like your type of baby boomer spring break? You’re in luck because there’s an expert in the house. Laura Martone, author of the guidebook, Moon Florida Keys, is here to advise us. Be sure to read to the end of the post to see how you can […]

Read More >

Don’t forget to sign up for our Road Trip Newsletter for the best road trip itineraries, interesting destinations, valuable tips and road trip gear. Subscribe by clicking here.