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.
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 […]
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 […]
A Taste of Kayaking in the Florida Keys
Are you looking for a fun place to visit in Florida with a dash of adventure? Kayaking Big Pine Key definitely qualifies. 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 […]
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 a panhandle road trip, 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 playing […]
Tips for a Dry Tortugas National Park Day Trip from Key West, Florida
Are you a boomer traveler who enjoys a national park adventure? Florida travelers, what about a remote trip that includes sailing to an off-the-beaten-path national park? 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 […]
Exploring Homestead, Florida for History, Food and Outdoor Fun
Florida is one of America’s most visited states. Known for its expansive beaches and multiple attraction parks, the Sunshine State really does have something for everyone. But, there are still some local spots that, although they may not receive droves of tourists, are still worth a trip — like Homestead. Come along as our guest contributor, […]
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