Our trip began in the wealthy little town of Tierra Verde. Surrounded by water, large condos, and ample sunshine, it’s no surprise that the waterways were stuffed with yachts varying in sizes from incredibly large to behemoth floating mansions. Heading northwest, we crossed over a large bridge and landed in the designated U.S. Historic district of Pass-A-Grille, a cozy, laid-back, slightly weathered beach town. I immediately fell for the chill vibe and decided that Pass-A-Grille would be my top choice if we came back to stay for a while.

Moving north, we got the opportunity to check out St. Pete Beach and Madeira Beach. Not only do both places boast incredible beaches, they’re also large enough that you’re just steps away from great food, shopping and entertainment at either of these adorable destinations.
Next we flitted through the famed Clearwater Beach, a much larger town than I’d imagined in my mind’s eye before the trip. Not only does it have the most beautiful beaches, but it’s got access to great foods, including Richard’s Foodporium, a fabulous place to stop and pick up some healthy grub on your trip.
When you arrive in Dunedin--the Spring Training spot for the Toronto Blue Jays--you’re going to feel like you stepped back into a simpler time. The cute little town seems to chug along at a pace all its own. It’s the kind of town you’ll want to get out and walk around in. Or perhaps, ride your bike along the renowned Pinellas Trail which runs right through the town. If you’ve got a big appetite, stop at Casa Tina’s Mexican restaurant where the atmosphere is authentic and the portions will last you through several meals.