I’ve decided I’m only going to do these travel pieces monthly, in order to hide the fact that I rarely leave the South. I’m also going to attempt to introduce you to places of which you may have never have heard, or encourage you to go when folks don’t, so you can be big in peace. For example, the absolute best time to go to Clearwater, Florida is in the dead of winter!

I pledge Allegiant

So, let’s talk about how I decided on Clearwater as my preferred Christmas destination: Allegiant Airlines. You see, Allegiant flies on-stop into Tampa-St. Petersburg Airport (PIE) for next to nothing. You get a cheap ticket, and then they nickle and dime you until you arrive upon a still reasonable plane ticket price.

Our first experiment was with Tampa, proper, where we stayed downtown and enjoyed some tasty food, but otherwise it was just a city. On the last day of that first trip, we set out to Clearwater to see what’s going on and discovered our next destination. The next year, we rented a 2015 Mustang Convertible and booked a house on the beach (that was actually cheaper than our Tampa Marriott hotel room).

Two things happened on that trip: I decided to buy said Mustang, and we discovered the perfect holiday destination.

What to do!

Well, hypothetically you can swim in the gulf. Although it’s December, the water isn’t terrible. We did spend some time basking on the beach, of which there are endless stretches. I actually enjoyed cruising at 5 MPH down the coastal stretch just taking in the palm trees and pleasant ocean breeze.

Do you like seafood? Then get you some seafood! Of course it’s fresh and delicious, you can see the giant body of water it came from! The local chain down there is Frenchy’s, and we partook of delicious refreshments and fried fish at Frenchy’s Rockaway Grill. You can, of course, visit the original Hooters, if you’re uh, a fan of wings.

Or stay in town and visit the Clearwater Marine Aquarium. I’m a huge fan of aquaria, particularly when they pull double duty as a marine hospital. Since this aquarium features extensive outdoor and open air exhibits, a nice cool December is the perfect time to go.

Last but not least, you should hit up Pan Filo’s Bar and Grill. They do a killer Mexican street taco, and the happy hour specials are no joke. I don’t think there’s a weak pour in Clearwater Beach, so if you enjoy your imbibables, then this may be the vacation destination for you!

Branch out

You’re also within a quick drive of lots of cool places like Dunedin, a town devoted to dogs. This dog friendly little town featured lots of canine art, in addition to a late night drag show that my wife thoroughly enjoyed. For me, we popped next door to St. Petersburg so I could visit the Salvador Dali museum, which just so happened to have a Frida Kahlo temporary exhibit that really elevated the experience.

We also booked it across Tampa to visit the Seminole Hard Rock Casino, because why not? The Tampa/St. Pete/ Clearwater metro is very drivable with a massive cornucopia of vacation experiences. So, pack your bags, put on some shorts, and set sail for adventure!

Posted by Damien

Big Guy Damien is a creative communications professional, who really likes starting projects. He has a dog named Mr. Buttons, who you will see featured from time to time.


  1. You’ve sold me on it! Sounds like a nice place. We haven’t been on a real vacation in a while, but we have been to other cities in florida. I am also a uh, fan of wings too ;).


  2. I would totally visit Florida just to see some Gators, man!


    1. That animals, yes! The football team, no… haha. Go Big Orange!


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