If you’ve followed along with our family’s travels, you know we’ve done our fair share of road trips and bucket list destinations.
For two years, we homeschooled on the road, which meant our classroom was wherever we happened to be – watching Old Faithful erupt in Yellowstone, standing beneath giant sequoias in Yosemite, and learning to haul lobster traps alongside fishermen in coastal Maine.
But sometimes you just want to get somewhere warm, park yourself by a pool, and not think too hard about logistics for a few days.
That’s exactly what Clearwater Beach delivered for us this December.
We stayed at the Wyndham Clearwater Beach Resort for the second time over the holidays, and I’m happy to report it’s earned a spot in our regular rotation.
Here’s why it’s become our go-to for a family-friendly Florida getaway.
The Pool Situation
Let’s start with what matters most when you’ve got three boys who would spend 23 hours a day in the water if you let them.
The pool at the Wyndham is large, heated, and, this is the key part, actually comfortable to swim in even when the December air is a little chilly.
Now, I should mention that the way the sun travels around the building means you’re in the shade most of the day at the pool. If you’re visiting in the dead of winter like we were, that can feel a bit cool.
Our workaround was pretty simple. We’d head down to the beach in the morning, where they had a couple of reserved chairs waiting for us, soak up some sun, and then migrate back to the pool in the afternoon.
That said, if you’re visiting in the summer when it’s hot enough to melt your flip flops to the pavement, being in the shade early in the day is actually a huge win. The way they have it arranged is really smart – you can relax all day getting a mix of sun and shade with an ocean view.
The hot tub was also a hit, particularly after the sun went down and the kids were finally starting to wind down. (Who am I kidding? They never wind down.)
The Room
We stayed in a two-bedroom suite, which is pretty much non-negotiable when you’re traveling with three boys.
The place felt high-end without being stuffy. Beautiful bathrooms. Really comfortable bed – which I don’t take for granted after some of the questionable mattress situations we’ve encountered on our road trips over the years.
Everything just felt clean and well thought out. It’s the kind of place where you walk in and think “Ok, this is nice” instead of immediately googling “hotels near me” as a backup plan.
Walkability
One thing I really appreciated about this property is how walkable everything is.
We spent a lot of time just strolling down the beach, checking out local spots, and never once felt like we needed to get in the car.
One of our favorite nights was walking about 15 minutes down the sand to Frenchy’s Rockaway Grill for dinner. We timed it for sunset, which was one of those moments that makes you feel like you’re experiencing something special you just don’t find back home in Ohio.
The atmosphere at Frenchy’s is lively but not over the top. Definitely a place you can bring the kids. We sat beachfront, ate fresh seafood, and watched the sky turn orange while the boys inhaled fried shrimp.
If there’s a wait, you just hang out and throw some football on the beach. It’s hard to complain about that.
Frenchy’s is a must-do if you’re staying in Clearwater Beach.
The ReliaQuest Bowl Bonus
We happened to be in town during the ReliaQuest Bowl, where Vanderbilt and Iowa were playing.
They had a super cool pep rally going on, and right there on the beach was this enormous sand carving featuring the logos of both schools. The kids thought it was awesome, and honestly, so did I.
It’s those little unexpected bonuses that can make a trip memorable. We weren’t there for the bowl game, but we got to soak up a little of the energy anyway.
For the Wrestling Fans
If you grew up watching wrestling in the 80s as I did, you’ll appreciate this.
Hulk Hogan’s bar, Hogan’s Hangout, is right there in Clearwater Beach. They’ve also got a little beach shop full of memorabilia – stuff for sale, but also plenty just to check out even if you’re not buying.
I may or may not have spent 20 minutes looking at signed photos and old championship belts while Sarah pretended not to know me.
Again, it’s all a 5-minute walk from the Wyndham.
The Verdict
Clearwater Beach isn’t going to give you the “wow” factor of standing at the rim of the Grand Canyon or watching a grizzly bear walk past your van in Yellowstone.
But that’s not what you’re going for.
You’re going for warm weather in December, a comfortable place to stay, a pool the kids will love, and the ability to walk to a great dinner without planning a military operation.
The Wyndham Clearwater Beach checks all those boxes.
We’ve now been twice, and I’d go back again without hesitation. If you’re looking for a family-friendly spot on Clearwater Beach, this is the one.
