This fall break, we traded the farm for the beach and headed to Clearwater, Florida for the very first time, and honestly, I can’t believe we hadn’t been sooner. We flew in on a Saturday and flew back out on Wednesday, and four days ended up being the perfect amount of time to soak up the sunshine, eat amazing food, and still come home rested.

It’s a direct flight from Nashville to Tampa, only about a 30-minute Uber ride once you land, and we didn’t need to rent a car the entire trip. Clearwater is the kind of place where you can walk to everything, from coffee shops to the pier to beachside dinners, which made it an easy, stress-free getaway for the three of us.

Where We Stayed

We stayed at the Wyndham Grand Clearwater Beach, and I can’t say enough good things about it. Our room had a balcony ocean view, and from one side we could see the harbor while the other overlooked the ocean. Every morning we’d step out with coffee in hand and watch the sunrise, and every evening we’d end the day watching the sunset over the water.

The hotel was spotless, the staff couldn’t have been friendlier, and it felt so family-friendly without being crowded. There were daily activities for kids by the pool, painting, coloring, and little games, and plenty of quiet spots for parents to relax.

The breakfast buffet was incredible: pancakes, omelets, yogurts, biscuits and gravy… basically everything you could dream of. For casual lunches, we loved Dock’s Pool Bar & Grill right on site, their wraps and burgers were perfect. For dinner, Ocean Hai (also inside the hotel) was absolutely delicious. We had a sunset meal there one evening and agreed it’s one of those spots that makes vacation feel extra special.

If you’re looking for a place that’s family-friendly, clean, walkable, and full of amenities, this is it.

Where We Ate

Clearwater has a huge range of restaurants within walking distance of the Wyndham, and we loved that we could mix things up every night depending on what we were in the mood for.

Crabby’s Bar & Grill — Great spot for lunch or dinner right on the beach. Super casual, fun, and perfect for seafood and people-watching.

Bavaro’s — If you love Italian food, this place is a must. Authentic, cozy, and such good pasta. It felt like a little date night tucked into our family trip.

King’s Pizza — After a long beach day, sometimes you just want something quick and easy. King’s Pizza hit the spot; hot, cheesy, and only steps from our hotel.

Ocean Hai & Dock’s Pool Bar — For when you want to stay close and still eat really well, both of these options inside the Wyndham were fantastic.

We also loved that there was a Starbucks just a two-minute walk from our hotel, and inside the Wyndham, there’s a coffee shop and café for early-morning lattes.

What We Did

We booked the Sea Screamer Dolphin Adventure — a big yellow speedboat that takes you out along the coast. It was such a highlight! The dolphins were literally jumping in our wake, and Sterling caught the cutest videos. The ride was exciting, affordable, and just long enough to feel like an adventure without taking up the whole day.

Right by the hotel, Pier 60 became our evening spot. We were surprised by how lively it was, with local artisans selling handmade jewelry, art, and beach goods, plus fishing opportunities if you want to cast a line (or just watch). The sunsets there were unreal, and the atmosphere was family-friendly but still relaxed.

Next time, we’re planning to visit the Clearwater Marine Aquarium and try swimming with manatees, which we learned is nearby.

What Surprised Us

Clearwater totally exceeded our expectations. We were surprised by:

How easy it was to walk everywhere, truly no car needed.
How friendly everyone was, from the hotel staff to shop owners.
How clean the beach stayed.
How many seashells you can find! Sterling spent hours collecting them.
The perfect mix of budget-friendly and elevated dining options, it works for any trip.

We also found a little Surf & Style Shop just steps from the hotel where we picked up a $10 sandcastle kit for Sterling. He played with it nonstop, and before flying home we gave it to the pool staff to pass on to another family.

What We Packed

We kept it simple for this trip and each took a carry-on suitcase, which ended up being perfect for four days. I wanted to travel light but still feel put together for dinners, so I packed:

Four dresses — one for each evening out.
Two pairs of sandals — one comfy pair for walking, one a little nicer for dinner.
My swimsuit and cover-up — which I basically lived in during the day.

The boys each packed:

Two pairs of swim trunks and swim shirts.
A couple of polos and shorts for dinner.

We’d rather be a little overdressed than underdressed when we travel, you never know the dress code at some places, but everything in Clearwater ended up being very relaxed and easygoing.

We pack all our toiletries into one travel bag to keep things organized and easy to grab.
👉 Here’s the toiletry bag we use and love.

If you’re traveling with a Type 1 diabetic, we can’t recommend this insulin travel cooler bag enough. It keeps everything safe and cool the entire trip and fits perfectly in a carry-on.

The Perfect Ending to a Perfect Trip

There’s something special about finding a place that feels effortless, where your biggest decision is whether to watch the sunset from the beach or your balcony. Clearwater gave us that kind of vacation.

We left with full hearts, sandy feet, and a new favorite family tradition in the making. If you’re looking for a trip that’s easy, beautiful, and full of memories waiting to happen, this is it.

Where We Stayed: Wyndham Grand Clearwater Beach
Must-Do Activity: Sea Screamer Dolphin Adventure
Favorite Restaurants: Crabby’s Bar & Grill, Bavaro’s, King’s Pizza, Ocean Hai

Four Days in Clearwater, Florida: Our New Favorite Family Beach Spot