Our Family Getaway to Seaside, Florida

We just got back from a wonderful family trip to Seaside, Florida…a place we have never been, but will now be visiting as much as possible! Finn and I planned this trip back in the fall when we knew we would be renovating our two upstairs bathrooms during the month of February. We figured it would be nice to get away from the dust of the construction, while also escaping the snow and cold of Chicago in the winter.

Our family trip to Seaside Florida

For years, my sister had raved about “30A”, a scenic road along the Florida panhandle with idyllic towns, and we finally listened to her and booked a trip. Never having been there ourselves, we didn’t really know what we were getting into and we randomly chose the town of Seaside. Holy smokes, it was one of the best trips I’ve been on and it was the perfect destination for our family with two young kids.

A Bit About Seaside, Florida

Our visit to seaside florida

Again, we went in kinda blind, only knowing that the weather would be better in Seaside, Florida than it was here in Chicago, which was good enough for us! Upon arriving at Seaside, we soon learned that it is just about the most adorable town you ever did see and we had eight days of perfect weather. In fact, it’s so idyllic that the town was used as the set for the movie, The Truman Show. We watched the movie on our last night of vacation, after seeing all of the hot spots that were filmed in town, and we could see why it was chosen for the film!

The cutest houses in Seaside Florida

Everything in Seaside is walkable, so it’s easy to get around, but you can bike ride or take a gulf cart too. (We rented both.) You really don’t need a car once you get there.

Enjoying the beaches in Seaside Florida

It’s located right on the water and it has the most beautiful beaches you ever did see with soft white sand and turquoise-blue waters. Seaside has the cutest little town square with ice cream shops, restaurants, and bookstores and we explored every inch of it.

How to Get There

Spending time in the sun and sand in Seaside, Florida

Seaside is located between Panama City Beach and Destin, and we ended up flying into Pensacola, because it had the only nonstop flight we could find from Chicago. We rented a car and then drove about an hour and a half to Seaside. My mom came a few days after us and she flew into Destin, which was a bit of a shorter drive. While we spent a majority of our time in Seaside, there are other cute towns along 30A that are only a short drive away!

Traveling With Kids

My mom and Rory at the airport

This was our first time traveling as a family of four (with a 22-month-old and 5-month-old), so we were a tad nervous going into it. Luckily, the flight was only two hours long and we had my sister’s help on the way there, and both my mom and sister on the way back. Four adults for two kids? Yes, please!

Ellis 5 months old

Even though we were nervous, the kids were wonderful. Ellis slept during both flights and Rory napped the entire way home. When she was awake, she read books, ate snacks, and checked out her new tablet. Rory isn’t quite two, but we bought her her own seat just in case she wouldn’t want to sit on our laps. Well, she was either on Dada or Grama’s lap the entire flight, but it was nice to have the extra seat just in case!

We have a long flight to Arizona next month, so we will see how that goes…

Renting Baby Items

Ellis napping at the beach in Seaside Florida

Traveling with kids means it’s tough to travel light. I swear, Finn and I spent an entire week packing because we were so nervous about forgetting something for the kids, and, of course, we barely gave a second thought to what to pack for ourselves. We ended up checking Ellis’ car seat and brought my mom’s stroller on the plane with us for Rory, while I wore Ellis in our baby Bjorn carrier.

Wearing Ellis in a baby carrier

Everything else we rented for our vacation. We used the new-to-us website, Babyquip, to rent cribs, a Baby Brezza bottle maker, booster seat for Rory, kid plates and cups, a beach tent, and more. It’s actually a pretty genius concept. You pick and choose the items that you need for your vacation and they are delivered to your location, set up, and then picked up when you’re done. It was a lifesaver and we’ll be using the company again for our upcoming Arizona trip.

Where We Stayed

Our cute VRBO

We found a wonderful Vrbo about a block from the beach and a seven-minute walk from the town square. The location was ideal and it was plenty roomy for our party of six, with lots of outdoor areas too. There are so many houses available for rent (some with pools!) and we liked being so close to all of the action. I highly recommend it!

What We Did

Getting ice cream
visiting black bear coffee shop

If you’re a parent of a little one, then you know that your days typically revolve around nap times. Our group was always up early and we would often go for a walk into town for coffee and breakfast.

Rory enjoying the beach
Enjoying our time in Seaside Florida on the beach
At the beach in Seaside, Florida

Then, we’d come back, so Ellis could nap, while we got ready to head to the beach. We’d spend a few hours at the beach, come home for a quick lunch, and get both kids down for nap time.

Enjoying our time in Seaside, Florida

Once the kids were up, around 3 pm, we’d get ready and head out for drinks and an early dinner. Our nights always ended a bit early, as we headed home around 6 pm for bath time and bed. Luckily, my mom and sister love a nice 8-9 pm bedtime too, so we weren’t the wildest group…ha!

Finn and I were even able to sneak in a date night while the ladies watched the kids, but only stayed out till around 8 pm. Who are we?!

Our visit to Seaside, Florida

We never made any plans and just went with the flow, which is my kinda vacation. The biggest thing on our agenda was figuring out where to eat for dinner each night. I loved having zero plans!

Where We Ate

Oysters at Old Florida Fish House
Rory getting ice cream

Speaking of eating, we enjoyed lots of yummy food during our trip. When in Florida, you gotta go for seafood, so I’d say our meals usually involved lots of that. Here are some spots we visited…

  • The Perfect Pig: This was my favorite meal of our trip and the restaurant was on the nicer side. Rory enjoyed her pasta and Ellis slept through dinner!
  • Seagrove Village Market: We grabbed some good fish sandwiches from this spot.
  • Bud & Alley’s: They have yummy crab cakes and the best view of the sunset.
  • The Hub: This was a quick drive from town, but it had a cool outdoor area with lots of restaurants and picnic tables. Rory loved running around here!
  • Old Florida Fish House: My mom and sister spotted this place on a bike ride and it was amazing! It’s the cutest outdoor spot, with lots of room for the littles to run around, plus great wine and food.
  • The Wine Bar: We went here on our date night for wine and charcuterie.
  • It’s Heavenly Ice Cream Shop: We definitely visited this spot more than once.
  • Great Southern Cafe: We got dessert here and brought it home…so yummy!
  • Black Bear Bread Co: We visited just about every morning for coffee and breakfast. It has outside tables in the most adorable shaded courtyard.
Getting Frose in town

Not to mention, the town square has the cutest food trucks and low-key restaurants where you can order at an outdoor window and get a drink or food to go. We loved how relaxed everything was, especially with two young ones in tow.

What to Pack

What to pack for your trip to Seaside Florida

We visited Seaside, Florida during the last week of February and it was in the 60s and 70s during our stay. While 60-degree weather might sound chilly, it would actually get pretty hot in the sun! My best advice is to pack lots of layers. We would usually start the day with leggings, a t-shirt, and a sweater…and then slowly take off layers as the sun came out. By noon, we were all on the beach in our swimming suits.

Rory's cute blue sundress

Finn liked to go in the water, but it was definitely super chilly in the ocean, so not a lot of swimming happened for anyone besides his brave soul. At night, we wore dresses or jeans and we always brought a jean jacket or sweater along. Again, everything is laidback, so we never got super dressed up.

Liz and ellis in the town square

Here are some things I packed for us…

We’ll Be Back Again Soon!

The beach at Seaside

Our trip truly was magical. It made my heart so happy to see our kids outside enjoying the weather and fresh air. (It has been a long winter here in Chicago!) We are planning to make this an annual family trip, so this certainly won’t be our last visit to this gorgeous place.


My travel guide to seaside florida

The Year of Casey

Hey there!

I’m Casey Finn, the voice behind The DIY Playbook. I’m a Chicago gal teaching you how to design, DIY, and maintain your home…by yourself! Learn more about me right here.

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