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First Beach Trip as a Family of 4!

6/10/2024

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We live to tell the tale...the tale of surviving our first beach trip as a family of 4 with our 2 littles. Littles that are 17 months apart. At the time of this trip, Cal just turned 2 and Addie, 8 months. What a time! Let's get into it shall we.
Here is what you will find!
  • Travel Options - Flight or Drive?
  • First Day - Arriving to the House, Room Assignments with Littles, Unpacking, Dinner
  • Second Day - Travel to Beach (and complications), Dinner Reservations at Old Florida Fish House
  • Third Day - Travel to Beach again (a bit better, less complications), Date Night Dinner Reservations at Cafe Thirty-A
  • Fourth Day - Guys played Golf, Gals walked around and went to the Pool, Birthday Celebration in PCB
  • Last Day - Breakfast in 30A, Travel Home Day! 

The Travel Options

Okay, we normally try to travel by plane anytime we go anywhere because, why not and with Southwest, they just make it so easy! Well, this time with Cal being 2, he would had needed his own seat. It was going to cost us upwards of $900 to fly and this time, it just wasn't worth it so we thought wed attempt THE DRIVE. The dreaded drive. I'm not going to lie, I was absolutely terrified of this part. The thought of being in the car with a 2 year old and an 8 month old (and my husband) for 8-9 hours. That was the real scary part but alas, that was the route that was upon us. Here's how it went down...
We traveled on a Saturday night/Sunday morning. Yes, we left at 3:00am. Do you remember going on family trips and that was always what you did? You left at the wee hours in the morning and slept in the car and then voilà , you were there! Well, this time...we are the "voila". We did a 4 night stay so our trip was arrive on Sunday, check out on Thursday. For our family, that's the perfect amount of time. As they get older, we may be able to do one more day but for now; that's justttt right for us. 

The thought process was that they would be asleep most of the drive by doing it this way and we'd get there early, yes, but not too early where it would be too long prior to check-in. You know, check-in is always late in the day, this time it was 4:00pm. Ek. So anyway:

The First Day

Left Sunday Morning at 3:00am

The kids woke up around 6-6:30am which is typical for them and also the sun was shining so bright in (my ole KY home) our car so I'm sure that woke them as well.

This is when we brought out some of our car tools. The trick is to make sure it's a fun new thing that they've not seen before or at least haven't in a while. That way it feels flashy and fun and new! 

Here are some recommendations for your beach road trip that we used! Everything is from Amazon so it's super easy!
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We made two stops; the first one was to eat breakfast. We ate at a Waffle House somewhere in Alabama around 7am. Second stop was not too far along for another potty break, oops! 
​

11:00am: We arrived into the 30a/Rosemary Beach area ​

We had lunch at a nearby place, Shades Bar & Grill, and had an absolutely amazing salad. It was much needed for me as I was already burning up. It was SO HOT already! 

Like I mentioned, we couldn't check in until 4:00pm so we had some time to kill. In true vacation fashion, we had lunch then thought, we need groceries, so we headed onto Publix. (No Krogers in FL).

1:00pm Grab Groceries at Publix
2:30pm: We were missing a few things so then headed to Target for a moment
3:00pm: Headed back to the condo. Addie was napping so we didn't want to get in and out too much. But that was fine because it really was only about 30 minutes until time to check in. We'd never been to this area before so we drove around a bit to get a lay of the land. It was great! We got to check out all the little shops around. The place so was great to be at and we're excited to return! 

What we found was if you did not want to drive around during your stay, the area really allowed itself to do that! It had so much. There were restaurants, shopping, breakfast places, live music, dessert places, the pool, and so much more! Most places around there included bike rentals and everyone bikes around the little community.

4:00pm: Finally 4:00pm rolled around and we were able to check into the house! We got there first as we were staying with another family (our aunt and uncle's family). We scoped the bedrooms and tried to figure out what would be best with our two little ones that are both in pack n plays right now. 
SLEEP: Now this was the tricky part. So, we had an encounter a few weeks before traveling for the first time with both of them away from home and we definitely learned what NOT to do. Still learning on what TO DO but hey. The first thing we learned is that, the pack n plays need NOT be right next to each other. Rookie mistake. 

So we found a room and it had a queen and a twin. This would be perfect in the event that one of the kids woke up and needed comforting. One of us could move to the twin bed and carry on with them there. Bonus, as it was set against the wall. Now, one of the biggest hurdles was also the light shining in. It doesn't get dark until late and the kids (at least Cal) is used to sleeping in a complete blackout room so that would be tricky. 

We did what any parent would do...we set up one pack n play in the closet and one by the big bed. Okay...does that sound weird? IN THE CLOSET? okay, well it's not like we're locking them in the closet and the door is cracked. I find this completely normal and know lots of parents who have done this or a bathroom or something like it! 
Anyway, after we got all squared away in the bedroom and all the groceries put up.

7:00pm: It was pool time then! We headed out to the pool around around 7pm. Yep, that's right. We were trying to salvage as much as the day that we still could! After all, it didn't get dark until around 8:30pm. 

We came back home changed and went out to dinner. It was late, I will give you that but we were hungry and didn't feel like cooking or eating a ham sandwich for dinner. So, we went out for dinner at 8:30pm. 

Here's one thing we just tried to keep in mind while on vacation; Will this mess with the kids schedule? Yes absolutely, but is it reasonable to adhere to a strict schedule like at home while on vacation? For us, no. There was no way we could keep everything the same, especially on travel day like this. So, we did what we could and packed our patience and let the kids lay where they fall. 

Cal fell asleep at dinner, rightfully so, it was 10:00pm. And he was so cute. Like I said earlier, we walked just about everywhere so where we went out for dinner that night, we walked it with the stroller. He fell asleep in the stroller and was just content as could be. 
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We got back to the house and put Cal right into the pack n play. Addie was awake, surprisingly, being a party animal! She did fall asleep shortly after arriving back "home". This was the first night and the roughest, to be expected.

Cal woke up around midnight but was able to get him back to sleep. Addie was basically up all night. It was a tough one. A friend of mine let us borrow her Slumber Pod but we did not spend the time trying to learn how to set it up that evening so we did not get to use it. It is below:
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That next morning, we decided it would be time to try and figure out how to set that up and use it the next few nights and boy, was I glad we did. That thing really works! At least it did for us. We did end up having to switch the pack n plays and put Addie's in the closet and Cals next to the bed (with the Slumber Pod on it) because;; SURPRISE, Cal showed us that he could climb out of it. So, that was a lot of fun! It was bound to happen, obviously, but it's not fun to have to learn to deal with while on vacation. 

I was so glad we had that Slumber Pod because it's essentially a black out tent over the pack n play and once it's set up, he couldn't really climb out of it.

Day Two

Regardless of the evening, we got up and worked on getting everything together and ready for the day. It was, after all, our first beach day! 

I ended up ordering a few rental items (stroller wagon and beach tent) from Babyequip.com and if you've never used baby equip, it's an online service where you can rent baby/kid gear from local families in whatever area you're in and you can either pick it up or they will delivery. Typically, they are a fraction of the price to rent. It's cool because each family/person's rental pricing and other details are different and what each host has is different but I think it's cool because you are also kind of supporting the local families you are renting from as well and you are not having to bring a ton of things on your trip! 
We had a small hiccup when we found out that just a few days prior they were not allowing wagons on the beach in which we had TWO. We had a stroller wagon and a wagon that was hauling all our other things but we still trotted along to the beach access, which was about 5 blocks. We got lucky with the guard and they allowed us to take the stroller wagon as it had the kids in it. We did end up having to carry the other items with some help with the family with were with thankfully! We wouldn't had been able to do it without them! 

We got on the beach around 11:00am and stayed until around 2:00pm. We had dinner reservations at 5:15pm so we wanted to make sure we got back home in a reasonable time to get, maybe a little nap, showers, get ready, and drive to the restaurant as it was about 15 minutes away. 

We packed a bunch of snacks, toys, sunscreen, and a bunch of other fun tools that were great for the beach with these little ones! See a bunch of those below along with photos of our first beach day! 
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Day Two - Dinner Reservations

Like I said, we did have dinner reservations at a place called 
Old Florida Fish House

It was so gorgeous and the food was fabulous! It's very family friendly and has so much to do and look at! After dinner, we just even walked around and shopped and had one more beverage, HIGHLY RECOMMEND this place and also HIGHLY RECOMMEND making a reservation because even at 5:15pm, they were super busy! 

Day Three

We learned a lot from the first day on the beach so we geared up and switched things around bit.

This time instead of bringing the wagons, we packed up what we could with our arms and hopped on the tram. In the little community we were staying in, they provide a tram that can take you to the beach access so we went that route this time. I strapped Addie onto me using my artipoppie carrier and away we went. 

We spent most of the day at the beach. Of course, we packed all the snacks, the tent, drinks, all the things! 

We were lucky enough to have family with us for this trip and they graciously said they'd watch the kids one night so we could go and have a nice little date night dinner, and tonight was the night!! 

Devon and I don't get to get just the two of us too much anymore so this was a treat for us for sure. We made dinner reservations for the Cafe Thirty-A at 8:15pm! We would had liked it for it to be earlier but that's all I could get because I made the reservation only about a week in advance. It was fine though. It allowed us to still get to spend tons of time together and then the kids would mostly be sleeping while we were at dinner! 

We ended up going on a Tuesday night and we did not know this until we arrived but every Tuesday and Thursday they do Tini Night and you can get $6 martinis at the bar all night! One of the perks of going on a weekday night! Be sure you look for those things, you can really get some specials by doing so. 
The food was freaking phenomenal, of course. But, I saw this on the menu and
​thought "ha, how funny!" 

"Well Behaved Children Are Welcome" 

Welp, that would NOT be my children right now but good to know! ​

Last Day

And on the last day, the boys golfed and the girlie-pops hung by the pool and did was walking around! 
We loaded up the kiddos and went to get crepes and did some walking around the little town. The kiddos were starting to get sleepy and one definitely fell asleep on the walk around, sweet girlie. Cal was getting a bit sleepy but we got him some shaved iced and he was in heaven! 
Speaking up having fun and what not, what was not so fun was trying on bathing suits postpartum! I hate it but I really needed to find some good new bathing suits, with better coverage. I had two littles back to back after all and one really on the go so I definitely needed something cute, that fit, but was going to be mom moving coverage. I found these awesome options on amazon! 
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Last Day - Traveling Home

Of course, this day had to come but the next morning was the day to check out! Check out was at 11:00am so we spent the morning basically repacking everything, loading up the car, cleaning out the fridge/pantry, and cleaning up! 

After all was done, we headed out to a breakfast joint, The Donut Hole!

It was a pretty cute little place and had corn hole out front while we waited. 

After breakfast, we drove for about 3 hours and then stopped just outside of Montgomery and found little park to let Cal run around for a bit. We stopped, ate, and chilled there for about 45 minutes. I do highly recommend doing this especially if your kids are as small as ours are right now. Really letting them get out, move around will do wonders for the rest of the trip! 

We got home around 7:30pm which is normally around bedtime but since we had been in the car practically all day, we let the kiddos stay up a little bit longer and get out wiggles. I know they were super excited to be home! 
Thanks for coming along to our family's first beach trip with the littles! We learned a whole lot and hope this may help you prepare a little bit if you're in the same boat! We are excited to keep sharing this trip as they get older and older! 
**if you click on some the photos with links, it may take you to a website on where to purchase the items. When doing so, I may receive a small commission on the products. I am not paid to advertise and have not been asked to promote specific items. These are my real opinions, ideas, thoughts, plans, and items purchased because I wanted to purchase them. Only items purchased here with links are items that I would want to share with you!*
1 Comment
Orlando cruise link
11/25/2025 08:51:17 pm

Thank for sharing this blog, very well written and structured.
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