Earlier this year when we scheduled our summer vacation days we knew we wanted to do a staycation in June to decompress, enjoy our new boat and enjoy where we live. We live in the Sarasota area which has lots of beautiful beaches, tons of stuff to do, etc. We always say, people pay thousands of dollars to vacation here and we don’t want to take that for granted.

I think we started a new summer tradition with that staycation but we also knew we wanted to travel in July. We scheduled time off but then Joe thought he had to travel that same week for work so we put off booking anything thinking worst case the kids and I will tag along with him and we will make it work. Long story short he was able to move his work travel at the last minute and the travel bug hit us quick so I went to searching where we could find somewhere to go without breaking the bank since it was so last minute.

We tossed around a few different ideas and places and ultimately, found what could have only been a cancellation on 30A and headed to Rosemary Beach, FL a few days later. Spoiler alert, we completely fell in love with this town and have not stopped talking about it since we got back. I documented our time and saved it to an IG highlight if you want to look there too but today, I thought I would recap here on the blog too since blogs are where I planned our trip from!

First things first, we found an Airbnb online and booked it really having no ideas where it would be. It was the space we needed and the in the price point we wanted and we were so pleasantly surprised to learn in was right in the thick of things when we got there. There are a few beach resorts/boutique hotels in and around Rosemary Beach (30A) but we loved have the Airbnb and there isn’t a shortage of them. The condo we rented was right behind Peddler’s Pavilion and a 5 minute walk to the town center so the location was perfect. Highly recommend staying as close to there as you can because it made everything in Rosemary Beach walkable and was within 20-25 mins of everything else we wanted to explore in 30A.

We arrived on Tuesday night after about 7 hours of driving. Joe and I both worked Tuesday morning and we hit the road around lunchtime so by the time we got to Rosemary Beach it was getting later and we were tired/hungry. We found the condo, walked around to get our bearings and then went to dinner.

I had a list of places I wanted to try but the place that caught our eye when we got there wasn’t on our list, ha! Lola’s was at Peddler’s Pavilion and was coastal Italian. We were so hungry and it looked to be the fastest so we ordered food and let me tell you — it was the first of many many delicious meals we would eat!

It felt like an underrated place because it wasn’t on any blog I found but we loved it. The calamari was the best I have ever had. And the drinks were so good. I will say it is a place to order and then sit yourself after you order. But, they bring your food to you and there is a great bar to grab drinks at. So definitely a casual place but exactly what we needed after traveling all day.

Day two rolled around and after a good nights sleep we set off for breakfast, groceries and to really get our bearings on the area. We had really no frame of reference to where we were so we wanted to drive around and peak at the area to make a plan for the 5 days we were there.

We went to breakfast at The Donut Hole and let me tell you, if I am going to eat gluten it has to be good and these were worth every bite. The girls and I had donuts and Joe had a full breakfast. The food was good, the service was good and we just loved the environment. It was busy but the line moved pretty fast. If you go, there are 2 different lines — one for dining in and one for ordering donuts to go so just pay attention you are in the right line.

Isn’t Peddler’s Pavilion the cutest? There was live music every night, lots of energy and a relaxed but really fun vibe.

After we explored and put away the groceries to bought (some lunches for the beach, quick snacks and a few things for grab and go breakfast plus drinks) we went back to the condo and changed to head to the beach. After the beach, we went to the pool where Joe swam with the girls and I enjoyed an afternoon nap!

Once we had enough of the sun we went back to get ready for dinner at Cowgirl Kitchen which was just as good as everyone said it would be. Be sure to get there early or be prepared to wait for your table for a bit. We took pictures and enjoyed the scenery while we waited. Just a quick note, most of the shops close around 5pm so while it would have been nice to poke around them they were closed when we were waiting around 6pm.

The girls were begging for ice cream so we headed back to Peddler’s and enjoyed ice cream at The Sweet Peddler which they had been eyeing all day. I just tasted theirs since I can’t eat dairy and the oatmeal cookie ice cream was out of this world. After some live music we were ready to go back to watch and movie and head to bed.

The next morning we walked to Amavida Coffee for the best coffee I have ever had. I went there everyday after this because it was the best latte I have ever had. I got a hazelnut latte with oatmilk. After we ate at the condo we went to the beach for a while then back to the pool again where we ordered pizza from Pizza by the Sea for lunch. Joe and the girls split a pie and I had the GF with a bunch of toppings and it was one of the best GF pizza’s I have ever had. If you aren’t catching on, the food is one of the best parts of the town.

After hours and hours in the sun we went back to the condo, relaxed for a while then got ready for dinner. The girls and I wanted to do a little exploring/shopping so we got ready first and then while Joe was getting ready we walked to the town center and did a little shopping.

For dinner we drove over to Alys Beach. It is totally walkable but we weren’t sure if it would rain or if the girls would be up for a ton of walking after all day in the water so we drove, it was 5-10 mins max. We ate at The Citizen which was one of the most recommended places and it did not disappoint. The whipped feta, oysters and ranch water were amazing…we all had something different for dinner and loved.

We went walking after dinner because there were so many beautiful places to take pictures and explore. Alys Beach to me was the most photogenic in the fact that every corner had a IG moment! We then hit up Charlie’s Delights for dessert. We went in for ice cream and because it was the end of the day they also gave us a bunch of donut holes too.

It still felt pretty early and it was drizzling so we decided to just get on 30A and drive! We went through Watersound and decided to stop at The Big Chill (I think it was called the Hub before) for live music and drinks. There are tons of little shops, food and stuff there. It was packed almost to an unenjoyable point if I am honest so we didn’t stay long but made a mental note to return another day earlier.

The next day we decided to go exploring 30A so we made our way to Seaside, walked around and enjoyed breakfast at Crepes du Soleil. We explored Seaside, took all the pictures, went in all the stores you see on IG, took the famous Post Office picture and then grabbed lunch at Bud and Alley’s which had great food and even better views. There was a ton to do in Seaside and it was much busier in activities than surrounding areas so we spent several hours just enjoying all it had to offer because heading back towards Rosemary.

We stopped at The Big Chill again to enjoy it before it go crazy crowded then went to relax a little at the condo before heading to dinner in Rosemary Beach at LaCo. LaCo is coastal latin and I had read that the lobster quesadilla was the best on the menu so I threw all my food allergies out the window and ordered it and enjoyed every single bite. We ended the night back at Peddler’s where we had more ice cream, I got some permanent jewelry from one of the vendors and we made friends with people around us.

The next day was our last day so we spent more time at the beach and it’s beautiful water. Let me tell you, I grew up in Florida so I am no stranger to pretty water but 30A is next level. The water is the perfect temperature and it is crystal clear. Dolphin everywhere. It is just beautiful and because you have to be a resident or renter, it stays so nice. There are very few public beaches in the area so while it can also feel a little crowded it was still really enjoyable.

We stayed out at the water most of the day and then headed to La Crema for dinner. This is a tapas style restaurant so just be warned that food comes out at all different times and sporadic. The wait wasn’t too long and the food was good I think we would have preferred it at lunchtime though.

We ended the night with a long walk around town and then to bed. We wanted to be on the road by 10am so that we still got home at a good hour to get ready for work the next day. On our way out we grabbed more coffee from Amavida and donuts for the ride at The Donut Hole and truthfully, none of us wanted to leave.

I am now dreaming of owning a place there and Joe/the girls tell everyone about it and can’t wait to go back so it’s safe to say we will be returning!

We loved Rosemary Beach and had the best 5 days there. We could have stayed longer and been just as happy but I wouldn’t recommend fewer days because believe me, you won’t want to leave!