Picture the most idyllic seaside town you’ve ever seen. Families biking to grab a snow cone, gorgeous architecture, sand so fine and clean you’d think it was flour, a small rainstorm every day that allows you to dip into a coffee shop for a cortado before heading back to the beach for more sunlight…

Got it pictured? Cool. That’s Seaside.

If you’ve been around here for a while you might know that my husband is a CPA and a partner in his firm. He works a ton and so when he came to me and said, “I’m ready for a beach.” It took about .5 seconds to decide on location and get it booked. In my season of life as a graduate student, the most stress I have is just dealing with meeting paper deadlines and so I really wouldn’t say I need vacations, but obviously…I’m never one to turn down a trip.

Adam wanted it as low stress as possible and so with a direct flight to Destin, FL that was the easiest option. I wasn’t crazy about Destin, but considering the adorable 30A beaches are only an hour away: vacation decided.

If you’re planning your trip to Seaside or 30A in general, I hope this itinerary is helpful! I’ll just go through what we did, day by day and then leave some tips and notes at the end. I hope it sparks some inspiration to go check out this gorgeous little nook of the U.S!

Day One

We flew on Allegiant and got to Destin around 11 a.m. We had rented a car from Enterprise – and I highly recommend renting a car – so we arrived with ease, got in our car and hit the road. Since it was still morning and we hadn’t eaten yet, we decided to head to The Donut Hole first thing. This place is pretty iconic and although a lot of out-of-towners go there, it has a really small town feel and my guess is they probably have plenty of regulars. I’m mainly going off of the fact that we overhead, “See you next time!” or “See you tomorrow!” a few times! If the locals go, you know it’s not an overrated tourist trap.

If you’re headed to Seaside or any of the surrounding 30A towns, The Donut Hole is an easy stop that’s just about midway. I had their Sunrise Bagel Sandwich, Adam ordered a burger and we got a Dutch Crumb donut to take to the beach with us for a snack.

After we got slightly-uncomfortable-in-a-bathing-suit style stuffed, we hit the road for Seaside! We rented an Airbnb that’s owned by the Cottage Rental Agency but since we weren’t able to check in until 4 p.m. we headed straight to the beach.

Fun fact, the to-go bags from The Donut Hole have water safety information on the back of them. In case, ya know, you’re simultaneously eating a glazed and wondering why there’s a blue flag up on the beach.

The coconut mojitos, however, come with no warning label at all whatsoever.

We did an extensive search on Airbnb for the perfect digs to stay in. If we had gone with a group (like we plan to next time), we would have loved to rent one of the larger houses, but with only two of us we were really drawn to Green Gables, a tiny little cottage. I’m going to be honest, it was adorable and I loved it. I loved the vibe, I loved the location and I loved that it came with coffee, a coffee pot, anything you’d need in a kitchen and two bikes! Bikes are a must in this area but I’ll get into that later in my tips and notes section.

This specific cottage is located on Forest St. which is right at the back of the town center so it’s so easy to get literally anywhere – shops, restaurants and straight down to the beach! Plus, directly behind the house is a shuffleboard court, tennis courts, sand volleyball, croquet pitch, kids pool and adult pool. The house comes with access to all of these and gives you the access code to the pools!

If you decide to use the Cottage Rental Agency, they supply you with a complimentary bottle of wine at check in, they have a ton of rentable DVDs and beach toys, plus they also gift you an insulated beach bag, two insulated beach cups, a football and beach towels!

For our first dinner, we went to 723 Whiskey Bravo (https://www.723whiskeybravo.com/) and I’ll be honest – the atmosphere is not what I thought it would be. It honestly looks like a lowkey sports bar. But the redeeming value is that the food was freaking delicious. We got the mussels in white wine cream sauce and seared scallops. So. Good.

Day Two

The day started with a cup of coffee on the screened in porch and listening to a tennis lesson in the distance. Then we biked to a MUST on everyone’s Seaside list – Bud & Alley’s (https://www.budandalleys.com/) – for breakfast. The rental car was good for exploring other 30A towns, but for doing anything in Seaside, we always took our bikes.

After breakfast, we went to Modica Market. Y’all NEED to go to this adorable little market. You can get general sundries, food to cook at home, food to grab and go for lunch or a picnic on the beach, any kind of drink you’d want and other fun stuff. You can even get an iced coffee or huge mimosa to go! We went and grabbed some local brews to take to the beach.

The good thing about building an itinerary for a beach trip is that it’s very simple. Breakfast, beach all day, dinner. For our second dinner we chose to go to the Surfing Deer. It was the number one most recommended place and it was also number one on my personal list after I did my research on the area. And it did not disappoint. It’s the exact atmosphere and vibe I was wanting, the food was incredible and it has a cute story behind the name. Surfing Deer alludes to a guy named Cube McGee, a local who lived in Seaside way before it was popular who had a pet deer named Bambi who would fish and surf with Cube!

Day Three

After spending the whole day at the beach the previous day, we were both a little crispy and decided to give our skin a rest. Thankfully, there’s no shortage of SHOPPING on 30A so we we literally went hopping from one beach to the next going treasure hunting in all of the fun boutiques. And we got quite a bit of bounty to bring back home! And also, there’s a great Farmer’s Market in Seaside on Saturday mornings so we started there first and picked up some local made soaps and dog treats.

Here’s a list of my shopping recommendations on 30A between Seaside and Rosemary.

Seaside:

• Fusion Art Glass
• The Seaside Style
• The Cabana Shops
• The Art of Simple
• Willow

Seacrest:

• the kiosks at Seacrest Village
• Bohlert Massey Interiors

Alys:

• Alys Shoppe
• Anne Hartley
• Mast

Rosemary:

• Patchouli’s
• Luminary (freaking love)
• HissyFits
• Willow
• Disco
• Oko
• Moonpize

Watersound:

• 13 Hub Lane
• Adaro Art
• A. Wickey
• Little Barn Apothecary
• Yellow Fly Trading Co.

When you get hungry in the midst of all of your shopping, stop in at George’s at Alys Beach for lunch. It’s fresh, healthy, delicious and they have great drinks!

After a full day of shopping, we went back to Seaside to get cleaned up and dress for dinner, but we headed back to Alys because we REALLY wanted to experience some eats there. We started with pre-dinner drinks at Neat (https://alysbeach.com/neat/), a cocktail lounge and bottle shop..

and then had dinner at Caliza. It was too dark to take pictures by the time we got there, but it was outrageously gorgeous. The restaurant surrounds a ritzy pool, has an excellent and thoughtful chef and is decadent in every sense of the word. Check it out: https://www.calizarestaurant.com/

We capped off the night with a bike ride around town to help digest dinner..but then couldn’t help ourselves and stopped at It’s Heavenly in the town square for some gelato.

Day Four

Just as our skins needed a break from the sun on day three, our wallets needed a break on day four LOL so it was back to the beach we went. The whole time in Seaside we had been eyeing a joint called Pickles. We had heard so many good things about it and so we went for breakfast. I think it was probably due to the fact that they recently had started serving breakfast, but we were not fans. Probably the most horrendous omelette I’ve ever had in my life and quite frankly it’s hard to screw up an omelette. I’m assuming they’re much better at lunches since they’re so wildly popular.

After we’d laid on the beach, played football in the ocean and felt like we needed a break, we came up to shop the Cabana market which is just the most adorable thing, y’all.

And then we grabbed some iced water at Modica to cool down and I had to venture over to get a snap of the idyllic and iconic Post Office. It’s original to the town and it adds such a quintessential essence to the place. Fun fact: the Jim Carey movie The Truman Show was filmed in Seaside and the post office makes the setting very recognizable!

Another notable spot in the town square is a coffee shop called Amavida. They roast beans that most restaurants in town use and we popped in for a flat white and cortado. You literally cannot walk by the shop without the smell of roasting coffee pulling you in. It’s impossible to walk by and no go in and order, no matter how hot it is outside.

For dinner that night, we had planned to go to Pescado in Rosemary but wound up being so content to stay in Seaside and not mess with dressing up and heading out that we got in some comfy clothes and went to the Pizza Bar by the main pavilion and WOW it was delicious. Hands down the best decision made that day!

Day Five

On our last day in paradise we woke up late and went to Great Southern Cafe for breakfast. For the life of me I have no idea why I didn’t snap a single picture of the place but it’s smack in the middle of town square and not only is it highly recommended, but it completely lives up to the hype. Our breakfast was so so good. And, since we’re children, we enjoyed that they had paper table coverings and a mason jar of crayons so we could play Hangman as we ate breakfast! We did our last minute shopping in town and grabbed some things we’d been eyeing and then, yes, we went to the beach.

For dinner that night we went to Fish Out of Water (https://www.foow30a.com/?NCK=8772563938) in the next town over – which was 100% not a mistake. That dinner was phenomenal and we had a gorgeous view of the ocean, which came with an even more gorgeous viewing of the sunset. I cannot recommend this place any higher to you!

We called it an early night since we had to be up at 4 a.m. to drive to Destin and catch our flight back home!

Y’all…I’ve got to say. I’ve been a lot of places and done a lot of things and I usually try to avoid “sitting on the beach and doing nothing” trips because I crave adventure and culture but MAN am I glad I did this vacation. There’s a reason everyone loves 30A. It’s adorable everywhere you look, it’s the cleanest sand and water that’s reminiscent of the Caribbean but way closer, the shopping and restaurants are top notch – but mostly, there’s just nothing better than lazy days of sun, quality time with my love, a good book and a recharge.

I hope our itinerary helps you plan a trip to Seaside so you can experience and fall in love with this darling little corner of the country. I put so much research, consideration and thought into planning our travel itineraries and I get so much joy out of sharing them with you. I do the work so you don’t have to!

Notes & Tips

• The #1 thing you need to get familiar with before going to Seaside is https://www.cabanaman.com/ – BOOK YOUR BEACH CHAIRS. You cannot book online the day before or day of, so you’ll want to do it in advance. And during peak season they fill up fast so if you want a front row seat, book early! We sprung for Club Cabana man on one of our days which comes with a side table and drink service (holla!)
• I really would suggest renting a car. Although most rentals come with bikes and there’s places to rent bikes outside of that, if you want to hop from town to town, a car is much easier (and cooler)
• The temps are in the 90s but feel much higher and the UV is around 11 or 12 consistently so it will be HOT and even if it’s overcast you will BURN if you do not take sunscreen. If you forget to pack it, you can buy some at Modica Market
• Surrounding towns have strict private beach access so if you’re staying in Seaside don’t expect to go spend time on the beach in Alys or Rosemary – it ain’t happening. You have to stay there to have access. But Seaside has public access points so if you stay somewhere else, you can still have access to that beach.
• It’s easy to spend a complete day on the beach, so bring a book! But if not, there’s an adorable book shop you can pop into to find something before heading to the water.
• Although the towns on 30A are maybe 5 minutes apart, each of them has a completely different aesthetic and vibe. Seaside is preppy and laid back, Alys is definitely ritzier and snooty (but I love it) and Rosemary has a quirky Bavarian feel to it! They’re all so fun and I would really recommend venturing out and exploring more than one town!

Cheers, y’all, and happy planning!

XOXO, Thessali

30A 30A travel guide florida seaside seaside florida travel guide