Seaside | Santa Rosa Beach

1.12.2018 – 1.16.2018 || Seaside | Watercolor || Santa Rosa Beach, Florida (Updated Jan 2019 and Jan 2023)

My childhood BFF, who lives in Bermuda, is a new homeowner of a fabulous beach house in Seaside, FL. Seaside is located on 30A between Panama City Beach and Destin in northwestern Florida.

Never heard of Seaside before? Seaside is best known as the location for the film The Truman Show starring Jim Carrey. Seaside started in the mid 1940s when the grandfather of the future founder bought 80 acres as a summer retreat for his family.

In 1979, the grandson inherited the land and transformed Seaside into an old-fashioned beach town and a master-planned community designed on the principles of New Urbanism (walk-able, housing and shopping in close proximity, etc.).

Seaside is a colorful beach side town where people slow down to enjoy the white sand beaches, perfect sunsets, specialty shops, wide open spaces and markets, and much more. Here, most people get around on foot, bike, or golf cart!

My friend was eager to show off her new town and arranged a weekend getaway. We were joined by four of her friends from Bermuda for a 4 night, 3 day adventure in Seaside.

I met the rest of the gang in Atlanta were we got the party started with some bubbly and the most interesting meet & cheese plate presentation, featuring still wrapped crackers, topped off with dried herbs!

After a quick 45 minute flight we landed in Fort Walton Beach and found our party bus transportation for the 45 minute drive to Seaside.


Not a lot of sightseeing happening when you arrive at 7:40pm in the winter. Our Sunshine Shuttle driver was very nice and stopped at the Publix grocery store so that we could pick up some staples before settling in for the night…


What to do when it is ~30 degrees in Florida?! Some of the activities that occupied our time included: indoor spa activities, shopping, and checking out the food & wine scene.

When it is unseasonably cold – feels like 27 – you try to stay as warm as possible until the shops open. My scarf doubled as a hat in the meantime.

First activity on the agenda was a visit to the nail salon. It was close by so we rode bikes/walked there.


In addition to renting bikes for the six of us, we had a golf cart to pick up. The golf cart was great for slightly longer distances and to pile all of six of in at once without having to worry about renting a car or ordering an Uber/taxi.

I was one of the first to be done at the nail salon so here I am picking the golf cart up in the parking lot behind the salon. I left my scarf/hat at the salon.

We were more than ready for brunch so we headed into town with Great Southern Café in mind. There was a lengthy wait so we explored the shops in the main square in search of warm gear.

Mercantile was a big hit! I bought this super soft Barefoot Dreams hat, which I showed some gratitude for on @champagneonplanes and then a couple of days later, the shop gave me (and all of their customers) this shout out! SO cool! The rest of the ladies bought some warm clothes to supplement their Bermudian winter wardrobes.

Time for Brunch! Great Southern Cafe has some (undocumented) signature dishes that were a hit, so were the mimosas!

After fueling up at brunch we hit the remaining shops around the Seaside square.

Three of the ladies getting into the shopping spirit! There were quite a few photo ops like this around Seaside.


One of the coolest shops in Seaside is Perspicacity, it’s described as a shopping bazaar showcasing a colorful array of women’s clothing & accessories in rows of cottages. We shopped around here at least 3 different times over the course of the weekend.

@perspicasity does a way better job showcasing the space!

The sunsets were stunning! I hope to visit again when it is warmer outside to enjoy the sunset at the end of a fun beach day.


Since we were biking, it was time to head back to the house with all of our treasures in tow!!

We spent the evening (mostly undocumented) out and about in Seaside and Grayton Beach.

The next day we headed to Rosemary Beach for brunch at Cowgirl Kitchen and more shopping. I heard about the Pearl Hotel and Rosemary Beach before arriving but it was even more stunning in person than I imagined!

The Pearl Hotel and the street below were used a backdrop in The Truman Show. It really did feel like there was a dream-like quality about this place and the beach was picture perfect.

After brunch we stayed around Rosemary beach for a little while longer. While shopping at Pish Posh patchouli’s, we learned how to prevent (and cure hangovers) from the twenty-year old sales girls, and we found mascara that comes off without having a raccoon face. She could have sold us anything.

We headed back to Seaside to hit the rest of the shops that we didn’t have a chance to explore the previous day, and to revisit Perspicacity. We also checked out some of the air stream trailers (food trucks) for some fresh juice and coffee.

This is the view of the Seaside square and the cutest Post Office I have ever seen.


We were treated to another stunning sunset from within the square this time.


We tried to stay out in town as long as possible because we had big plans to surprise our host, but most of the shops close at 5pm on Sunday and she was starting to catch on to us so we headed back to the house.

I took over as the golf cart driver for the last couple blocks to the house and we blindfolded her so that she wouldn’t have any clues until she was inside. SO FUN!

We pulled it off and completely surprised her by organizing a private chef to cook dinner! One of the girls had the idea and found Chef Jekyll, and the rest came together rather seamlessly once we selected a theme.

We had a four-course Mexican themed meal and we provided the margaritas. I have never hired a private chef before but this was amazing for many reasons.

Here are a few that we discussed:

  1. It was too cold to go back outside
  2. Most restaurants don’t take reservations
  3. The Chef did all of the prep
  4. The Chef served each course
  5. The Chef also cleaned up!

After a super fun evening in, we had a relaxing third and final day planned. We started the day with breakfast and mimosas at a diner named Pickles before hitting the shops again, and spending the rest of the day relaxing at the spa!

Pickles is one of the many low key options along the square for quick service so that you can get back to the beach, or in our instance, back to leisure activities.

Caught a glimpse of one last sunset while biking home.

We had a wonderful (undocumented) dinner out at Café 30A. This was one of the only restaurants that offered reservations. It is amazing how reliant we are on apps to make reservations in order to avoid waiting!

Even in the brisk January temps Seaside is a super charming town with tons of shops and restaurants, perfect for a girls getaway! Looking forward to many returns and to visiting my new friends in Bermuda!

Where we stayed:

Where to Eat Breakfast:

  • Amavida – Seaside (2018, 2019, and 2023) Local chain serving coffee and pastries
  • Black Bear Bread Co – Grayton Breach (2019)
  • Pickles – Seaside (2018 and 2019)

Where to Eat Lunch:

  • The Citizen – Alys Beach (2023) Coastal cuisine with a great drink menu that believes in mimosas with a splash of OJ
  • Cowgirl Kitchen – Rosemary Beach (2018 and 2019) Great hangover food
  • Fish Out of Water – Santa Rosa Beach (2023) Located at the Watercolor Inn overlooking the gulf
  • Great Southern Café – Seaside (2018, 2019, 2023) My favorite for brunch and mimosas with a splash of OJ

Where to Eat Dinner:

What to Grab Drinks:

  • AJ’s – Grayton Beach (2019) Local hangout with live music
  • The Big Chill –  30A (2023) Grab drinks, watch a game, shop
  • Bud & Alley’s Pizza Bar – Seaside (2018 and 2019) Grab drinks or dinner with an ocean view
  • Chiringo – Grayton Beach (2019) Grab dinner or drinks
  • Holiday Cafe –  Alys Beach (2023) After brunch at The Citizen, grab drinks while shopping at Parasol and connected furniture store
  • The Wine Bar – Watercolor/30A (2023) Daily happy hour wine specials

What to Do:

Question: What’s your favorite thing to do at the beach when it’s a bit chilly?

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