St. Augustine Beach Trip

Now that my little dude is quietly sleeping in his crib and my husband is out for a guy’s dinner, I finally have some time to catch up on some writing!

For my birthday this year, my husband Matt planned a thoughtful surprise getaway to St. Augustine, Florida, which I’ve always loved because of the combination it’s historical roots and proximity to the beach. He invited our immediate family to fly or drive in from Pennsylvania, Wisconsin and North Carolina to join us as well! In the northeast I was surrounded by historical places all the time, but they are much more rare in Florida, which makes it one of my favorite places to visit.

Legend has it that Ponce de Leon landed in St. Augustine in 1513 looking for the Fountain of Youth. He was followed by Spanish admiral Pedro Menéndez de Avilés who officially founded St. Augustine in 1565, which has remained the oldest continuously occupied European-established settlement within the United States. In 1672, the Spanish began construction of the Castillo de San Marcos fort on the shores of Matanzas Bay to protect the city, which can be visited today a United States National Park. Other historic sites include the Oldest House, Oldest School House, Fort Matanzas, and the beautiful campus of Flagler College.

 That being said, my favorite thing to do in St. Augustine is to wander the streets of the old city admiring the mixture of Spanish and old Florida architecture, and stopping in at the cool little shops, bars and restaurants you will find along the way. If you pop over the bridge, you will find yourself at either beautiful Vilano beach to the north, or St. Augustine beach to the south.

This year matt rented a charming sky-blue beach cottage in Vilano beach, which was only a quick 10 minute car ride to old town St. Augustine.



The cozy cottage was able to hold 12 of us, and the path down to the beach wasn’t too long to lug all the chairs and beach supplies down. The distressed white wood furniture and laid back décor gave out the perfect beach vibe.  There was a large second story balcony area and then another lookout on the 3rd floor, which was perfect for watching the sunsets.

We spent our first full day playing on the beach with Max. This was his first time seeing the ocean so he was a little bit timid at first, but once he got the hang of things he couldn’t get enough of it. Max would walk straight out into the water and I would have to pick him up and back him out of the water over and over again.

Morning snuggles with Grandma.


For the most part he was able to keep his footing really well as the waves would break, and we took his kiddie pool down to the beach so that he could have a calmer alternative as well. When he wasn’t in the water, Max’s cousins were awesome, showing him all their tricks to build sand castles (although Max mostly just knocked them down).

That night we went into down and had a great dinner at the Columbia House Restaurant, where Max celebrated with a happy birthday song and flan (yes, he ate flan), and danced to the Spanish music playing the background. After dinner we walked around the streets and grabbed amazing popsicles at The Hyppo for desert.

Pregame before dinner in at Columbia House in Old Town St. Augustine.



Hanging out in Old Town St. Augustine with my little sis!


The next morning we drove back down to to Old Town St. Augustine in the morning and toured Castillo de San Marcos, where Max earned his first Junior Ranger Badge from the National Park Service, and then returned back to the cottage for lunch and more beach time.

These adorable trunks, swim shirt and chambray hat were available this summer from Baby Gap.

TORY BURCH ONE PIECE | SIMILAR HAT




My extended family from Jacksonville came to visit that afternoon while we all played in the sand some more, and then that night Matt cooked a fantastic dinner of chicken, shrimp, steak and lots of other things for 19 people!  We also had a family birthday cake for Max since his birthday was only a few days away.

Sitting on Pap Pap’s lap.


Watching the sunrise with MeMaw…

I know that there was a lot of damage to the area after Hurricane Matthew the very next weekend, so I am hoping that our little blue cottage didn’t fare too badly. It was really the cutest little place, and I fell in love with the beach in that area. If felt like I was a million miles away from everything during our walks, and we were only 2 hours from home.


In all, it was a great birthday weekend and Mr. Max really loved his first trip to the beach. I can’t wait to take him back!  Click HERE more information about the St. Augustine area.

One thought on “St. Augustine Beach Trip

  1. Patty Jassak says:

    Kristy- thanks for sharing your birthday celebration. Love the history of the area you provided. Pictures were delightful and scenic/beautiful ocean/beach views and sunsets.

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