We live about 30 minutes from one of Florida’s best little cities and we like to visit as often as we can. In fact, two years ago we had made it a point to visit monthly calling it St. Augustine in 2014. Here are a few ideas of what to see and do when checking out St. Augustine, the oldest city in the US. (Check out the great outfits I’m wearing! Chico’s supplied me with the pieces but I love them all on my own! Details at the bottom.)
Where to Stay
If you want to go for a splurge then I recommend the Casa Monica hotel. Taylor Engineering’s Founder’s Day Ball (which just so happened to coincide with St. Augustine in 2014) was held in this beautiful, historical hotel two years ago. It is a popular place for weddings!
A very romantic city, St. Augustine has many quaint bed and breakfast inns to choose from. We stayed At Journey’s End because it received great reviews, is in walking distance from the main square and the Casa Monica Hotel, the site of the ball.
Another favorite of ours is the Hilton Bayfront Hotel. We had wanted to stay at this hotel overlooking the bay and the Bridge of Lions so one day Michael surprised me by pulling in after a day of hanging out at the beach. He had packed my suitcase and had it hidden in the back of the car. That evening we tried out several new-to-us places. (Check out Where to Eat and Drink). The inside is so very Spanish with dark wood and majolica tile.
Where to Eat
There are so many places to recommend and we are still finding new places! Below is a short list of some of our favorites.
La Pentola – fine Italian dining. I hardly EVER eat at Italian Restaurants but I liked this place.
The Columbia – Spanish/Cuban cuisine in a beautiful location.
Cellar 6 – Bistro-type wine bar. You can sit outside at one of the road-side tables and watch the people go by. Feels like you are on a small street in Spain!
O.C. White’s – We love the outdoor seating in this centrally located restaurant!
Pizza Alley – Some of the best pizza in St. Augustine, located right on St. George Street!
The Conch House – Located on Anastasia Island, across the Bridge of Lions. Caribbean inspired cuisine. We like to grab a tiki hut and eat outside overlooking the marina. My kids first tried gator here!
If you have time, try out Villano Beach which is on the north side of the inlet. Our favorite over there is Cap’s on the Water but Michael likes Aunt Kate’s too.
Where to Drink
Some of our favorite places in St. Augustine are where you can grab a great drink!
The Ice Plant 
Probably one of my favorite drink places in St. Augustine, the Ice Plant is housed in an old plant where they would make the ice for the shrimp boats when they would come in with their catch. They have completely restored it with period items.
All their cocktails are handcrafted and EVERYTHING is made from scratch – even the ketchup!
We just happened to run into Michael Macklemore, the owner, Patricia’s, father. He showed us around a little bit. This is the liquor cage. Pretty cool!
And upstairs is the bar area. The bartenders and waitstaff dress in period costumes. The place has a speakeasy sort of feel to it.
JP Henley’s – We last came here for a work-related social and had a few beers. The dark interior feels more like a clubhouse to me.
The Prince of Wales British Pub – This place is so picturesque! I love the look and feel of the place. Pretty authentic food and beer!
Harry’s Seafood Bar and Grille – Although this is also a restaurant, we’ve only been here for drinks. And boy were they good! There’s outside, shady seating!
Cellar 6 – Wine, cocktails. You name it.
San Sebastian Winery – The winery is up the road from the Ice Plant. They have a large upstairs terrace where you can have a glass of wine and see the view of downtown. Especially fun at Christmas time when all the lights are on!
What to Do
If you have never visited St Augustine, it’s a good idea to take a tour of some kind. There are many to choose from: walking, trolley, Segway (read about our experience here!), carriage ride, The Tasting Tours, Graveyard or Ghost Tour. This will help you get the lay of the land and provide you with informative history. Over the years we have done several different kinds. 
Our latest tour was the Vino and Victuals tour with the Tasting Tours. We visited 4 different locations, sampled different food and wines and had a blast with the other visitors in our own horse drawn wagon.
A visit to the Castillo de San Marcos fort is a must. It’s really fun to visit when the re-enactors are shooting off the cannons. 
Check out the visitor’s center for art exhibits. We saw American Masters who were coming down to St. Augustine to paint and I know they had a Picasso exhibit as part of the 450 Anniversary but unfortunately we missed that one!
Across the Bridge of Lions is Anastasia Island which has the beautiful St. Augustine Lighthouse that is worth a climb to see the views of downtown and the inlet. Another fun thing to do on the island is visit the Alligator Farm. We have even ziplined over all the reptiles!
The Lightner Museum is housed in one of Henry Flagler’s hotels. It’s such a cool building with a cafe’ located where the indoor pool used to be!
Flagler College was also a Henry Flagler hotel. You can take a tour of this beautiful college campus. 
Explore the side streets, not just St. George Street. The houses are so pretty and you’ll find hidden gardens and fountains!
Now let’s chat a bit about the great outfits I’m wearing. Chico’s provided me with the pieces but the opinions are all my own. Here’s what I’m wearing:
So Slimming Petite Girlfriend Alabaster Ankle Jeans – I love that the petite size is PERFECT on me! I didn’t have to roll or hem these pants. The material is super soft and a perfect weight. Heavy enough to not be see-through but light enough to wear in summer. I also like that the rise is a bit higher than some of my other jeans but they are not high-waisted. I.love.these.jeans!
Petite Double Layer Tank in Majestic Blue – I love this tank! I really, really do! It’s super lightweight but again, not see-through. I don’t have to wear a cami under it! I think the length is perfect. Very flattering. I also love that I can wear a regular bra under it without any peekaboo going on! It’s perfect on its own or layered under the jacket.
Geometric Bi-Color Jacket – Although the days are really hot here (it was 97 degrees with high humidity on the 4th of July!), the air conditioning is set really low so I often bring a sweater or a jacket if I’m going to be inside a building for any amount of time. This jacket is perfect for layering *and* making a bold statement!
Classic Petite Rosemary Dress – This dress is part of the Travelers Line which means that it doesn’t wrinkle! The ruching is quite forgiving. This dress can easily be dressed up or down, making it a very versatile piece when traveling.
Petite Bayleigh Fringed Pullover – This is my favorite piece. I love the color and how unique it looks. It’s like a poncho and tank all rolled into one and it’s also a cold shoulder piece (my first!). It’s knit, like a sweater, but it’s so loosely knit that it breathes and keeps you cool. I wore this when we went on a horse-drawn Vino and Victuals tour. It was hot, but I stayed cool and collected.
Willow Collar Necklace – The links of this necklace are made to look like pieces of bamboo. It has a nice heft to it. I like how the polished silver adds a little extra something to whatever you wear it with. As you see, I’ve styled it with all three outfits and it looks great with each!
I confess that I had never shopped at Chico’s before. I “met” them at the B@M Conference I attended and was so pleased to do a collaboration with this brand! Since then I have learned a few things about this clothing company.
- They have regular *and* petite sizes. I love it when I can find petite sizes! They just fit me better! (I’m 5’1″)
- They have different collections such as the Traveler’s Collection which keeps you wrinkle-free while you travel and the Black Label Collection which has chic black and white pieces.
- I like that many of their models are not in their teens or twenties. That speaks to me because, hey, I’m not in my teens or twenties either!
- They have bold, modern pieces – from clothing, to bathing suits, to jewelry. I encourage you to check them out!
awesome post…love all your outfits and I really enjoyed reading about this town and seeing it too. My fave outfit is that teal cold shoulder poncho!
It was a Spanish colony before any of the British ones so it’s the oldest city in the US! That’s my favorite too!
St. Augustine is my go-to place when I need a Europe fix! It just has that feel! I’ve never shopped in Chico’s, but I’m going to have to scope them out! There’s one at the Tanger near my house. Thanks for all the gorgeous pictures! You look marvelous, and the clothes do too!
Agreed. St. Augustine feels a little bit like my beloved Taormina. Michael was my photographer. He did well, no?
He did VERY well!
Great post! I would love to spend more time in Florida. We’ve only been to visit Disney World! All of your outfits are so pretty – love the off the shoulder poncho. So unique!
Disney is a great destination, but St. Augustine is a great destination for a beach week! Besides the beach, there’s so much to see and do (and eat and drink…)
Now I really want to visit St. Augustine! You did a wonderful job convincing me and looked awfully cute while you did!
Haha! Thanks Whitney! Let me know when you want to go! I will have two kids off at college in August so plenty of space for guests!
Love this post! Off to pin this and loving all of the pictures you got of yourself, you are too cute lady.
Thanks Sarah!
You look dazzling all over St. Augustine. I remember going there when I was young and eating some kind of delicious bread outside the old town. And having a special conversation with my father there. Good memories. Would like to visit again. My granddaughter is leaving for a week there tomorrow with her dad and his family. You featured some many pretty places, I will share your post with them.
Oh how fun! Thanks for sharing my post with her!
Back again. This time as part of the Scavenger Hunt. I am so hungry and the mention of pizza brought me here.
Bwahaha! I sure do love me some pizza!