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  • Writer's pictureCassandra Thomas

Soaking Up St. Augustine

Updated: Jan 22, 2023

A weekend jaunt through the oldest city in the United States.


Nestled on the western shore of Matanzes Bay and over the Bridge of Lions, one will discover a quaint city that looks as if it were built from a painted postcard. St. Augustine may be 450 years old but remains a popular hotspot for tourists and locals alike.


My extended weekend in St. Augustine was a last minute but worthwhile decision in November of 2020. It was Thanksgiving weekend and, for the first time in years, I found myself single and with no amazing city to eat turkey in. A road trip was in order and St. Augustine had always been a place on my Florida bucket-list. And while I initially thought this would be a trip where I would work to mend my broken heart, it ended up being an experience that assured me my heart was indeed still beating.


Flew or Drove: Drove

Total Trip Duration: Four Days


The Hotel

Pros: This new and modern resort comes with ample space, courteous staff, and stunning views. The main lobby is decorated in refreshing neutrals that open up to a courtyard complete with fire pits that are set ablaze just in time for the nightly live music and evening relaxation. The onsite farm-to-table restaurant, Harvest and Wheel, is nestled next to a indoor spacious bar, Rhum Bar, that specializes in rum-based cocktails. And when poolside, there is an additional bar, Castaway Cantina, which serves an incredible agave margarita. I stayed in the King Suite with a Balcony, which was the size of a small apartment and had picture perfect views.


Cons: I wouldn't suggest this resort to any of my single or solo traveling friends. This hotel is ideal for families that want the access to St. Augustine but from a distance. It becomes very quiet in the early evening hours and is not within walking distance to the historic downtown area nor any superb restaurants. Staying here means you need a vehicle, an early bedtime...and possibly a small child.

The Eats

Sunday Gathering Table: When I reminisce on this bright bohemian eatery, I suddenly hear Lionel Richie crooning in my ear. Located in the laid-back area of Uptown, this gorgeously simple cafe served up an aromatic French Press Coffee and flavorful Avocado & Arugula Toast (with egg). Offering both indoor and outdoor seating, the small restaurant specializes in sourdough, fresh local ingredients, and excellent people.


PK's Roosevelt Room: I have had many a delicious quiche but none have compared to the Ham & Leek Quiche from PK's Roosevelt Room. This buttery, almost creamy, yet savory quiche is served with a fresh green apple salad and roasted tomato puree. I easily could have eaten more than one slice but had to settle for topping off my meal with a Pomogranate Mimosa, which was tartly sweet and so refreshing.


Burrito Works Taco Shop: Before hitting the road, I researched some must-try dishes from other bloggers and none came up more than the famous Mexican UFO from Burrito Works Taco Shop. This crunchy, chewy, cheesy, messy goodness is a tostado, taco, and burrito all in one neatly packaged and pressed tortilla. Biting into it, you get all of the amazing ingredients housed inside (friendly tip: choose "The Works" - you won't regret it!). Surrounded by local surfers, I enjoyed my meal outside of this beachy establishment with a cold beer and a huge smile.


Shmagel's Bagels: There is nothing better than a freshly made bagel. Shmagel's Bagels caught my attention while roaming through historic St. Augustine...on a full stomach. I had literally just finished a light breakfast but couldn' pass up on trying their scratch-made jalapeno cream cheese. The bagel itself was soft and chewy with a slightly crunchy exterior, but the homemade spread ad fresh sliced tomatoes were the definite stars.


Prohibition Kitchen (not pictured): I would have loved to have included a picture of the most incredible burger I have ever eaten BUT...it was literally just that good. If ever in St. Augustine (and a carnivore), one must not leave without trying the PK Signature Burger. This burger features a half pound blend of Short Rib, Brisket and Sirloin paired with Smoked Bacon Red Onion Jam, Fried Egg, and Red Dragon Cheese. Amazing. Delicious. Incredible. Phenomenal. I could go on but my mouth is watering just thinking about it.

The Activities

This was a great way to spend a few hours in the heart of St. Augustine. The distillery tour was short and sweet, consisting of delicous tastings of gin and creative cocktails.


An initimate rooftop bar, San Sebastian Winery is the perfect place to unwind with a delicious glass of red (or white), live acoustic sounds, and a nice gentle breeze.


This quaint spa is nestled in Uptown, the quiet residential side of downtown St. Augustine. I enjoyed a delicious brunch before walking to this day spa, where I indulged in a facial and massage.


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