Our St. Augustine Getaway

The nation’s oldest city offers a charming downtown, amazing food and drink options, and beautiful beaches. Ryan and I will definitely be back to this Florida gem!

LSS ST AUGUSTINE

Our recent trip to St. Augustine, Florida was pretty random! We had an existing flight credit (we had to change some flights around last fall due to a hurricane) that was set to expire, so we opted for a flight to Orlando that cost the exact amount of our credit. We didn’t know exactly what we wanted to do once we got there, but, we had a booked flight! In hindsight, we definitely would’ve flown into Jacksonville instead, but we didn’t know where we were headed at the time.

After a thorough Pinterest and Google search of new towns to visit in Florida, we finally decided we were going to stray outside of the Orlando area and drive up to St. Augustine.

LSS ST AUGUSTINE AIRBNB
LSS ST AUGUSTINE AIRBNB
LSS ST AUGUSTINE AIRBNB

There are lots of bed and breakfasts and boutique hotels in the area, but ultimately we opted for an Airbnb located just one block from all the restaurants, bars, and sights! And, it was nice to able to spread out a bit, have more privacy, and enjoy some wine on our quaint porch. If you’d like to book the same Airbnb for your stay, you can find it here. There was another larger unit available in our building (large historic home) as well! It was well decorated, had a massive kitchen, and allowed for easy street parking!

LAURA SWAN SIECKMAN AVILES STREET

Self check-in at our Airbnb was a breeze, and after freshening up a bit, we walked over to Cellar 6 for their happy hour! I would highly recommend stopping here as it was an amazing value for drinks and small plates. We enjoyed $4 glasses of wine, $6 Old Fashioneds, $5 Truffle Fries, and a couple other items off their shareable menu! Afterwards we stopped by a cigar bar called Stogies, which offers you a free cigar with your first draft beer, and then over to Odd Birds, where we ended up spending the rest of our evening! We met a crew of locals that we drank with, sang with, and danced with on the outdoor patio and had SO much fun!

LSS CELLAR 6 ST AUGUSTINE
LSS ODD BIRDS ST AUGUSTINE

The next morning we snuck in a quick workout at a local gym (not walking distance, but easily driveable), snagged a sandwich, and made it a beach day! We headed over to St. Augustine Beach and found easy public parking next to a hotel complex just north of the pier. The beach was wide open, pristine, and very swimmable! There were lots of people boogie boarding and surfing as well. It was so relaxing to lay out on the sand, listen to the water, and take a cat nap. There were outdoor showers right by where we parked too, so it was easy to rinse the sand off of us before leaving!

LSS ST AUGUSTINE BEACH PIER

Later in the day we showered and changed, and then walked over to the meeting spot for our Corks + Forks food +wine tasting tour! Our tour guide Marcy was the nicest southern mama, and we had a blast visiting restaurants and shops we normally wouldn’t have visited! The food was delicious and the wine was plenty, so it was WELL worth the ticket price. Our favorite stops were The Ancient Olive, Old City House Inn + Restaurant, and Casa de Vino 57!

LSS ST AUGUSTINE WINE BAR
LSS ST AUGUSTINE FOOD TOUR
LSS DOWNTOWN ST AUGUSTINE

After our tour (which wrapped up just before 8PM), we roamed around the historic downtown streets (St. Augustine feels like a mix between Savannah, GA and New Orleans, LA to me!), stopped in a few shops, and then parked ourselves at Prohibition Kitchen for live music and build-your-own Old Fashioneds. I would recommend snagging a seat at the bar if it is just the two of you - it was fun to chat with the bartenders about different bitters and syrups you could try in your drink! My favorite combo was Elijah Craig Bourbon with Peychaud’s Bitters and Simple Syrup.

LAURA AND RYAN
LSS PROHIBITION KITCHEN ST AUGUSTINE

The next morning was a repeat of the last - workout, lunch, and beach! We took up the same spot on the sand as the day before because we loved it so much. That evening, we started off by visiting the Medieval Torture Museum, an intense showcase of torture devices from various centuries. I was a little disappointed by some of the informational descriptions / plaques throughout the museum (they were a little vague on how each piece was used), but generally speaking, you could use your imagination on what each piece was for based on its’ setup. I’m really happy that I was born in the 1980’s - I probably would’ve been tortured as a witch if I had been alive in any other century. Eeek!

LAURA SWAN SIECKMAN ST AUGUSTINE

After the museum, we walked nearby to Catch 27 for an amazing seafood dinner! I would recommend getting a reservation here as the place was filled within minutes of them opening for dinner service. We enjoyed fresh guacamole, chowder, salad, scallops, and flounder at our meal and it was phenomenal! They also made a damn good cocktail.

LSS CATCH 27 ST AUGUSTINE
LSS CATCH 27 ST AUGUSTINE
LSS CATCH 27 ST AUGUSTINE

After dinner, we picked up some beer and wine and snagged a quick UBER over to Vilano Beach Pier for an adults-only BYOB sunset cruise on the water! The boat fit about 30 people or so, and we saw dolphins and views of the downtown while sipping drinks and listening to music. It was SO relaxing, and the crew was awesome. The cruise lasted about an hour and a half, and once we returned, we finished the rest of our drinks on the pier (not quite sure if that was actually legal or not) and watched the fisherman. We even saw someone catch (and throw back) a baby shark!

LSS DOWNTOWN ST AUGUSTINE

There’s a fun beach bar (ironically) called Beaches at the end of the pier that is great for views of the water and a couple of cold ones. We finished a couple of beers here before taking an UBER back downtown and calling it a night. It was the perfect end to our trip!

LSS ST AUGUSTINE
LSS ST AUGUSTINE BEACHES BAR

The following morning we packed up and set out back to Orlando for our flight home. We were SO glad that we ended up choosing St. Augustine as our “random” destination for this trip, as it ended up high on our list of favorite spots. We’ll be back for sure! Have you visited? Leave me a comment below and tell me your favorite spots!

XOX LAURA

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