Did you know St Augustine by record, is the oldest city in America? It just so happens to be one of my most favorite spots to visit.
One of my besties spoiled me for my birthday to an overnight stay at the Hilton St. Augustine Historic Bayfront. What a treat that was. 🥰
We had a corner room with a wrap around balcony overlooking the backstreets of the Historic downtown area and a view of the St John’s River. Prime location, walking distance for all of downtown.Â
We started off with my first visit to Forgotten Tonic. This is for sure a must stop while visiting St Augustine. It’s considered a local, hidden neighborhood gem offering American comfort food, an extensive wine list, hand-crafted cocktails & captivating southern hospitality.
My first cocktail of the afternoon was their signature drink, the “Forgotten Tonic”. Navy strength gin, french herbal liqueurs, quinine, lime, seltzer..I loved this cocktail, it was smooth, light and very refreshing which was perfect for this extremely hot, Florida afternoon. Pricing is scaled towards the higher end, but you get what you pay for here. Quality over quantity for sure. Mixology, true craft cocktails.$$
We then headed over to 1 of my regular spots, Pizzalley’s Chianti Room! We were starving and wanted all things cheesy!! We started off with the mozzarella moons and captured 1 heck of a cheese pull!! The marinara dipping sauce was a struggle to share, it’s the perfect marinara sauce for me 🥲 Â
I’ve got a picky bestie, so we went for the Extra cheese pizza and I’m not mad that we did. The cheese on this pizza has to be Grande, which is my favorite and easy to identify. If it’s not, it’s just as delicious…and perfect for another award winning cheese pull! 🏆 (am I the only one who is obsessed with cheese pulls)? $$Â
Next we stopped at Sangrias Wine & Tapas Bar and I ordered… a sangria… but of course ! And a strong sangria it was. I went with the Reilly’s Rojo, red wine base, with cranberry, apple and a hint of peach. I think I would stick with a classic next time. Great balcony spot for people watching for sure. You have to stop by at least once and sit outside on the balcony. They have small bites, wine, sangrias, bottled and draft beers. $$
Off to the popular, local dive bar Trade Winds Lounge. Visit their website https://tradewindslounge.com/about/ to learn more about their history. They always have great, live music entertainment and $5 rum punch that we actually enjoyed!
We sipped and enjoyed music, singing along, and people watching until it was time to head out for dinner.Â
We didn’t want to be on a schedule so we didn’t make reservations. We stopped in at Auggie’s Draft room for a burger. They have 24 Self-Serve Taps, 10 big-screen TVs, and a menu that offers lots of burger choices including, build your own. I ordered the Auggie’s Jr Bacon Cheeseburger, it was the perfect size and it was delicious, hit the spot! Sports fanatics will love this spot. Service was fast, even on a Saturday night! $
We then walked over to another favorite spot of mine, the Tini Martini Bar. I have worked my way through the martini menu, and my favorite remains the salted caramel martini. And do NOT WASTE the caramel in the glass when the martini is gone. Trust me! You get 2 pours per order, and it’s beautiful lit with torches and strung lights at night time. Side note, they do not serve food. Do not go hungry. $
We were going to go to the room, early 9:30, but got a 2nd wind and screamed YOLO! We headed back to Trade Winds Lounge to finish the night. We paid a $5 cover fee for the band Live Stream. I have to say they were phenomenal! Every song was a sing along. They played anything and everything from Bon Jovi to Led Zeppelin, to Journey. We had an absolute blast, it’s always a good time, I feel like I’m missing out if I don’t at least pop in for a drink.Â
We rested well in our room, the bed was super comfy. We woke up around 7 and didn’t get moving until a little after 8 Sunday morning. We took our time getting ready, checked out and decided to skip breakfast and have an early lunch at Burrito Work Taco Shop.Â
After admiring and stalking people at the Tini Martini Bar the night before, who were smashing on these delicious looking wrap like soft maybe crunchy on the inside tacos? We weren’t sure, so we asked… LOL and they all had what’s called the UFO, and that’s what we ordered.Â
I split that with my daughter, we ordered the works and the chicken was our protein. I’m embarrassed at how much we enjoyed this and can’t wait to have it again! We also ordered the Rasta Sampler: Guacamole, Queso, Salsaand Chips and the 3 of us couldn’t finish it but everything was delicious!!! $(shareable portions)
We stopped at a few boutiques including one of our very favorites, the Red Pineapple, I bought 2 new pieces of jewelry.Â
We stopped in Kilwins for a scoop of delicious ice cream, I had 2 scoops the salted caramel and a toasted coconut I believe it was. I always get the coconut flavor here! I couldnt finish it all, but I had to have 2 flavors, Lol. Their ice cream is yummy and homemade, with 32 flavors to choose from. They have all kinds of delicious assorted candy, caramel, chocolate coated apples and they’re also known for their in store made fudge with right around 11 flavors to choose from.Â
Our last stop was the bar located at the Auntie Anne’s spot, I forget the name of it, it’s newer, outside seating with live music, it used to be Mi Casa, we ordered a frozen lemonade margarita and it was delicious and refreshing as it was a pretty hot afternoon. We enjoyed the one man and and oscillating fan at a shaded table.Â
There’s a lot more to do than eat & drink, but for this weekend that was our agenda and we made the most of it.Â
The Spanish fort is a site to see, you have to do at least one ghost tour, and you definitely need to visit during the holidays when the Nights of Lights is featured.Â
Lots of shops, novelty stores, boutiques, bed and breakfasts, art galleries, so much to see and do all within walking distance.Â
🎶 Be sure to checkout the smaller amphitheater right in the heart of downtown -Colonial Oak Music Park at night time. Concerts usually start around 7.Â
Be sure to head over the bridge and tour the well known light house marked as 1 of the most haunted landmarks in the world! We did a night time tour there and it was definitely a scare and something fun to do at least once!
Other restaurant mentions;Â The Floridian, 1 of my favorites, fresh ingredients, vegetarian options, fresh made to order. $$
Pizza Time, casual, counter service, cash only with an ATM inside. Their pizza is one of my absolute favorites! $
St George Inn Restaurant, reservations recommended. European-Influenced American Cuisine, a little more upscale, exceptional service and dining experience. $$, $$$
Auggies Mini Donuts- freshly made, warm and scrumptious 🥲 $
Pks Roosevelt Room for brunch-chefs strive to showcase the finest local farmers, fishermen, butchers & bakers$$
Prohibition Kitchen- Tapas, soups, salads, sandwiches and burgers, and a great bar, busy, but cool, happening spot!$$
And a place near and dear to my heart, Milltop Tavern, a family favorite for years, casual bar/restaurant, live music $Â
Osteens- have to get their fried shrimp and the tiger sauce is out of this world! Cash only and it’s a dry restaurant. Diner, family style environment. $
Columbia Restaurant, beautiful inside, been there many times with my Dad. Most famous for the 1905 Salad! $$
Harry’s Seafood Bar & Grille- Cajun, creole, and southern flavors infused. Beautiful lit up courtyard at night. Love their crab cakes.
For lodging, I recommend checking out  Airbnb, and Vrbo, lots of affordable, cute cozy choices.
St Augustine, a beautiful city, so much history lots to see and do! During the holiday season be sure to check out the Nights of Lights from Nov 19th, 2022, to Jan 31, 2023.Â