Guest Post: Sippin Gypsy In St. Augustine

Posted On April 6, 2018

St. Augustine Guest Post by Sippin Gypsy

St. Augustine has been a new attraction to me as of late, I have seen so many people visit this beautiful, historic town. Therefore, it has been added to my bucket list and I wanted some more information from someone who has been there.

Bring in Kristin, from Sippin Gypsy, who had the opportunity to fill me in some more.

Sippin Gypsy’s time in St. Augustine

Cheers Travelers! This post comes to you while enjoying my Sippin Gypsy Spicy Vodka Sip featuring St. Augustine Vodka inspired by my visit to the Distillery in  St. Augustine, Florida.

St. Augustine is one of the oldest cities in America founded in 1565. Also known as The Ancient City, this charming community has held on to the beauty of her Spanish roots. It’s conveniently nestled along the eastern coast of Florida giving you the best of both worlds, a relaxing day at the beach, and carefully preserved historic sites and architecture.  Convenient for someone like me who loves seafood and southern cuisine, St. Augustine has packed in a cornucopia of delicious spots to accompany a walk through history.

The Ancient city packs in so much to experience within the few blocks of the historic district.   

There are restaurants, shops, a distillery, a winery, museums and historic sites to explore. When I first arrive to any city, I always enjoy an overview of history by doing the tourist thing and exploring through an organized tour.  The Old Town Trolley Tour not only gives you insights and history, but also allows you ‘on and off privileges’ which means you can use the trolley to also get around between destinations.  The Oldest Wooden School House as well as the Oldest House Museum take you into structures that have been carefully preserved to show you what life was like in colonial St. Augustine. The Lightner Museum was originally one of the luxury hotels but now is an airconditioned retreat that takes you through the centuries of successes and turmoil St. Augustine has endured.  

Since there is so much to do while in St. Augustine, I found it very helpful to download the Visit St. Augustine app to assist me in selecting what to do and navigating the attractions. One of my favorite places to visit in St. Augustine is the St. Augustine Distillery. 

I try to support local when I travel, and the St. Augustine Distillery offers a tour, sampling and the ability to stock up on several spirits including Gin and Vodka.  I prefer to start at the St. Augustine Distillery on my drive into the historic area of St. Augustine. I always pick up a few bottles of their gin and other liquors for my home bar, and its easier to take them directly to my car instead of lugging it onto the trolley and back to the hotel.  While at the St. Augustine Distillery, come hungry and visit one of my favorite spots in all of Florida…the Ice Plant Bar above the distillery. The food is flavorful and cocktails are creative and delicious.

St. Augustine has no shortage of restaurants and bars.  

If you are in St. Augustine over a weekend, the San Sabastian Winery  hosts tours and has a beautiful rooftop lounge to catch the sunset while enjoying wine and live music.  In continuing my pursuit of supporting local and enjoying flavors indigenous to an area, The Floridian and Preserved offer wonderful plates from locally sourced farms.  

One of the truly fun things about St. Augustine is the surprising locations that offer something to sip on.  Crucial Coffee is literally a wooden shack that has coffees and other refreshing blended non-alcoholic drinks.  

At night, Odd Birds bar is one of my other favorite spots in St. Augustine.  Eclectic and unassuming, this charming spot crafts some of the best cocktails I have had in Florida.  It’s easy to wander up and down the streets of the historic district in St. Augustine and find a lively spot with great music.  I personally enjoy the live music and ambiance at Prohibition Kitchen, but each bar hosts a variety of entertainment and most will offer live music on the weekends.  

If your travels take you to St. Augustine in the winter, the whole town transforms with millions of lights for an event called Nights of Lights.  Lit up homes and historic buildings make for a very magical holiday getaway and a truly memorable way to experience St. Augustine.  Just after Thanksgiving the Nights of Lights begin. I like to arrange a two or three night getaway in early December to enjoy the lights and do some holiday shopping.

One of my travel indulgences is to stay in posh lodgings that place me right in the heart of the historic districts of any city I’m visiting.  

St. Augustine has so many beautiful and comfortable Bed and Breakfast options that place you within footsteps of historic sights entertainment.  Carriage Way Bed and Breakfast and 44 Spanish Street Inn Bed and Breakfast are two truly elegantly appointed historic homes that are that a perfect blend of comfort and retreat. Both homes are for adult guests, so they are perfect for a romantic getaway or a girls trip! It’s always nice to have a warm homecooked breakfast every morning before getting your day started.

My other favorite lodging in St. Augustine is the historic Casa Monica Hotel .  Every hallway and and corner in this impressive structure is adorned with historic art and lavish details.  I love the location of the Casa Monica, we were able to walk to everything in the historic district in the evenings.  The hotel also has its own restaurant and bar which was nice when first checking in before heading out for the day. One of my favorite spots is the rooftop pool at the Casa Monica.  Mornings were great here to catch a little reading time in the sun before exploring.

In Conclusion

St. Augustine is a town I am fortunate enough to get to visit often.  Although small, The Ancient City packs in so much to see and do especially if you love history!   When your travels bring you to the eastern coast of Florida, plan on a few days in St. Augustine and enjoy experiencing her journey through time and the hospitality and flavors she offers! Cheers!

Meet Kristin

Kristin started Sippin Gypsy as a way to catalog her experiences and offer helpful tips from her travels as she explores the world sip by sip. See more Sippin Gypsy travel suggestions as well as cocktail recipes inspired by each location at  


  • Salut, je m'appelle Alexis et j'ai 35 ans. Je suis un passionné de voyage et je partage mes aventures sur mon blog depuis maintenant plusieurs années. Mes destinations préférées sont celles qui sortent des sentiers battus et qui offrent une immersion dans la culture locale. J'aime aussi beaucoup les voyages en solo, qui me permettent de me déconnecter du monde et de me recentrer sur moi-même. En dehors de mes voyages, j'aime aussi beaucoup la randonnée et le camping, et j'essaie de passer autant de temps que possible dans la nature.