St. Augustine: Florida's Oldest Happy Hour

We’ve visited St. Augustine several times over the years. It’s a field trip for most Central Florida fourth graders - visiting Castillo de San Marco and the Fountain of Youth are must-sees for children studying Florida history. 

The oldest city in the U.S., St. Augustine has a deep and sordid history that one can hardly keep up with. The Spanish, the English, the pirates, the railroad, and civil rights all converge on this one spot. It’s really something you have to take in with a drink. So here are our liquid highlights and musings on the historic city located just an hour and a half from Sanford.

Our Favorites

St. Augustine Distillery

Our visits to St. Augustine usually begin at the St. Augustine Distillery (go figure) to pick up a few bottles of their award-winning vodka, gin, rum, and bourbon. They distill in Florida’s oldest ice plant. The distillery tour is a MUST to see more history, the process, and to partake in a tasting before you exit through the gift shop. It’s one of the best distillery tours we’ve done and it’s free!

We absolutely love St. Augustine gin - it’s perfect for a Martini with a twist, and we especially enjoy it in a Bee’s Knees.

Ice Plant

Located in the same building as the distillery is Ice Plant bar and restaurant. They take their ice, cocktails, and farm-to-table cuisine seriously and you won’t be disappointed no matter what time of day you visit. The cocktails change seasonally and the Mr. appreciates the drawings of the glass the cocktail will be served in displayed next to each name and list of ingredients. Yes, this sometimes always affects what he orders.

They do not take reservations so time your visit before or after the usual meal time rush.

Odd Birds

For another round of delicious cocktails head to Odd Birds. Here “the rule is oddness in a relaxed and chill environment.” We’d like to add on to that rule and tell you it’s important to go early, particularly on weekends. The place tends to get pretty packed later into the evening and you’ll miss out on chatting with the skilled bartenders who enjoy adding an extra flair to each drink. Our other piece of advice is to trust your bartender and let them make you something unexpected based on just a couple of preferences. We’ve never been disappointed. Oh, and order the arepas to pair with your cocktails!


Sanfordites and historic preservation buffs will enjoy brunch at Preserved. This restaurant completely transformed the historic Victorian-style building (and surrounding neighborhood) from a seedy convenience store into a beautiful setting to enjoy Southern dishes. You won’t find the hard stuff here but there’s a good beer and wine list. For brunch, have a Shrubmosa - sparkling wine and a splash of shrub, consisting of pressed juice and apple cider vinegar from a farm in Jacksonville. Preserved is so nice that we went twice in one weekend!

You’re sure to find other spots to your liking - make dinner reservations at The Floridian or Catch 27. Hang out at the breweries and stroll Old Town with an ice cream cone. 

And a really great way to eat and drink your way around town is with a food tour. We did one a couple years ago with family and had a blast with Lynn, our tour guide. Each tour stops at five restaurants, all within walking distance of one another. Along the way your guide will weave in the history of St. Augustine and pair it with the food and drink you’re having from that particular culture. 

But Wait, There’s More!

  • Attend a concert at St. Augustine Amphitheater. This is our favorite music venue!
  • Soak in some history at the Lightner Museum. Browse antiques in this former hotel built by famous Florida industrial/railway tycoon Henry Flagler.
  • It would definitely be difficult to miss the Castillo de San Marcos, the oldest masonry fort in the continental United States. Visit in the early morning when it’s cooler and less crowded. 
  • Head across the intracoastal to visit the St. Augustine Lighthouse & Maritime Museum for great views (the 219 steps up to the top of the lighthouse are not for the faint of heart).

Random (But Useful) Tips

  • Even for Floridians, summers in St. Augustine are HOT. If you must visit in the summer we recommend making it more of a beach trip and don’t leave home without your sunscreen. But cooler weather can bring the crowds to the historic city and all the traffic pains that come with it. If visiting in the nicer months, park the car for your stay and see the town on foot.
  • And if the historic bed and breakfasts are out of your budget, check out AirBnB for cute properties just blocks away from all the history, food, and drink. We've stayed in several - email us if you'd like a recommendation!