If you have 3 days in St. Augustine, Florida, then do a dance because you’re going to have an awesome time! I recently spent a long weekend in St. Augustine (yay girl’s weekend!), and came up with an awesome 3 day itinerary for you; it’s a great mix of history and of course, yummy food & drinks.
Day 1 | Chocolate, Wine, & Ghosts
Your first stop NEEDS to be at Whetstone Chocolate Factory because chocolate…need I say more? Make sure to get there early enough in the day to hop on a tour. They’re only $8, and you get plenty of yummy samples! Side note: you get some excellent hair nets to wear. See this lovely photo of us!
After your chocolate tour, you’ll probably need to wash it down with some wine, so mosey on over to the San Sebastian Winery. They have FREE WINE TASTINGS, which is basically my idea of heaven. On the weekends, tastings are self-led, so you basically walk around with your little wine cup begging for samples from various locations. It was kind of amazing. However, those small cups really weren’t doing it for me, so after the tasting, we popped up to the rooftop bar for a nice goblet sized drink with gorgeous views!
Lastly make sure to save some time in the evening for a haunted pub crawl. We joined one that brought us to a haunted graveyard and then four haunted bars. Hint: everywhere in St. Augustine is haunted, and your ghost detectors will definitely light up! If you’d prefer the non-pub crawl version, check out this awesome ghosts and gravestones tour.
Day 2 | History & Craft Cocktails
Get your history on in the morning while everyone else is still asleep. Start your day at the Castillo de San Marcos, an old fort with a ton of cool history. Make sure to check out their musket and cannonball demonstrations! I’d recommend going to the fort right when it opens because it gets incredibly busy throughout the day (and hot in the summer!)
A few other cool stops are the municipal marina (because it’s pretty) and the oldest schoolhouse. Some of my favorite lessons from the 1872 rules at the schoolhouse:
- After 10 hours in school, the teachers may spend time reading the bible or other good books.
- Any teacher who smokes, drinks, frequents pool halls or pubs, or gets shaved in a barber shop gives good reason to suspect his worth, intention, and integrity.
- After 5 years of faithful service, a teacher will be given a 25 cent raise per week.
All in all, being a teacher in 1872 sounds horrible. They apparently were also in charge of the chimney cleaning, coal scuttling (still unsure what this is), and making pens for their students.
All that learning will make you thirsty, so spend the afternoon on a DIY craft cocktail tour through St. Augustine! We started off at Odd Birds, then the Tini Martini Bar, took a distillery tour, and finished up at the Ice Plant. In all honesty, I could have spent a day at each of them since there were SOOOO many good drinks to choose from. Some of my personal favorites were the key lime martini and the Florida Mule.
Day 3 | Architecture, Shopping, & Beaches
In the morning, pencil in some time to walk around Flagler College and the Lightner Museum. The museum wasn’t open when we were strolling around, but it definitely looks like an awesome spot to explore!
Next up is St. George Street, a wonderful pedestrian only area filled with shops and lots of ice cream stores (there are two Kilwins, which is basically the best ice cream store ever!) While you’re in the area, hop over to Spanish Street, home to some gorgeous old homes and bed & breakfasts. I kind of fell in love with this little area.
After your morning explorations, pack up a picnic and drive to Anastasia State Park for some quality rest and relaxation. Enjoy your picnic, read a book, take a nap, and just enjoy the peace of the beach!
If You Have Extra Time…
If you move through activities quickly or have more than 3 days in St. Augustine, consider adding in some of these additional things to do:
- Trolley Tour – So this would probably be useful even as part of this 3 day St. Augustine itinerary, but consider investing in a hop-on, hop-off trolley pass. It can get pretty hot in St. Augustine, so even though the distances are short, you can get worn out walking around.
- Fountain of Youth – This is the likely 1513 Florida landing site of Spanish explorer Ponce de Leon…more great Florida history here!
- The Old Jail – This is one I definitely want to do next time because jails are super fascinating. Take a guided tour through the prisoners’ cells and you even get to visit maximum security from back in the day!
- St. Augustine Beach – If you have some extra time, add in St. Augustine Beach and make a day of it!
- Oldest Store – If you haven’t caught on yet, St. Augustine has a lot of “the oldest” things, including this store that is set in the early 1900s…I’ve added this tour to my to-do list!
Where to stay in St. Augustine: St. Augustine has so many adorable bed & breakfasts so this would probably be my first choice. Check out Victorian House or Casa de Solana, which are both in the city center. If you’re like me and wait to book a place to stay until two weeks before a long weekend, the bed and breakfasts will probably be booked so check out the TRYP by Wyndham. It’s slightly further from town, but still walking distance, plus it has free parking and a hot tub! One more option is to check out Airbnb and stay in a local’s house or apartment! (Use my link for savings on your first stay!)
Cheap Flights to Jacksonville: I’d recommend checking out Momondo. They scan tons of different travel discount sites and let you filter by cheapest, best, and shortest.
St. Augustine Car Rentals: You won’t need a car too frequently to get around town, but if you’re flying in for your visit, you might want to have access to one to get to the beaches. As far as rental cars go, you can’t go wrong with CarRentals.com . They pull from a number of different car companies, and definitely provide good deals. If you’re looking for a luxury rental, try Sixt –they provide some legit deals on premium and luxury rentals!
For further reading on Florida, make sure to check out the following guides!
- Sarasota, Florida Guide – Discover some of Sarasota’s most unique activities, as well as top hotspots for food & drink!
And there you have it, an epic 3 days in St. Augustine! Have you been to St. Augustine before? What were some of your favorite things to do?
P.S. This post contains affiliate links. If you click on one and make a purchase, I might make a little extra spending money, at no extra cost to you. As always, all opinions are my own.