3 Days in St. Augustine: Your Perfect Itinerary

Planning a trip to St. Augustine and not sure where to start? With 450 years of history, stunning Spanish-inspired architecture, and a laid-back coastal vibe, this city has a little bit of everything. St. Augustine is the kind of place where you can spend hours getting lost in the historic streets—or just lounge on a sunny beach with a good book.

For your 3 days in St. Augustine, I’m going to break down the best things to do in St. Augustine so you can make the most of your visit. From must-see landmarks to hidden gems, this guide will cover it all without leaving you with a case of FOMO. Whether it’s your first time here or you’re making a return trip, you’re sure to find something new to love. So, let’s dive in and make those three days count!

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Day 1: Sweet Treats, Stunning Views, and Spooky Sips

Whetstone Chocolate Factory

Let’s be real—starting a trip with a chocolate tour is peak vacation behavior, and I have zero regrets. At the Whetstone Chocolate Factory, you get to tour the facility and sample chocolate like a professional—which to my understanding means eating as much as possible without looking desperate. It’s the sweetest way to kick off your 3 days in St. Augustine adventure (pun intended).

Whetstone Chocolate in St. Augustine, Florida

St. Augustine Lighthouse

After all that chocolate, it’s time to work off a few calories by climbing 219 steps to the top of the St. Augustine Lighthouse. The view is incredible, and once you catch your breath, you’ll get a panoramic look at the city and the beach. There’s also a maritime museum if you’re a fan of old shipwreck stories—but if you just came for the Instagram-worthy views, who am I to judge how you’re spending your 3 days in St. Augustine?

St. Augustine Lighthouse

San Sebastian Winery

By now you have done sooo much work (those lighthouse stairs are no joke!), so it’s time for a wine break. The San Sebastian Winery is a local favorite and offers free tastings, which is basically the wine-lover’s version of finding a hidden treasure. You can also head up to the rooftop bar for some live music and more wine—because why stop at just a tasting?

San Sebastian Winery in St. Augustine, Florida

Haunted Pub Crawl Tour

Lastly, make sure to save some time in the evening for a haunted pub crawl. St. Augustine is famous for its ghost stories, and hitting the city’s creepiest bars with a guide who knows all the spooky details is a great way to mix history and happy hour. If you’d prefer the non-pub crawl version, check out this awesome ghosts and gravestones tour.

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Day 2: Forts, History, & Craft Cocktails

Castillo de San Marcos

Get your history on in the morning while everyone else is still asleep to kick off the day 2 of your 3 days in St. Augustine. 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!)

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The Oldest Schoolhouse

After your stop at Castillo de San Marcos, I’d recommend checking out 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.

DIY Craft Cocktail Tour

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.

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Day 3: Architecture, Charming Streets, & Beachy Bliss

Flagler College

Kick off the last of your 3 days in St. Augustine with a bang. Flagler College looks more like a European palace than a college campus. Originally built as a luxury hotel by Henry Flagler, it’s all grand staircases, stained glass, and those fancy ceilings you’re almost scared to walk under.

Flagler College drone shot from above in St. Augustine, Florida
Flagler College

Lightner Museum

Next, head over to the Lightner Museum, which was also built by—you guessed it—Henry Flagler. It’s housed in another former hotel, so expect more grand architecture, fountains, and a feeling that you should have worn fancier shoes. Unfortunately, it wasn’t open when I was there, but judging by the exterior, it’s worth a visit. The building is absolutely gorgeous, and if the inside is half as pretty, you’re in for a treat.

Lightner Museum in St. Augustine, Florida

St. George Street

Next up is St. George Street, a wonderful pedestrian only area filled with shops and lots of ice cream stores (there are two Kilwins shops – my favorite ice cream store!) While you’re in the area, hop over to Spanish Street, home to some gorgeous old homes and bed & breakfasts. If you’re a fan of historic charm with a side of souvenir shopping, this is your spot.

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Anastasia State Park

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! There’s no better way to wrap up your 3 days in St. Augustine.

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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!
  • 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!
  • Oak Canopy at Magnolia Road – This is one of the most picturesque spots in St. Augustine, and you can’t help but grab a few snaps for your Instagram!
Oak Canopy at Magnolia Road in St. Augustine, Florida - one of the top Instagram spots in St. Augustine
Oak Canopy at Magnolia Road

St. Augustine packs a lot of punch for a small city, with haunted pubs and enough historic sites to satisfy your inner history nerd. It’s the perfect place for a long weekend escape—whether you’re chasing ghost stories, indulging in chocolate, or just enjoying the laid-back Florida vibe. With 3 days in St. Augustine, you can get a taste of the city’s best without needing to take a vacation day to recover. And hey, if you’re anything like me, you’ll leave with a full camera roll and a lingering suspicion that you might have had a drink with a ghost!

Where to Stay in St. Augustine

When it comes to planning where to stay for your 3 days in St. Augustine, bed and breakfasts are where it’s at. They offer a cozy, charming vibe that fits perfectly with the historic feel of the city. Plus, nothing beats waking up to a homemade breakfast in a centuries-old building. Here are a couple of my favorite B&Bs:

Victorian House: Step back in time with a stay at Victorian House, a charming bed and breakfast in the heart of the historic district. This cozy spot is full of antiques, beautiful woodwork, and a welcoming atmosphere that makes you feel right at home. Plus, it’s just a short stroll away from some of St. Augustine’s best attractions.

Casa de Solana: Casa de Solana offers a little slice of Spanish-inspired paradise right in downtown St. Augustine. This historic bed and breakfast has been around since the 1700s, giving it a unique blend of history and modern comfort. It’s an intimate retreat that feels like a hidden gem.

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20 Comments

  1. I’ve been here and loved it! You found some chocolate, too (which I missed). And I must say I love, love, love your blue outfit. You look so pretty in your photos!

  2. I’ve never heard of St. Augustine but it actually sounds awesome! Nice mix of history, nature and alcohol! What’s not to like?! Definitely need to look into this as I don’t know much about Florida apart from the usual suspects!

  3. Hi! Thanks for sharing, this will definitely come in handy next week when I visit. Could you tell me which haunted pub crawl tour you took? Going to a haunted graveyard sound awesome!

    1. It’s called the Original haunted pub crawl, so much fun! The pub crawls all seemed relatively similar (we kept seeing the same group lol), so I don’t think you can go wrong with any of them!

  4. Grew up in Saint Augustine and any readers I can assure you- this is a pretty great itinerary!

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