Day Trip Guide: St. Augustine, FL

Ice Plant - St. Augustine, FL is a must stop for craft cocktails

Since moving to Central Florida in 2012, day trips have sort of become my jam. Living in a state where people regularly come for their yearly vacations means an endless supply of things to do, and I’m making a commitment to explore more this year and in the future. Day trip guides feature locations accessible in 2.5 hours or less that are small enough to be enjoyed in just one day.

St. Augustine, FL

The Basics

St. Augustine, located on the East coast south of Jacksonville, is the oldest city in the United States. Ornate buildings, narrow cobbled streets, and rich history can be found at every turn and there are numerous attractions to visit.

You could easily spend a week in St. Augustine visiting every attraction, but if you’re visiting for the day (still totally worth it!) you’ll want to do some prior planning and choose just a few activities. I recommend arriving early (8:30-9:00am) as many of the attractions are closed by 5pm. Plan for a 2 hour drive (each way) from Orlando.

Flagler Memorial Presbyterian Church, St. Augustine, FL

What to Do

Old Town Trolley Tours
A trolley ride is the ideal introduction to the city, especially if this is your first visit. The trolley runs daily with 23 stops throughout town, starting and ending at The Old Jail. When purchasing your trolley ticket, you can add on attraction tickets for the places you’d like to visit (at a slight discount). If you’re visiting for the day, choose no more than 3, otherwise you’ll feel rushed.

While on the trolley, you’ll get a full history of the area from your trolley driver. You can opt to stay on the entire route to get the full history in one go, or hop on and off throughout the day at designated trolley stops. It’s your mode of transportation and an informational tour all in one!

Flagler College / Ponce de Leon Hotel
After 3 visits, this remains my favorite tour in St. Augustine. Flagler College, originally the Ponce de Leon Hotel, was commissioned by Henry Flagler (a major pioneer of Florida’s development) and built in an impressive 18 months. His vision was for a grand, luxury hotel, still standing today and restored to its former glory. If you’re not in awe from simply stepping into the courtyard (with its central fountain that doubles as a sundial) then you’ll certainly be wowed when entering the building and gazing up at the Tiffany stained glass and intricate ceiling paintings.


The hotel (which ceased operations in the late 1800s) is now Flagler College, a liberal arts school, and all tours are led by students. You’ll learn about what the hotel was like in its glory days, and gain access to the private Flagler Room (containing original furniture, artwork, and more), while learning about the college.

The Old Jail
A bit cheesy, but fun! Your guide will lead you on the tour as if you’re an actual prisoner – explaining what to expect (like ridiculously long workdays, a monthly bath where everyone uses the same water, and all of the critters that will be joining you in your cell) while giving a history of the jail. The end of the tour leaves time for you to explore the main cell block along with old photographs and a weapons collection. The tour only lasts about 40 minutes and is a nice thing to do at the end of the day before dinner.

staugustinefl-distillerySt. Augustine Distillery
Relatively newer to the area, the distillery opened up in 2013. Distribution laws still limit purchases to 2 bottles per person PER year, but it’s better than nothing. The distillery offers tours for FREE everyday and that includes free samples of the alcohol. I can’t speak to the tour as I arrived after the last tour of the day, but there’s a wonderful museum onsite which includes much of the information given on the tour. You can also visit their gift shop for free samples.

staugustinefl-streetsExplore on foot
The best thing you can do when visiting St. Augustine for the day is to leave a little breathing room in your schedule. When afternoon rolls around, leave a break in between tours to simply walk around admiring the old homes and buildings, colorful foliage, and narrow streets. This is the best way to appreciate the beauty of St. Augustine and it’s completely free. It’s also a great way to discover where to stop for lunch.

More options
Castillo de San Marcos is a fort located right on the water that also happens to be the oldest masonry fort in the U.S. Definitely worth visiting, just give yourself at least a few hours to see everything. Also of interest is the Flagler Memorial Presbyterian Church for it’s stunning dome and beautiful architectural details. If you don’t mind getting home late, stick around after dark for a walking ghost tour.

Where to Eat

Cousteau’s Waffle and Milkshake Bar
My mom and I spotted Cousteau’s while riding by on the trolley, both saw the word “milkshake” and exchanged a knowing look. We made our way to Cousteau’s after lunch (tacos – are you surprised?) and once inside I noticed the whole place is themed after Jean Cousteau and the Wes Anderson movie The Life Aquatic. You even get a discount if you wear a red beanie! The “Stevezie” milkshake was amazing with huge hunks of cookie dough. I will be back for a decadent waffle…

Cousteau's Waffle & Milkshake bar in St Augustine, FL

Ice Plant Bar
Ice Plant is attached to the distillery and while the cocktail and food menu may look intimidating at first, have faith that anything you order will be fantastic. If all else fails, just get yourself a cocktail and an order of soft pretzels and you’ll be happy. (Still having dreams about that white cheese dip.) Craft cocktail bars can occasionally be both intimidating and pretentious, but Ice Plant is neither of those things. The bartenders are eager to answer questions and help you choose a cocktail you’ll enjoy, and same goes for the food.

Cocktails at the Ice Plant in St. Augustine are a MUST!Dinner at Ice Plant in St. Augustine, FL

For cocktails, I had the Ping Island (my favorite) and the Dusk Til Dawn, and my mom was a big fan of the Florida Mule and Grandma By the Pool. Dinner was a bowl of Carrot Ginger Soup and Shrimp Ceviche–both delicious–but the Wagyu burger that John, my mom, AND my stepdad ordered was also a crowd pleaser. This is a pricier option for dinner, but 100% worth it.

Yes, you’re going to do a double take when you pull up and notice that Carmelo’s is attached to a gas station. But trust me on this! Of the foods I consider myself to know well, pizza is in the top 3, and this is some of the best pizza I’ve had. I was put off by the gas station situation but all fear melted away once I took in the friendly and warm atmosphere. Nothing tastes better than a hot calzone or a giant pizza after a long day of trekking around in the Florida sun.

Raintree Restaurant
Set in an old Victorian home, Raintree is an upscale dining option where you can continue your immersion in history after the historical sites have closed down for the evening. The home is beautifully kept, the atmosphere romantic, and the food savory and delicious. I’m a huge fan of the bruschetta (extra points for artful presentation).

Raintree Restaurant - St Augustine, FL

Tips / Getting Around

Avoid the pressure of feeling like you need to see everything. Instead, prioritize what you’re interested in. History and architecture buffs will love the Flagler College Legacy Tour, Castillo de San Marcos, and the Flagler Memorial Presbyterian Church. Foodies and cocktail lovers will delight in a food tour or a visit to the St. Augustine Distillery / Ice Plant restaurant. Ghost tours shouldn’t be missed if you don’t mind getting home late or decide to stay the night.

St. Augustine, FLParking is FREE at The Old Jail making it a great place to ditch your car for the day. It’s about a mile from town.

When it comes to shopping and dining, St. George Street is a main draw. While it’s definitely worth a stroll, it’s always packed. Avoid the massive crowds and navigate the side streets instead. There are still plenty of boutiques and eateries to be discovered there!

What to do, where to eat/drink, and tips for getting around the nation's oldest city

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