How to Spend a Weekend (or longer!) in St. Augustine, Florida

How to visit St. Augustine Florida | St. Augustine itinerary | a weekend in st. Augustine | USA travel | visit Florida I’ve written before about St. Augustine, Florida, and why it’s my favourite destination in the United States. I’m convinced that if you visit, it’ll be one of your favourite destinations too. It’s a fairly small city but has something for everyone, whether you’re a beach bum or culture buff.

The great thing about St. Augustine is that it’s the perfect weekend getaway, but you can easily spend weeks there and not feel bored. The following itinerary is intended for a 3-day weekend in St. Augustine, but can be extended by adding extra beach days or taking more time to visit attractions in the historic downtown area.






Practicalities: Getting in and where to stay

St. Augustine is located in northeast Florida, on the Atlantic coast about halfway between Jacksonville and Daytona. Both Jacksonville and Orlando airports provide easy access to St. Augustine. For the most freedom during your stay, I’d recommend renting a car, as it’s about an hour’s drive from Jacksonville or two hours from Orlando. However a St. Augustine airport shuttle does exist from Jacksonville – I can’t vouch for them as I’ve never had to use them, but they do brag about being environmentally conscious!

One of my favourite things about travelling to St. Augustine is that there’s such a wide range of accommodation options for any budget and travel style. Budget hotels are easy to find in and around both the historic downtown and the beach area. For an upscale, luxury stay, try the Casa Monica downtown. I’ve never stayed here, but I have walked through the lobby and visited the spa, so I can tell you that it’s absolutely breathtaking.

If living like a local is more your thing (it is for me!), try out one of the many vacation rental properties in St. Augustine Beach. Every time I visit, I stay at the SeaWinds Dreams. Full disclosure: my parents own it, but the two-bedroom condo is beautifully decorated, steps from the beach and a short drive from shopping and downtown.

A weekend in St. Augustine, day 1: Beach bum

St. Augustine Beach

Maybe it’s because I’m from Toronto where the weather sucks for eight months of the year, but I love to start my St. Augustine trips off at the beach! If you stay at SeaWinds or almost any of the beach hotels, you’ll have private access to an extremely uncrowded beach.

Start the morning off with a walk along the shore towards Eleventh Street (you may have to GPS this since you can’t tell what street you’re on from the beach) in search of food. Most of the east-west streets provide access to the beach as well, so once you’ve figured out which street is Eleventh, you’ll be able to access it easily.

By this point, you’re probably hot and hungry, so make your way west on Eleventh Street and stop into Cafe Eleven for some food. I love the food here – it’s the lightest and healthiest (though they have desserts too) that I’ve been able to find in St. Augustine, and it’s delicious. They offer all kinds of options for meat-eaters and vegans alike. If your day one here happens to be a Saturday, you’re in luck because you’ll be walking into the restaurant for their amazing brunch buffet.

After filling up on food and smoothies, spend the afternoon lazing on the beach and soaking up the sun. For dinner, head to Salt Life on A1A Blvd. They have amazing drinks, bowls, salads, and sushi, with live entertainment playing on weekend evenings.

A weekend in St. Augustine, day 2: Culture vulture

The grand entrance to Flagler College, once a high-end hotel, now a college.

Spend day two soaking up the history of the old town and taking in the gorgeous Spanish colonial architecture. Stop into Le Macaron on Cathedral Place for an authentic French brunch of crepes or savoury croissants before heading out to wander the streets.

Check out the pedestrian-only St. George Street, and dodge into some of the quirky local shops along the sides. After a few minutes of walking, you’ll come to the Oldest Wooden Schoolhouse, a schoolhouse from the 18th century. With admission costing just $5 per person, it’s totally worth going in to check out the property, which for the most part is the original structure. You can go inside to learn about the history of the schoolhouse, and what it was like to be a student in the 1700s and 1800s.

The back courtyard and the schoolhouse building at the Oldest Wooden Schoolhouse.

Once you’ve had your fill of exploring the cobblestone streets on your own, pick up some tickets for the Old Town Trolley Tour, and hop on for a guided tour of the city. The tour will take you to places like the Fountain of Youth, Flagler College, wineries and distilleries, and several museums and churches, explaining the history behind each building and area of town. The tour is hop-on-hop-off style, so feel free to hop off the trolley to explore anything of interest – just be aware that the last trolley leaves at 4:30 pm!

After the tour, head to Harry’s for dinner with a view of the best patio I’ve ever seen. They serve Creole-style food, mainly seafood. Their vegan and vegetarian menu options are pretty limited, but if you ask, they’ll be able to make a special dish for you.

harry's st. augustine
The entrance to Harry’s Seafood Bar & Grille, and the most beautiful patio I’ve ever experienced.

A weekend in St. Augustine, day 3: Shop til you drop

Shoppers paradise: St. Augustine has no shortage of malls for you to explore. Conveniently, there are two different outlet malls on either side of I-95: St. Augustine Outlets and St. Augustine Premium Outlets. Between the two, you’ll find a mix of high-end and more mid-range stores to browse through.

For lunch, eat your weight in pancakes at IHOP next to the Premium Outlets. You’re probably laughing at this recommendation if you’re from the US, but we only have like, two IHOPs in Canada, so being so close to one is exciting for me! Alternatively, there are restaurants as part of both the outlets.

Beachcomber Restaurant

Continue shopping for the afternoon, or head back to the beach to put the finishing touches on your tan. For dinner, bid farewell to the beach life at Beachcomber, serving classic beach food shack eats. Sit on the patio to eat, drink, and watch the sun go down.

Extending your stay

Like I said, there’s actually a ton to do in and around St. Augustine, and really, a weekend is not quite enough. If you want to stay in town longer, add more beach days into the mix, or take some time to go into any of the downtown attractions you saw on the trolley tour.

If you want to explore further afield, take a day trip to Orlando (Disney World, anyone?) or to Jacksonville for more shopping, food, and a different kind of history – on one trip I visited Kingsley Plantation to learn more about the painfully sad slave history in the US.

So, have I convinced you to visit my beloved St. Augustine yet?

About Erica

My wanderlust was ignited when I booked my first solo trip to India in 2015. Since then, I've developed a passion for ethical and sustainable travel, and I'm here to help you learn how to make a positive impact through your travels.


  1. I haven’t heard too much about St. Augustine (I guess it gets shadowed by the bigger cities in Florida) but it looks like a relaxing place to vacation! I love how it has malls but also ocean!

    • The fact that it gets overshadowed is part of the reason I love it – it’s like a hidden gem! It’s a great place though, highly recommend 🙂

  2. Anjali w

    St. Augustine seems like a beautiful getaway for a relaxing vacation. Would love to make a visit there someday! Thanks for sharing the itinerary. I am saving it for my future visit:)

  3. The city has such a rich history it is overwhelming. While talking to a local ship captain we found out there are still several ships out in the Atlantic that you can dive on! How cool?

Leave a Reply

Your email address will not be published. Required fields are marked *

CommentLuv badge