Spend a Weekend in St. Augustine!

A mélange of history and culture; St. Augustine is distinguished with scattered bits of architecture resembling Spain’s Andalusia, colonial U.S. cities and San Juan, Puerto Rico. Why, you ask? St. Augustine is known to be the oldest occupied settlement of European origin in the United States – and by European we mean Spanish, although it flip-flopped back and forth for several centuries. Its rich history began in 1565 when the town was founded by the Spanish admiral Pedro Menéndez de Avilés. Sometime in 1740, the British forces attacked Spanish Florida and took over St. Augustine; later on, Spain regained the land in 1783. Fast forward to 1819, Spain ceded Florida to the United States and became an official state in 1822.

How to get to St. Augustine?

The nearest airport is the Jacksonville International Airport, which is about an hour ride from downtown St. Augustine. There are a few options for transport. The most affordable way is to rent a car one way and drop it off upon arrival at St. Augustine – this could be as low as $30. Several airport shuttle services start at $75; you can book a shuttle here or this service with airport express.

Once you’ve gotten the logistics down, it’s time to plan for a weekend in Northern Florida. You can easily cover this one of a kind city in 2 to 3 days of venturing. Here’s a sample itinerary of how to spend a weekend in St. Augustine. We’re splitting everything into two categories by area: mainland St. Augustine and Anastasia Island.

Where to Stay

There are a few things to know when choosing a place to stay in St. Augustine. The most popular of course is the Colonial Quarter in mainland St. Augustine and centered around the famed St. George street. In simple terms, this is a 2-acre stretch of historic buildings, entertainment, restaurants and other attractions. Lots of charming Bed & Breakfast options here as well as several chain hotels.

If you’re looking for something a bit more low key and away from the busy restaurants and bars in the evening, then consider finding accommodation in the northern area of Anastasia Island. The Bridge of Lions conveniently connects the island to the heart of St. Augustine and the historic Lincolnville. As long as you stay close to the bridge, you’ll be a short 10-minute walk away from the city center. Now, be ready for some wet Florida weather, have an umbrella or raincoat handy at all times – you never know when the sky is going to open up.

What to Do in St. Augustine (mainland)

Mainland St. Augustine is extremely pedestrian-friendly and it’s where most of the city’s biggest attractions are. After spending a long weekend we concluded that the best way to hit the best attractions of St. Augustine is by grabbing an Old Town Trolley tour. The hop on hop off trolley gives you the flexibility of exploring all parts of the city without worrying about getting around. Here’s what you’ll see!

Castillo de San Marcos

The largest and oldest fort in the U.S., Castillo de San Marcos’ construction began in 1672 and has been going strong since. Try to get to the fort early in the morning or around sunset, as it can get very crowded with all the tours roaming in St. Augustine. You can also catch a cannon show every other hour from the upper deck of the fort starting at 10:00 am!

St. George Street

Smack-dab the middle of the colonial quarter is the very famous picturesque St. George Street. This is where all the fun is, stacked with restaurants, antique shops, gardens and lots of history. You can opt to go on a “full colonial experience” around town with this tour, or just wander the streets on your own!

Old City Gates

Right at the edge of St. George Street are the old city gates, built by locals in 1808 using coquina blocks. After a few hours in St. Augustine you’ll learn that everything was made of coquina blocks, which are essentially compacted fragments of shells.

Oldest School House

As you venture into the quarter, you can find the oldest wooden schoolhouse in the USA built around 1716. Enjoy a tour of the buildings, old classrooms, sculptures of famous educators and an outdoor garden.

St. Photios Greek Orthodox Shrine

Hidden in the quarter is this quaint shrine dedicated to the first colony of Greek people who came to America in 1768. It’s quite small, but the exquisite frescoes inside make for a wonderful quick (& free) visit.

Colombia Restaurant

Yet another historical mark, this restaurant is known for its Spanish/Cuban cuisine but more importantly for being one of the oldest restaurants in all of Florida.

Flagler College

Wander west out of the colonial quarter and you’ll reach the very magnificent Flagler College. Another thing you’ll learn while in St. Augustine is that Henry Flagler either owned or built most of what we see of St. Augustine today. One of those being the Flagler Hotel, now a private liberal arts college. The photos speak for themselves, do yourself a favor and walk through this massive campus.

Lightner Museum

Directly across from the college, is the Lightner Museum – once the Alcazar Hotel constructed in 1888 (also built by Flagler) now a museum of an assortment of artifacts, Victorian styled rooms, and the world’s largest indoor pool among other things.

Villa Zorayda Museum

Somewhat of a replica of Alhambra Palace in Granada, Spain, this small museum is an artifact in and of itself from its beautiful exterior to the intricate details and décor inside.

Memorial Presbyterian Church

Just a few streets behind Flagler College & the Lightner Museum is a stunning church. Another Flagler construction (remember this gentlemen built what seems like half of the city’s more recent structures), this memorial church is dedicated to his daughter who passed away at an early age.

Cathedral Basilica of St. Augustine

Walk down King Street towards the bridge and you’ll peek the Basilica of St. Augustine to your right. One of the settlement’s first cathedrals and yet another national historic landmark.

Aviles Street

Hidden across King Street is Aviles Street, the oldest street in the US. Another cobblestone road of shops, museums and galleries. This is also the beginning of the historic town of Lincolnville, still within the St. Augustine district.

Bridge of Lions

You won’t miss the lions! Connecting the mainland with Anastasia Island is this relatively new bridge. Enjoy a walk across, or stroll through its gazebos and publicly accessible dock!

A bit out of downtown are the San Sebastian Winery and St. Augustine Distillery (where the Ice Plant is located). Both establishments offer free tasting tours and guided history tours! This should not be missed by any means. You can easily access these with the Old town trolley- so keep that in mind as you plan.

The Shine

Officially known as The Shrine of Our Lady of La Leche at Mission Nombre de Dios, the shrine grounds are massive and much like a holy stroll through a park. Check out the 204-foot cross and of course the lusciously green chapel. If you’re lucky, you could catch sight of peacocks strutting around.

Magnolia Avenue

Speaking of greenery, named one of the most beautiful streets in the U.S. – Magnolia Avenue! Home to the entrance of the Fountain of Youth Archaeological Park, this street deserves its own praise. The park is famed for being a landing point for Spanish explorers and extends to over 15 acres of attractions, and a variety of shows and living history reenactments.

Where to eat in St. Augustine

The mainland is swarming with locally run restaurants, some of which carrying immense history, harvests of nearby farms, and eccentric cuisine. Here are some of our favorite places to munch!

Stop by Maple Street Biscuit Company, The Blue Hen, or City Bistro for excellent brunch selections. Yearning for something sweet? Grab a gourmet popsicle at The Hyppo!

For coffee connoisseurs, visit the Australian chain Kookaburra, City Perks Café, or Relámpago Coffee Lab. If you’re looking for fine dining experiences, head over to the Ice Plant or The Floridian.

And if you’re yearning for a nice southern meal, stop by The Gourmet Hut for excellent Po’boys and check out their Secret Garden in the evenings for live performances and a cozy atmosphere.

Nightlife suggestions? Almost all the restaurants turn up at night, but we loved hanging out with locals at Odd Birds (and especially loved their outdoor terrace and rooftop). Prohibition Kitchen is also yet another famous venue, with a full-on stage and evening entertainment.

Now before we close out the mainland portion, we have to praise the Ghost Tours. First off, you get to avoid a few entry tickets to the Old Jail House for example and the oldest pharmacy known as Potter’s Wax Museum. Second, it’s a nice evening activity – not scary but you get to see another side of the city’s history and supposed paranormal activity. There are many options for the Ghost tours, but we went ahead and purchased a combined ticket with our Old Town Trolley tour.

What to Do on Anastasia Island

Anastasia Island is a bridge away from the mainland; it’s a bit more spread out so consider renting a car for this portion or grabbing an Uber.

Probably the most exciting site on Anastasia Island is the St. Augustine Lighthouse. Get ready for some cardio because you’ll need to climb a whopping 219 steps to reach the observation deck. Thankfully there are resting areas in between floors.

Nearby, is the Alligator Farm a large zoo dedicated to… yes, alligators. Even more thrilling is the Crocodile Crossing attraction. Zip through the air right over the crocodiles and through the treetops on one of their many zipline courses.

If you’re feeling hungry while exploring Anastasia Island, head over to the Conch House for fresh seafood, and if you’re free on a Sunday, enjoy their Reggae party entirely performed on a barge.

For a lighter bite, we recommend Osprey Tacos – because we always recommend tacos. If fancy dining strikes you, go to Llama Restaurant!

Venture into the Island a bit and visit Fort Matanzas. Yes, another fort. But you’ll need to grab a small ferry to get to this one.

Since you can’t visit the sunshine state without indulging a bit in some sea & sand, make your way over to the St. Augustine Beach & Pier. Check their schedule and maybe you can attend one of the many beach front performances and concerts.

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