A Weekend Guide to St. Augustine, FL

Castillo de san Marcos

St. Augustine is not just a beach town. It is also the oldest continuously inhabited city in America and full of compelling history, great restaurants, and cool shops. And it has beaches. What more could a person want?

After years of hearing everyone from my sister-in-law to my hairdresser rave about St. Augustine, we decided to go see what the fuss was all about.

Now that we’ve spent a long weekend there, we get the hype. Here is our guide to the best things to do, see, and eat in St. Augustine:

Things to Do in St. Augustine

Anastasia Island

Saint Augustine Beach

The beach is obviously St. Augustine’s biggest draw. We spent most of our time at St. Augustine Beach on Anastasia Island, which is only a short drive from downtown.

The waves are pretty intense, so it is a great place to surf or boogie board. The undercurrent can be vicious though, so I’d caution against venturing too deep into the water if you aren’t a strong swimmer.

Since I swallowed roughly half the Atlantic attempting to surf in Portland, Maine, earlier this year, I decided to enjoy the ocean from the comfort of my beach chair.

A free beach parking lot is located in front of the Pit Surf Shop and Stir it Up burritos. Space is limited, so we recommend arriving early if possible.

Castillo de San Marcos

Castillo de san Marcos

Visiting the Castillo de San Marcos is a must when in St. Augustine. The fort’s construction began in 1672, which makes it positively ancient by American standards. It has at intervals belonged to the Spanish, the English, the Confederacy, and ultimately the United States of America. Its long history is well documented in the exhibits throughout the fort.

There are also people in costume which always makes cool places so much better.

Admission costs $10 for adults (16 and up) and is free for children (15 and under).

1 S Castillo Dr, St Augustine, FL 32084

Cathedral Basilica of St. Augustine

Cathedral Basilica of St. Augustine

Originally built in the late 1800s, the Cathedral Basilica of St. Augustine is the oldest church in Florida. The interior is quite impressive and deserves a quick look around.

Admission is free.

38 Cathedral Place St. Augustine, FL 32084

Further Reading: 7 Best Weekend Destinations in the Southeastern USA

Plaza de la Constitucion

Plaza de la Constitucion

Keeping with the theme, Plaza de la Constitucion in downtown St. Augustine is the oldest public park in the United States. Not only is it old (which is typically reason enough for visiting a monument, building, or obscure plot of land), but it was also the setting for many important events, including Florida’s transfer from Spain to the United States.

Bridge of Lions

Bridge of Lions

The Bridge of Lions spans the Intracoastal Waterway, connecting Anastasia Island to downtown St Augustine. Walking the length of the bridge makes for a nice evening stroll.

George Street

George Street

George Street is really the heart of St. Augustine. Always bustling with activity, it is a great place to eat, shop, or people watch.

Where to Eat in St. Augustine



Beachcomber is located roughly 4 steps away from St. Augustine Beach. So though a bit pricey, we loved Beachcombers for the sheer convenience.

Sam recommends the fish tacos.

Mains from $11-$21

2 A St, St Augustine, FL 32080

Burrito Works

Burrito Works Taco Shop

For a cheap and casual meal, we recommend Burrito Works Taco Shop, which serves up tasty West Coast-style burritos, tacos, and quesadillas.

Mains from $7-$11

Several locations throughout St. Augustine.

 Pizza Time

Pizza Time

For a ginormous slice of NY-style pizza roughly the size of your torso, head to Pizza Time on George St. Though a bit chaotic, the pizza was delicious. Cash only.

Slices for $3-$5

124 Saint George St, St. Augustine, FL 32084-3610


The Hyppo

The gourmet ice pops from The Hyppo are the perfect cold treat on a hot day. With an enormously long list of flavors, you’re sure to find one that tempts you. Be sure to get it dipped in chocolate, because everything is better dipped in chocolate.

Ice Pops from $3-$4

48 Charlotte St., St. Augustine, FL 32084

 The Kookaburra

 The Kookaburra

For a caffeine fix, head to The Kookaburra. Even Sam was impressed, and he’s a total coffee snob!

24 Cathedral Place, St. Augustine, FL

 Where to Shop in St. Augustine

 Two Sparrows

 Two Sparrows

Two Sparrows—a women’s clothing store—reminds me a lot of Anthropologie. Not only are the products stylish and high quality, but they are also displayed beautifully. I was tempted to buy basically everything in the store, which is the highest endorsement I can give.

21 King St, St Augustine, FL 32084

 Red Pineapple

Red Pineapple

Red Pineapple was another store we (okay, I…) enjoyed browsing. It sells everything from women’s clothing to soap to notebooks. If you’re wanting to take home a cool souvenir, this is a good place to look.

120 St George St, St Augustine, FL 32084

 Earthbound Trading Co.

Earth Bound

This shop definitely gives off an eclectic, boho vibe. It sells fashion, jewelry, and home goods.

108 Saint George St, St Augustine, FL 32084

 What is on your St. Augustine bucket list?

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A Weekend Guide to St. Augustine

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