What To Do in The Uptown District of St. Augustine

While St. Augustine downtown, along St. George St, earns all the accolades and attention, there’s so much to see and do if you skip just north a few blocks and enter uptown. Give the ancient city your love when you stay at one of our St. Augustine oceanfront Beach condo rentals.

The uptown district is rewarding in its own right and a worthy place to check out for a calm afternoon out. What Is the Uptown District?

The uptown district, definitively, refers to anything north of the downtown city entrance at St. George St. Geographically, this includes the many shops, galleries, and restaurants along San Marco Ave before it turns into Anastasia Menendez along downtown. It is within walking distance of the fort Castillo de San Marcos which sits on the northern edge of downtown. Ripley’s Believe it or Not Museum and the Visitor’s Center a block over acts as the informal divide between the two main areas. 

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What Can You Do There?

RainTree Restaurant

Raintree restaurant sets the tone. Thick foliage swoops over the outside courtyard while the water trickles delicately amongst a few dazzling waterfalls. It’s all about setting the stage for romance and delight in this historic steak and seafood diner.


Step a few blocks over and check out Luli’s Cupcakes, tucked away in an old white and blue historic home. The café has vegan options, mini cupcakes for those who simply want a tease, and even icing shots. And if you love historic sites, we suggest you make a list of top historic places to see in St. Augustine!

Anastasia Books

We love the classic vibes and quiet demeanor of Anastasia Books. Splashes of red and brown next to some reading chairs make this shop memorable. With a number of classics, old and new, as well as used and new items, Anastasia Books is a treat for book lovers.

There are lots of little hidden spots along San Marco Ave. in uptown. We suggest keeping your eyes and ears open as you traverse north and hit the end- only to turn around and come back on the other side.

Favorite Local Boutiques

Uptown has a handful of really popular and special boutiques. We highlight our three current favorites.


Declaration prioritizes quality over quantity, giving you just enough options to come home happy. It specializes in bath products, bright sundresses, and coffee. It is the quintessential boutique shop in uptown for adorable apparel and handmade organic products.

A Step Back in Time

A Step back in Time is possibly the top antique shop in the neighborhood. It is filled to the brim with every possible item you could ask for, including jewelry, gemstones, clothing, wall art, and much more.

West and East

You can find an eclectic assortment of homemade items here, encompassing bright wall art, glassware, stone decorations, and furniture. 

Other Shopping Areas To See

For more fun under the sun, check out some more of St. Augustine’s top shopping areas. Walk right on over to the main downtown district for a whole new selection of boutique shops. We also recommend heading beachside, with its focus on vintage antique shops and surf shops.

Plan Your Vist to St. Augustine

We adore the city. Come and see for yourself what makes it so magical. Take some time out of your afternoon to play a few games at our on-site St. Augustine Beach and tennis resort. And of course, walk right down to the Atlantic any time.