One thing I love about living in Orlando is there are so many places to travel nearby for a quick staycation or even a date night! For example, why not a quick date night in St. Augustine?

Recently my husband and I celebrated our 16th wedding anniversary. There are so many places to visit, sights to see, and food to eat. This historic city really has something for every couple.  After all, it is the oldest city in the United States.

For the Historians newspaper with a pint of beer, newspaper reads "Roosevelt ends Prohibition", date night in St. Augustine

Who doesn’t love a good story? Or appreciate how old a building or tradition is. A perfect date night in St. Augustine is getting to learn about the oldest city in the United States. The pirate lore, the romantic stories, everything about St. Augustine is perfect for a history-lover!

Historic buildings and roadways

Take a leisurely stroll along St. George Street, lined with historic buildings, shops, and restaurants. Enjoy the romantic ambiance of the cobblestone streets and historic architecture.

Castillo de San Marcos 

Explore this historic distinctive star-shaped fortress together. It includes a drawbridge, moat, and rooms used for various purposes, such as living quarters, storage, and a chapel, just to name a few. The views from the top are spectacular, especially during sunset.  

Castillo de San Marcos, date night in St. AugustineCastillo de San Marcos, date night in St. Augustine

Oldest Wooden School House 

You can tour this school house turned museum and even receive a diploma. The Oldest Wooden School House is recognized as the oldest surviving school building in the United States.  

Nighttime Ghost Tour 

 If you are into ghostly things AND you also enjoy learning about history then join a nighttime ghost tour to explore the spooky side of the city together. St. Augustine is known for its haunted history. It can be a unique and thrilling experience. 

boat in front of restaurant reads "SS Melliser", date night in St. AugustineFor the Foodies 

Florida often gets a bad reputation because it doesn’t have as many Michelin-star or Bib Gourmand-award restaurants, but I can assure Florida will satiate any food craving you have. The perfect date night in St. Augustine is not complete without visiting one of these amazing restaurants. 

Barley Republic

Irish eatery that offers pub food and an ample beer selection. There is family seating downstairs with a full menu. They do have additional seating upstairs, but it is a limited menu, however they do have a full bar.

Prohibition Kitchen

If you are looking for a place that offers delicious cocktails and gourmet pub-like food while listening to live entertainment this is the place for you. I would recommend getting there early as seating tends to fill up quickly, especially when there are special events going on in the area. My favorite item off the menu is the Poutine.  

Maple Street Biscuit Company

While this restaurant is a franchise this particular location is very cute and quaint. They have so many options to accommodate every type of breakfast, lunch, or brunch foodie.  

little girl with father-figure walking with other people in between rows of shops. St. George's Historic Walk, date night in St. AugustineFor the Shoppers

There are so many shops and too many to list but here are a few favorites to round your date night in St. Augustine. 

Bath Junkie 

Here you can make your own bath products. Ranging from lotions to oils to scrubs and washes.  There are SO many ducks in this shop! Tiny ducks, small ducks, big ducks, & massive ducks. 


Do you like honey? Stubbees has an entire store filled with different types of honey. Raw, Infused, Whipped, and Traditional Blossoms. We were able to try a few different choices before deciding on the perfect honey for us. Who knew ‘honey tasting’ was a thing? The Blackberry Bourbon Infused is amazing on pancakes and is a wonderful replacement for traditional sugar or sweeteners. 

entrance to St. George's Row, date night in St. Augustine

Heritage Walk on St. George St. is a shopping mall that has an array of different types of shops.  From comic stores to clothing and jewelry stores. 

Known as the oldest street in the United States, Aviles Street is home to art galleries, antique shops, and specialty stores. It’s a great place to explore if you’re interested in unique and locally made items.  

For the Spirits (not the ghostly kind)

Of course we couldn’t leave out the spirits, you lush! If you’re staying the night or only want to finish your date night in St. Augustine with a night cap, these are the perfect places to visit. 

St. Augustine Distillery Tour

If you and your date enjoy spirits, consider taking a tour of the St. Augustine Distillery. Learn about the local distilling process and enjoy some tastings together. 

The Tipsy Duck Parlor

They keep the ‘make your own feel’ going on this side also. Except here you can create your own hard soda (or non alcoholic soda also). They also have an array of cocktails and beer available.  Each drink comes with, you guessed it, a duck!  

Casa de Vino 57

If you want to enjoy a charcuterie with a bottle of wine while listening to live music, this is the place for you. Their secluded courtyard gives the romantic ‘only 2 people in the world’ feeling while keeping you right in the middle of downtown. You can check their website for their calendar of music and events.

Overall, St. Augustine is one of the most romantic cities where you can enjoy a date night. If you happen to take a date night during the holiday season I would recommend walking halfway across the Bridge of Lions and looking back at the beautiful downtown scene all lit up.  

Join us for an INDOOR Egg Hunt!


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