St. Augustine, FL is the perfect city to explore on a little “date-cation”. This cute town is loaded with history and holds unique places for you and your partner to experience.

Recently, my girlfriend Maddie and I explored America’s Oldest City (yes, you read that correctly) and we even turned our adventure into a podcast! Here are 7 things we did on our trip to St. Augustine.


1) Climb Up the St. Augustine Lighthouse

Perhaps the most picturesque structure on the First Coast, the St. Augustine Lighthouse can be seen for miles. This black and white spiraled lighthouse is more than just a sight – it’s an experience! Visitors can actually go inside the structure and climb all 219 stairs to the top. One of my favorite parts was reading the signs as we ascended to the top of the lighthouse. I got to learn about lighthouse nuggets, like the story of Smokey the cat.

Aside from the lighthouse, you can also explore the Maritime Museum on property. The museum describes the history of the lighthouse and explains what life was like for the lighthouse keepers and their families.


2) Walk Around the City

One of my favorite parts about St. Augustine is that the city is very walkable! Right when we got into the city, Maddie and I immediately took some time to explore the town on foot. Our walk down St. George Street placed us in the heart of the historic city among restaurants, galleries, bakeries and shops.

Aside from St. George Street, we also explored some side streets. The narrow roads hold adorable bed & breakfasts and uniquely constructed homes. During our expedition through St. Augustine’s side streets on foot, we bumped into a few neat sites like the Plaza de la Constitucion and the Gonzalez-Alvarez House, which is believed to be the oldest surviving house in St. Augustine.


3) Grab some Grub

There is no shortage of tasty eateries around America’s Oldest City. From quick food to fine dining to barbeque to seafood – you’ll find it all!

Maddie and I decided we would grab lunch at Meehan’s Irish Pub & Seafood House. Our outside seating gave us a wonderful view of the Matanzas River and the beautiful Bridge of Lions. The menu featured authentic Irish dishes, and when the food arrived it exceeded our expectations.


4) Take an Old Town Trolley Tour

In addition to exploring the town on foot, hopping on the Old Town Trolley is a wonderful way to get to learn the city! Old Town Trolley Tours take you through St. Augustine, making plenty of stops at the city’s most historic spots.

The Old Town Trolley in St. Augustine has over 20 stops, and you can get on and off at your leisure. The trolley guides are extremely knowledgeable and will provide you with tons of historic nuggets about the city.


5) Explore the Fort

If you’re only going to do one thing in St. Augustine, it has to be a visit to Castillo de San Marcos, the oldest masonry fort in the continental United States. Construction on the fort began in 1672, 107 years after the city’s founding. Exploring Castillo de San Marcos was Maddie’s favorite stop in St. Augustine. She loved learning about the history as we walked through the different rooms throughout the fort.

When we walked into the fort, it felt like we went back in time. The National Park Service has done a great job of preserving the fort and describing the fort’s ownership and use throughout different time periods. From the fort’s early beginnings to the weaponry that was used to historic baseball at the fort, I was fascinated by Castillo se San Marcos’ unique history.


6) Sip Some Spirits

If you and your date are 21 or older, you will most certainly want to stop by City Gate Spirits and take part in their complimentary spirit tasting. City Gate Spirits is conveniently located on St. George Street near many of St. Augustine’s best attractions and shops.

At City Gate Spirits, you’ll go into the tasting room to sample house made craft spirits. At the different tasting stations, knowledgeable staff members will talk you through the spirits you’ll sample. My personal favorite stop was at the final station where Maddie and I sampled moonshine. All products are made on site, and if you’d like to purchase some fine spirits you can certainly do so!


7) Drive up A1A

Whether it’s at the crack of dawn as the sun rises over the Atlantic or sometime during the second half of the day, the drive on A1A between St. Augustine and Ponte Vedra will be a classy addition to your St. Augustine adventure.

This scenic stretch of 2-lane road provides views of stunning homes, beautiful beaches and preserved interconnected habitats. Don’t hesitate to make your way to Mickler’s Landing, Ponte Vedra, or Jacksonville Beach for some additional experiences to add to your date-cation.


Destinations Beyond Expectations is the podcast designed for students of travel. You can find the show wherever you listen to podcasts – make sure to subscribe! Also, don’t forget to stay up to date by following the show on Facebook and Instagram.