How to Spend a Fun Weekend in St. Augustine

When it comes to one of the oldest places in the United States, there’s no shortage of ways to spend the weekend in St. Augustine, Florida. 

Initially established by the Spanish in 1565, St. Augustine is considered the oldest continuously occupied European settlement in the country. Through its long history, it’s seen a number of transformations first as a military colony and most recently as a prime vacation destination. These days, it’s the perfect place to visit for sun, history, and excellent food! 

Check below for all my favorite ideas on where to go and eat for an amazing weekend.

Where to Go for Your Weekend in St. Augustine

Castillo San Marcos National Monument

If you only manage to do one thing during your weekend in St. Augustine, it has to be visiting Castillo de San Marcos. It’s older than the United States itself, having been built to be a masonry fort between 1672 and 1795 when Florida belonged to Spain. Besides its 450+ years of history, one of the most intriguing things about the fort is its design. It’s one of the only forts made with coquina, which is a sort of limestone made from shell fragments. 

All you need to do is pay an entrance fee and then you can walk around to learn more and take in the views.

Check out St. Augustine’s many historic streets.

St. George Street

To be right in the heart of St. Augustine, just head over to pedestrian-only St. George Street. Starting in the Historic District and ending in Lincolnville, you’ll find tons of interesting landmarks as well as innovative restaurants and local businesses. Come over after visiting Castillo San Marcos and start with the Old City Gates. Keep an eye out for places like the Oldest Wooden Schoolhouse and the Cathedral of Basilica of St. Augustine, aka the oldest Catholic church in the country.

Aviles Street

Aviles Street has the honor of being not only the oldest street in St. Augustine but the oldest in the whole nation. It runs a few blocks parallel to St. George’s Street, beginning from King Street and ending at Bridge Street. Back in the day you could find everything from schools to the second Spanish Military Hospital, but today it’s known as the town’s main arts district. In between visiting art galleries and landmarks like the St. Augustine Historical Society, be sure to pop into Peace Pies for a nice ice cream sandwich.

Lincolnville Museum and Cultural Center

Black history in St. Augustine is quite unique and can best be seen amongst the numerous exhibits at the Lincolnville Museum and Cultural Center. 

Start with the very first Black people, both free and enslaved, to come to Florida with the Spanish in the 1500s. Then learn more about Fort Mose which was founded in 1738 as the first “legally-sanctioned community for people of color.” Yes, you read that date right – enslaved people in British North America could find freedom in Spanish Florida so long as they pledged allegiance to the Spanish King and converted to Catholicism. 

Move on to 1866 and the founding of Lincolnville following the end of the Civil War. Many newly-freed slaves settled in St. Augustine and created a thriving community that would go on to play a significant role in the Civil Rights Movement of the 1960s. Through it all, the arts and culture of Lincolnville rivaled that of NYC’s Harlem and even a certain, famous blind musician learned to read braille and music while attending school here. Wonder how often his home state was on his mind while he was studying!

If you want even more Black history, a great place to visit nearby is Lenny Foster’s Gallery One Forty-Four. There you can see his “Where We Stand” exhibit, which was inspired by his move to Lincolnville where he soon learned all about its long history.

Sailing with St. Augustine Eco Tours

No visit to St. Augustine is complete without getting out on the water! Of course, you can head to any of its beaches for a swim, but why not head out on the water for an eco tour? Not only will you get to learn more about all the various creatures who call these waters and islands home, you’ll get fantastic views of the city from afar. For those that want a little exercise with their trip, choose the kayak adventures; and for those that would rather sit back and relax, pick from their boating tours and sailing excursions. 

Lightner Museum

Step back into the Gilded Age at the stunning Lightner Museum. Once a resort hotel commissioned by Henry Flagler to appeal to wealthy tourists, it’s now a museum showcasing various exhibits related to this opulent era. After less than 50 years of operation as a hotel, it closed and was later bought by Otto C.Lightner. He turned it into his own hobbies museum where he could display his collection of Victorian art before turning it over to the city of St. Augustine a year later in 1948. It’s truly a cool museum full of an eclectic mix of curiosities!

Flagler College

Across the street is another former resort hotel, only this time it was turned into Flagler College. Once a Spanish Colonial Revival resort hotel, it was also commissioned by Henry Flagler to attract wealthy tourists. Even though it’s a college, you don’t need to be a prospective student to join a tour! The college offers historic tours so regular visitors can enjoy the campus’s stunning architecture too.

Villa Zorayda

Villa Zorayda Museum (sometimes nicknamed Zorayda Castle) is another grand Gilded Age building in St. Augustine. It was commissioned by Boston millionaire Franklin W. Smith to be his winter home and was inspired by the Alhambra in Granada, Spain. The name even comes from a character in Tales of the Alhambra by Washington Irving. If you see any buildings designed in the Moorish Spanish Revival style in the city, know that this villa was the influence. Today you can take a self-guided audio tour to learn more about the villa’s history over the last century. 

St. Augustine Lighthouse

What’s a visit to a coastal city without checking out its lighthouse? The St. Augustine Lighthouse, located on nearby Anastasia Island, does not disappoint. Sitting at 165 feet high, its spiral design is hard to miss! The current lighthouse was built at the end of the 1800s and like Castillo San Marcos, it was constructed with coquina. Check out the museum to see what life was like for its keepers before climbing 219 steps up to get an epic view of St. Augustine from above.

Fountain of Youth Archaeological Park

If you ever wonder how Florida was first founded, then you’ll want to pay a visit to the Fountain of Youth Archaeological Park. Back in the 1600s, Juan Ponce de León was on the hunt for these mythical springs to regain some of his youth. He apparently landed in the current spot the park occupies in 1513 when it was a village for the Timucua people. Over the years the park has transformed from claiming to be the location of the Fountain of Youth to being an important archaeological site where you can learn more about the Timucua Native Americans as well as the city’s earliest history.

Where to Eat During Your Weekend in St. Augustine

Asado Life

Learn the art of the asado at Asado Life! Asados are South America’s version of barbecues, and they were first introduced to St. Augustine thanks to Urban Asado founder Nick Carrera, who’s father is from Argentina. What started out as creating his own asado grill soon turned into a business which turned into weekly asados. Asado Life is simply the further evolution of the business! Instead of a weekly event, this newly opened waterfront restaurant is well worth the visit. Check out their lunch hours or, for the true experience, come for a 4-course dinner al fresco. 

Llama Restaurant

For a twist of transitional Peruvian dishes, make a reservation at Llama Restaurant. Founded by Chef Marcel Vizcarra, the restaurant blends dishes from his hometown of Lima with his Japanese training and LeCordon Bleu education. Whatever you do, don’t skip any of the ceviche offerings.

Columbia Restaurant

The Columbia Restaurant in St. Augustine is one of seven locations around Florida. Founded by Spanish Cuban immigrant, Casmiro Hernandez, Sr., the St. Augustine restaurant is located right in the heart of the Historic District. Pick from any number of its Spanish-Cuban dishes including its famous Spanish bean soup and original 1905 salad. 

Preserved Restaurant

For some seriously deliciously authentic Southern cuisine, head over to Preserved Restaurant. Located in Lincolnville, it’s actually housed in an 1800s Victorian home that once belonged to Thomas Jefferson’s granddaughter. All ingredients are fresh and regionally-sourced and you can bet there’s plenty of Southern hospitality to match the dishes!

And there you have it – all my favorite ways to spend an incredible weekend in St. Augustine. Any ideas I’m missing? Feel free to share below!

If you want to see more things to do in Savannah, check out our “St. Augustine” episode of Season 6’s “Samantha Brown’s Places to Love”.