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The Perfect Weekend in St. Augustine

St. Augustine certainly has a lot of labels attached to it -America's most historical city, America's most haunted city, America's most romantic city... In a way, I can see how all of them are true at once. It is a captivating blend of old town charm, natural beauty, and ominous history.

Along its cobblestone streets, you will find endless art, unique museums you can't find anywhere else, and delicious, one of a kind restaurants. It doesn't matter whether you're a history buff, a ghost hunter, a romantic, a foodie, this city makes for a perfect little getaway and will certainly captivate your heart. So let's dive into an action packed weekend in America's oldest city!

Day 1

1. Castillo De San Marcos

This one is perfect for you history lovers out there. The Castillo De San Marcos is the nation's oldest masonry fort, built in 1695. Just walking along its centuries old walls is like time traveling back in history. You will get a glimpse into the soldier's life in America's early ages learn all about the imperial struggles that Florida faced as a Spanish colony. And you'll see some pretty cool canons.

Once you get to the top, you'll have a magnificent view of the city and the shores that surround it. Looking out, you can imagine the pirates that once sailed through the bay attempting to attack the impenetrable fort. My toxic trait is thinking that I could have made my way into the fort, despite it surviving centuries of enemy attack.

2. Harry's sea food bar and grille

After a long day of time traveling and fort-overthrow plotting, step into St. Augustine's yummiest restaurant, Harry's Sea Food Bar and Grille. It's delicious and beautiful, with its string lights hung on their outdoor patio so you can enjoy a picturesque dinner with fresh air. I'm not kidding when I say that I actually fell in love with their crab cakes and iconic shrimp po-boys.

The wait for a table might be pretty long, so it's a fun idea to go out and explore the neighboring downtown area while you wait.

3. The love trees of St. Augustine

There's an old local myth in St. Augustine revolving around a few of their trees. It looks like a normal oak tree from far away, but once you get closer you realize there's something special about it. Inside the oak tree, a palm tree grows. It turns out, the weather and humidity in the area make it not uncommon to find trees growing through each other.

An oak tree with a palm tree growing in it is covered in Christmas lights, next to a green house covered with the same lights
the love tree, courtesy of Atlas Obscura

Locals say that lovers who share a kiss underneath the tree will share an everlasting relationship and eternal love. Old couples often routinely come under the tree to kiss and renew their love each year, It's a perfect, highly romantic spot to come with your special person and share a kiss that you will remember forever.

I went with my ex so I guess the love spell doesn't work on everyone LOL! But with or without a romantic interest, it's still a pretty cool sight to see a palm tree actually growing through an oak tree. Plus, there's a little gift shop right by the tree so you can buy a little lovely souvenir to commemorate your everlasting love and weekend in St. Augustine.

a skeleton hangs in an iron cage, illuminated by yellow lights
poor guy, courtesy of Medieval Torture Museum

4. Torture museum

Keep the romance going with a little trip to the Medieval Torture Museum! Nothing says romance like gazing at wax figures of people dying in horrendous ways.

But all in all, this is truly a one of a kind museum that enlightens you with its dark history, all while fulfilling that grotesquely curious side of you. It's actually quite impressive with it's intricate characterizations of Medieval torture and makes you think "thank God I wasn't born in the 1400s".

5. A riverwalk sunset walk

After a disturbing evening at the torture museum, it's time to truly soak in the city and all of its beauty. On the same street as the Castillo de San Marcos is a side walk along the bay. We went for a sunset stroll and watching the sun descend over St. Augustine's iconic "Bridge of Lions" was the perfect way to end a fulfilling day.

three red rocking chairs on a balcony in the sunlight in St. Augustine
St. Francis Inn Bed and Breakfast, courtesy of Tripadvisor

Where to stay

The St. Francis Inn Bed and Breakfast is honestly one of the coziest places I've ever stayed at and enhanced my weekend in St. Augustine so much. It was the perfect distance from the city and it gave perfect, peaceful, cottage vibes. I remember waking up and spending the morning on the balcony, which was surrounded by beautiful plants and bamboo.

They gave us a free brownie as we checked in, and it that doesn't sell it for you I don't know what does. And it's supposedly haunted!

Day 2

6. Exploring Flagler College

A weekend in St. Augustine would not be complete without exploring one of its most iconic structures, Flagler College. They offer historic tours there for $16, but we went the old fashioned way and just walked in. Once you're up close, you'll see that the architecture is actually quite impeccable. The pink-roofed campus was originally built as a luxury hotel, and you can definitely see the work put into it when you're up close.

A pink, castle-like building stands in the distance over a shroud of green trees
Flager College, from a distance (forgot to take pictures up close)

7. The Fountain of Youth

If Spanish explorer Ponce de Leon searched hundreds of miles to find the Fountain of Youth, you certainly must make time to visit it on your trip to St. Augustine.

The so called Fountain of Youth is a scenic park a few minutes drive from Flagler College. There, you can enjoy a scenic walk on the boardwalk, learn about fascinating Spanish and Native American history, and even drink the water that is said to give you eternal youth and life (it tasted a little metallic). There, you also will find an array of peacocks and interesting birds wandering about the grounds.

We went and explored their planetarium show, which was a beautiful and fun experience.

a red sign that leads directions to the so called "fountain of youth"
the way to the Fountain of Youth, courtesy of Fountain of Youth Archaeological Park

a black and white lighthouse with a red top stands over a wilderness of green trees
courtesy of St. Augustine Lighthouse & Maritime Museum

8. St. Augustine lighthouse

The historic, black and white St. Augustine Lighthouse was built in 1874 and is iconic to the city's landscape. They also have daily activities and exhibitions you can explore while you're there, incase you don't feel like climbing.

It is also supposedly haunted, so you might be able to see some lightkeeper ghosts!

9. End your weekend in St. Augustine with a sunset stroll on the beach

Memorialize your fun-filled weekend in St. Augustine with a peaceful stroll and reflection on one of St. Augustine's beaches. We went to North Beach Pavilion & Park, which was a quiet, tranquil little beach. It was the perfect way to just watch the sun slowly dissolve over the horizon and feel the soothing sea breeze.

While walking to the beach, we came across what is known as the "love bridge," (I guess there's a lot of love in St. Augustine).

the ocean stands after the end of the bridge, which is covered in mesh and have locks all in between the mesh spaces
St. Augustine's love bridge

It's a bridge that holds hundreds of locks on it, each one representing one's story with their loved ones. Just to stroll along it and see the years worth of couples commemorating their relationship on there was such an adorable reflection of humanity.

It definitely made the perfect end to an educational, historical, and romantic trip and gave me memories that I can hold dear into the future.

In Conclusion

It's difficult to squeeze such an exciting city into just two days. From ghosts, to romance, to history, to iconic architecture, St. Augustine certainly has a little bit to offer for everyone. No matter how short your duration in the city it, it will never fail to impress.


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