Hey there, adventurers! It is I, The Monthly Traveler, your go-to guide for uncovering the best places to visit. This time, we’re diving into the epic, sun-soaked streets of St. Augustine, Florida—a city with a past as rich as its sunsets.
St. Augustine isn’t just any old town—it’s the oldest continuously occupied European city in the U.S., founded way back in 1565 by Spanish conquistador Pedro Menéndez de Avilés. That means you’re literally walking through over 450 years of history. So grab your walking shoes, an appetite for adventure (and some delicious food), and let’s explore this city’s fascinating mix of old-world charm and laid-back coastal vibes. I’ve got some hidden gems up my sleeve that you definitely don’t want to miss!
For those of you looking to escape California’s beaches (but still want to stay near a beach—let’s be real), St. Augustine offers a delightful mix of historic streets, ancient forts, and some seriously jaw-dropping food. And it’s all wrapped up in the unmistakable charm of Spanish culture. Ready for a whirlwind few days? Let’s dive in!
A Glimpse into St. Augustine’s Rich History
Before diving into the enchanting sights awaiting us, let’s pause to appreciate the fascinating history of St. Augustine—our nation’s oldest continuously occupied European settlement! Founded in 1565 by Don Pedro Menéndez de Avilés, this remarkable city emerged 42 years before Jamestown and 55 years before the Pilgrims landed at Plymouth Rock.
As you stroll through its charming streets, you’ll encounter 36 original colonial buildings and 40 reconstructions, each inviting you to step back in time. The narrow streets and balconied houses whisper tales of a rich cultural tapestry woven over centuries.
St. Augustine also played a vital role in the Underground Railroad. In 1738, it became a sanctuary for escaped slaves, establishing Gracia Real de Santa Teresa de Mose, the first legally recognized community of freed slaves in the U.S.
And let’s not forget the majestic Castillo de San Marcos! Completed in the late 17th century, this fortress stood strong against sieges, including a dramatic British attack in 1702. A visit to St. Augustine isn’t complete without exploring its thick coquina walls and scenic waterfront views. As you wander through this incredible piece of history, you can feel the weight of the centuries upon you.
Day 1: History and Culinary Delights
First Stop: Castillo de San Marcos – A Fortress Like No Other
Alright, let’s kick things off with a bang—Castillo de San Marcos, baby! This colossal fortress is where history and adventure collide. Built in the late 1600s, it’s stood strong through wars, invasions, and—most importantly—time. As we wander through the coquina stone walls (yep, made of seashells!), imagine what it was like when Spanish soldiers defended this stronghold. Bonus: The views of Matanzas Bay are pretty breathtaking too.
Let’s be honest—standing in a fort this old feels like a scene out of an adventure movie, doesn’t it? And if you’re anything like me, The Monthly Traveler, you’ll definitely want to get that classic cannon photo for the ‘Gram. Because what’s a trip without a little historical flex?
St. George Street – Your Portal to the Past
Now, it’s time to swap fort walls for cobblestones as we head over to St. George Street. This is your pedestrian-only playground, packed with charming shops, art galleries, and local eats. Trust me, you could spend hours just wandering, but don’t get too distracted by the shops (although those handmade crafts are calling your name). This street feels like a journey back in time, with colonial-style houses that make you feel like you’ve stepped into another century.
Pro tip: Keep an ear out for some live music, and if you’re lucky, you might catch a street performer or two. Nothing like some tunes to accompany your stroll through history, right?
Check-In at St. George Inn – Your Home Away from Home
After soaking in all that history, it’s time to check into the St. George Inn. Nestled on the picturesque, pedestrian-only St. George Street, this charming boutique hotel serves as your gateway to St. Augustine’s rich past. With captivating views of landmarks like the Castillo de San Marcos and City Gate, the inn’s cozy accommodations offer a perfect blend of comfort and elegance. Picture yourself relaxing in a room adorned with thoughtful features, and maybe even enjoying a lovely balcony view. It’s the ideal spot to recharge for our adventure!
Time for Lunch! Columbia Restaurant – A Feast of Spanish Flavors
Okay, after all that exploring, it’s time for a serious refuel. Let me take you to Columbia Restaurant, the oldest restaurant in Florida. Established in 1905, this place is an institution. And believe me when I say, the food? Chef’s kiss. You absolutely have to try their famous 1905 Salad—it’s practically legendary. If you’re in the mood for something heartier, go for the paella. Trust me, it’s a party on a plate.
Oh, and while you’re here, don’t sleep on the sangria. It’s been a house specialty for over a century for a reason. The Monthly Traveler approves of this place for a solid dose of Spanish flavor—served with a side of history, of course.
Fountain of Youth – Let’s Take a Sip, Just for Fun
And now, onto the mythical stop that everyone secretly hopes will work—The Fountain of Youth. Legend has it, Ponce de León was searching for this magical spring, hoping to unlock eternal youth. And while I can’t promise you’ll leave looking five years younger, I can guarantee it’s a fun and fascinating spot to explore. Take a sip of the spring water—you know, just in case! There’s also a great park with peacocks strutting around like they own the place and some incredible Timucua Native American history that adds to the richness of the experience.
I’ll just say this: whether the Fountain works or not, a little stroll around here is sure to leave you feeling rejuvenated.
Michael’s Tasting Room for Dinner
As the sun starts to dip, it’s time to treat yourself to a culinary masterpiece at Michael’s Tasting Room. The restaurant offers a casually elegant dining experience that showcases the best of coastal Spanish-inspired cuisine. With its cozy, intimate atmosphere and an award-winning wine list, Michael’s is perfect for a more refined dinner. Opt for their tasting menu, where each course is paired with a carefully selected wine. Trust me, this meal will leave you talking about it long after you’ve left town.
Time to Rest at St. George Inn
After a fabulous first day of exploration, it’s time to return to the St. George Inn. Settle into your comfortable room, and let the day’s adventures wash over you as you drift off into dreamland. Tomorrow promises even more excitement!
Day 2:
Breakfast at St. George Inn – A Cozy Start
Rise and shine, fellow explorers! Let’s kick off Day 2 with a small breakfast at St. George Inn. They offer a delightful selection of pastries, fresh fruit, and coffee to get you fueled up for another exciting day ahead. There’s something so comforting about enjoying breakfast in a place that feels steeped in history, don’t you think? With your energy renewed, it’s time to head out and uncover more of St. Augustine’s treasures!
Mission Nombre de Dios – A Quiet Stop for Reflection
With your belly full and your spirits high, let’s head to one of the most peaceful spots in St. Augustine—Mission Nombre de Dios. This mission is where the first Catholic mass was celebrated in the U.S., dating back to the same year the city was founded. As you walk through the tranquil grounds, you’ll see the giant cross that marks the site. It’s hard not to feel a sense of calm and history here. Take a moment to reflect on everything we’ve seen so far—this city is bursting with stories, and we’ve only scratched the surface!
St. Augustine Distillery – Time for a Sip of the Local Spirit
Next stop? The St. Augustine Distillery. Don’t worry, this tour doesn’t involve too much walking, but it does involve plenty of tasting! At this local gem, they’re making small-batch spirits like bourbon, vodka, and gin—all crafted from Florida-grown ingredients. I’ll let you in on a secret: the cocktails here are divine. Go ahead, take a sip of their bourbon while learning all about how it’s made. It’s the perfect way to toast to our adventure so far.
Dinner with a View at Pesca Rooftop Kitchen & Bar
As the sun sets on another day of adventure, there’s no better way to wind down than with a memorable dinner at Pesca Rooftop Kitchen & Bar. Perched high above St. Augustine, this rooftop gem offers panoramic views of the city and bay, setting the stage for a stunning dining experience.
Indulge in the freshest seafood while watching the sky transform with vibrant evening hues. The ceviche is a standout, bursting with refreshing, citrusy flavors that pair perfectly with a handcrafted cocktail. As you sip and savor, the combination of fresh cuisine, cool breezes, and breathtaking views creates a magical evening atmosphere.
After dinner, with the city lights twinkling below, it’s the perfect time to relax and reflect on the day’s adventures before heading back to the St. George Inn for a restful night.
Time to Rest at the St. George Inn
After savoring the last of your dinner, it’s time to wind down and head back to the St. George Inn for some well-deserved rest. The charm and comfort of the inn welcome you with open arms after a full day of exploring. With its picturesque courtyards and cozy rooms, it’s the perfect place to relax and recharge for more adventures to come.
Day 3:
Breakfast at St. George Inn – Fuel Up for More Adventures
Good morning, adventurers! After a restful night at the charming St. George Inn, it’s time to kick off Day 3 with another cozy breakfast. As you savor fresh pastries, fruit, and a steaming cup of coffee, you’ll be soaking in the serene atmosphere that only this historic inn can offer. It’s the perfect way to prepare for a new day of exploration in St. Augustine. With the sights and sounds of the city waking up around you, there’s a sense of excitement in the air—today’s adventures are calling, and we’re ready to answer!
St. Augustine Beach – Sun, Sand, and Serious Relaxation
Feeling the need to unwind after a full day of sightseeing? Let’s hit the beach! St. Augustine Beach is just a short drive away, and it’s the perfect place to sink your toes in the sand and soak up some rays. Whether you’re here for paddleboarding, surfing, or just lounging under an umbrella, this beach has it all. Plus, the Atlantic Ocean has a way of washing away any stress you didn’t even know you had.
Lunch at Bourbon & Boards – Relaxation After the Beach
After spending a sun-soaked morning at St. Augustine Beach, there’s nothing quite like cooling off and grabbing lunch in the heart of the historic district. Our next stop? Bourbon & Boards, where charcuterie and jazz make for the perfect midday pick-me-up.
This charming spot, just a short drive from the beach, invites you to unwind after a morning of sun and surf. Known for its beautiful charcuterie boards stacked with savory meats, cheeses, and colorful garnishes, Bourbon & Boards serves up a relaxing lunch that hits the spot. Pair it with one of their craft bourbon cocktails, and you’ve got a meal that’s both refreshing and satisfying.
With live jazz filling the air, this is the perfect place to sit back, sip a drink, and let the laid-back vibe carry you into the afternoon. It’s just the kind of easy-going atmosphere you crave after a morning of beach fun—like a cozy little retreat in the heart of St. Augustine.
One Last Stroll Down St. George Street
Before we bid farewell to this incredible city, there’s one more stop that simply can’t be missed—another leisurely stroll down St. George Street. This historic thoroughfare feels like the heart of St. Augustine, where the charm of the past meets the vibrant energy of the present.
As we wander through the pedestrian-only lanes one last time, you’ll feel the undeniable magic in the air. The cobblestone streets are lined with colonial-style buildings housing unique boutiques, art galleries, and cafés. It’s the perfect spot to pick up a last-minute souvenir or two, whether it’s a piece of handmade jewelry, a local work of art, or a fresh-baked treat to enjoy on your journey home.
There’s something so timeless about St. George Street that no matter how many times you walk through, it always offers something new to discover. Soak in the atmosphere, listen to the street musicians playing nearby, and enjoy this final moment in St. Augustine before we part ways.
Wrapping Up Our Adventure
Well, fellow explorers, that’s the grand tour of St. Augustine! As Hispanic Heritage Month comes to a close, there’s no better place to reflect on the rich culture and history that we’ve just experienced. From the fortress walls of Castillo de San Marcos to the fresh sea breezes at the beach, St. Augustine offers a perfect blend of past and present, culture and coastal relaxation.
It’s been a joy guiding you through this unforgettable city. But don’t worry—I’ll be back soon with another adventure. Until then, Stay curious!
