Why St. Augustine is My Dream Eccentric Winter Escape

As a New Englander, winter can feel like living inside a snow globe, but not in the dreamy kind of way—more like the “frozen in time, fighting for warmth” type of way. So, when the cold settles in like a long, unwelcome guest, I crave a refuge that balances the quirky with the luxurious—a place to rediscover myself and indulge every whim. St. Augustine, Florida, is my ideal winter escape where I can indulge all my eccentric interests and lifestyle. From history to wellness, nature to food and art, or a dash of mystery, this town never disappoints.

I didn’t just stumble upon this city—it’s a place that chose me, as much as I chose it. When I attended Flagler College, I had the privilege of studying in a historic city, even living in the Ponce de Leon Hotel, like many of the United States' presidents and leaders did. I could feel their stories pulsing through the architecture today. It was here I realized that, just like me, St. Augustine has a soul made of contradictions: a deep reverence for history mixed with a very modern, eclectic energy that feels welcoming without being overbearing.

Here’s why St. Augustine is the perfect setting for everyone’s eccentric winter retreat, full of quirky delights and unexpected experiences.

History, Haunts, and Mystery: An Adventure for the Curious Soul

St. Augustine is, after all, the oldest city in the United States. There’s history around every corner. But I don’t just mean your typical colonial landmarks—no, no. I’m talking about the weird and wonderful corners where history and mystery blur into one big, intriguing puzzle. Castillo de San Marcos, with its ancient stone walls, makes for an epic photo op—but dive a little deeper, and you’ll hear ghost stories, secret passages, and tales of pirates. There’s something irresistible about wandering the cobblestone streets, where every building could tell a scandalous tale. I’ve spent hours at the Lightner Museum—not just to admire its stunning collection of Victorian art but to drink in the gorgeous, slightly eerie ambiance of the old hotel-turned-museum.

And let’s talk about the Ponce de Leon Hotel, where I had the pleasure of studying at Flagler College—because, after all, this city is inextricably linked to two titans of history. Henry Flagler, the railroad magnate, built the Ponce de Leon Hotel in 1888 as one of the finest luxury hotels of its time, a testament to his vision for transforming the area into a resort haven for the elite. And who stayed there? Only the most famous names of the Gilded Age—like John D. Rockefeller, Thomas Edison, and even Henry James—a roster that reads like a who's-who of the wealthy and influential of the time.

The most fascinating part? Even today, you can still see remnants of the hotel's early days, including some of the electrical wiring from Thomas Edison himself. It's surreal to think that you're walking beneath the same roof where these historical giants once roamed, discussing everything from industry to the future of electricity.

But if you think the history here is just something to read about, think again. St. Augustine is known for its lively reenactment culture, which takes over the streets of downtown at certain times of the year, bringing the past back to life in the most immersive way possible. One of my favorite events is the Sack of St. Augustine, a reenactment of the 1702 raid where the streets are filled with roaring cannons, soldiers in period costumes, and a vibrant crowd of spectators. It’s like walking into a living history book—except with more cannon smoke and less homework.

If you're into the paranormal, there’s the Old Jail, where the ghosts of old-time criminals still make their presence known, and the Spanish Military Hospital Museum, where haunted histories often take center stage. But don't let the spooky vibes scare you away; the city has a magnetic energy that invites curiosity and playfulness—mystery and history are part of the charm.

Surf, Sun, and Wellness: A Healing Adventure for Body & Soul

Now, let’s talk about surfing and that wonderful St. Augustine Beach—which seems like it stretches on forever. Seriously, you could walk for miles and still feel like you’re discovering something new. The beach has always been one of the best East Coast surf destinations, and honestly, this was one of the things that first drew me to St. Augustine. When those blustery New England winter days seem to linger on forever, I can imagine nothing better than heading out to St. Augustine Beach for a few hours on the board, feeling the warm, salty water lapping at my skin.

The waves aren’t as massive as they are in California, but they’re just big enough to feel playful and exciting when the swell’s right. After all, this New England surfer didn’t come here just for the historic sights—I came for surf, sun, and salty freedom. There's something magical about riding a wave in 70-degree waters with dolphins cruising nearby when you’ve spent months buried under snowdrifts up north. It’s the perfect antidote to those long, cold winters.

But surfing isn’t just about the waves—it’s about finding that balance between adventure and rest. After a morning of catching some waves, there’s no better way to refuel than by grabbing a bite at Creative Juices Natural Café. It’s my go-to place for a post-surf feast, especially the quinoa feta burger, which is always fresh, flavorful, and exactly what my body craves. If you’re feeling extra fancy, they also have a killer smoothie selection to hydrate and replenish.

And let’s not forget wellness. The St. Augustine vibe isn’t just about history and waves—it’s also about healing. I love swinging by The Standard, a wellness oasis offering organic juices, mindful therapies, and a peaceful atmosphere. Whether I’m indulging in a detox, partaking in a calming yoga session, or treating myself to a moment of mindfulness, The Standard is my go-to sanctuary. On a quick escape, I might even indulge in a foot massage at Chinese Herbal Foot Massage & Reflexology in downtown St. Augustine, where they welcome you with open arms (and gentle reminders to drink more water after those soul-soothing sessions!).

Local Cuisine with a Side of Quirk: For the Unconventional Foodie

You know that feeling when you stumble upon a quirky little restaurant that’s not trying to impress anyone but just be itself? That’s St. Augustine, and nowhere is this more true than in its thriving food scene. Whether you’re a localvore or just someone who loves fresh, imaginative cuisine, this city delivers on flavor—and it’s all wrapped in a bit of local charm.

The Floridian is a standout in town, offering a menu that’s focused on locally sourced ingredients—seasonal produce, fresh seafood, and products from nearby farms are the stars here. The restaurant’s dedication to being food allergy-friendly makes it an especially great spot for those with dietary restrictions, offering safe and delicious options without sacrificing flavor. From farm-to-table salads to creative entrees, The Floridian manages to make fresh, healthy eating feel indulgent.

Then there’s The Kookaburra, a quirky little Aussie café that has become one of my go-tos for a mid-day caffeine fix or a casual bite. With their classic meat pies, veggie options, and perfectly brewed coffee, The Kookaburra is a unique blend of comfort food and casual charm that captures the spirit of St. Augustine. It's a place to relax, soak in the local vibe, and enjoy something simple but satisfying.

And, of course, Mojo’s Tacos—where, if you haven’t had their tacos, you’re missing out. Their signature tacos feature cheese melted between two taco shells (yes, you heard that right!)—making them a crispy, cheesy delight that’s sure to satisfy any taco lover’s cravings. It’s the perfect blend of flavor and fun, and a classic stop for those in the know.

St. Augustine’s food scene is as eclectic as its history. Whether you're craving a hearty meal, a light bite, or something more unique, this town has a bit of everything, with restaurants that prioritize local ingredients and diverse flavors. You’re never far from something that’ll leave you feeling satisfied and inspired.

Art, Music, and First Friday: A Celebration of the Creative Spirit

Every first Friday of the month, I head out to downtown St. Augustine for one of my favorite rituals—the First Friday Art Walks. Imagine strolling cobblestone streets, popping in and out of galleries, sipping on free wine, and letting the rhythm of live music sweep you into the night. The art scene here is alive with color, texture, and stories that defy convention. From abstract masterpieces to hand-crafted jewelry, every corner is brimming with creative energy.

On any given night, you’ll find spontaneous performances, whether it’s jazz at The Blue Hen or indie rock at The Colonial Quarter. For me, this city has a way of weaving art and music into the very fabric of life—much like the way the city’s history is never far from your thoughts. It’s a place where the old and the new meet, and you can’t help but feel a sense of inspiration every time you step outside.

Quirky Shops, Antique Finds, and Vintage Delights

If you’re anything like me—someone who can happily spend an entire afternoon lost in a thrift store or vintage boutique—St. Augustine will not disappoint. This city is a haven for all things quirky and nostalgic, from antique shops overflowing with forgotten treasures to boutique stores showcasing one-of-a-kind finds. One of my favorite places is Antique Emporium, where you can easily lose track of time sifting through old postcards, vintage maps, and obscure memorabilia.

I’ve always loved hunting for the perfect souvenir, something that’s not just a trinket but a piece of history—and here, there’s no shortage of treasures. Whether it’s a retro postcard from the 1950s or a handmade journal crafted by a local artist, there’s always something that feels like it was made just for you.

Nature, Trails, and Quiet Reflection: Finding Solitude in St. Augustine's Green Spaces

Even in the heart of this vibrant city, St. Augustine manages to preserve its natural beauty, and nowhere is this more evident than at Anastasia State Park. For me, this park is my sanctuary—a secluded escape where I can soak in the quiet stillness of nature and reset. Tucked away from the hustle and bustle of downtown, it’s the perfect spot to breathe in the salty air, feel the sand between my toes, and watch the waves roll in without a crowd in sight.

Anastasia State Park offers miles of trails, both on land and water, that wind through dense maritime forests, salt marshes, and along pristine beaches. One of my favorite things to do is grab my paddleboard and explore Salt Run, where the water is calm and the air is crisp, a perfect contrast to the bustling city just a few miles away. For nature lovers, it's a dream come true: birdwatching, kayaking, and fishing are all available, as well as the occasional sighting of dolphins or even manatees in the more tranquil waters.

But it’s the beaches that make Anastasia particularly special for me. While the main St. Augustine Beach can get a bit crowded—especially on sunny weekends—Anastasia offers a sense of seclusion that’s rare to find. Whether it’s lounging with a book, walking the shoreline, or watching the surfers catch waves, it’s easy to lose track of time here. The quiet solitude is exactly what I need to escape the winter chill up north and recharge. No loud crowds, no big tourist traps—just nature and space to breathe.

Anastasia is also a perfect place for those who love to escape into history while surrounded by the beauty of nature. The Anastasia Island lighthouse stands as a sentinel over the park, reminding me of the area's long and rich maritime heritage. Walking along the shore at dusk, I’ll often think back to the stories of pirates and explorers, of ships coming into harbor after long sea voyages. This deep connection between history and nature feels like the ultimate fusion, and I love how St. Augustine’s past continues to weave itself into my present experience of the city.

Whether I’m hiking through the serene dunes, kayaking in the salt marshes, or simply sitting on the beach and letting the world drift away, Anastasia State Park always feels like a personal retreat. It's the perfect counterbalance to St. Augustine’s busy downtown—a hidden oasis where you can truly escape and reconnect with yourself. If you’re looking for a place to reflect, reset, or just enjoy the beauty of Florida’s coastline, Anastasia is my go-to spot, and I promise it won’t disappoint.

A Soulful City for Every Side of You

St. Augustine is my eccentric winter escape, and I’m convinced it’s a place for everyone who craves variety, adventure, and inspiration. Whether you’re strolling through its historic streets, getting lost in its artistic spirit, catching waves, savoring a perfectly crafted meal, or simply letting nature speak to you in its quiet, peaceful way, this city has something for every side of you—and every side of me.

So, if you haven’t yet experienced the magic of St. Augustine, consider this your invitation to escape, discover, and indulge your most unconventional desires. After all, isn’t that what winter is for?