Hey adventurers! I’m The Monthly Traveler, here to guide you through St. Augustine, Florida—a sun-soaked city rich in history and charm. Founded in 1565 by Spanish explorer Pedro Menéndez de Avilés, St. Augustine is the oldest continuously inhabited European settlement in the U.S.
Step into over 450 years of history as you explore its historic streets, ancient forts, and vibrant coastal vibes. Whether you crave adventure, great food, or hidden gems, this city has it all. If you’re seeking a fresh beachside escape beyond California, St. Augustine’s unique blend of Spanish culture and stunning scenery awaits. Ready to explore? Let’s dive in!
A Glimpse into St. Augustine’s Rich History
Let’s start strong with Castillo de San Marcos, a massive fortress where history meets adventure. Built in the late 1600s from coquina stone—made of seashells—it has withstood wars, invasions, and centuries of time. Walking its walls, imagine Spanish soldiers defending this iconic stronghold while enjoying stunning views of Matanzas Bay.
Standing inside this ancient fort feels like stepping into an adventure film. And if you’re like me, The Monthly Traveler, you’ll want to snap that classic cannon photo for the ‘Gram—because every trip deserves a historical highlight.
St. Augustine also holds a powerful legacy as a sanctuary on the Underground Railroad. In 1738, it became home to Gracia Real de Santa Teresa de Mose, the first legally recognized freed slave community in the U.S.
No visit is complete without exploring Castillo de San Marcos—its thick coquina walls and scenic waterfront truly bring history to life.
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Day 1: History and Culinary Delights
First Stop: Castillo de San Marcos – A Fortress Like No Other
Kicking off our journey with a true icon—Castillo de San Marcos. This massive 17th-century fortress is where history and adventure collide. Built from coquina stone (yes, actual seashells!), it has withstood centuries of battles, invasions, and time itself. As you stroll through its weathered walls, picture Spanish soldiers defending their post, with panoramic views of Matanzas Bay adding to the experience.
Exploring this ancient stronghold feels like stepping into a real-life adventure film. And let’s be real—you’ll definitely want that classic cannon shot for your Instagram feed. Because what’s a trip without a little historical brag?
St. George Street – Your Portal to the Past
Next, trade fort walls for cobblestones as you explore St. George Street—a vibrant, pedestrian-only hub at the heart of St. Augustine. Lined with colonial-style buildings, this historic street blends old-world charm with modern flair. Browse unique shops, local art galleries, and tempting eateries, all while soaking in the timeless atmosphere.
It’s easy to lose track of time here, especially with handmade crafts and sweet treats around every corner. Stay alert for live music or street performers—there’s no better soundtrack for your stroll through centuries of history.
Check-In at St. George Inn – Your Home Away from Home
After a day steeped in history, unwind at the St. George Inn—an inviting boutique hotel tucked along the charming, pedestrian-only St. George Street. Just steps from iconic landmarks like Castillo de San Marcos and the City Gate, this cozy retreat blends classic elegance with modern comfort.
Enjoy well-appointed rooms, some with balconies overlooking the historic district, offering a peaceful place to recharge. Whether you’re sipping morning coffee with a view or resting up for your next adventure, the St. George Inn is the perfect home base for exploring St. Augustine.
Time for Lunch! Columbia Restaurant – A Feast of Spanish Flavors
After all that exploring, it’s time to refuel—and there’s no better place than Columbia Restaurant, Florida’s oldest dining establishment, founded in 1905. This iconic spot delivers bold Spanish flavors in a setting rich with history.
Start with the legendary 1905 Salad—fresh, zesty, and unforgettable. Craving something heartier? The paella is a flavor-packed feast you won’t forget. And don’t skip the sangria, a house favorite for over a century. Columbia Restaurant is where tradition meets taste, earning The Monthly Traveler’s stamp of approval for a truly historic dining experience.
Fountain of Youth – Let’s Take a Sip, Just for Fun
Next up is a legendary stop that sparks everyone’s curiosity—the Fountain of Youth. According to myth, Ponce de León searched these grounds for the magical spring promising eternal youth. While I can’t guarantee a rewind on the clock, the experience is definitely worth the visit.
Take a sip from the spring—just in case—and explore the lush park, where peacocks roam freely and centuries of Timucua Native American history come to life. Whether or not the waters work their magic, a walk through this historic site is sure to leave you refreshed and inspired.
Michael’s Tasting Room for Dinner
As the sun begins to set, indulge in an unforgettable dinner at Michael’s Tasting Room. This intimate, casually elegant spot delivers coastal, Spanish-inspired cuisine at its finest. With an award-winning wine list and warm ambiance, it’s the ideal setting for a refined evening out.
For the full experience, choose the tasting menu—each course thoughtfully paired with a curated wine selection. Every bite is crafted with care, making this a meal you’ll remember long after your St. Augustine adventure ends.
Time to Rest at St. George Inn
After a full day of discovery, head back to the comfort of the St. George Inn. Unwind in your cozy room, reflect on the day’s adventures, and let the charm of St. Augustine lull you to sleep. Rest up—another exciting day awaits tomorrow!
Day 2:
Breakfast at St. George Inn – A Cozy Start
Rise and shine, explorers! Start Day 2 with a light yet satisfying breakfast at the St. George Inn—fresh pastries, seasonal fruit, and rich coffee set the perfect tone for the day. There’s something special about savoring a quiet morning in such a historic setting. With your energy recharged, it’s time to dive back into the timeless charm and hidden gems of St. Augustine!
Mission Nombre de Dios – A Quiet Stop for Reflection
With your belly full and spirits lifted, make your way to one of St. Augustine’s most serene landmarks—Mission Nombre de Dios. Established in 1565, it’s the site of the first Catholic Mass in the U.S. and a powerful symbol of the city’s deep-rooted history.
Stroll through the peaceful grounds and take in the towering Great Cross that marks this sacred place. It’s the perfect spot to pause, reflect, and appreciate just how much history surrounds you. And believe it or not, we’ve only begun to uncover St. Augustine’s incredible story.
St. Augustine Distillery – Time for a Sip of the Local Spirit
Next, visit the St. Augustine Distillery—a local favorite where tasting takes center stage with minimal walking. This small-batch producer crafts bourbon, vodka, and gin using Florida-grown ingredients, offering a true taste of the region.
Sip on expertly crafted cocktails as you learn about the distilling process. It’s a delicious way to celebrate our journey so far and raise a glass to the spirit of St. Augustine.
Dinner with a View at Pesca Rooftop Kitchen & Bar
As the sun sets on another adventure-filled day, unwind with dinner at Pesca Rooftop Kitchen & Bar. This rooftop hotspot offers sweeping views of St. Augustine and the bay, creating a breathtaking backdrop for your meal.
Savor the freshest seafood—especially the citrusy ceviche—paired perfectly with a handcrafted cocktail. The blend of delicious flavors, cool evening breeze, and stunning scenery sets the tone for a magical night.
Afterward, enjoy the city lights twinkling below as you reflect on the day before returning to the St. George Inn for a restful night.
Time to Rest at the St. George Inn
After enjoying your dinner, return to the St. George Inn for a well-earned rest. Its cozy rooms and charming courtyards provide a peaceful retreat, welcoming you to relax and recharge after a day full of exploration. This inviting inn is the perfect base to prepare for the adventures ahead.
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, start Day 3 with a cozy breakfast of fresh pastries, fruit, and steaming coffee. Enjoy the peaceful ambiance unique to this historic inn as the city comes alive around you. With energy renewed and excitement building, you’re ready to dive into another day of exploration in St. Augustine. Let the adventure begin!
St. Augustine Beach – Sun, Sand, and Serious Relaxation
Need to relax after a full day of sightseeing? Head to St. Augustine Beach, just a short drive away. Sink your toes into the soft sand, soak up the sun, or enjoy paddleboarding and surfing. Whether lounging under an umbrella or catching waves, the Atlantic Ocean’s calming energy is the perfect way to melt away stress and recharge.
Lunch at Bourbon & Boards – Relaxation After the Beach
After a sun-soaked morning at St. Augustine Beach, cool off with lunch in the historic district at Bourbon & Boards. This cozy spot is known for its stunning charcuterie boards, featuring savory meats, cheeses, and vibrant garnishes—perfect for a satisfying midday bite.
Pair your meal with a craft bourbon cocktail while live jazz sets a relaxed, inviting mood. Bourbon & Boards offers the ideal blend of flavor and atmosphere, making it the perfect retreat after a morning of sun and surf in St. Augustine.
One Last Stroll Down St. George Street
Before saying goodbye to this incredible city, take one last leisurely stroll down St. George Street—the heart of St. Augustine where history and vibrant energy meet.
Wander the pedestrian-only cobblestone lanes lined with colonial-style buildings, unique boutiques, art galleries, and cafés. It’s the perfect place to grab a final souvenir—whether handmade jewelry, local art, or a fresh treat for the road.
St. George Street’s timeless charm means every visit reveals something new. Soak in the atmosphere, enjoy the street musicians, and savor this final moment in St. Augustine before you depart.
Wrapping Up Our Adventure
That wraps up our grand tour of St. Augustine, fellow explorers! As Hispanic Heritage Month concludes, it’s the perfect time to reflect on the rich culture and history we’ve uncovered. From the steadfast walls of Castillo de San Marcos to the refreshing ocean breeze, St. Augustine beautifully blends history, culture, and coastal charm.
It’s been a pleasure guiding you through this unforgettable city. Stay curious—I’ll be back soon with another adventure!
Frequently Asked Questions
What is St. Augustine Dream – The Monthly Traveler about?
It’s a travel guide exploring the rich history, culture, and attractions of St. Augustine, Florida, blending historical sites with modern experiences.
Who is the target audience?
Travelers and adventurers interested in history, culture, coastal escapes, and unique local experiences in St. Augustine.
What are the must-see attractions featured?
Highlights include Castillo de San Marcos, St. George Street, Mission Nombre de Dios, and St. Augustine Beach.
Does the guide cover dining options?
Yes, it features local favorites like Columbia Restaurant, Michael’s Tasting Room, Bourbon & Boards, and Pesca Rooftop Kitchen & Bar.
Is the guide suitable for families?
Absolutely! The guide offers attractions and activities that appeal to travelers of all ages.
When is the best time to visit St. Augustine?
Spring and fall offer pleasant weather with fewer crowds, ideal for exploring.
Does the guide include tips for accommodation?
Yes, it highlights charming stays like the St. George Inn, perfect for an authentic experience.
Are there any cultural or historical insights?
The guide delves into St. Augustine’s Spanish heritage, including its role in the Underground Railroad and Native American history.
Conclusion
St. Augustine offers a captivating blend of rich history, vibrant culture, and stunning coastal beauty that makes it a must-visit destination for any traveler. From exploring ancient forts and charming cobblestone streets to savoring delicious Spanish-inspired cuisine, every moment in this city feels like stepping into a living storybook.
Whether you’re seeking adventure, relaxation, or a deeper connection to America’s past, St. Augustine delivers unforgettable experiences at every turn. So pack your bags, and get ready to create your own St. Augustine dream!