St. Augustine: The City We Keep Coming Back To

My wife and I first went to St. Augustine on a romantic weekend getaway, not really knowing what to expect. By the end of that first trip, we were hooked—it instantly became one of our favorite destinations. Since then, we’ve been back several times, and it never disappoints. The best part about St. Augustine is how easy it is to just park the car and forget about it. The city is designed for walking, which makes exploring stress-free and allows you to soak up the atmosphere at every turn. From our base at the Casa Monica Resort & Spa, with its Moorish Revival architecture and old-world elegance, we were able to wander to nearly everything worth seeing, eating, and experiencing.

Castillo de San Marcos National Monument

History feels alive in St. Augustine. On one visit, we started at the Castillo de San Marcos, the oldest masonry fort in the continental US. Walking its coquina walls overlooking the Matanzas Bay, it’s easy to picture the battles and centuries of stories that unfolded there. Just down the street, the Colonial Quarter offered another immersive glimpse into the past. Climbing the watchtower, watching demonstrations, and strolling past reconstructed 16th–18th century buildings made us feel like we’d stepped back in time. Every corner of the city seems to have a story, and discovering those layers of history together has been one of the most memorable parts of our trips.

Of course, food has been just as much of a highlight. St. Augustine is filled with incredible dining options, from casual pubs to fine dining with a historic twist. We’ve enjoyed hearty pub fare at Bull & Crown on St. George Street, where the atmosphere is as lively as the people-watching. One night we dressed up for dinner at the iconic Columbia Restaurant, famous for its Spanish-Cuban cuisine and historic setting. On another evening, we grabbed drinks and dinner at Prohibition Kitchen (PK St. Aug), a speakeasy-style gastropub that always has great live music. Even casual meals stand out—One Twenty Three Burger House quickly became a favorite for its burgers and wood-fired pizzas.

Brunch in St. Augustine

No trip feels complete without a stop at the St. Augustine Distillery, where we’ve learned about (and sampled) locally crafted spirits. Right next door is the Ice Plant Bar, housed in a restored 1927 building where they once made ice. Their craft cocktails and farm-to-table menu are the perfect nightcap after a day of exploring.

St. Augustine Distillery

Learn about bourbon

Beyond the history and food, what makes St. Augustine so special to us is its charm. The people are friendly and welcoming, the city is dog-friendly—meaning we stop often to pet the many pups out on their walks—and there’s a laid-back vibe that makes it easy to relax. For us, the combination of history, atmosphere, and amazing food has turned St. Augustine from a one-time getaway into a tradition. Every visit feels just as magical as the first, and every time we leave, we’re already planning when we can come back.

For more inspiration and insider recommendations, visit our St. Augustine page.