Discovering Romance and History in St. Augustine, Florida

If you’re searching for a romantic, history-filled escape by the sea, St. Augustine, Florida, is a dream come true. My husband and I recently celebrated our 25th wedding anniversary in this timeless coastal town, and it truly felt like a step back into history. The serene beauty of the ocean complemented our experience.

Where to Stay: The Saint Augustine Beach House

We found our perfect retreat at The Saint Augustine Beach House. This cozy, charming three-story property is nestled right on the oceanfront. Our corner unit on the second floor offered breathtaking views of the Atlantic through wide bay windows and from the private balcony. Mornings were particularly magical, especially on Sunday, when a crowd gathered on the beach for sunrise worship. Watching that peaceful moment from above, coffee in hand, was a beautiful experience.

A Cozy Room for Couples

The room featured a king bed, hardwood floors, and a kitchenette with a table and chairs. It was perfect for laid-back breakfasts or evening wine. The air conditioning kept things crisp, and the vibe was clean, modern, and calming. This atmosphere is ideal for couples looking to reconnect.

Getting Around: Trolley Tour of the Historic District

We highly recommend purchasing the St. Augustine Trolley Tour Pass. It’s a convenient hop-on, hop-off experience. This allows you to explore the rich history of America’s oldest city at your own pace. We opted for the Grand Tour, which included all-day access and entry to several historic landmarks. It was an excellent way to see the city without the stress of driving and parking.

Exploring the City’s Charm

With the trolley pass, you can easily access various sites. Each stop is filled with unique history and character. We learned so much about the city’s past, from its founding to its notorious figures. The knowledgeable guides shared stories that brought St. Augustine’s history to life.

Must-See Stop: The Old Jail

History buffs—don’t miss the Old Jail. Built in 1891 and surprisingly in operation until the 1950s, this site delivers a mix of eerie charm and real insight into past life in St. Augustine. Guided tours by costumed actors make the experience even more engaging.

A Glimpse into the Past

With preserved jail cells and original artifacts, you get a true sense of what incarceration was like a century ago. It’s both chilling and fascinating—and definitely worth the stop if you love a good (and slightly spooky) story.

Don’t forget to ask about the infamous inmates during your visit!

A Wild Ride: The Medieval Torture Museum

Now, for something completely different… the Medieval Torture Museum. Equal parts terrifying and theatrical, this attraction is like stepping into a very twisted history lesson. Wax figures in disturbing poses, hands-on torture devices, and interactive exhibits will leave you thinking, “People really did this?!”

Laughter and Unease

You’ll laugh, you’ll squirm, and you might even take a selfie in a torture cage—because, hey, what’s romance without a little shared trauma? It's an entertaining and educational experience for thrill-seekers. Just be prepared for some unsettling sights!

Where to Dine: River & Fort

For an unforgettable dining experience, head to River & Fort. This gem is located right at the main intersection in the heart of historic St. Augustine. The rooftop restaurant and bar offer open-air seating, coastal breeze, and stunning views overlooking the Matanzas River and the Castillo de San Marcos. It’s the perfect place to sip, savor, and people-watch as the city moves around you.

A Dining Experience to Remember

We were lucky enough to sit at the bar, where we met Austin, an incredible bartender who made the entire experience even better. My husband ordered the Blacksmith, one of their specialty cocktails—smoky, bold, and full of character. If you go, ask for Austin and try the Blacksmith—you won’t regret it!

River & Fort features locally inspired dishes, a refined but relaxed vibe, and an ambiance that perfectly captures the spirit of Florida.

More Dining Options to Explore

If you have time, explore other local dining options. From casual seafood shacks to upscale restaurants, St. Augustine's culinary scene is diverse and exciting. Each restaurant has its unique twist, making every meal a new adventure. Don’t miss out on trying fresh, local ingredients!

Final Thoughts

St. Augustine is the perfect blend of romance, history, and quirky charm. From peaceful mornings on the balcony to slightly spooky adventures and unforgettable meals, this city has something for every couple. Whether you’re in the mood for love, laughter, or learning something new together, St. Augustine delivers.

Let Soul Quest Travel help you plan your next romantic getaway. You deserve a love story with an ocean view!