Romantic Getaway Guide to St. Augustine, Florida By Christi Kisling – Soul Quest Travel

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—blended with the serene beauty of the ocean.

Where to Stay: The Saint Augustine Beach House

We found our perfect retreat at The Saint Augustine Beach House—a cozy, charming three-story property 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.

The room featured a king bed, hardwood floors, and a kitchenette with a table and chairs—perfect for laid-back breakfasts or evening wine. The air conditioning kept things crisp, and the vibe was clean, modern, and calming—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 hop-on, hop-off experience that 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.

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. With costumed guides, preserved jail cells, and original artifacts, you’ll 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.

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?!” 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?

Where to Dine: River & Fort

For an unforgettable dining experience, head to River & Fort, located right at the main intersection in the heart of historic St. Augustine. This rooftop restaurant and bar offers 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.

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.

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.

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