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Unique Date Night Activities in St. Augustine

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Whether you’re in a relationship, celebrating years of marriage, or going on that very first date, St. Augustine has activities for all types of romance. The “Old City” features a number of romantic date night activities waiting to be discovered. Few cities across America offer couples such a rich unique history, beautiful beaches, eclectic dining, fresh seafood and locally inspired farm to table restaurants, all in one location. The charming change of pace in St. Augustine is just one of many reasons why couples love getting lost in the city.  Here’s just a few of our favorite date night activities across St. Augustine! 

Ghosts & Gravestones Night Tour

For couples interested in a romantically spooky adventure, Ghosts & Gravestones Night Tour offers the perfect unique date night activity.

Listed on the Florida and National Registers of Haunted Places, there’s plenty of hair-raising to be had in the nation’s oldest city. Explore the paranormal aboard the Trolley of the Doomed, while your Ghost Host gives you a glimpse into the grim history of St. Augustine. Discover the secrets of the Tolomato Cemetery. Be sure to keep a watchful eye while passing by the old City Gates. You might catch a glimpse of Elizabeth, a child victim of the yellow fever, waving to passersby. Face your fears in Potter’s Wax Museum’s Chamber of Horrors and enter the town’s most haunted building, the Old Jail, for an up close and personal encounter. Arrive early to explore Cromwell’s Parlour of Paranormal Curiosities, St. Augustine’s only collection of the paranormal and unexplained. Listed as one of USA Today’s Top 10 Best Ghost Tours in the country, this unique date night experience gives you the perfect reason to cuddle up close to your loved one for safety.

Michael’s Tasting Room

For the best romantic meal in St. Augustine, visit Michael’s Tasting Room.

The menu consists of dishes created using local and seasonal ingredients, as well as an award-winning wine list. When you book your dinner reservation, be sure to ask about their unique Date Night Experience. It begins with an amuse bouche and a toast of sparkling wine for two. Chef Lugo then serves up a three-course dinner accompanied by the perfect wine pairing.

Horse-Drawn Carriage Ride

For a unique date night experience, try exploring downtown St. Augustine by a horse-drawn carriage.

The staff at Southern Carriages will make you feel as if you’ve stepped into a fairytale as you ride through town in their lighted white carriage. You can bring your own bottle of wine or have them take care of all the details for you. Give your partner this incredibly romantic memory that will last a lifetime.

Schooner Freedom Charter

Rated as one of the Top 10 Attractions in St. Augustine by USA Today, you will want to add this to your to-do list.

Each Friday evening, Schooner Freedom Charters offers a one-hour-and-15-minute moonlight cruise. While you sail, you’ll enjoy complimentary drinks and unbelievable views of the town. Let the reflection of the moon glistening over the water be the backdrop to your unique date night experience. Keep in mind, reservations must be made in advance.

The St. Augustine Food Tour

Let history come alive as you savor the diverse and delicious flavors of the Old City.

The St. Augustine Food Tour is perfect for the foodie couple on the search for a unique date night experience. This three-hour, all-inclusive tour stops at five participating restaurants. You’ll dine on four delectable dishes and one dessert. Beer and wine are also available to purchase if you’re looking for the perfect beverage to pair with your meal.

Craft Cocktails

There’s no denying date night planning can get stressful. Why not take the edge off with some delicious craft cocktails?

St. Augustine is known to have a number of unique date night locations; but we recommend Ice Plant and Odd Birds for some of the finest craft cocktails in town. Try the Ice Plant for a historic setting with a modern vibe and expertly mixed craft cocktails that are sure to impress. Odd Birds features a slightly more lively atmosphere as they often feature live music by local performers on their patio.


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Bike Ride Across St. Augustine

Another unique date night activity is discovering the beauty of St. Augustine at night on a romantic bike ride.

Visit St. Augustine Bike Rentals and rent a pair of bicycles for yourself and your partner. From downtown to the beach to our beautiful parks, there’s an abundance of biking opportunities in St. Augustine. Make your own map and let the road be your guide as you see a different side of the Ancient City.

Old Jail After Dark

Discover the grim history of St. Augustine’s Old Jail After Dark with Old Town Trolley’s brand new paranormal tour.

Recognized as one of the most haunted buildings in the country, the Old Jail is shrouded in mystery and lore. Explore a different side of the Ancient City on this spine tingling tour and take part in an actual paranormal investigation. Their expert guides will teach you how to use the latest ghost-hunting equipment. See what makes this iconic landmark so spooky after dark during this intimate and unique date night experience.

There’s no question that St. Augustine boasts a number of unique date night activities. With so many options to choose from, it’s no wonder why couples keep coming back for romantic getaways. Whether you’re exploring the rich history of the Ancient City by horse and carriage, or simply strolling through the streets hand-in-hand admiring the historical architecture of the city, the opportunities for romantic date night experiences are limitless. Hopefully, the examples above are just enough to get your romantic date night planning started!