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Romantic Places to Visit St. Augustine

There’s something magical about strolling hand in hand down cobblestone streets gazing at sights that have been enjoyed by other couples through the centuries. If a getaway, whether for a day or a week, in…

There’s something magical about strolling hand in hand down cobblestone streets gazing at sights that have been enjoyed by other couples through the centuries. If a getaway, whether for a day or a week, in a locale that has charm, history and culture around every corner sounds like your cup of tea, revel in the romance that is St. Augustine, Florida.

With more than 500 years of history, a stroll around the city will bring with it a sense of old-fashioned courtly romance. The idyllic warm weather in north Florida also makes St. Augustine a destination that can be enjoyed year-round. Whether you’re looking to ignite that spark, have an adventure or a little R&R, grab your loved one by the hand and saunter on down to one of the most romantic spots in Florida.

For the History Buff

Wine and Carriage Tour

Walk (or ride) in the footsteps of those who came before us with a sightseeing tour by a horse-drawn carriage. The sway of the carriage and sounds of the horses “clip-clopping” on the streets will transport you back to times past while your private guide points out notable sights and stories along the way.

Amp up the romance even further by combining a horse-drawn tour with a wine or food tasting. You and your loved one can wine and dine your way through the historic center of St. Augustine while cuddling under a blanket or feeling the warm breeze flowing through your hair. Companies like The Tasting Tours offer a variety of packages that are sure to please any wine lover or foodie.

For the Foodie

Preserved Restaurant.

Declared by Southern Living as the South’s best food town, St. Augustine has an exceptional culinary scene that reflects its coastal location and diverse heritage. Farm-to-Table restaurants serve fresh food with locally sourced ingredients to feed your appetite and ambiance to feed your soul. If you’re looking for dining to impress your sweetheart, take a look at Michael’s, Preserved, Collage, Old City House.

Whetstone’s Chocolate

To satisfy your sweet tooth, there is nothing much more synonymous with romance than chocolate and wine. The Whetstone’s Chocolate factory tour is a fun and delicious activity that will take you through the art and history of chocolate making. The bonus – you can do a tasting where a guide will show you the subtle differences between the chocolates. Afterward, head down the block to the award-winning San Sebastian Winery to further refine your palate. Savor the wines and head upstairs to their Jazz and Blues Bar to enjoy lively music and an amazing view of the historic district.

For the Music Lover

Colonial Oak Music Park

The Colonial Quarter is St. Augustine’s largest outdoor venue and offers free concerts and shows every week. The area is right off historic St. George street and is modeled after what the area originally looked like 500 years ago. Cozy up under the big Oak tree lit up by dozens of lanterns and listen to some of the best music around.

For the Artist

Aviles Street art galleries and cafés

St. Augustine has been a backdrop inspiring artists of all kinds for hundreds of years. In fact, the local art galleries are an attraction in themselves as they regularly debut new collections and host events like “Get to know the artist” series, art walks and wine tastings paired with viewings. For a more casual outing, grab a cup of coffee and spend the afternoon browsing the unique works of art throughout the town. Here is an art gallery map to help plan your route.

Sleep Tight

Courtyard at The Collector Luxury Inn & Gardens historic bed and breakfast

Whether you’re nearby and want a “staycation” or you are traveling from out of town, there is no better way to end your day of exploration than coming back to a cozy spot that combines modern comforts with a fascinating history. There are more than two dozen historic bed and breakfasts that are within walking distance to many of the items above.