Romance is easy to come by in a whimsical city of lights, Spanish history, and quaint cobbled streets. It’s Europe in America, so to speak, and it’s oozing with charm. That's why we’ve compiled a guide to our favorite romantic streets in St. Augustine. All of these walkable spots are ideal for lovely couple strolls (in the historic district and the surrounding area). So, grab your beau, get your walking shoes on, and feel the love in the air.
Downtown St. Augustine Walks
St. George Street
Any time of day, St. George Street is teeming with life and activity. Donned with ice cream and fudge shops, cozy boutiques, and side alley surprises, there is no shortage of places to stop in for a drink or a romantic bite along this pedestrian corridor.
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Try any one of the many listening rooms and live music venues to achieve the right romantic vibes, like at Bin 39, Stogie’s, or Pierre’s Pub. Or, have a nice sit-down meal at the iconic Columbia restaurant.
Pro tip: Try this romantic street in St. Augustine during the morning hours to avoid the crowds. You might just have the place all to yourselves!
Bayfront Promenade
St. Augustine’s waterfronts are dotted with numerous restaurants, bars, and rooftop lounge spaces to accompany any strolling date. The most romantic of them all, perhaps, is the waterfront walk along the bayfront promenade.
On this romantic street in Augustine, you will pass the mighty Castillo de San Marcos. You'll also see multiple entrances to the Colonial Quarter, not to mention the lineup of old fashioned horse-and-buggies waiting for couples just like you along the bayfront wall.
Be sure to make a stop at the adorably decorated Crucial Coffee Cafe. Or, do a free walk-through tasting tour of whiskey, rum, and vodka at City Gate Spirits.
For waterfront meal times, look to Harbor View Cafe for breakfast, or drinks at the lovely Casablanca Inn (home of the Tini Martini Bar and Nero’s Waterfront Cafe), or Casa Reina’s rooftop overlooking the bay.
Plaza de la Constitución
The central plaza between King Street and Cathedral Place paves the path through the historic district towards the bayfront and the Bridge of Lions. Expect to see various statues, gazebos, and greenery along this romantic street.
Along both sides of the Plaza, find upscale shops, restaurants, Ancient City Brewing, and the indelible Casa Monica Hotel, where you must walk in to view the Arabesque lobby. The interior lounge spaces are stunning, so it’s worth popping in for a cocktail.
Throughout the year, Plaza de la Constitucion hosts numerous seasonal events, so you never quite know what to expect.
Aviles Street
Famed to be the oldest street in the United States, here you'll see places like the Spanish Military Hospital Museum and other worthy landmarks. But the real reason to head down this romantic street in St. Augustine is to find some hidden gems for eats and drinks that, typically, tourists don’t venture out to see.
Among the list and not soon forgotten is the Forgotten Tonic, where vintage vibes greet you, happy hour surprises you, and the drink list… well it’s going to knock your socks off. Cut up towards the waterfront after cheers with cocktails to walk the bayfront back to your car.
Walk Across the Bridge of Lions
Typically taking only 5-10 minutes to walk across, the ornate drawbridge at the Bridge of Lions is a right of passage to stroll, some locals may say. Take this stroll at a leisure pace, stop for photos of the water and, if you’ve got the gusto to go another five minutes past the bridge, do yourself a favor and drop in for a cocktail at Odd Birds.
The view of the boats will inspire your imagination to sail away with your beloved first mate.
Where to Park Downtown
Paid public parking is available at 1 Cordova Street in the Historic Downtown Parking Facility garage, or limited street parking is available.
St. Augustine Beachside Strolls
Anastasia Island
Who doesn’t love long walks on the beach, eh? Pick up some take-out from Nalu’s food truck (just outside the gates to Anastasia Island State Park) and park down at the beach lot, which has ample parking.
The park offers watercraft rentals and surfing. Plus, it has an onsite grill that serves adult beverages as well. Pssst… if you love this romantic locale, book a beach camping experience to walk into the wee hours.
St. Augustine Beach
Loaded with beachside restaurants and bars, seek one of the many beach access parking lots, like at Ocean Hammock Park Walkway or Pier Park. And don’t forget to grab something from Kookaburra Beachside coffee before you head down to the sand.
More Romantic Streets in St. Augustine Near Downtown
Fort Mose Walkway to Freedom
Only a few minutes north of town, Fort Mose offers a beautiful pathway along the marshy waters of the Tolomato River. Yup, it's perfect for a romantic stroll. It’s called the “Walkway to Freedom,” and here you’ll have opportunities for bird-watching and soaking in nature. This is also one of the fascinating historic places to visit with kids.
It’s a really lovely spot on a weekend morning. Park at the fort lot (which, by the way, there is no actual fort there but there is a museum). Visiting the walkway is free.
Stroll by the Love Trees
St. Augustine has several love trees, where two different species of trees have intertwined and grew stronger as one. Legend has it that if you kiss your sweetie under a Love Tree, you’ll have everlasting love. A popular love tree is by Bar Harbor Cheesecake Company.
Magnolia Avenue's Picture-Perfect Path
Among the most photographed streets in America, according to National Geographic, stroll along Magnolia Avenue. Arguably the most romantic street in St. Augustine because of its picture-perfect backdrop, couples often venue to Magnolia Avenue for engagement pictures.
No matter where you wander, love is in the air in St. Augustine!
