The Perfect Getaway: A romantic long weekend in St. Augustine, Florida
Bayfront sunsets, Old Town strolls, trolley tours, and special dinners offer a charming escape in the Ancient City.
Edited by Kaitlyn Dreyling | January 21, 2026
The city of St. Augustine, on the northeast coast of Florida, welcomes couples to slow down and savor a weekend of lantern-lit streets, cobblestone lanes, and bay breezes. Stay at Hilton St. Augustine Historic Bayfront, a waterfront retreat in the Historic District. The hotel’s colorful Spanish Colonial-style architecture, Avilés Restaurant & Lounge, and guest rooms with views of Matanzas Bay create a sense of place that feels timeless and inviting. From this central location, you’ll find recommendations and insider tips for making every moment feel special.
Friday
Morning
Arrive in St. Augustine and let the city’s relaxed rhythm set the tone. Drop your bags with the front desk at Hilton St. Augustine Historic Bayfront — valet parking makes it easy to park once and explore on foot. Start with a gentle stroll along the bayfront, then pause for coffee at a nearby café, then wander the picturesque streets to orient yourself.
Afternoon
Once you’ve checked in, set your sights on the Castillo de San Marcos National Monument, the oldest masonry fort in the continental United States. Late afternoon visits typically offer a quieter experience as well as beautiful light for photos. The coquina walls glow in the golden light, and the views from the seawall are especially romantic as the day winds down. Take your time exploring the ramparts, then linger for sunset along the bay.
Evening
As twilight falls, stroll through the Colonial Quarter, where lanterns flicker and live music drifts from courtyards. Reserve a table at Avilés Restaurant & Lounge for a candlelit dinner — fresh local seafood, steakhouse favorites, creative coastal fare, and an extensive wine list are highlights. Afterward, take a slow walk along the waterfront before returning to your room.
Saturday
Morning
Take a drive across the Bridge of Lions to Anastasia Island and make your way to St. Augustine Beach for an early sunrise stroll on powdery-white sand. The morning is quiet and cool, perfect for sharing coffee at a local spot before returning to the Historic District.
Afternoon
Hop aboard the Old Town Trolley for a narrated sightseeing loop of the city’s top spots. The trolley is hop-on, hop-off, so you can explore at your own pace and choose which stops interest you. Pause at the St. Augustine Distillery for a whiskey tasting, take a tour of the San Sebastian Winery, or head to the Ponce de Leon’s Fountain of Youth Archaeological Park.
Evening
For a special evening, reserve a table at Harvest & Reel at Embassy Suites St. Augustine Beach Oceanfront Resort near St. Augustine Beach. Enjoy shore-to-table coastal cuisine, with a menu that features locally sourced seafood and seasonal produce. The dining room’s floor-to-ceiling windows frame golden-hour views of the Atlantic, making it an ideal spot to watch the sun set.
Sunday
Morning
Ease into your final day with a leisurely brunch. Stroll to the Lightner Museum or join a tour of nearby Flagler College to admire stained glass, grand courtyards, and Gilded Age architecture.
Afternoon
Spend the afternoon browsing Old Town’s boutiques and galleries for unique keepsakes. When you’re ready, make your way back to Hilton St. Augustine Historic Bayfront for one last coffee on the terrace or a quiet moment in your guest room overlooking the bay before check-out.
Until next time!
St. Augustine’s allure lingers long after you leave. Whether you return for summer sun or holiday lights, this city always welcomes you back for another chapter of romance and discovery.
Disclaimer: We used AI assistance to generate this content. All information was reviewed by Hilton's team to ensure it meets our standards for accuracy and ethics, allowing us to better match your travel needs and connect you with the right stay.
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