Weekend in St. Augustine, Florida: Ideas for every traveler
Follow your curiosity through the Ancient City, from the charming streets of the Historic District to the white quartz sand of Anastasia Island.
Edited by Taylor Cahan | January 21, 2026
Morning by the sea, afternoon in the past — St. Augustine, Florida invites you to slow down and explore the city’s neighborhoods at your own pace. Park once and wander the pedestrian-only Historic District or cross the Bridge of Lions for a beach day on Anastasia Island. Rainy afternoon? Anchors like the impressive Castillo de San Marcos, downtown’s St. George Street and the boardwalks of Vilano Beach make it easy to tailor your trip.
In this article: Things to do in St. Augustine
Adventure in the Historic District
Culture, cuisine, and music in Lincolnville
Adventure in the Historic District
Start your day at Castillo de San Marcos, where early entry helps you beat the lines and enjoy the cool morning breeze along the scenic Matanzas Bay. Wander the pedestrian-only stretch of St. George Street, lined with historic facades, local shops, and inviting cafés. Families might linger in downtown’s hands-on living history exhibits or hop on the Old Town Trolley for a sightseeing tour, while couples can relax in lush courtyards or stop by the St. Augustine Distillery for a midday whiskey tasting. If the forecast predicts rain, Villa Zorayda and the Lightner Museum’s galleries provide a cozy retreat filled with Gilded Age pieces. For a seamless experience, Hilton St. Augustine Historic Bayfront puts you steps from St. George Street and the bay, with colorful Spanish Colonial-inspired architecture and a heated outdoor pool overlooking the water.
Beach day on Anastasia Island
Begin your morning with a climb up the 219 steps of the historic 1874 St. Augustine Lighthouse, where panoramic views reward your effort. If you prefer to stay grounded, the Maritime Museum features fascinating exhibits and hands-on activities for kids. Later, head to Anastasia State Park for a sun-soaked afternoon — rent a kayak, stroll the trails, or simply relax on the sand. If the weather shifts, the St. Augustine Alligator Farm Zoological Park provides a lively, weather-flexible option. For a restful night, oceanfront suites at Embassy Suites by Hilton St. Augustine Beach Oceanfront Resort offer direct beach access, a resort-style pool, free made-to-order breakfast, and a shore-to-table restaurant on site.
Culture, cuisine, and music in Lincolnville
Discover the heart of St. Augustine’s Black history in Lincolnville, a storied neighborhood that served as a cornerstone of the Civil Rights Movement. Spend your afternoon exploring interactive exhibits at the Lincolnville Museum and Cultural Center, then walk the ACCORD Freedom Trail or admire the neighborhood’s Victorian-era homes. As evening falls, catch live jazz or blues in a courtyard or sample Southern-inspired fare at a neighborhood eatery. If rain interrupts your plans, nearby museums and galleries around King Street provide a cozy alternative. For longer stays or small groups, Homewood Suites by Hilton St. Augustine San Sebastian, just across the San Sebastian River, features spacious suites with full kitchens and an outdoor pool with marina views.
Boardwalk sunset at Vilano Beach
Just over the Francis and Mary Usina Bridge, you’ll find the laid-back Vilano Beach community. Plan for a late-afternoon stroll along the Vilano Beach Nature Boardwalk, where the wide shoreline is perfect for shelling and sunset views. Add a daytime stop at Fort Mose Historic State Park for a glimpse into history or simply unwind by the water. As the sun dips, the iconic fishing pier offers a peaceful spot to end your day, with fresh seafood and local flavors nearby. Hampton Inn and Suites St. Augustine-Vilano Beach is a serene seaside base providing free hot breakfast, complimentary bike rentals, and an outdoor pool for relaxing after your adventures.
Bonus: Winter fun at Nights of Lights
If you’re visiting St. Augustine in the winter, don’t miss Nights of Lights. The renowned event transforms the city into a glowing wonderland from November through January, with millions of lights illuminating the Historic District. For the best experience, plan to visit on a weeknight and use the city’s free park-and-ride shuttles, then experience the festive atmosphere on foot. DoubleTree by Hilton St. Augustine Historic District offers convenient downtown access, an outdoor pool, an on-site restaurant, and the signature warm DoubleTree cookie welcome.
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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