The Perfect Getaway: 3 days in St. Augustine for history buffs
Plan your stay with this walkable itinerary that explores the history of St. Augustine, Florida, from Castillo de San Marcos to Flagler College and St. George Street.
Edited by Karen Johanson | February 5, 2026
St. Augustine, Florida rewards those who explore on foot. Centuries of Spanish colonial planning created a walkable grid within its compact Historic District, where eras overlap at every turn. Experience the city’s layered history with minimal transit and maximum discovery. By anchoring your stay at Hilton St. Augustine Historic Bayfront, you’ll have the city’s most iconic sites just steps away — St. George Street, the Bridge of Lions, and Matanzas Bay are all within easy reach. Spanish Colonial-inspired architecture reflects the city’s past while offering modern comfort. Aviles Restaurant & Lounge is an ideal destination for both guests and locals, with farm-to-table produce, locally caught seafood, and global influences. If you arrive before check-in, simply drop your bags at the front desk and step right into the city’s living history.
Friday
Morning
Begin at the City Gates, the historic entrance to colonial St. Augustine. Stroll south along St. George Street, a pedestrian thoroughfare lined with coquina structures, shaded courtyards, and some of the city’s oldest shops. Pause in the Cathedral Basilica plaza to take in the Spanish facade and the sound of church bells.
Afternoon
Head to Castillo de San Marcos, the oldest masonry fortress in the continental United States. Avoid lines by arriving near 9 am, when they open, or during the early afternoon lull. Spend about an hour exploring the star-shaped bastion and learning how this architectural style absorbed cannon fire and protected the city for centuries. Afterward, stroll Avilés Street — the oldest street in the United States, with roots dating back to the early 1600s — and experience historical reenactments of the 17th and 18th centuries in the Colonial Quarter.
Evening
Near sunset, walk the waterfront promenade toward the Bridge of Lions to experience the warm glow on the water and the city’s historic facades. Hear stories of pirates and hauntings in after-dark themed walking tours — a popular way to experience St. Augustine’s storied streets. For dinner, return to Aviles Restaurant & Lounge for a relaxed meal and toast to the day’s discoveries.
Saturday
Morning
Begin your day with a guided tour of Flagler College, which was previously Hotel Ponce de Leon. Marvel at the Louis Comfort Tiffany stained-glass windows and the soaring Spanish Renaissance architecture. Tours are popular, so consider securing tickets in advance for one of the two daily tours. As you exit, trace King Street’s grand sightlines toward the Bridge of Lions.
Afternoon
Walk to the Lightner Museum, housed in the former Hotel Alcazar, for an immersion in decorative arts and Gilded Age design. If you have time, pair this stop with a visit to the Villa Zorayda Museum, an opulent example of Moorish Revival architecture, or the Oldest House Complex for a look at the history of St. Augustine. Take a midday break back at the hotel, with a dip in the outdoor pool or a quiet moment in the lounge.
Evening
As evening falls, browse the galleries and artisan shops along Avilés Street, soaking in the city’s creative energy. Stroll the bayfront promenade at sunset, then settle in for dinner, dessert, or a nightcap at Aviles Restaurant & Lounge, before returning to your room.
Sunday
Morning
Start your final day with a self-guided walk through Lincolnville, a neighborhood central to St. Augustine’s civil rights history. The ACCORD Civil Rights Museum and the Lincolnville Museum and Cultural Center mark pivotal moments with displays, documentaries, and books. For a deeper dive, consider a quick rideshare to Fort Mose, the first legally sanctioned free Black settlement in what is now the United States.
Afternoon
Return to the Historic District for a stroll through the Mission Nombre de Dios grounds, where the city of St. Augustine and the first Catholic Franciscan mission in the continental United States were founded. If you’re curious about archaeology and first-contact stories, the Fountain of Youth Archaeological Park offers reconstructed Timucua village exhibits that bring Indigenous history to life. Shaded areas and museum interiors offer a comfortable break from hot, humid weather and save longer walks for later in the day.
Until Next Time!
Time your visit to the St. Augustine Lighthouse for late afternoon or early evening, when the climb rewards you with sweeping views over the city, Matanzas Bay, and the Atlantic Ocean. Before heading home, reflect on your explorations of Spanish colonial streets, Gilded Age masterpieces, centuries of maritime history, and the ongoing narrative of America’s oldest city.
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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