A Weekend Getaway Guide to Historic St. Augustine: A Detailed Itinerary for a 2-3 Day Trip
Welcome to St. Augustine, Florida, the oldest continuously inhabited European settlement in the United States, founded in 1565. With its cobblestone streets, Spanish colonial architecture, and vibrant history, this charming coastal city is the perfect destination for a weekend getaway. Whether you’re a history buff, a foodie, or simply seeking a relaxing escape, St. Augustine offers a delightful blend of historic sites, cultural experiences, and modern amenities. This detailed 2-3 day itinerary will guide you through the best things to do, where to eat, and where to stay for an unforgettable trip to America’s Ancient City.
Why Visit St. Augustine?
St. Augustine is a treasure trove of history and culture. From the imposing Castillo de San Marcos to the enchanting Nights of Lights (if you visit during the holiday season), the city is packed with attractions that cater to all interests. Its compact historic district makes it easy to explore on foot, while nearby beaches and state parks offer opportunities for outdoor adventures. Plus, the city’s culinary scene is a delightful mix of fresh seafood, Southern comfort food, and international flavors.
This itinerary is designed for a 2-3 day trip, ideal for a long weekend. If you’re staying for just two days, you can follow the core plan; if you have three days, I’ve included bonus activities to enhance your experience. Let’s dive into your St. Augustine adventure!
Day 1: Exploring the Historic Heart of St. Augustine
Morning: Start with History at Castillo de San Marcos
Kick off your weekend getaway at the iconic Castillo de San Marcos National Monument (9 AM – 5 PM, $15 per adult, free for children under 15). This 17th-century Spanish fortress, built from coquina stone, is the oldest masonry fort in the continental United States. Wander through its rooms, climb the ramparts for views of Matanzas Bay, and catch a musket or cannon demonstration (check the schedule online). Plan to spend about 1.5-2 hours here to soak in the history.
Pro Tip: Arrive early to beat the crowds, especially in summer, as the fort can get busy by mid-morning.
After the fort, stroll across the street to the City Gate, the historic entrance to the old city. Snap a photo and head down St. George Street, a pedestrian-only thoroughfare lined with shops, cafes, and historic buildings. Grab a quick coffee at Crucial Coffee (open 8 AM – 8 PM), a cozy spot with outdoor seating and delicious lattes.
Lunch: The Floridian
For lunch, head to The Floridian (39 Cordova St, open 11 AM – 9 PM), a local favorite known for its fresh, Southern-inspired dishes made with sustainable ingredients. Try the “Fancy Grilled Cheese” with pimento cheese or the shrimp and grits. The outdoor courtyard is perfect for a relaxed meal. Expect to spend $15-25 per person.
Afternoon: Flagler College and Lightner Museum
Next, dive into the Gilded Age with a guided tour of Flagler College (74 King St, tours at 10 AM and 2 PM, $17 per adult). Originally the Hotel Ponce de Leon, built by railroad tycoon Henry Flagler in 1888, this Spanish Renaissance masterpiece boasts Tiffany stained-glass windows and a jaw-dropping domed lobby. The 45-minute tour offers fascinating insights into St. Augustine’s transformation into a winter resort destination.
Just across the street, visit the Lightner Museum (75 King St, 9 AM – 5 PM, $17 per adult). Housed in the former Alcazar Hotel, this museum showcases 19th-century art, antiques, and curiosities, from taxidermy to Tiffany glass. Allow about 1-1.5 hours to explore its eclectic collections.
Evening: St. George Street and Dinner at Columbia Restaurant
As the sun sets, return to St. George Street to enjoy its lively atmosphere. Browse quirky shops like the Pirate & Treasure Museum gift shop or indulge in a sweet treat at Whetstone Chocolates (open until 7 PM). If you’re visiting from mid-November to January, the Nights of Lights festival illuminates the historic district with millions of twinkling lights—perfect for an evening stroll.
For dinner, make a reservation at the Columbia Restaurant (98 St. George St, open 11 AM – 9 PM), a St. Augustine institution since 1905. This Spanish-Cuban eatery is famous for its paella, sangria, and the “1905” salad, tossed tableside. Entrees range from $20-35, and the ambiance, with its tiled courtyard and live music, is unbeatable.
Where to Stay: Check into The Collector Luxury Inn & Gardens (149 Cordova St), a beautifully restored historic property within walking distance of the historic district. Rates start at around $200 per night, offering modern comforts in a serene setting. For a budget-friendly option, try Southern Oaks Inn (2800 N Ponce de Leon Blvd), with rates from $100 per night and a free shuttle to downtown.
Day 2: Culture, Nature, and Sunset Views
Morning: Fountain of Youth and Colonial Quarter
Start your second day at the Ponce de León’s Fountain of Youth Archaeological Park (11 Magnolia Ave, 9 AM – 6 PM, $19 per adult). This quirky attraction claims to be the 1513 landing site of the Spanish explorer. Sip from the “fountain,” watch a blacksmith demonstration, and explore exhibits about early Spanish and Timucua life. The park’s peacocks and scenic grounds add to the charm. Spend about 1.5 hours here.
Next, head to the Colonial Quarter (14 S Castillo Dr, 10 AM – 5 PM, $14 per adult). This living history museum brings 16th- to 18th-century St. Augustine to life with musket drills, a climbable watchtower, and interactive exhibits. It’s a great spot for families and history lovers alike. Allow 1-1.5 hours.
Lunch: O.C. White’s Seafood & Spirits
For lunch, walk to O.C. White’s Seafood & Spirits (118 Avenida Menendez, open 11 AM – 9 PM), a waterfront restaurant with views of the Bridge of Lions. Try the crab cakes or fresh catch of the day, paired with a craft cocktail. Meals cost $15-30 per person, and the breezy patio is ideal for a sunny day.
Afternoon: St. Augustine Lighthouse and Anastasia State Park
Drive or take a short Uber to the St. Augustine Lighthouse & Maritime Museum (100 Red Cox Dr, 9 AM – 6 PM, $15 per adult). Climb the 219 steps for panoramic views of the coast, explore the keeper’s house, and learn about shipwrecks. The site also offers kid-friendly activities and a spooky “Dark of the Moon” ghost tour (book in advance for evenings). Plan for 1.5-2 hours.
If you’re craving nature, head to Anastasia State Park (300 Anastasia Park Rd, 8 AM – sunset, $8 per vehicle). This pristine park features 4 miles of beaches, tidal marshes, and trails. Rent a kayak, hunt for shark teeth, or relax by the water. Spend 1-2 hours here to unwind.
Evening: Sunset Cruise and Dinner at Cap’s on the Water
Cap off your day with a sunset cruise on the Schooner Freedom (111 Avenida Menendez, departs around 6 PM, $60 per adult). This 72-foot tall ship offers a 1.5-hour sail along Matanzas Bay, complete with stunning views and a chance to spot dolphins. Bring a jacket, as it can get chilly on the water.
For dinner, drive to Cap’s on the Water (4325 Myrtle St, open 4 PM – 9 PM), a rustic waterfront restaurant just outside downtown. Savor dishes like the calamari Vilano or blackened mahi-mahi while watching the sunset over the Intracoastal Waterway. Entrees range from $20-40, and docking is available if you arrive by boat. No reservations, so arrive early to avoid a wait.
Day 3 (Optional): Beaches, Distilleries, and More History
If you have an extra day, use it to explore St. Augustine’s beaches, modern attractions, and hidden gems.
Morning: St. Augustine Beach and Alligator Farm
Start at St. Augustine Beach (350 A1A Beach Blvd), a wide, sandy stretch perfect for a morning walk or shelling. Parking is free, and the vibe is laid-back. If you’re traveling with kids or love wildlife, visit the St. Augustine Alligator Farm Zoological Park (999 Anastasia Blvd, 9 AM – 5 PM, $35 per adult). This historic zoo houses every species of crocodilian, plus exotic birds and mammals. Don’t miss the daily wildlife shows or the zip line (additional cost). Spend 2-3 hours here.
Lunch: Sunset Grille
Grab lunch at Sunset Grille (421 A1A Beach Blvd, open 11 AM – 9 PM), a casual beachfront spot known for its fish tacos and key lime pie. Meals cost $10-20 per person, and the ocean views are a bonus.
Afternoon: St. Augustine Distillery and Fort Mose
Head back to the historic district for a free tour and tasting at the St. Augustine Distillery (112 Riberia St, 10 AM – 6 PM). Housed in a restored ice plant, this award-winning distillery crafts bourbon, gin, and rum using local ingredients. The 45-minute tour is engaging, and the cocktail bar serves creative drinks. Allow 1 hour.
Next, drive to Fort Mose Historic State Park (15 Fort Mose Trail, 9 AM – 5 PM, free entry, $2 for museum). This site, the first legally sanctioned free African settlement in what is now the U.S., offers a glimpse into a lesser-known chapter of history. Watch the short film and explore the grounds. Spend about 1 hour.
Evening: Ghost Tour and Dinner at Harry’s
St. Augustine is famously haunted, so why not end your trip with a Ghost Tour? Book the Ghosts & Gravestones Trolley Tour (departs 7 PM, $35 per adult) for a 90-minute journey through the city’s spookiest sites, including the Old Jail. It’s fun, slightly creepy, and packed with stories.
For your final dinner, head to Harry’s Seafood Bar & Grille (46 Avenida Menendez, open 11 AM – 10 PM). This New Orleans-inspired eatery serves crawfish étouffée, jambalaya, and fresh seafood in a charming courtyard. Entrees range from $15-30, and the live music adds a festive touch.
Practical Tips for Visiting St. Augustine
- Getting There: St. Augustine is a 45-minute drive from Jacksonville International Airport (JAX) or a 2-hour drive from Orlando. A car is recommended for flexibility, but the historic district is walkable.
- Parking: Use the Historic Downtown Parking Facility (10 Castillo Dr, $15 per day) for easy access to attractions. Some hotels offer free parking or shuttles.
- Best Time to Visit: Spring (March-May) and fall (September-November) offer mild weather and fewer crowds. Winter is great for Nights of Lights, but book accommodations early.
- What to Pack: Comfortable walking shoes, sunscreen, a hat, and a light jacket for evenings. Bring a reusable water bottle for eco-friendly hydration.
- Budget: Expect to spend $100-150 per person per day on food, attractions, and activities, excluding lodging.
Where to Stay in St. Augustine
- Luxury: Casa Monica Resort & Spa (95 Cordova St, from $250/night) – A historic Moroccan-inspired hotel with a spa and central location.
- Mid-Range: Hilton St. Augustine Historic Bayfront (32 Avenida Menendez, from $180/night) – Cozy rooms with bay views, steps from downtown.
- Budget: Bayfront Marin House (142 Avenida Menendez, from $120/night) – A charming B&B with waterfront cottages and free breakfast.
- Beach Option: Ponte Vedra Inn & Club (200 Ponte Vedra Blvd, from $300/night) – A 5-star resort 30 minutes away, perfect for a splurge.
Final Thoughts
St. Augustine is a destination that effortlessly blends history, culture, and relaxation. In just 2-3 days, you can explore centuries-old forts, savor fresh seafood, and sail into the sunset. Whether you’re wandering the historic district or lounging on the beach, the city’s charm will leave you longing to return. So pack your bags, book your stay, and get ready for a weekend getaway to remember in America’s oldest city.