Nestled along Florida's picturesque Northeastern coast, St. Augustine blends old-world charm with vibrant local culture, making it the perfect weekend escape!
With centuries of history, stunning waterfronts, and a savory culinary scene, this historic gem has something for everyone. Whether you're a foodie, a history buff, or simply seeking a relaxing coastal getaway, this curated weekend itinerary highlights the best of what St. Augustine has to offer!
Day 1: History, Shopping & Seafood by the Bay
🛍️ Late Morning Stroll: Head straight to St. George Street, the heart of the historic district. This pedestrian-only thoroughfare is lined with boutique shops, local art galleries, and charming cafés. Grab a refreshing iced coffee or smoothie along the way and do a little souvenir shopping while taking in the sights and sounds of colonial-era streets. You'll walk past the Oldest School Wooden House and several other historically preserved spots!
🌴 Afternoon Exploration: Take a guided tour of the iconic Castillo de San Marcos, the oldest masonry fort in the continental U.S. It sits directly on the bayfront, with stunning views of Matanzas Bay and the Bridge of Lions.
🍷 Dinner with a View: Make your way to OC Whites for a delicious seafood dinner with a historic twist. Located in a restored 18th-century home with a charming garden patio, it’s a perfect way to wind down your first day. It's just a short walk from the fort!
👻 Evening Ghost Tour: St. Augustine is known for its ghostly legends, so end your night with a spooky (but fun!) ghost tour. Whether you choose a walking tour, hearse ride, or haunted trolley, you’ll get a thrilling perspective of the city’s past.
Day 2: Beachside Bliss & Sunset Sails
☀️ Morning Beach Walk & Brunch: Start your day with a peaceful sunrise walk on Porpoise Point Beach. This serene stretch of sand offers panoramic views where the Matanzas River meets the Atlantic Ocean—perfect for a tranquil morning and some incredible sunrise photography. Afterward, grab brunch at The Kookaburra Beachside, known for Aussie-style coffee and breakfast pies.
⛲ Afternoon Leisure: Head to the St. Augustine Lighthouse & Maritime Museum to climb the tower for panoramic views. Then, unwind with some shopping at Uptown St. Augustine, filled with indie boutiques and vintage treasures. After, make a wish at the famed Fountain of Youth Archaeological Park, located nearby! This historic site is believed to be where Spanish explorer Ponce de León landed in 1513. Wander through lush gardens, sip from the legendary spring, and explore fascinating exhibits on early colonial life and Native American history.
⛴️ Sunset Adventure: Book a sunset sail on the Schooner Freedom or opt for a dolphin-watching boat tour. Watching the sky change colors over the water is pure magic!
🌊 Dinner & Drinks: Cap off the evening with dinner at Cap's on the Water, a beloved waterfront restaurant perched along the Intracoastal Waterway. Known for its romantic ambiance, live oak canopy, and fresh seafood offerings, Cap's blends upscale Southern coastal cuisine with rustic charm! Savor dishes like oysters on the half shell, pecan-crusted catch of the day, or shrimp and grits as you dine under the stars with water views that are nothing short of enchanting.
Day 3: Coffee, Culture & Departure
☕ Morning Caffeine & Culture: Grab a quick bite and locally roasted coffee at DOS Coffee & Wine before diving into your last bit of sightseeing! Visit the Lightner Museum, located in the former Alcazar Hotel, to enjoy fine art and Gilded Age artifacts.
🍊 Farewell Lunch: Finish your trip with lunch at The Floridian, where farm-to-table meets southern comfort. Their seasonal menu and vibrant vibe are a great send-off!
👋 Check-Out: Say goodbye to your Staylah home and St. Augustine—for now... We know you’ll be back!
Ready to book your next getaway? Browse through Staylah’s curated collection of premium vacation rentals in St. Augustine here at staylah.com! Whether you crave beachside bliss or historic charm, we’ve got the perfect Florida escape for you!
🚨 BONUS... 🚨
✨ If You’re Staying an Extra Day
- Explore the St. Augustine Wild Reserve 🐅
- Try Escape U’s interactive escape rooms 🧩
- Catch a show at the Limelight Theatre 🎭
- Visit the Old Jail or Potter’s Wax Museum 🕰️
🧳 Tips for the Best Weekend Ever
- Book dinner reservations in advance—weekends fill up fast
- Wear comfy shoes; there’s lots to explore on foot.
- Check event calendars for live music, art walks, and seasonal festivals!
