St. Augustine Weekend Guide: History & Haunts
St. Augustine at a Glance
St. Augustine, the oldest continuously inhabited city in the United States, is a walkable destination with cobblestone streets, Spanish colonial charm, and a vibrant local culture. It’s the perfect place for memorable photos in any one of it’s many unique settings. Whether you are traveling solo, with friends, or family, expect to find friendly locals, historic sites, and a relaxed pace. St. Augustine is perfect for sightseeing, weekend getaway’s, and soaking in the charming atmosphere. It boasts top attractions, historical B&Bs, and plenty of lively activities suited for all visitors. All within easy reach, making it simple to experience the best of the city in just a weekend.
Best Time to Visit
• Spring (March-May): Mild weather, blooming gardens, and numerous festivals.
• Fall (September–November): Fewer crowds, warm days, and beautiful sunsets.
• Winter (December–February): Mild temperatures and the Nights of Lights festival.
• Summer (June–August): It’s hot and humid but great for the beach.
Tip: Book your accommodations early for spring and holiday visits—top B&Bs fill up fast.
Where to Stay
St. Augustine offers many lodging options, from historic inns, to modern hotels, and vacation rentals. Popular choices in the historic district include:
• St. Francis Inn: Historic charm, gourmet breakfast, pool, and central location.
• Casa de Sueños: Romantic rooms, jetted tubs, private balconies, and free parking.
• Bayfront Westcott House: Waterfront views, gourmet breakfast, and elegant decor.
• Casa Monica Resort & Spa: Iconic luxury hotel in the heart of the historic district.
• Hilton St. Augustine Historic Bayfront: Upscale lodging with bay views.
Consider options like Guy Harvey Resort on St. Augustine Beach or Embassy Suites by Hilton at St. Augustine Beach for a beachfront stay.
My favorite stays have been at B&Bs. The charm of the restored homes, the proximity to the local attractions, and the owners who host you make for a wonderful weekend experience you won’t soon forget.
Weekend Itinerary
Stroll down St. George Street, a pedestrian-only thoroughfare lined with colorful storefronts, historic balconies, and lively shops. This is one of the best spots in the city for vibrant street photography and people-watching.
Day 1: Historic Heart & Haunts
Start your day at Castillo de San Marcos, the oldest masonry fort in the U.S. Walk the ramparts, admire the coquina stone walls, and snap photos of the scenic waterfront—especially at sunset when the light is golden and perfect for Instagram.
Pop into one of the many alleyway shops to discover old arcade games and fortune tellers machines such as “Zoltaire” or “The Hat” it is alway good fun!
Take a Flagler College Historical Tour to marvel at the Gilded Age architecture and the stunning Tiffany stained glass windows (tours at 10:00 a.m. and 2:00 p.m., $17). The grand lobby and dining hall are among the most photographed interiors in St. Augustine. It is stunning to see!
Visit the Lightner Museum, which houses a collection of 19th-century art and curiosities in a grand historic hotel with beautiful architecture.
Wander Aviles Street, the oldest street in America, and don’t miss a photo on Treasury Street, the narrowest street in the U.S., just seven feet wide.
Need a afternoon break visit Pierre’s Pub in the historic center for live music and great drinks. Follow the smell of the Auntie Annie Pretzels and you will find the secret spot.
For dinner, enjoy rooftop dining at River + Fort or Nonna’s Trattoria for Italian Cuisine. Catch the sunset at the Bridge of Lions—another iconic photo spot with its dramatic drawbridge and waterfront views.
End your evening with a ghost tour or live music in the Plaza. St. Augustine’s historic district is especially lively at night, with lantern-lit streets and costumed guides leading ghost tours. I have taken this tour several times over the years and it never disappoints! It is great for all ages.
Not into the paranormal, may I suggest a lovely horse drawn carriage ride that will instantly transport you back in time as you travel the brick paved roads of St. Augustine and the drivers will give you insider details and storytelling along the way.
Side note: If this is a romantic getaway this is a great activity!
Day 2: Beyond the City Gates
Start your morning on Magnolia Avenue, famous for its ancient live oaks draped in Spanish moss. It is one of the most picturesque spots in the city and a must for early-morning or golden-hour photos.
Tip:(Do not take or handle moss, it could have mites) I know it is tempting!
Cross the Bridge of Lions to Anastasia State Park for nature trails, birdwatching, and beach access. The park’s sandy shores and dunes are perfect for relaxed, natural photos. The vibe across the bridge is less touristy.
Climb the St. Augustine Lighthouse for panoramic views of the coast and city—an excellent spot for sweeping landscape shots. Climb 219 steps to the top. If you are brave experience a family-friendly guided ghost tales tour of the lighthouse. Other tours are available throughout the year. This is one of my favorite activities!
Food and Refreshments:
Forgotten Tonic is a great way to end your weekend getaway. Reservations are recommended. Forgotten Tonic features a creative and extensive cocktail menu along with a diverse wine selection. The historical cozy setting is the perfect backdrop for the twist on American comfort food. One of the city’s vibrant culinary scenes.
Catch 27 is a popular farm-to-table seafood restaurant steps from St. George Street. Relaxed, chill vibe, outdoor dining known for the locally sourced seafood. Vegetarian options are available. Must try the the homemade desserts. Reservations recommended on weekends.
Visit the St. Augustine Alligator Farm to see all 23 crocodilian species and try the high ropes course.
Explore the quirky Villa Zorayda Museum, inspired by Spain’s Alhambra, and the legendary Fountain of Youth Archaeological Park with its lush gardens and interactive exhibits.
You can pick up handmade crafts, chocolates at Claude’s Chocolate, or antiques at Spanish Main Antiques.
Relax at St. Augustine Beach or visit historic Butler Beach for a quieter coastal vibe.
Top Tours & Activities
St. Augustine is known for its rich history and unique experiences. Consider these popular options:
• Hop-on Hop-off Trolley Tour: See all the major sights with unlimited stops at 22 locations. I highly recommend this especially if you are spending the weekend. It comes in handy for transportation and sightseeing.
• Ghost Tours: Spine-tingling stories and haunted sites, including ghost hunts at the lighthouse or historic district. I have taken these tours multiple times and they never disappoint! Always great time.
• Boat Cruises: Scenic, sunset, and dolphin cruises along the coast. Check weather in the summer months. (Rainy season)
• Walking Tours: Explore history, food, and local culture with expert guides.
• Nights of Lights Tour (seasonal): Experience the city’s magical holiday lighting. Highly recommend!
Free & Donation-Based Activities
• Fort Matanzas: Free entry and ferry ride.
• Fort Mose: First free African-American settlement (museum $2).
• Art Association Gallery: Free exhibits.
• First Friday Art Walk: Free gallery tours and live music.
• San Sebastian Winery: Free wine tastings and self-guided tours.
• St. Augustine Distillery: Free spirits tastings and guided tours.
Distance from Major Florida Cities:
- Orlando: 107 miles (2 hour drive)
- Tampa: 190 miles (3 hour drive)
- Miami: 311 miles (5 hour drive)
- Tallahassee: 203 miles (3 hours, 15 min)
St. Augustine Weekend Guide: Final Thoughts
Now you’re ready to make the most of your St. Augustine weekend—step into history, savor the culture and capture unforgettable moments. For more travel tips and real-time inspiration, follow @Soloherway on Instagram, TikTok, Pinterest, and Facebook! A new podcast is posted on soloherway.com to answer your travel questions and needs each month. Have a question? Reach out. I am here to support your travel goals.
