Planning a weekend trip to St. Augustine Florida? Whether you’re into charming cities, haunted tales, historic architecture, or tiki cocktails, this walkable, coastal gem has it all—plus it’s incredibly easy to explore in just a couple of days.
Here’s everything you need to know for an unforgettable weekend visit to America’s oldest city.
Plan your Ultimate Weekend Trip to St. Augustine, the Oldest City in America—Filled with History, Lighthouses, Wine Tastings & Coastal Charm.
✨ What Makes St. Augustine Unique
Founded in 1565, historic St. Augustine is the oldest continuously inhabited city in the U.S. From Spanish forts to charming cobblestone streets and the Atlantic Ocean just minutes away, every corner here feels like a storybook come to life. The best part? You can enjoy sunset boat tours on the Matanzas River, explore centuries-old sites, and still kick back on the beach—all in one weekend.
Want to see even more while you’re there? We used the trolley! 🎟️ Book a St. Augustine trolley and museums tour here with GetYourGuide – it’s a fun and informative way to dive into the city and get around!
🏨 Where to Stay in St. Augustine for Your Weekend Trip (Top 5):
Here are our 5 favorite top-rated places to stay—perfect for a romantic weekend getaway in St. Augustine or a fun escape with friends:
1. Cedar House Inn
We absolutely loved this Victorian-style bed and breakfast! Our suite was cozy, welcoming, and just steps from the action. You’ll love the homemade breakfasts and charming decor. Great for couples or solo travelers who want that “home away from home” vibe. Read Reviews and Book Cedar House Here!
2. The Collector Luxury Inn & Gardens
A boutique inn made up of historic buildings with lush courtyards, complimentary happy hour, and luxurious touches. It’s ideal for travelers who want charm with a bit of bougie. Read Reviews and Book Here!
3. Casa Monica Resort and Spa – Marriott
This luxurious hotel is in the center of the historic district and part of Marriott’s Autograph Collection so you can use points! Read Reviews and Book Casa Monica Here!
4. Old City House Inn
A cozy bed and breakfast with an amazing courtyard and terrace! It’s located steps from St. George Street shopping. Don’t forget to try the quaint restaurant too! Read Reviews and Book Old City Inn Here!
5. St. George Inn
Located right on pedestrian-only St. George Street, this inn offers balcony views of the historic district. Perfect if you want to stay in the middle of the buzz and walk to everything. Read Reviews and Book St. George Inn Here!
Tip: ✨If you have a larger group this amazing 2 br house rental from VRBO is in the Historic District!
🏰 What to See in St. Augustine: Historic Gems + Must-Visit Spots
If you’re looking for the best things to do in St. Augustine on a weekend, don’t miss these iconic stops:
Castillo de San Marcos
- The oldest masonry fort in the U.S. Take a self-guided tour or catch an amazing view of the river from the top of the fortress.
St. Augustine Lighthouse & Maritime Museum
- Climb to the top of this beautiful lighthouse for panoramic views, then explore exhibits on shipwrecks and lighthouse keepers. We also did the ghost hunt here and loved it.
- Also, see our Road Trip Guide to Florida’s Best Coastal Lighthouses for even more inspiration!
Lightner Museum
- Set in a former hotel built by Henry Flagler , it’s filled with Gilded Age oddities and antique treasures like Tiffany glass and unique artifacts.
Oldest House Museum Complex
- A peek into everyday colonial life in Florida’s oldest surviving home.
Colonial Quarter
- Living history with reenactments, blacksmiths, and hands-on learning.
Pirate & Treasure Museum
- Great for families or anyone who want to learn about the swashbuckling history of pirates on Florida’s coast.
Fountain of Youth Archaeological Park
- Yep, you can sip from the legendary spring! ✨ See where Ponce de León supposedly found the legendary waters.
Anastasia State Park – Pristine beaches
- Discover the beautiful beachfront, kayaking, camping, nature trails, and maybe even spot a manatee!
🛍️ Stroll & Shop on St. George Street
- Don’t leave without strolling St. George Street, a walkable lane packed with unique shops, old-world architecture, and ice cream stops. Whether you’re after handmade art, pirate gear, or a cozy café, it’s the heart of historic St. Augustine.
🍳 Where to Eat and Drink on a St. Augustine Weekend
Exploring works up an appetite! Here are the best places to eat and drink during your St. Augustine weekend itinerary:
🍽️ Ice Plant Restaurant
Located in an old ice factory, this spot is known for incredible cocktails (we loved them all!) and farm-to-table eats. Get the shrimp and grits! Tip: We got here and to the winery below on the hop on hop off trolley!
🎷 Prohibition Kitchen
Live music, speakeasy vibes, and creative comfort food—We had the chicken and waffles or the PK burger and both were great!
☕ Café Alcazar
Tucked inside the side entrance to the Lightner Museum, Café Alcazar is one of the most unique places to dine in St. Augustine. This elegant café is literally built in the deep end of what was once the largest indoor swimming pool in the world, back when the building was the opulent Hotel Alcazar built by Henry Flagler. We had light bites here and listened to live music in this unique setting!
🍹 Tradewinds Tropical Lounge
The oldest tiki bar in the oldest city! Chill with a mai tai, great live music, and some classic local character.
🍷 We also loved the wine tasting at San Sebastián Winery (included with some trolley passes!) and enjoyed the rooftop bar views.
🎟️ What to Do in St. Augustine: Fun, Unique & Ghostly
Looking for unique things to do in St. Augustine for your weekend trip? These experiences are what set this city apart:
- Hop-On, Hop-Off Trolley Tour – It’s the easiest way to explore the city. Book a day pass here and jump on and off at 20+ stops.
- 🍷Wine Tasting at San Sebastián Winery – Free tastings and local wines with a rooftop view.
- Ghost Hunt at the Lighthouse – We loved the lighthouse at night ghost tour at one of the most haunted places in the South!
- Matanzas River Sunset Cruise – Soak in the golden hour views on a peaceful boat tour.
- St. Augustine Beach – Just 10–15 minutes from downtown. Bring your beach gear and catch a sunrise or sunset over the Atlantic.
- We also did a Golf Cart Tour of the historic city center and they even picked us up!
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🌅 Wrapping Up Your Weekend Trip in St. Augustine
From ghost tours, to shopping, to wine tastings, historic forts to coastal sunsets, your weekend trip to St. Augustine Florida will be packed with charm, discovery, and maybe even a few ghostly vibes (ours was!). It’s the kind of place that lingers in your memory and makes you want to come back again and again. We are already planning another weekend!
👉 Ready to plan your perfect St. Augustine escape?