3 days you’ll remember in St. Augustine, Florida.
Saint Augustine is the kind of place that makes time feel like a suggestion. As the oldest city in the U.S., it wears its history with pride—cobblestone streets, Spanish colonial architecture, and centuries-old secrets tucked behind every vine-covered wall.
But don’t let the age fool you—Saint Augustine pulses with life. From ghost tours to craft cocktails, live music to golden beach days, it’s a rare blend of old soul and coastal cool. You’ll wake up with the church bells and wind down to the sound of waves hitting the sand.
This weekend itinerary is your chance to slow down and savor the stories that made America’s oldest city unforgettable. Let’s take it from the top.
Itinerary inspired by the Foresyte community.
📍 Old Stones, New Stories
Day 1: Sunset Cruise
“Drift into the golden hour, sea breeze in your hair, and history painting the skyline.”
Day 1: Dinner @ Forgotten Tonic
“Craft cocktails and vintage vibes in a tucked-away spot that feels like a whispered story.”
Day 2: History Tour
“Cobblestone alleys, centuries-old forts, and tales that come alive with every step.”
Day 2: Lunch @ Salt Life Food Shack
“Laid-back bites by the beach, where fish tacos meet frozen drinks, and the soundtrack is waves.”
Day 2: Adventure Tour
“Pedal, paddle, or zip your way through town. This is history with a side of adrenaline.”
Day 2: Dinner @ Llama Restaurant
“Peruvian flair in the heart of the oldest city. Bright plates, bold flavors, and pure charm.”
Day 3: Brunch @ The Blue Hen Café
“Southern comfort with a funky twist. Brunch here is practically a local ritual.”
Day 3: Airboat Adventure
“Hold on tight, this wild ride through marshy backwaters is equal parts thrill and nature tour.”
Day 3: Bites @ Castillo Craft Bar
“Sip something bold just steps from the fortress walls, historic flavor, modern edge.”
Day 3: Scenic Boat Ride
“Gentle waters, hidden coves, and a new view of the city you thought you knew.”
Day 3: Dinner @ Michael’s
“Romantic ambiance and culinary finesse. Spanish fusion done with quiet confidence.”
St Augustine Itinerary FAQ.
What are the top attractions in Saint Augustine for a weekend trip?
Must-sees include Castillo de San Marcos, St. George Street, the Lightner Museum, and the historic district’s ghost tours and local shops.
When is the best time to visit Saint Augustine for a weekend getaway?
Spring (March–May) and fall (September–November) bring mild weather and fewer crowds, making them ideal for exploring the city.
Is Saint Augustine walkable for weekend visitors?
Yes, the historic downtown is extremely walkable, with most sights, restaurants, and shops located within a few charming blocks.
What is Saint Augustine known for among weekend travelers?
It’s known for its rich history, Spanish colonial architecture, romantic ambiance, and unique blend of museums, beaches, and ghost lore.
Where should I stay in Saint Augustine for a weekend trip?
Look for accommodations in the historic district for easy access to attractions and unbeatable ambiance, or stay beachside for ocean views.
How many days do you need in Saint Augustine for a full weekend experience?
Two to three days is perfect to explore the city’s history, enjoy local cuisine, relax on the beach, and soak up its unique charm.
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