Family Fall Break Vacation Itinerary in St. Augustine

Discover the charm and history of St. Augustine, the oldest city in the U.S., and explore the captivating destinations of Northeast Florida this fall. From historic landmarks to beautiful beaches, this itinerary promises a fantastic family getaway filled with adventure and relaxation.

Day 1: Arrival and Historic St. Augustine
Morning: Arrive in St. Augustine and check into your accommodations. Choose from charming condo or modern family-friendly vacation rental right in the heart of the city.
Afternoon: Start your exploration with a stroll through St. George Street, the city’s historic pedestrian street lined with quaint shops, cafes, and historic buildings. Visit the Castillo de San Marcos, the oldest masonry fort in the continental U.S., and soak in the stunning views of the city and harbor.
Evening: Dine at a local favorite like The Columbia Restaurant, where you can savor delicious Spanish cuisine in a beautiful setting. After dinner, enjoy a leisurely walk along the waterfront or take a ghost tour to uncover the city’s spooky side.

Day 2: Exploring Historic Landmarks
Morning: Visit the Lightner Museum, housed in the former Alcazar Hotel, to marvel at its eclectic collection of art and artifacts. Next, head to the Flagler College campus for a tour of its stunning architecture and history.
Afternoon: Explore the beautiful gardens and historical exhibits at the Oldest Wooden School House. Then, head to the nearby St. Augustine Alligator Farm Zoological Park, where you can see crocodiles, alligators, and exotic birds up close.
Evening: For dinner, enjoy a family meal at Harry’s Seafood Bar & Grille, known for its vibrant atmosphere and delicious Southern cuisine. Afterward, relax at your accommodations or enjoy a nightcap at a local pub.

Day 3: Beach Day at St. Augustine Beach
Morning: Spend a fun-filled day at St. Augustine Beach. Enjoy sunbathing, swimming, and beachcombing along the beautiful shores. The beach is perfect for building sandcastles and playing in the waves.
Afternoon: Grab a bite at one of the beachfront eateries like Beachcomber Restaurant, offering casual dining with ocean views. Continue your beach day with a visit to the St. Augustine Pier, where you can fish, picnic, and take in panoramic ocean views.
Evening: Head back to the city for a casual dinner at a family-friendly spot like The Manatee Cafe, offering comfort food and a relaxed atmosphere.

Day 4: Day Trip to Jacksonville
Morning: Drive to Jacksonville for a day of exploration. Start with a visit to the Jacksonville Zoo and Gardens, where the kids can enjoy animal encounters and interactive exhibits.
Afternoon: Head to the Jacksonville Museum of Science and History (MOSH) for engaging exhibits and hands-on activities. Afterwards, stroll through the Riverside Arts Market, where you can find unique crafts and enjoy live entertainment.
Evening: Dine at a waterfront restaurant like The Fish Company, offering fresh seafood and beautiful views of the St. Johns River. Return to St. Augustine in the evening for a relaxing night.

Day 5: Nature and Outdoor Adventures
Morning: Explore the natural beauty of Anastasia State Park. Enjoy hiking, bird-watching, and perhaps a paddleboarding adventure in the park’s serene salt marshes and tidal waters.
Afternoon: Visit the nearby Fountain of Youth Archaeological Park, where you can learn about the area’s history and legends. Enjoy the interactive exhibits and the beautiful grounds.
Evening: Treat your family to dinner at The Kookaburra, known for its tasty Australian pies and relaxed vibe. Afterward, take a scenic drive through the historic district to admire the beautifully lit buildings.

Day 6: Relaxing at Ponte Vedra Beach
Morning: Head to Ponte Vedra Beach for a relaxing day by the ocean. Enjoy the tranquil atmosphere, beach activities, and perhaps a round of golf at one of the nearby world-class courses.
Afternoon: Lunch at a local spot like The Surf Deck Grille, offering casual dining with a beachy vibe. Spend your afternoon strolling along the beach or exploring the nearby Guana Tolomato Matanzas National Estuarine Research Reserve.
Evening: Return to St. Augustine for a final dinner at The Cellar, a charming restaurant with a historic ambiance and a menu full of delectable dishes.

Day 7: Departure and Reflection
Morning: Spend a leisurely morning reflecting on your memorable trip. Enjoy a final breakfast at a local cafe and perhaps a last stroll through the city’s charming streets.
Afternoon: Prepare for departure, cherishing the wonderful experiences and adventures you’ve had in St. Augustine and Northeast Florida.
Evening: Head home with your hearts full of cherished memories and a newfound appreciation for the historic and natural beauty of Northeast Florida.

Immerse yourself in the rich history and natural beauty of St. Augustine and Northeast Florida this fall. With charming attractions, scenic beaches, and family-friendly adventures, your fall break will be unforgettable!

Heading to the Southwest coast of Florida this fall break? Check out our Southwest Fall Break Guide for the best tips and recommendations!