Step back in time this year as St. Augustine, Florida, celebrates an incredible milestone — its 460th anniversary! Founded in 1565, St. Augustine proudly holds the title of America’s oldest continuously inhabited city, blending centuries of history with stunning coastal views, cobblestone streets, and Spanish charm.
Just a scenic two-hour drive from Orlando, St. Augustine makes for a perfect day trip or weekend getaway for guests staying in one of our Orlando vacation rentals or Florida vacation homes near Disney. And in 2025, the city is going all out to honor its rich past with special events, historical reenactments, music, and family fun.
A Celebration 460 Years in the Making
Every September, St. Augustine commemorates its founding with vibrant cultural celebrations — and this year promises to be bigger than ever. Visitors can expect a blend of parades, live music, traditional ceremonies, and art festivals that bring the city’s history to life.
From the famous Founders Day events in the historic district to open-air markets and concerts near the bayfront, the 460th anniversary will showcase the city’s enduring beauty and deep cultural roots.
Families staying in Davenport vacation rentals or Orlando villas can easily make the trip for a full day of sightseeing, dining, and celebration by the sea.
Historic Charm Meets Coastal Beauty
St. Augustine is a city where history and modern comfort go hand in hand. Stroll through St. George Street, explore Castillo de San Marcos, and visit centuries-old landmarks that still tell stories of explorers, pirates, and settlers.
Then, unwind along the waterfront — where you’ll find seaside cafés, boutiques, and views of the iconic Bridge of Lions. For couples and families alike, it’s the perfect mix of history and relaxation.
Family-Friendly Events and Activities
The 460th celebration will feature something for everyone:
- Historical reenactments honoring the city’s Spanish founders.
- Cultural festivals with live performances, dance, and cuisine from around the world.
- Art shows and markets featuring local crafts and traditional goods.
- Family-friendly tours and activities that make learning history fun for kids.
And since St. Augustine’s weather is mild and coastal year-round, you can enjoy walking tours, trolley rides, and beach strolls in comfort.
A Perfect Day Trip from Orlando
One of the many advantages of staying in Orlando vacation rentals or Florida vacation homes is how easy it is to reach other incredible Florida destinations. St. Augustine is less than two hours away by car — making it an ideal day trip from Central Florida.
Start your morning exploring the historic district, grab lunch at a waterfront restaurant, and finish the day watching the sunset along the bay. It’s a trip that adds a whole new layer of magic to your Florida vacation.
The Best of Both Worlds: History and Modern Comfort
While St. Augustine lets you step into the past, your vacation rental near Disney ensures you return to modern comfort and convenience. After a day of exploring ancient forts and coastal streets, you can relax in your private pool, prepare a family dinner, or enjoy a quiet evening in your Orlando villa.
With our trusted property management in Orlando, every home is prepared and guest-ready, giving you peace of mind and the space to unwind after your adventure.
Make History Part of Your Florida Vacation
In 2025, St. Augustine’s 460th anniversary invites visitors from all over the world to celebrate America’s oldest city in style. It’s the perfect blend of history, culture, and fun — all within reach from your Orlando vacation home.
✅ Explore centuries of history and culture
✅ Enjoy live events, parades, and local festivals
✅ Stay close to the action in comfort and style
Make this year’s Florida getaway one for the history books — celebrate St. Augustine’s 460th Anniversary, and experience the magic of the past and present in one unforgettable trip.
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