How to Plan the Perfect Trip From Orlando to St. Augustine

Escape the ordinary and treat yourself to an adventure in St. Augustine! This gorgeous city is widely known for its centuries-old architecture, iconic cultural sites, and miles of unspoiled beaches. For an experience like no other, a drive from Orlando to St. Augustine should be at the top of your list! For the ideal start to your road trip, we suggest taking the scenic route from Orlando to St. Augustine. The drive along scenic Highway A1A is just over two hours,and it’s jam packed with beautiful coastal backdrops. Once you arrive in the nation’s oldest city, the fun begins! Use our complimentary Vacation Guide to find the best things to do in St. Augustine and make your trip from Orlando unforgettable!

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The Ultimate Orlando to St. Augustine Trip Itinerary

Step Into the City’s Rich History

St. Augustine is widely regarded as the nation’s oldest city. With that title comes an extended and rich history that you won’t find anywhere else.  Wherever you go, you’re bound to discover another piece of the story that makes St. Augustine so unique. The city is filled with extraordinary museums that  offer a glimpse into another era. 

These are the best museums in St. Augustine: 

Explore the Country’s Oldest Monument

Castillo de San Marcos was constructed by the Spanish to protect and defend Spain’s territory in the Americas. The grand structure was completed in 1695, and is regarded as the oldest Masonry Fort in the United States. Now, this massive stone fortress is a national monument that attracts visitors from all over the world. The monument hosts daily programs, weaponry demonstrations, and ranger-led tours. Plus, as you explore the site, you may even run into a re-enactor. If you do, feel free to ask them anything about the Fort’s importance and historical significance over its many centuries of activity. 

Take a Historic Tour at Flagler College 

For a chance to admire the magnificence of Spanish Renaissance architecture, you have to visit Flagler College! The college offers a walking tour through the historic campus that delves deep into the story of it’s meticulously crafted 19th-century buildings. The historic site was built in 1888 by Henry M. Flagler and initially opened as Hotel Ponce de Leon. During this remarkable tour, you will have the opportunity to see the site’s most iconic features including Tiffany stained glass windows, hand-carved oak caryatids, beautiful hand-painted murals, and a series of Austrian crystal chandeliers. 

Stay at Agustin Inn Bed & Breakfast Primrose Suite

After wandering through the charming streets of St. Augustine on your getaway from Orlando, get your rest at the Agustin Inn. When you wake from your undisturbed slumber in the Duchess Room, enjoy a delicious breakfast and help yourself to our endless cookie jar! Our quaint inn is located near downtown and gives you easy access to all of the best restaurants, local boutiques, and attractions. Stay as long as you like and take in all that this magical place has to offer.

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