St. Augustine – The Most Historic City in America – Perfect Florida Road Trip

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St. Augustine, Florida – Historical Marvel

No city in North America has more historical relevance than St. Augustine, Florida. When the King of Spain sent Don Pedro Menendez de Aviles to colonize Florida in 1565, little did he know for the next 250 years the British, French and Spanish would fight for control of the region (and most of Florida). This Florida road trip encompasses more history than most.

Under Spanish rule, fortification was as important as finding food. Defending the colony from disease, and appeasing the Native Americans were key to survival.

The fort Castillo de San Marcos (at one point renamed Fort St. Mark) stands at the entrance to the city of St. Augustine. The fort was started in 1572 and refortified many times as the continuing conflicts with the French and British battered the fort many times.

 

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Apaches at Fort Castillo St. AugustineApaches at Fort Castillo St. Augustine

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Over the years St. Augustine and the fort was a haven for run away slaves, a mission for Native Americans, a prison for those same Native Americans, briefly controlled by confederate troops in the civil war and later a prison for deserters in the Spanish-American War. The narrow streets, coquina-built homes and Spanish influence is evident throughout the city of St. Augustine.

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Henry Flagler Brings St. Augustine to Modern Times – For the 1800’s

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Narrow St. George Street St. Augustine
Narrow St. George Street, St. Augustine

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In the late 1800’s Henry Flagler invested in St. Augustine and the region in many ways. He built the Ponce de Leon Hotel, purchase a railroad to serve Florida’s east coast, bought another hotel, and built a bridge over the St. John’s River to facilitate travel. Today Flagler College stands where the then elegant Ponce de Leon Hotel stood. Flagler’s holdings went beyond St. Augustine. He built or bought hotels up and down Florida’s coast from Jacksonville to Miami.

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Today, you can roam the downtown St. Augustine area and see the many old buildings reminding you of almost 500 years of political and economic change for St. Augustine. As you wander, some of the “streets” are no more than well-preserved alleys. On St. George St. you will find a wide selection of shops, restaurants, a good crop of museums with plenty of quaint novelty stores to occupy your time.

Things to see and do on Your St. Augustine Florida Road Trip

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Things to do include taking a tour in a horse-drawn carriage. Visiting the old Fort Castillo de San Marcos and the Government House Museum. Stroll up St, George Street to see the many shops lining both sides of this street (no cars, just walking!). Along the way end your hunger at the Prohibition Kitchen. This place is huge with a novel menu.

Of course, Harry’s Bar is the local’s favorite for dinner. Just a refreshment? Try the Tini Martini Bar – a six seat fun bar.

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Room at Casa Monica Hotel
Room at Casa Monica Hotel

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If you plan to stay overnight, there are the normal Best Western’s, Holiday Inn’s and the rest. However, for a little more upscale experience, try the Casa Monica Hotel in the middle of downtown. As part of the Marriott collection, this grand old hotel, once owned by Henry Flagler, has been restored to its original elegance.

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St. Augustine is about 45 minutes south of Jacksonville, about 3 1/2 hours from Tampa/St. Petersburg area, two hours from Orlando and about 5 hours from Miami area. A Florida vacation or road trip from anywhere in Florida is fun.

For more information about St. Augustine, Read more in our One Day of things to do in St. Augustine.

 

The Oldest House is a view of living in the 18th century.
The Oldest House in St. Augustine dates back to the early 1700's. Great glimpse of a hard life.
St. Augustine History
St. Augustine had many soldiers stationed there - French, British, Spanish and American troops have protected St. Augustine.
St. Augustine Prohibition Shake
A guest trying one of Prohibition Kitchen's Fabulous shakes.
Prohibition Kitchen at St. Augustine
Sports action is live on one of the many TV's at Prohibition Kitchen.

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