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St. Augustine – The Most Historic City in America

St. Augustine, Florida – Most Historic City in America

The most historic city in America is clearly 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).

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

Apaches at Fort Castillo St. Augustine

Apaches at Fort Castillo St. Augustine, most historic city in America
Native Americans relied on the fort for protection from warring parties.

Over the years, St. Augustine and the fort was a haven for runaway 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.

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

Narrow St. George Street St. Augustine most historic city in America
The narrow St. George Street is now a shopping mecca.

In the late 1800s, Henry Flagler invested in St. Augustine and the region in many ways. He built the Ponce de Leon Hotel, purchased 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.

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, and a good crop of museums with plenty of quaint novelty stores to occupy your time.

Things to See and Do in St. Augustine

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.

Room at Casa Monica Hotel most historic city in America, St. Augustine
Elegant but dated rooms at Casa Monica make a great stay.

If you plan to stay overnight, there are the normal Best Westerns, Holiday Inns 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 it’s original elegance.

St. Augustine most historic city in America is about 45 minutes from Jacksonville and about 3 1/2 hours from Tampa/St. Petersburg area, two hours from Orlando and about 5 hours from the Miami area.

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