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As the country’s oldest city, Saint Augustine, Florida, has plenty of historic charm. Henry Flagler turned the town into a winter resort in the late 19th century, headquartering his Florida East Coast Railroad there. His influence can still be seen in the architecture of the buildings he constructed, such as the Ponce de Leon and the Alcazar Hotel, which are now City Hall and the Lightner Museum. Even modern homes here have adopted the Old Florida style, with wraparound verandas, an open floor plan that maximizes air circulation, and a metal roof with a cupola to allow heat to escape.

The neighborhood of Anastasia Island is nestled against the 1,700 acres of Anastasia State Park, which is protected from development. The park has nature trails, canoe rentals and campsites. Saint Augustine Beach has beachside condominiums and 18 miles of pristine sand. You can enjoy surfing and fishing year round and stroll among shops and restaurants along the beachfront. Concerts are even held near the dunes. Marsh Creek is a private golf course community with patio homes and villas. The golf club also has a tennis program, a fitness center, and a variety of social events. The surrounding salt marshes and preserves provide miles of scenic hikes and kayaking experiences.

The downtown area is a mix of restaurants, inns, and boutiques, which you can explore on foot or in a horse-drawn carriage on narrow cobblestone streets. The Spanish Quarter of Old Town will give you a feel for what life was like here in the early 19th century, with some landmarks dating back to the 16th century. St. George Street, the main shopping street in Old Town, is filled with cafes and shops but also a living history museum where you can see various cottage crafts along with a blacksmith working wrought iron. Stop by the Sebastian Winery inside of one of Henry Flagler’s old railroad offices and sample several Florida wines; the rooftop features a jazz and blues bar. If you like your history on the supernatural side, Old Town has plenty of spooky stories to tell on a Ghost Tour. Overlooking the Intracoastal Waterway is the old Spanish fort Castillo de San Marcos, which is now a National Monument. Nearby is the picturesque Bridge of Lions, adorned with stone sentinel lions that are replicas from Florence. With mild, sunny weather all year round to enjoy all that Saint Augustine has to offer, this quaint historic town is a great place to live.

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