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St. Augustine's neighborhoods are fairly compact. Most include a stretch of waterfront—whether ocean, river, or creek—which, along with Mediterranean architectural details like curves, archways, and red-tile roofs gives the city its relaxed semitropical aura. Neighborhoods range from centuries old to mere decades, but all have sights worthy of attention.

It can be confusing to see references to the "Old City," "Old Town," and "Historic District." The Old City, like the Big Apple, refers not to a neighborhood but to the entire city of St. Augustine. Old Town is a small neighborhood, with the Plaza de la Constitución at its northern border, a row of shops and restaurants along King Street, many award-winning B&Bs, and the Oldest House museum toward the south. Old Town is actually within a larger neighborhood, the Historic District, a 144-block area filled with many of the city's most popular attractions, including museums, parks, restaurants, nightspots, shops, and historic buildings.

St. Augustine's Uptown is filled with the shops, restaurants, and galleries along San Marco Boulevard, as well as museums, parks, and historic structures, all of which attract crowds. The narrow streets and hustle and bustle make for a vibrant atmosphere.

Heading east across the Bridge of Lions, you enter Anastasia Island, much of which is within city limits. In the 1920s, real estate developer D.P. Davis had big plans for a Mediterranean-style development here, but the Florida land boom went bust. Today Davis Shores has a mélange of styles and a casual beach vibe.

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