Uptown

Bordering St. Augustine’s Historic Downtown, Uptown features historic properties and neighborhoods, as well as motels and hotels — including Villa 1565. Locally, Uptown along San Marco Ave. is known for boutique shops, art galleries, antique stores, as well as local eateries from pizza to elegant restaurants — such as the Raintree Restaurant.

The Uptown region extends west from the Matanzas River to a block or two shy of U.S. 1; and from Grove Avenue north to the Vilano Causeway, Uptown is worth a visit by auto or on foot. Attractions include The Fountain of Youth Archeological Park, the site of the first Spanish settlement in the new world; and The Old Jail, built by Henry Flagler in 1891 to move the jail farther from his Ponce de Leon Hotel (now Flagler College).

If you appreciate architecture from the 1800s to the 1920s, you'll want to walk through a number of charming neighborhoods listed on the National Register of Historic Places. These include the Abbott Tract Historic District, roughly bounded by Matanzas Bay, Pine, San Marco, and Shenandoah Aves., and the Nelmar Terrace Historic District, site of a Timucuan Indian village, a British plantation, and a development in the 1910s after a trolley car route was built along San Marco Avenue.

Wander the 1.5 miles from the Plaza de la Constitución to the Fountain of Youth, or take a bike, scooter, car, or any of the local transportation options. Parking can be found on the street, and in lots owned by the attractions, stores, or restaurants.