Castillo de San Marcos National Monument

The most logical place to start a visit to Old Town is at the Castillo de San Marcos National Monument (1 S. Castillo Dr., 904/829-6506, www.nps.gov/casa, 8:45 a.m.–5:15 p.m. daily, $6 adults, children 15 and under with adult free). Built in 1695 and constructed of coquina, the Spanish fort withstood the multiple attacks the English launched from Charleston and Savannah, and like many other territories in northern Florida, it changed hands often.

When Confederate troops took the fort, it was manned by a single Union soldier who wouldn’t surrender until he was given a receipt for turning it over. Today, the Castillo overlooks a much more peaceful Matanzas River, and reenactments and walking tours give visitors an opportunity to understand some of the area’s complex history. Even better, there’s a metered parking lot out front; cross the street and you’re within the loosely defined boundaries of Old Town.

Colonial Spanish Quarter Museum

The Colonial Spanish Quarter Museum (53 St. George St., www.historicaugustine.com, 904/825-6830, 9 a.m.–5:30 p.m. daily, $6.95 adults, $4.25 students, children under 6 free) is one of the first major sights you’ll see, and like many other attractions in St. Augustine, it valiantly recreates the life of the town’s early colonists. The focus is on mid-18th-century Spanish families, and the staff here demonstrate activities like candle making, carpentry, blacksmithing, and more.

Cathedral Basilica

The Cathedral Basilica (38 Cathedral Pl., 904/824-2806) looms large over Old Town and stands as a memorial to the city’s 400 years of Catholic tradition. Built in 1797 after the destruction of two previous parish churches and expanded in 1887 and 1966, the church is the oldest Catholic parish in the United States. Tours aren’t given, but services are held regularly, and guests are welcome in the sanctuary.

Villa Zorayda

Half a dozen blocks away is the more whimsical Villa Zorayda (83 King St., 904/829-9887, www.villazorayda.com, 10 a.m.–5 p.m. Mon.–Sat., $10 adults, $8 seniors, military, and students, $4 children 8–12, children 7 and under free). Located across the street from the beautiful campus of Flagler College, the Villa Zorayda was originally built in 1883 as a winter residence and modeled on a Moorish-era castle in Spain but at a tenth of the size. Audio tours provide a somewhat excessively detailed history of the property and its many owners and renovations. A puzzling variety of artwork, antiques, and artifacts are on display. Accented in bright colors, the villa is hard to miss. Worth noting: Paid admission to the museum entitles you to a full day of free parking in their lot.

Flagler College

Were it not for the expansionist entrepreneurialism of Henry Morrison Flagler, it’s hard to imagine when, how, or even if modern Florida would have developed. Today, Flagler’s legacy is essentially the east coast of Florida. A more tangible monument to his impact on the state can be seen a block south of the Villa Zorayda on the campus of Flagler College (74 King St., St. Augustine, 904/823-3378, www.legacy.flagler.edu, tours 10 a.m. and 2 p.m. daily, $6 adults, $1 children 11 and under).

The liberal arts school’s hallmark building is Ponce de Leon Hall, which was originally the Ponce de Leon Hotel, the beginning of Flagler’s long and influential role as one of modern Florida’s founders. Designed by John Carrère and Thomas Hastings in the Spanish Renaissance style, the poured-concrete structures — with their red-tile roofs and arched windows — provided the visual foundation for much of the Mediterranean revival architecture that would come to dominate buildings in Florida for the next century.

Lightner Museum

The Lightner Museum (75 King St., 904/824-2874, www.lightnermuseum.org, 9 a.m.–5 p.m. daily, $10 adults, $5 children 12–18, children under 12 free) is a three-story facility that emphasizes its collection of Louis Comfort Tiffany stained glass and a wide range of Gilded Age antiques and oddities (particularly interesting are the odd turn-of-the-20th-century machines and musical instruments). The Lightner is somewhat refreshing in that it’s one of the few historically-oriented sites in St. Augustine that bridges the gap between the colonial era and modern times.

Historical Homes

Two sights that make no such attempt are the Ximenez-Fatio House Museum (20 Aviles St., 904/829-5375, www.ximenezfatiohouse.org, 11 a.m.–4 p.m. Tues.–Sat., $5 adults, $4 children 6–17, $3 seniors) and the Father Miguel O’Reilly House Museum Garden (32 Aviles St., 904/826-0750, www.oreillyhouse.org, 10 a.m.–3 p.m. Wed.–Sat., free). Located on the same narrow street just south of King Street, these are two of the more interesting “house museums” in Old Town. Of the two, the Father O’Reilly house is the oldest; in fact, it’s the second oldest building in St. Augustine after the Castillo de San Marcos. Both museums do an excellent job putting the houses into Augustine’s historical context, but the O’Reilly house’s lessons on the history of Catholicism in the city provide additional illumination.

Walking a few blocks farther south, you’ll arrive at the Oldest House Museum (14 St. Francis St., 904/824-2872, www.staugustinehistoricalsociety.org, 9 a.m.–5 p.m. daily, $8 adults, $7 seniors, $4 students, children 5 and under free), which, despite the nomenclature, does not contain the oldest house in St. Augustine; that would be the O’Reilly House. The house on this museum’s property only dates back to the early 18th century, and the site has been continuously occupied since the early 1600s—it was once the site of the oldest Spanish colonial dwelling in the country—so the “oldest house” designation is less inaccurate than it is misleading.