Monasterio de San Francisco#8 in Best Things To Do in Santo Domingo
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During the day, this Zona Colonial ruin isn't much to look at. After all, the Monasterio de San Francisco has been steadily crumbling since a 16th-century demolition squad and a 17th-century earthquake practically decimated it. But your opinion might change when you see how nighttime floodlights illuminate its cracks and crevices. Definitely swing by for a picture or two if you're in the Zona Colonial in the evening.
And if you're into odd history, you may want to make a special visit to this site. Although used mainly as a monestary, after it was rebuilt following a second earthquake in the 18th century, officials decided to convert the space into a mental asylum. Once again, though, Mother Nature intervened (this time in the form of a hurricane), resulting in the mental asylum's closure in the 1930s. To this day, portions of chains used to secure inmates are still visible.
Keep in mind, though, that entrance into this gated ruin is a bit of a hit-or-miss. Although some prior visitors have been able to gain access to wander the grounds, most were disappointed to go and find the gates locked without property hours displayed. Still, due to the gate's wider bars, many travelers note that snapping photos is absolutely doable.
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#1 Zona Colonial
Partially barricaded by stone walls, accented with baroque architecture and lying on cobblestone streets, Santo Domingo's Zona Colonial marks the area where Columbus settled in the New World. Visitors say it's definitely a must-see, considering the city's best known historic sites are located here. But this UNESCO World Heritage Site also shelters many hotels, bars and restaurants. Best of all, you can explore the area entirely on foot: For all that's crammed inside, there's really only 11 blocks worth of sights.
So where should you start? Perhaps the Catedral Primada de America, which is located near the heart of the zone (look for the statue of Christopher Columbus). From there you can trek a little farther west to Fortaleza Ozama, located along the mouth of the Río Ozama in the southeast quadrant. Next, walk along the Calle Las Damas (the oldest street, a pedestrian-only zone) to the Alcázar de Colón palace and museum.
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