When it comes to Spanish-style colonial charm, few cities in the Western Hemisphere can rival Old San Juan. But that doesn’t mean that Puerto Rico’s historical significance is exclusively within the capital city’s walls. Roughly 100 miles southwest of San Juan, the lovely town of San Germán holds the venerable distinction of being Puerto Rico’s second oldest city.

Founded in 1573 and named after King Ferdinand the Catholic’s second wife Germaine of Foix, San Germán became the island’s first settlement outside of San Juan. Its significance was such that the island was first divided into the San Juan Party and the San Germán Party. The town also became the focal point from which other settlements were established, thus earning the nickname ‘Ciudad Fundadora de Pueblos’ (roughly, Town-Founding City).

But while San Juan went on to grow exponentially beyond the old city walls and other cities like Ponce, Mayagüez, Arecibo or Caguas grew in population and importance, San Germán remained a sleepy colonial town and one of the best-kept secrets within the island.

From a historical perspective, San Germán’s most famous landmark is Porta Coeli Church. One of the earliest examples of Gothic architecture in the Americas, the chapel was originally built as a convent in 1609 by the Dominican Order. It was reconstructed during the 18th century and expanded with a single nave church of rubble masonry. Listed in 1976 in the U.S. National Register of Historic Places, Porta Coeli was restored by the Institute of Puerto Rican Culture and now houses the Museo de Arte Religioso, which showcases religious paintings and wooden carvings dating back from the 18th and 19th centuries.

Porta Coeli overlooks quaint Plazuela Santo Domingo, an elonganted, cobblestoned square enclosed by pastel-colored, colonial-style houses. A block away sits the town’s main square, Plaza Francisco Mariano Quiñones, where the operational church of San Germán de Auxerre is located. Both Porta Coeli and San Germán de Auxerre are part of the San Germán Historic District, which was also listed in the U.S. National Register of Historic Places in 1994 and includes about 100 significant buildings.

Though San Germán has long since lost its 16th-century designation as Puerto Rico’s most important city after San Juan, the town is nonetheless a regional powerhouse in southwestern Puerto Rico, housing important insitutions as the main campus of Universidad Interamericana (Interamerican University). Sports enthusiasts will also appreciate that the city is considered “The Cradle of Puerto Rican Basketball” as it is home to one of the island’s oldest and most succesful basketball franchises, Atléticos de San Germán (San Germán Athletics).