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East of Old San Juan lies the upscale tourist oriented neighborhood of Condado, which occupies land that used to be owned by entrepreneur Pablo Ubarri Capetillo, a Spanish railroad developer and Count of San José de Santurce under the Spanish colonial period.

Beaches such as nearby Ocean Park, popular with swimmers, surfers and kitesurfers, are found all along the district's Atlantic coastline which is also the locus of numerous hotels.

Near Condado are two separate business districts, Santurce and Miramar. Miramar is mainly a residential area rising south of the Condado Lagoon. It comprises the former barrio of Miraflores, as well as drained marshland and landfill over which was built San Juan's first airport, the Isla Grande airport, which was renamed Fernando Luis Ribas Dominicci Airport in honor of Major Fernando Luis Ribas-Dominicci (USAF). Miramar now hosts the Puerto Rico Convention Center as well as some of San Juan Harbor's cruise ship piers. In 2005 Miramar was designated an historical district of Puerto Rico.

Santurce, originally named San Mateo de Cangrejos (Saint Matthew of the Crabs), was a settlement for freed African slaves during the early days of the city. After Pablo Ubarri sought permission to link San Juan with Río Piedra proper via steam tramway in 1878, the time it took to travel between both points were shortened and thereby stimulated the colonization and growth of the district. At the beginning of the twentieth century an electric trolley was installed, the township was split into three parts, and its main settlement, merged with the city, was renamed using the Spanish spelling of Santurtzi (Saint George in Basque), Ubarri's birthplace in Vizcaya, Spain. The "Museo de Arte de Puerto Rico" (Puerto Rico Museum of Art) and other important cultural venues are located in Santurce.

Looking down an Old San Juan street towards the bay

South of Santurce is Hato Rey, part of the former municipality of Río Piedras. Hato Rey was grazing ground for cattle owned by the royal government (hence its name, the King's Herd in Spanish) as early as the 16th century, and is now considered the financial center of the island. A section of this district is often referred to as the "Golden Mile" (actually 0.47 miles/0.76 kilometres long) due in part to the many banks and businesses located there.

In the southern part of the city is the socially diversified community of Río Piedras. Founded in the mid 1850s, Río Piedras was a separate town which hosted sugar cane plantations and the estates of some of San Juan's wealthiest inhabitants (as well as their working class staff). The Spanish colonial governors also had their summer home there on land which eventually gave way to the main campus of the University of Puerto Rico. In 1951 the municipalities of San Juan and Río Piedras were merged to redefine San Juan's current city limits. Today Río Piedras comprises the largest area of the municipality of San Juan. and is home to the renowned, traditional “ Plaza del Mercado” (Río Piedras Marketplace), the main campus and the Medical Sciences campus of the University of Puerto Rico and the San Juan Botanical Garden.

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