Old San Juan is the second oldest city in the Americas. It dates back to 1509 when Spanish settlers moved here after the failed attempt to establish a settlement in Caparra.  The Cathedral of San Juan Bautista was begun in 1521and is one of the oldest buildings in San Juan and the second oldest cathedral in the Americas.  Casa Blanca, the first residence of the first Governor Juan Ponce de Leon, was also begun in 1521.  The construction of the Castillo San Felipe del Morro began in 1539 when King Charles V of Spain authorized its construction, including the surrounding walls.  The purpose of the fort was to defend the bay of San Juan from invaders and prevent enry into the harbor.  Most buildings in Old San Juan are centuries old, like El Convento which was once a convent in the 17th century and is now a fully restored hotel in the heart of the old city.   The city has  narrow cobblestone streets, sidewalks and alleys and a never-ending flow of automobile traffic in and out of the city.

Old San Juan is built on an island, called Isleta de San Juan, that  was originally hilly. The island is attached to the modern city of San Juan via causeways.   The highest part of the Old San Juan  is  the north side. There are no beaches in the Old City, but there is one approximately a mile away, El Escambron Beach, which is part of the internationally acclaimed Blue Flag Beach Program.   At the north of the city is the Atlantic Ocean. At the south,  San Juan Bay.

The City layout is very staightforward, although some streets might appear like a big maze. Streets run parallel with the compass points. Vertical streets go north/south, and horizontal streets go east/west. If you walk toward the bay - you can see cruise ships, etc- you're heading south. If you walk  up the hill, you're going north.

Because San Juan was a stop-over for Spanish galleons, a replenishment station for Spanish ships, supplying them with water and foodstuffs for the voyage to Spain, the city was built around its ports. A 50+ feet wall surrounds the whole north and west side of the city, and part of it still stands in the southern and eastern side. It was built to protect the city from attacks from the English,  Dutch, pirates and corsairs from the 16th to the 18th centuries. Many ships containing gold, silver and goods from the New World came from South America,  Peru,  Mexico, etc.

Buildings are attached to each other in rows.  Today, one can easily determine one building or residence from another by the different vibrant colors . It is rare to find a hotel with window for all of the rooms.   Perhaps 70% of all hotel rooms in Old San Juan do not have windows, except for the modern  Sheraton Hotel (formerly a  Wyndham hotel) because it was built  in a wider open space area near the cruise ship docks. Those who stay in one of the historic, smaller hotels will probably find street noises filtering up to their rooms, while those rooms that are windowless tend to be very quiet.  Old San Juan's architecture is very similar to that of Spanish cities in the Andalucia Province of southern Spain.  The old city makes you feel like you could be in Toledo, Cordoba or Sevilla.  Even the lamposts, wrought iron railings and the tile street signs on the buildings are identical.  Behind the doors of many residences lie interior  courtyards, some with a well, others with trees and plantings and decorated with colorful mosaic tiles.

Streets are very narrow, some of them still have the original blue cobblestone, which originally was ballast from the ships.  The city has started a restoration program where it plans to re-brick every street of Old San Juan. The work is  expected to be completed by 2015. There are wide open spaces, called "Plazas" where people sit and relax; small parks with trees around, but completely tiled. The names of  some include:  Plaza Colon, Plaza de Armas, Plaza Salvador Brau (or Barandilla) and Plaza San José. You can just sit there and relax as long as you want. Don't worry about security. Old San Juan is one of the safest places in Puerto Rico.  After all, the Governs mansion, La Fortaleza,  is in Old San Juan.  Aside from being a walled city there were  fortifications build to protect the city like: Castillo de San Felipe del Morro, Castllo San Cristobal and  La Fortaleza.

Today, Old San Juan is the jewel of Puerto Rico and the Caribbean.  It is a major tourist destination, with millions of cruise ship passengers, locals  and tourists visiting annually.  OSJ has a plethora of historic sites, museums, art galleries, boutiques, outlets, restaurants, pubs and nightclubs.