The city's tumultuous history saw ups and downs in its role as a trade center, centuries of wars, sieges, bombings, fires, natural disasters and fierce political conflicts. A fortified military town, San Sebastian was twice demolished by fire: first in 1489, and again in 1813 when the Portuguese and English troops bombed heavily the French forces that held the city and burned it to the ground after they took it. Only a few buildings on the Calle de la Trinidad, today's Calle 31 de Agosto, survived. The survivors gathered in Zubieta and made the decision to rebuild the city from scratch.

In 1863 the city walls were demolished and San Sebastian became capital of the province of Gipuzkoa. Miramar Palace was used as a royal summer residence by the Queen Regent Maria Cristina. A casino was built, and in the early 20th Century the city developed fast as a cosmopolitan place, attracting illustrious visitors from all over Europe. It lived the glamour of the Belle Epoque before World War I when celebrities such as Ravel, Trotsky and Mata Hary were frequent visitors of the casino, and famous opera singers and ballet companies delivered performances.

Gambling was banned in 1925, the casino was closed down, and the glory of San Sebastian as a summer resort went into decline, but its importance as an industrial and administrative center continued to grow. Franco spent a month there each summer from 1940 to 1975, placing it back on the map of beach resorts.

Of the old buildings preserved on Calle 31 de Agosto, you can visit the Santa Maria church and the one-time Dominican Convent, today the San Telmo Museum. The central square - the historical Plaza de la Constitution is flanked by arcades on all four sides. Interestingly, the balconies of the surrounding buildings have numbers on them, bringing back the times when bullfights were held in the square and the balconies were used by the spectators.  The square has witnessed celebrations, political upheavals, royal proclamations, parades and fairs. Miramar Palace, built in the place of an old San Sebastian church, rises between Ondarreta Beach and La Concha Beach, dividing the long seafront promenade. The Castle of Santa Cruz de la Mota on Mount Urgull offers a beautiful panoramic view of the city and the bay. San Sebastian harbour between the old town and La Concha Beach today mostly receives pleasure boats. The area is full of small shops and cozy restaurants.