Ayuntamiento (City Hall / Former Casino)

The building in front of you is where the city council debates budgets, planning applications, and parking regulations. It is also a former casino where Leon Trotsky gambled. Let that contrast settle for a moment.

Built in eighteen eighty-seven and inspired by the casino at Monte Carlo, this was the social epicentre of Belle Epoque San Sebastian. Queen Maria Cristina herself attended the inauguration on July first of that year. The gaming tables attracted European royalty, industrialists, and political figures -- the Shah of Persia played here, Baron Rothschild played here, and yes, the Russian revolutionary Leon Trotsky sat at these same tables before he went on to help overthrow the Tsar.

The party ended abruptly in nineteen twenty-four when dictator Primo de Rivera banned gambling across Spain. Overnight, the casino lost its reason to exist. The building sat in a kind of limbo for over two decades before the city government moved in, converting it to a town hall in nineteen forty-seven. The ornate Belle Epoque interiors -- designed for champagne and roulette -- now serve as the backdrop for municipal meetings.

If you look closely at the facade, you can spot something darker. There are bullet holes from the Spanish Civil War still visible in the stonework. Nobody has filled them in. Whether that is preservation or oversight depends on who you ask, but the effect is powerful -- a building that went from royal casino to war zone to city hall in the space of sixty years.

The location is perfect, sitting right where the Old Town meets La Concha promenade, with the bay spreading out behind it. The architects knew exactly what they were doing when they put a pleasure palace here.