Set at the end of a narrow lane, this is a smart bar that boasts a pleasant outdoor terrace and a certain amount of medieval charm inside. Built on Roman foundations, an old stone wall dominates the interior, making for a special atmosphere. A decent drinks list and excellent tapas attract a well-heeled clientele – get in line early.

It may seem odd to recommend an Irish pub in a city with such a rich Spanish history, but make an exception for O'Brian's if you get tired of vermouth and tapas. A treasure trove of old street signs, posters, newspaper clippings and more from the old country, there are some good beers on tap, not to mention Guinness – which you're unlikely to find anywhere else in Toledo.

A cool place for a drink, a bite to eat and a bit of table football is Taberna Maxi's, a poky, laid-back establishment a stone's throw from the cathedral. Apart from the great bar snacks, or para picar, the wide range of drinks and hip furniture, there are screens showing sporting events for those into that sort of thing (they love their football here).

Formerly known as the Dodici Café Teatro, La Nuit is where Toledo's hot young things gather to hit the dancefloor and shake their bits. If you don't like Vodka shots, 'til-dawn clubbing and anthemic DJs, this place probably isn't the place for you. But in in a relatively small city with limited late-night options, it's a welcome new addition.

Formerly called Garcilaso – a local legend of a discoteca dating back to the 1960s – this venue reopened its doors in 2012 with a fresh direction. Big on rock music and with regular live bands gracing its stage, Los Clasicos is also a nightlcub open Thursday to Sunday from 1900 until dawn. There's a wide selection of beers and cocktails to choose from, too.

There are few live music venues as grand as this in the whole of Spain, let alone Toledo. The Circulo de Arte Toledo is based out of a converted church, and is stunning from top to bottom, with great acoustics to boot. The unique venue offers live music (blues, jazz, soul, rock, pop) by night, frequent clubnights, as well as a pleasant café and art space by day.

This poky, blink-and-you'd-miss-it spot down a dark street in the old town is worth seeking out. El Ultimo hosts lives blues and jazz bands from the city and sometimes far beyond, and is easily one of the coolest joints in Toledo. Things don't get started until late at El Ultimo, so early evening drinks are best sought elsewhere.

At the Pícaro Café Teatro, you may find up-and-coming pop, rock and reggae bands playing depending on the night. The handsome venue is one of Toledo's livelier spots, with performances on almost daily. But with its stylish interior and atmospheric lighting, plus a wide range of drinks, it's worth stopping in even when there's no concert.