Anchoring the city's alternative entertainment district, which is recognisable thanks to all the wild graffiti just east of downtown, is this classic bar and club. The crowd is young and laid back, and here to enjoy live bands and a legendary beverage menu that lists more than 200 cocktails. The food's good, too.

Prostitution is legal in Costa Rica, and the sex tourism scene is centred on San José's (in)famous, frosted pink Hotel Del Rey, home of the Blue Marlin Bar. While it's geared to single gentleman – as are several businesses in the surrounding blocks, collectively known as the Gringo Gulch – everyone is welcome to enjoy the small casino and expensive drinks. If you'd rather avoid that scene, now you know where it is.

If you're in the mood for a more elegant aperitif, take a cab into the mountains of Escazú to fabulous La Cava. The underground bar, with magnificent views over the starry Central Valley, is part of pricey Le Monastere Restaurant, one of the capital's long-time favourite splurges. The bar is a bit more relaxed, but offers truly inspired bocas and a very full bar, including an excellent wine list. Open from 1830-0200 on Fridays and Saturdays.

This San José institution has been the capital's hottest spot for Latin dance for years. Castros has three throbbing floors of DJs serving up spicy rumba, reggaeton, and of course salsa to a crowd that knows how to dance, and there's usually karaoke on as well. It's away from the city centre (take a taxi, as Barrio Mexico can be dodgy), but gets a fair number of tourists.

One of San José's oldest gay and lesbian clubs, La Avispa remains the epicentre of the scene, with a huge dance floor, great music, and straight-friendly vibe that brings in a diverse, stylish crowd from across the country.

Dress to impress at Costa Rica's top dance club, considered a destination by party people from all over Central America. Unless you're looking really good, you'll wait in line for a while before being admitted to the unremarkable-looking warehouse. It's worth this bit of Studio 54-style theatre to enjoy two huge dance floors, with live DJs, spinning electronica, trance, and more.

This relaxed venue, owned by a local film celebrity, is decorated with a cinema theme. Though it is perhaps best known for screening cool movies within the cavernous interior, El Observatorio is also a great place to see live music. The crowd is mixed, the food is good, and the entertainment schedule listed on its Facebook page.

The polished, elegant Jazz Café is every capitaleño's favourite place to see live music, with a reliably good line-up of top regional and international talent. The crowd is older, the music better, and the drinks and food pricier than on nearby Calle Amargura. A newer Jazz Café has opened in Escazú on Próspero Fernández Highway; reservations are recommended.

This Los Yoses institution may not be pretty, but the classic dive bar often has lines out the door for its popular live shows. The dance floor is huge and sound system loud, the better to broadcast cover bands playing rock and heavy metal from the 1970s, 80s, and 90s. On off nights, a huge video screen keeps kids in black t-shirts entertained.

San José's graceful National Theatre is considered the city's most beautiful building; guides will tell you that Costa Ricans criminalized war rather than risk hurting it again. Designed during the 1890s and fuelled by full-bodied coffee profits, the city's main stage is wrapped in French sophistication, with a soaring façade and classical art. The theatre hosts performers from all over the nation and world, and is home to the Orquesta Sinfónica Nacional (National Symphony Orchestra).

Inside the enormous red, white, and blue Centro Cultural Costarricense y Norteamericano (Costa Rican and North American Cultural Center), the Eugene O'Neill Theatre stages all sorts of plays, musicians, movies, and many other events, most with a North American flavour. It also offers plays, puppet shows, activities for children, as well as various workshops and classes.