Tosca Cafe

The glorious gay rights film Milk aside, there’s not many things in life you can be thankful to Sean Penn for, really, is there? But clearly time spent as the Mayor of Castro Street got to Mr Penn’s soul, and it’s thanks to him and an influx New York money that this iconic venue is still up and running. So, taking a moment to be grateful the great moody Oscar winner, treat yourself to a little class in this authentic 40s style cocktail bar, all high ceilings and red vinyl booths. As you rub shoulders with a frequently star-studded crowd in one of the city’s oldest bars, potent martinis and cosmopolitans are the order of the day. The venue does a nice range of classics, with signature drinks including Al’s Cut (Tanqueray gin, elderflower liquor and lime), San Francisco Fresca (Absolut Mandarin vodka, Triple Sec and Ginger ale delicious!) or for the sweet of tooth, a chocolate martini. The wine and champagne list is sufficient rather than extensive, and they also serve a reasonable range of beers (be warned before you order, it’s a cash only bar, though they do have an ATM inside if you’re stuck). Often doubling as a film set, you may find yourself on the casting couch before the night is through or if all that seems a bit sleazy (though we’re not judging), enjoy one of their literary nights. The venue also hosts special events including live bands. And Sean is a regular when he’s in town, so if you see him, be sure to say thanks.