To spend an evening the way most Iraklians do, stroll and then sit in a cafe and watch others stroll by. The prime locations for the latter have been Plateia Eleftheria (Liberty Sq.) or Fountain Square, but the crowded atmosphere of these places -- and some overly aggressive waiters -- has considerably reduced their charm.
For a more relaxed atmosphere, go to Marina Cafe, at the old harbor (across from the restored Venetian arsenali). For as little as 2€ for a coffee or as much as 9€ for an alcoholic drink, you can enjoy the breeze as you contemplate the illuminated Venetian fort, which looks much like a stage set. Another possibility if you're looking to have a late meal and hang out with a younger crowd is to try the small cafe/restaurant right on the 1866 Street (the Market street), Peninda-Peninda.
An alternative is Filos Sophias Roof-Garden Cafe (tel. 2810/222-333); enter through an interior staircase in the shopping arcade on Fountain Square. It attracts younger Iraklians, but travelers are welcome. The background music is usually Greek. You get to sit above the crossroads and, with no cover or minimum, enjoy anything from a coffee (2€) or ice cream (from 3€) to an alcoholic drink (from 4€).
There is no end to the number of bars and discos, featuring everything from international rock 'n' roll to Greek pop music, although they come and go from year to year. Disco Athina, 9 Ikarou, just outside the wall on the way to the airport, is an old favorite with the young; or try any of the clubs along Epimenidou -- the Villa Lokka or Privilege -- or Vogue or Envy along the seafront.
Most Class A hotels now host a Cretan Night, when performers dance and play traditional music. For more of the same, take a taxi to either Aposperides, out on the road toward Knossos, or Sordina, about 5km (3 miles) to the southwest of town.
During the summer, Iraklion's arts festival brings in world-class performers (ballet companies, pianists, and others), but mostly featured are ancient and medieval-Renaissance Greek dramas, Greek-themed dance, or traditional and modern Greek music. Many performances take place on the roof of the Koules (the Venetian fort in the harbor), Kazantzakis Garden Theater, or Hadzidaksis Theater. Ticket prices vary, but are well below what you'd pay at such cultural events elsewhere. Maybe you didn't come to Crete expecting to hear Vivaldi, but why not enjoy it while you're here? The festival begins in late June and ends in mid-September.
Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.