The bar and cafe scene in Kalamata is thoroughly Greek: the evening volta (the evening stroll) along the seafront promenade is a social institution, and by 10pm the bars along Navarinou Street come alive with locals dressed up for a summer night. The crowd is predominantly Greek domestic tourists and locals rather than international visitors, which keeps prices reasonable and the atmosphere unpretentious.
The Greek coffee culture means that cafes are serious — a freddo cappuccino or freddo espresso (both served over ice) is the standard summer drink, and you will find good coffee at virtually any kafeneion in the old town. Traditional kafeneia still exist in Kalamata, particularly around the market area, where older men play backgammon over small cups of strong Greek coffee. Ouzo with a small plate of mezes — olives, sardines, maybe some grilled octopus — is the standard early-evening drink, and the seafront is the right place to do it at sunset.