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The historic district beneath the castle features picturesque lanes with cafés, ouzerias, boutiques and taverns. Every Saturday, the weekly market offers Kalamata's famous olives and other products from the surrounding region such as figs and raisins. The silk weaving mill of the nuns from the Kalograion monastery, whose cloth is a precious commodity throughout Greece, is another famous site. The cloth can be bought from stalls around the Church of the Ypapanti. The beach at Kalamata, which extends for five kilometres along the bay toward Verga, deserves particular mention. Both the city and the beach offer a particularly lively night life.

Historic Sparta is nearby and definitely worth a day trip for any history buff. Eleven kilometres away is Messini, where an entire ancient town has been discovered and excavated. Kalamata also plays host to a famous annual dance festival at the castle. Fans of historic feats of engineering will enjoy the Railway Museum. Visiting the city around Easter? Check out the wild goings-on at Saitopolemos, when young people set off home-made fireworks in public. This custom is thought to date back to the struggles for independence from the Turkish occupying forces that had their start in Kalamata.