The history of Kalamata begins with Homer who mentions Pherai, unimportant in Antiquity. The site continued in obscurity until middle Byzantine times. It experienced a period of prosperity in the 11th–12th centuries. Following the Fourth Crusade, Kalamata was conquered by Frankish Crusaders and remained in Frankish hands until near the end of the Principality of Achaea, coming under the control of the Byzantine Despotate of the Morea in 1428. Kalamata was occupied by the Ottomans from 1481 to 1685. The Venetian Republic ruled Kalamata from 1685 as part of the "Kingdom of the Morea". During the Venetian occupation the city was fortified, developed and thrived economically. The Ottomans reoccupied Kalamata in the war of 1715 and controlled it until the Greek War of Independence in 182. Kalamata was the first city to be liberated on 23 March 1821. In independent Greece, Kalamata was rebuilt and became one of the most important ports in the Mediterranean Sea.
There are numerous historical and cultural sights in Kalamata. The point of reference par excellence is the legendary “castle of Isabeau” where the renowned International Dance Festival takes place annually. It is amphitheatrically constructed on the site of the Pherai acropolis offering a bird’s eye view of the city. No less beautiful is the exquisite Palia Poli (Old City) at the foot of the Castle. The wider region boasts the Metropolitan Panagia Ipapanti church (1873), the 12th century Kalograion Monastery with the renowned silk weaving workshop, and the Byzantine church Agioi Apostoloi (13th century) with the brick enclosed masonry. Other attractions include the Benakeion Archaeological Museum with findings dating from the Bronze Age to the Roman period. The spacious central Vassileos Georgiou (King George) square with many coffee shops and the pedestrian walkway of Aristomenous Street, the Folklore and History Museum, with traditional objects and relics from the 1821 Greek War of Independence.The seaside road in front of the city’s extensive beach (4 km length with crystal clear waters.
Near-by destinations include beaches at Verga (8 km E), Mikri Mandineia (10 km SE), Avia (12 km SE) and Kitries (17 km SE), which in recent years have developed into resorts with significant tourist facilities and a vibrant nightlife in the summer. The mountain villages on the Western slope of Mt.Taygetos, on the road to Sparti. The Ancient Messini is a few kilometres outside Kalamata, in the Municipality of Ithomi. It's a recently-discovered archeological site that astonishes visitors with its size and good condition; in fact, it is considered the best preserved archeological site.
Kalamata is renowned as the land of the Kalamatianos dance and of the Kalamata olives and oil, other local specialties to be tried Lalagia, Diples (dessert) and Pasteli (dessert).