There are numerous historical and cultural sights in Kalamata, such as the Villehardouin castle, the Ypapanti Byzantine church, the Kalograion monastery with its silk-weaving workshop where the Kalamata scarves are made, and the municipal railway park. The Church of the Holy Apostles is where Mavromichalis declared the revolt against Ottoman rule in 1821. Art collections are housed at the Municipal Gallery, the Archaeological Museum of Messenia and the Folk Art Museum.
Interesting sites in or near Kalamata are the following:
- Benakeion Archaeological Museum of Kalamata, located in the heart of the historical centre of Kalamata.
- Cultural events, such as the Kalamata International Dance Festival
- Kalamata Castle from the 13th century AD.
- The marina and the Port of Kalamata, located SW of the city centre, is the main and largest port in Messenia and the southern part of the Peloponnese.
- The Railway Museum of the Municipality of Kalamata, a railway museum which first opened since 1986.
- Ancient Messene, 20 km north-west of modern Messini.