Kalamata is one of the best-positioned cities in Greece for day trips to extraordinary places. The southern Peloponnese is dense with ancient sites, Byzantine towns, and wild landscape within two hours' drive.
The Mani Peninsula
The Mani — the middle finger of the Peloponnese — is the most distinctive landscape in mainland Greece. A barren, rocky peninsula with tower-houses that look like they were built to withstand siege (they were), centuries of blood feuds, and a culture so fiercely independent that it was never fully conquered by the Ottomans. The outer Mani is dramatic and accessible; the inner (Mesa) Mani is bleaker and more extraordinary. Areopoli, the main town, is under an hour from Kalamata.
Mystras
The ruined Byzantine city of Mystras sits on a steep spur of the Taygetos mountains about 65 km from Kalamata (near Sparta). It was the last great flourishing of Byzantine culture before the fall of Constantinople, and the frescoes in its churches — some dating to the 14th century — are among the finest medieval paintings in the Balkans. Allow a full morning; the site involves considerable walking on steep paths.
Ancient Messene
About 25 km north of Kalamata, the ancient city of Messene has some of the best-preserved Classical Greek fortifications anywhere in the world. The walls stretch for 9 km and the site is only partially excavated — what has been uncovered includes a theatre, stadium, and the Arcadian Gate, a remarkably intact round gateway. Far less visited than Olympia or Mycenae and worth every minute.