Otranto is at its best in May, June, and September, when the sea is warm enough to swim, the light is sharp, and the old town is not yet packed. July and August are very busy — Italians from across the country book the Salento months in advance, and prices in the historic centre rise sharply.
The town's biggest event is the Festa dei Santi Martiri on 13–15 August, marking the anniversary of the 1480 massacre with processions, a re-enactment of the siege, and fireworks over the castle. Outside summer, April through early May is quiet but pleasant for walking the coast, and the cathedral and castle are uncrowded.
Winter is mild but most beach restaurants close from November through March; the historic centre stays open year round but with a much shorter list of working trattorias.