Santorini

The Santorini Experience is Santorini's premier sports-tourism event, drawing professional and amateur athletes from across the world. The trail routes begin in Oia and pass through Imerovigli and Firostefani - essentially the caldera-rim path at racing pace, with views that make most road races look dull. The swim starts from the volcanic islet and finishes at Fira's old port. Mid-October is the sweet spot for the island: temperatures have dropped from summer peaks, the tourist crowds are largely gone, accommodation prices are lower and availability is good. Registration is open at santorini-experience.com. Even if you are not racing, Oia on race morning is worth watching.

This is a genuine locals-first event that takes place after most tourists have left for the season. The Church of Agia Matrona (built 1859) is decorated with palm leaves on the eve; rosemary and rose geranium are scattered in the alleys; coloured flags hang in the squares. Traditional foods include xelouristo (salt cod with onions, olive oil and potatoes), gamopilafo rice and meat from wood-fired pots. Vespers begin at 7pm, the panigiri proper starts around 9pm with traditional music bands. The celebration continues until sunrise, with a morning service and icon procession the following day. The Greek Gastronomy Guide confirms it as a food-forward event; the santorini-islandguide.com calendar confirms the date. Worth the drive from Fira if you are on the island in late October - a rare window into off-season Santorini life.

Oxi Day (Epeteios tou Ochi) is one of Greece's two national days. In Santorini, the solemn parade with schoolchildren and veterans takes place in the morning in Fira. The mood is patriotic but relaxed; visitors are welcome to watch. Archaeological sites and museums - including the Museum of Prehistoric Thera (one of the finest Cycladic museums in Greece) and the Akrotiri archaeological site - are free to enter. If you are already visiting Santorini in late October, time your museum visits for this day. The weather in late October is typically mild and the island is quiet, making it a good day for the caldera walk from Fira to Oia.

Santorini in December is a very different island from the summer version: most tourist businesses are closed, prices are a fraction of peak-season rates and the caldera villages have their own unhurried rhythm. The Christmas Village in Fira's square (opening typically in the first week of December) includes a tree, food stalls, local crafts and family events. On Christmas Eve, groups of children carry metal triangles door-to-door singing kalanda (carols) in exchange for small gifts or coins. New Year's Eve sees hotels and restaurants host private dinners with caldera-view fireworks; the Vasilopita cake is cut at midnight. Epiphany on 6 January (Theophania) brings the cross-diving ceremony at Fira's port and in Ammoudi, closing the festive season. A good time for travellers who want Santorini without the crowds, but verify that your preferred accommodation and restaurants are open.