Chora’s street plan was designed to be disorienting — a defense against pirates who couldn’t navigate the narrow, winding alleys. The result is a town that rewards wandering but punishes planning: the more deliberately you try to navigate it, the more likely you are to end up somewhere you didn’t intend and miss what you were looking for. The walk described here is a loose route, not a strict itinerary. Allow two to three hours, start early, and let it run over its schedule.
Starting Point: The Old Harbor (Alefkandra)
Begin at the old harbor on the western side of town. The working fishing harbor — where the small boats dock — is at the northern end of the waterfront. Between approximately 6am and 8am, the night’s catch arrives. The market that occasionally forms here is informal and brief, but worth seeing if you’re up early.
From the harbor, walk north along the waterfront past the row of pelicans (Petros the pelican is the island’s unofficial mascot; there are usually two or three in this area) to reach the Alefkandra square.
Little Venice and the Windmills
The row of old sea captains’ houses built directly over the water along the Alefkandra waterfront is what is known as Little Venice — the nickname is fanciful but the architecture is genuine, dating from the 18th century. The buildings were originally merchants’ residences; their ground floors extended over the water to allow direct loading from boats.
From Little Venice, a path climbs to the Kato Myli (lower windmills). The six windmills on this promontory are 16th-century Venetian construction, restored in the 20th century. Walk around their base for views south toward the sea and north toward the Kastro.
The Kastro Neighborhood
The Kastro is the oldest part of Chora, on the northern edge of the town above the harbor. The streets here are narrower than the rest of town, the buildings are taller, and the traces of the Venetian fortification wall are still visible in places. The neighborhood has almost no tourist infrastructure — a few residential buildings, a small church, some cats.
Paraportiani church is at the entrance to the Kastro. It is actually five small chapels built at different times against and around each other, creating the asymmetric white mass that photographs well from every angle. The interior of the main chapel is open at irregular hours.
Matogianni and the Central Streets
Matogianni is the main commercial artery of Chora — boutiques, jewelry shops, restaurants, bars. It runs for about 200 meters and is often described as one of the most expensive shopping streets in Greece in summer. Walk it once and then take any of the parallel streets one block to the east: the same neighborhood, the same architecture, fewer people, and restaurants that serve the same food at 15–20% lower prices.
Practical Tips
- The walk is most enjoyable between 7am and 9:30am. By 10am in peak season, the main streets are too crowded for comfortable walking.
- Wear shoes with grip — the Mykonos stone paving is smooth and becomes slippery when wet or when worn smooth by foot traffic.
- The town is almost entirely flat; the only real elevation is the windmill promontory and the Kastro, both of which are short climbs.
- Most churches in Chora are open only for services; the main exception is Paraportiani, which is open to visitors (at unpredictable hours) and doesn’t require a fee.