Anchoring Off Folegandros: A Sailing Log

Day one: Milos, and the walk to Sarakiniko

We left the marina at Lavrio in the early afternoon and reached Milos by evening, anchoring in a bay short of the main port. The island's Sarakiniko coast, a stretch of white volcanic rock eroded into something closer to a lunar landscape than a typical Greek beach, is a twenty-minute walk from the anchorage. We went at sunset, once the day-trip boats from the port had mostly cleared out.

Day two: the crossing to Folegandros

A longer sailing day, most of it spent on open water between Milos and Folegandros, with the wind cooperative enough to sail rather than motor most of the way. Folegandros gets a fraction of Santorini's visitor numbers despite sitting one island over, mostly because it has no airport and a limited ferry schedule — the same isolation that keeps its Chora, a cluster of whitewashed houses on a clifftop, genuinely quiet even in August.

Day three: the cliff path

A full day given to Folegandros itself: a hike along the cliff path connecting Chora to the Panagia church above it, then an afternoon left unscheduled, which the group mostly spent reading on deck or swimming from the boat directly, off a bay with no other vessels anchored in it. This was the log's best day by general agreement, and the least eventful — worth noting, since it suggests the itinerary's looser days are doing real work.

Day four: Sikinos and Kimolos

Two smaller islands in a single day, neither with much in the way of formal sights, both worth the stop precisely for that reason. Sikinos's port has a handful of tavernas and little else; dinner was fish bought that morning by the boat's cook directly from a fisherman at the dock, cooked aboard that evening.

Day five: Santorini, kept brief

Santorini earns its reputation — the caldera view from Oia is genuinely remarkable — but the crowds earn their reputation too, and the itinerary gives it one day rather than the two or three a first-time visitor might expect. We timed the Oia sunset viewing carefully, arriving early to claim a position before the tour-bus crowds arrived, and left the island the following morning.

Day six and seven: back toward the quiet islands

The final two days retraced toward Kimolos and a last night at anchor off Milos, a deliberate choice to end the trip on the quieter islands rather than close on Santorini's crowds. It's a small piece of itinerary design, but it changes what the week feels like in memory — the last thing logged isn't a crowded caldera view, it's an empty anchorage at dusk.