Classic yachts in the Cyclades carry a particular appeal around Ios, where the island’s ancient cemetery, its Homeric connection as the burial place of Homer, and the timeless landscape of white cubic architecture create a setting that resonates with vessels whose own history stretches back decades. A timber ketch or a traditional schooner at anchor off the Ios Chora produces one of those images that defines Greek island sailing. Eight classic yachts charter in Greek waters, and the Cycladic circuit is among the most popular itineraries for their guests. Classic yachts in the charter fleet range from 20-metre ketches with hand-laid teak decks to 30-metre schooners with fine woodwork and restored interiors. They carry four to six guests across three or four cabins, with crew of two or three who are often passionate boat builders and ocean navigators as conventional charter skippers. The atmosphere on board is intimate and unhurried, reflecting the character of the vessels themselves. Charter rates for classic yachts around Ios begin around 50,000 euros per week for a smaller vessel in early summer, rising toward 180,000 euros for a prestigious historic yacht in peak season. The provisioning allowance of around 30 percent covers fuel, berthing, food and drinks. The classic Cycladic circuit from Ios takes in the ancient ruins at Delos, accessible by tender from a Mykonos anchorage, the marble quarry caves of Paros, the medieval Venetian Kastro at Naxos, and the lighthouse and sea caves of Folegandros before returning south to Ios.