Naples and the Bay of Naples have a long association with classic yachts: this was one of the key stops on the nineteenth-century grand tour for those who could travel by private vessel, and the anchorage off Posillipo retains a particular beauty at dusk that photographs from a century ago still capture. Chartering a classic yacht here today means arriving at Capri or Positano in the manner that wealthy travellers of another era did: under canvas or on a slow passage with a wooden hull, the cliffs above and the sea below. Four classic yachts in the collection operate in these waters, ranging from elegantly maintained motor sailers to pure sailing vessels with a century or more of history between them. Guest capacity is typically four to ten, and the pace of travel favours long anchorages over multiple stops in a single day. Weekly rates run from approximately 67,500 to 224,000 euros, with the advance provisioning allowance of around 30 percent adding for fuel, food, and berthing. September and October are the preferred months for classic yacht charters in the Bay of Naples: the summer crowds have thinned, the light is lower and more golden, and the berthing fees in Capri and Positano smaller harbours are more accessible. The crew on each classic yacht brings specialised knowledge both of the vessel and the historical and architectural heritage of the ports, making these charters well suited to guests who want a guide as much as a capable sailing crew.