A sailing week based in Sicily is, in practice, a week in the Aeolian Islands. Of our 452 boats, 264 are at Portorosa and Capo d'Orlando on the north coast, and both of those bases exist because the archipelago is a short sail offshore: seven volcanic islands — Lipari, Vulcano, Salina, Panarea, Stromboli, Filicudi and Alicudi — named after the Greek keeper of the winds and listed in their entirety as a UNESCO World Heritage Site.
The distances are genuinely small. From Portorosa it is about 22 miles to Lipari, then roughly 10 on to Panarea, 12 more to Stromboli and 21 back across to Salina. That is a complete week with no leg longer than a morning, and two of the islands have volcanoes that are actively, visibly erupting while you watch.
The practical catch is depth. These islands rise abruptly out of deep water, which leaves very little shelf to anchor on at sensible depths. You can anchor in most of the bays and the holding is generally good, but the usable spots are smaller and fewer than the chart suggests, and at Stromboli the moorings are expensive — well over a hundred dollars — and come with a man in a dinghy to help, because the hawsers are too heavy to handle alone.
The wind explains the islands themselves. Almost every settlement is on the eastern side of its island, because that is the side sheltered from the strong and frequent mistral. Plan your anchorages the same way the Aeolians planned their villages.
The rest of the fleet is on the western end — Palermo, Marsala and Trapani — which opens a different week toward the Egadi islands. The whole regional fleet averages 14.6 metres with 222 monohulls, 180 catamarans and 32 gulets.