Mediterranean (Sicily & Lipari)

The stretch of water between Sicily's north-eastern coast and the Aeolian archipelago is compact enough to day-sail comfortably yet varied enough to feel genuinely different on each tack.

Summer brings the maestrale down from the north-west most afternoons, rarely gusting above 20 knots in June and July, which makes the 20-odd nautical miles from Milazzo to Lipari a relaxed first passage — enough wind to sail, short enough to arrive before lunch. Come August the wind softens and the anchorages fill, so an early start pays dividends.

The Aeolians are the core of it. Lipari itself is your natural charter base, with decent provisioning at the supermercato near the marina and straightforward fuel. Vulcano's Porto di Levante smells of sulphur and looks like another planet; anchor there overnight only if the scirocco stays away, as the southern roadstead turns uncomfortable fast. Panarea has expensive mooring buoys and extraordinary thin-crusted pizza to justify them.

The real prize is arriving off Stromboli at dusk and watching the crater flash orange from the cockpit — sail east of the island to avoid the worst of the swell rebound.

Sicily's mainland ports anchor the wider circuit. Syracuse, with its Ortygia waterfront, earns a two-night stay for the Greek theatre alone; the marina is functional and secure. Taormina is best done as a side trip by bus from Giardini Naxos, since anchoring in any swell off that exposed coast is a miserable business. Etna's silhouette trailing smoke makes a fine backdrop for a dusk passage south.

May and early June offer the best balance of settled conditions and space; a bareboat ticket requires ICC certification, and experienced skippers considering single-handed passages should carry an anchor light bright enough for the ferry traffic.