The Tyrrhenian circuit from the Amalfi Coast south to the Aeolians is one of those passages that keeps reminding you why you went sailing in the first place. The coast itself runs roughly northwest to southeast, so you'll generally be reaching or running on the prevailing northwesterly sea breeze as you work down from Naples toward Salerno — a generous gift on most summer afternoons.
The mornings are calmer, which makes them ideal for anchoring off Positano's pastel terraces or nosing into the cove below Ravello before the tourist ferries arrive. Swell wraps around the headlands more than charts suggest, so choose your anchorage carefully; exposed lunette bays that look perfect on paper can be rolly by evening.
The passage south to the Aeolians — roughly 80 nautical miles from Salerno to Lipari — is best done overnight, leaving late afternoon to catch the land breeze and arriving at first light. Lipari's main harbour is straightforward to enter and well-provisioned, making it the sensible base for the chain.
From there you work the islands anticlockwise or clockwise depending on the scirocco and libeccio forecasts, both of which can build quickly and render some anchorages untenable overnight. Stromboli demands a night approach: watching lava spill down the Sciara del Fuoco in darkness is genuinely arresting.
Most charters depart from Naples, Salerno, or Milazzo on Sicily's north coast. Bareboat licences are accepted for competent sailors with a recognised certificate; the Italians check paperwork properly at some marinas, so carry originals. Provisioning is excellent throughout, though expensive in the smaller ports.
May and September suit experienced sailors best; July and August bring crowded anchorages, higher prices, and the full theatre of Italian summer.