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Guiding Winds
Pastel houses of an Amalfi coast village seen from the water

Salerno · Tyrrhenian Sea · Mediterranean

Italy · Amalfi & Aeolian. Capri at sunrise, dinners that ruin you for hotels.

Length

5 to 7 nights

Guests

Up to 12

Starts at

$3,650/ guest

The voyage

Capri at sunrise, Positano on the water, the volcanic Aeolian chain - dinners ashore that ruin you for hotel restaurants forever.

In the price

  • All meals aboard, cooked fresh (Italian-leaning galley menu)
  • Snorkel gear, paddleboards
  • Private cabin with ensuite head
  • Fuel and moorings
  • Crew

Not included

  • Flights to Naples (NAP) / from Catania (CTA)
  • Travel insurance
  • Off-boat dining (we cover one shore dinner; others on you)

The coast

Capri at sunrise. Anchorages that ruin you for hotels.

The week, day by day

A sample itinerary. Weather and mood get a vote.

  1. Day 1 · Saturday

    Embarkation · Salerno

    We stay tied up at the marina this first night, so everyone can get settled aboard before we head out in the morning.

  2. Day 2 · Sunday

    Amalfi & Atrani

  3. Day 3 · Monday

    Positano

  4. Day 4 · Tuesday

    Capri

  5. Day 5 · Wednesday

    Stromboli (overnight passage)

  6. Day 6 · Thursday

    Panarea

  7. Day 7 · Friday

    Lipari

  8. Day 8 · Saturday

    Disembarkation · Milazzo

From the field

What it looks like.

A mix of guest photography and licensed imagery while we add to Dodie's library through the 2027 season.

Positano cliffs and pastel houses rising above the Tyrrhenian
Capri and the grottos at Marina Piccola
Stromboli volcano lit up at night in the Aeolian Islands
Panarea
Lipari harbor in the Aeolian Islands

Before you go

Questions guests actually ask.

The full 23-question FAQ covers everything. If something isn't there, just ask.

How does Italy compare to BVI?
Less swimming-pool turquoise, more "you're in a postcard." Longer passages, more shore time, more dinners ashore. Higher price reflects Mediterranean dockage and provisioning costs.

Availability

A limited runSee the open weeks

We sail every week we're open, then the boat heads back across the Atlantic. A limited run.

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