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Guiding Winds
Whitewashed Cycladic village above the Santorini caldera at sunset

Athens · Aegean · Mediterranean

Greece · Cyclades. The Cyclades at the pace they were meant to be sailed.

Length

Typically 7 days

Guests

Up to 12

Price

Price depends on duration and season.

The voyage

Athens to Santorini by way of Kythnos, Serifos, Sifnos, Folegandros and Ios, the chain at the pace it was meant to be sailed.

In the price

  • All meals aboard, prepared together (Greek-leaning menu)
  • Snorkel gear, paddleboards
  • Private cabin with ensuite head
  • Fuel and moorings
  • Hosted by Clint

Not included

  • Flights to Athens (ATH) / from Santorini (JTR)
  • Travel insurance
  • Off-boat dining (we cover two shore dinners; others on you)

The Aegean

The Cyclades at the pace they were meant to be sailed.

The week, day by day

A sample itinerary. Weather and mood get a vote.

  1. Day 1 · Saturday

    Embarkation · Athens (Alimos)

    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

    Kythnos · Kolona

  3. Day 3 · Monday

    Serifos

  4. Day 4 · Tuesday

    Sifnos

  5. Day 5 · Wednesday

    Folegandros

  6. Day 6 · Thursday

    Ios

  7. Day 7 · Friday

    Santorini

  8. Day 8 · Saturday

    Disembarkation · Santorini

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.

Whitewashed Cycladic village above the Santorini caldera at sunset
Kolona, the twin-bay sandbar anchorage at Kythnos

Before you go

Questions guests actually ask.

The full 27-question FAQ covers everything. If something isn't there, just ask.

How long is the trip?
Charters typically run 7 days, one-way from Athens (Alimos) to Santorini through the Cyclades. Shorter charters are available. Specific weeks are available - see the calendar.

Availability

A limited run See the open weeks

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

Call us

Off-grid catamaran voyages

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Book a 30-minute intro call