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Adventure ★ 5.0 · 1 reviews

Cyclades Sailing & Sunsets

Eight days island-hopping the Cyclades under sail — Santorini, Ios, Naxos and Paros, sleeping aboard.

Duration
8 days
Group size
max 12
Departures
3 dates
Destination
Greece
Cyclades Sailing & Sunsets — Santorini Oia Cyclades Sailing & Sunsets — Coastal Cove Cyclades Sailing & Sunsets — Beach Chairs

About this trip

A skippered crossing of the central Cyclades on a 15-metre yacht, twelve guests maximum. You are not expected to know how to sail; you are expected to be happy swimming off the back of a boat and eating in a different harbour every night.

Day by day

Boarding in the afternoon, safety briefing, and a first night in the marina.

Night
Selected 4★ hotel or similar
Meals
Dinner

A four-hour crossing north with the meltemi behind us, anchoring off Manganari for the afternoon.

Night
Selected 4★ hotel or similar
Meals
Breakfast, dinner

The longest sail of the week, arriving under the Portara at dusk.

Night
Selected 4★ hotel or similar
Meals
Breakfast, dinner

Koufonisia and Schinoussa — the quietest water of the trip.

Night
Selected 4★ hotel or similar
Meals
Breakfast, dinner

Naoussa harbour, and an evening ashore.

Night
Selected 4★ hotel or similar
Meals
Breakfast, dinner

The cave in the morning, beaches in the afternoon.

Night
Selected 4★ hotel or similar
Meals
Breakfast, dinner

A long, fast reach back towards the caldera.

Night
Selected 4★ hotel or similar
Meals
Breakfast, dinner

Breakfast aboard, then transfers.

Meals
Breakfast, dinner

What’s included

Included

  • Skipper and hostess
  • All berths aboard
  • Fuel and harbour fees
  • Accommodation as described
  • Daily breakfast
  • All transfers and transport in destination
  • English-speaking local guide
  • All entrance fees listed in the itinerary
  • 24/7 emergency contact while travelling

Not included

  • International flights
  • Travel insurance
  • Visa fees where applicable
  • Lunches and drinks unless stated
  • Tips and personal expenses

Departure dates

  • 12 Sep 2026

    back 19 Sep

    only 2 left

    ₦3,300,000

    Book
  • 9 Nov 2026

    back 16 Nov

    7 seats

    ₦3,696,000

    Book
  • 10 Jan 2027

    back 17 Jan

    10 seats

    ₦3,300,000

    Book

What travellers said

Eight days, four islands, zero stress

I had never sailed before and it did not matter at all. The skipper made it easy, the food on board was better than half the tavernas we ate in ashore, and Koufonisia was the quietest water I have ever swum in.

Lena Fischer

Cyclades Sailing & Sunsets

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