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A two-masted sailing yacht under way below an island headland at dusk

Tour · Greece · By boat

Length8 daysFrom$2,720Leaves6 JuneSeats6 leftBook this tour

The tour · Cyclades

Eight days under sail between five islands, swimming off the stern and eating where the fishermen eat.

This is a sailing week for people who have never sailed, and for people who have and miss it. Nobody has to pull a rope. Anyone who wants to steer, trim a sail or learn the knots will be handed something within the hour.

The pace depends on the wind, which is the point. Most days are two to four hours under sail, a long swim stop, and a harbour or an anchorage by late afternoon. Day five is on land. If the meltemi blows hard we change the order of the islands, not the number.

What makes it is the size of the boat. Fifteen metres, four guest cabins and a keel shallow enough for coves the ferries and day boats cannot use. Eleni eats where the fishermen eat, and on two nights that is a table with no menu.

The itinerary · 8 days

Cast off from Naoussa

Day 01 / 08Paros

Cast off from Naoussa

Aboard at five. Cabins, a swim off the stern and dinner in the harbour.

By boat · night in harbour

Route, day by dayDrag the line to travel it

What you pay for

Included

  • Seven nights aboard in a double or twin cabin
  • Breakfast and lunch aboard every day, and four dinners ashore
  • Skipper, fuel, harbour fees and bed linen
  • Snorkels and two paddleboards
  • Your guide

Not included

  • Ferries or flights to Paros and home from Milos
  • Three dinners ashore
  • Travel insurance
  • Tips for the skipper
Eleni Vardaki in a rust coat on a cobbled street

Your guide

Lead guide, Greece · Apollonia, Sifnos

Her grandmother ran the bakery in Apollonia. She knows which path is open and whose table has room.

tours led

Meet Eleni

Departures

  • 6 June 2027$2,720per person6 leftBook
  • 27 June 2027$2,880per person8 leftBook
  • 5 September 2027$2,880per person4 leftBook
  • 19 September 2027$2,720per person8 leftBook

Prices are per person in a shared room. No booking fee.

Travellers on this tour

“I have booked group tours before and always felt herded. This felt like travelling with a friend who had done all the homework.”
Daniel OkaforThe Cyclades by sailboat, June 2026
A two-masted sailing yacht under way below an island headland at dusk

Tour · Greece · By boat

Length8 daysFrom$2,720Leaves6 JuneSeats6 leftBook this tour

The tour · Cyclades

Eight days under sail between five islands, swimming off the stern and eating where the fishermen eat.

This is a sailing week for people who have never sailed, and for people who have and miss it. Nobody has to pull a rope. Anyone who wants to steer, trim a sail or learn the knots will be handed something within the hour.

The pace depends on the wind, which is the point. Most days are two to four hours under sail, a long swim stop, and a harbour or an anchorage by late afternoon. Day five is on land. If the meltemi blows hard we change the order of the islands, not the number.

What makes it is the size of the boat. Fifteen metres, four guest cabins and a keel shallow enough for coves the ferries and day boats cannot use. Eleni eats where the fishermen eat, and on two nights that is a table with no menu.

The itinerary · 8 days

Cast off from Naoussa

Day 01 / 08Paros

Cast off from Naoussa

Aboard at five. Cabins, a swim off the stern and dinner in the harbour.

By boat · night in harbour

Route, day by day

What you pay for

Included

  • Seven nights aboard in a double or twin cabin
  • Breakfast and lunch aboard every day, and four dinners ashore
  • Skipper, fuel, harbour fees and bed linen
  • Snorkels and two paddleboards
  • Your guide

Not included

  • Ferries or flights to Paros and home from Milos
  • Three dinners ashore
  • Travel insurance
  • Tips for the skipper
Eleni Vardaki in a rust coat on a cobbled street

Your guide

Lead guide, Greece · Apollonia, Sifnos

Her grandmother ran the bakery in Apollonia. She knows which path is open and whose table has room.

tours led

Meet Eleni

Departures

  • 6 June 2027$2,720per person6 leftBook
  • 27 June 2027$2,880per person8 leftBook
  • 5 September 2027$2,880per person4 leftBook
  • 19 September 2027$2,720per person8 leftBook

Prices are per person in a shared room. No booking fee.

Travellers on this tour

“I have booked group tours before and always felt herded. This felt like travelling with a friend who had done all the homework.”
Daniel OkaforThe Cyclades by sailboat, June 2026
A two-masted sailing yacht under way below an island headland at dusk

Tour · Greece · By boat

Length8 daysFrom$2,720Leaves6 JuneSeats6 leftBook this tour

The tour · Cyclades

Eight days under sail between five islands, swimming off the stern and eating where the fishermen eat.

This is a sailing week for people who have never sailed, and for people who have and miss it. Nobody has to pull a rope. Anyone who wants to steer, trim a sail or learn the knots will be handed something within the hour.

The pace depends on the wind, which is the point. Most days are two to four hours under sail, a long swim stop, and a harbour or an anchorage by late afternoon. Day five is on land. If the meltemi blows hard we change the order of the islands, not the number.

What makes it is the size of the boat. Fifteen metres, four guest cabins and a keel shallow enough for coves the ferries and day boats cannot use. Eleni eats where the fishermen eat, and on two nights that is a table with no menu.

The itinerary · 8 days

Cast off from Naoussa

Day 01 / 08Paros

Cast off from Naoussa

Aboard at five. Cabins, a swim off the stern and dinner in the harbour.

By boat · night in harbour

Route, day by dayDrag the line to travel it

What you pay for

Included

  • Seven nights aboard in a double or twin cabin
  • Breakfast and lunch aboard every day, and four dinners ashore
  • Skipper, fuel, harbour fees and bed linen
  • Snorkels and two paddleboards
  • Your guide

Not included

  • Ferries or flights to Paros and home from Milos
  • Three dinners ashore
  • Travel insurance
  • Tips for the skipper
Eleni Vardaki in a rust coat on a cobbled street

Your guide

Lead guide, Greece · Apollonia, Sifnos

Her grandmother ran the bakery in Apollonia. She knows which path is open and whose table has room.

tours led

Meet Eleni

Departures

  • 6 June 2027$2,720per person6 leftBook
  • 27 June 2027$2,880per person8 leftBook
  • 5 September 2027$2,880per person4 leftBook
  • 19 September 2027$2,720per person8 leftBook

Prices are per person in a shared room. No booking fee.

Travellers on this tour

“I have booked group tours before and always felt herded. This felt like travelling with a friend who had done all the homework.”
Daniel OkaforThe Cyclades by sailboat, June 2026

Plan a trip

WhereAnywhereWhenAny monthTravellers2 travellersFind a tour
Call us+44 20 7946 0412

Booking 2027 departures

A travel planner answers within a day

Plan a trip

WhereAnywhereWhenAny monthTravellers2 travellersFind a tour
Call us+44 20 7946 0412

Booking 2027 departures

A travel planner answers within a day

Plan a trip

WhereAnywhereWhenAny monthTravellers2 travellersFind a tour
Call us+44 20 7946 0412

Booking 2027 departures

A travel planner answers within a day

Tour operator and travel agency

Lisbon · local time

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Booking 2027 departures

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Tour operator and travel agency

Lisbon · local time

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Booking 2027 departures

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Tour operator and travel agency

Lisbon · local time

--:--

Booking 2027 departures

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