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Yacht sailing holidays & skippered tours in Greece

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

93

experiences

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4.9

Fast cruising Cicladi Occidentali

Duration:

6 days - 7 nights

Greece:

Cyclades

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+11 travellers

have booked

€925

Per person

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4.8

Catamaran in the sea of Ulysses - All inclusive

Duration:

6 days - 7 nights

Greece:

Ionian Islands

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+15 travellers

have booked

Starting from

€1,250

Per person

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4.7

Big and luxurious 60ft catamaran in Cyclades - best local experience

Duration:

6 days - 7 nights

Greece:

Cyclades

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+10 travellers

have booked

Starting from

€1,650

Per person

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5.0

Dodecanese, outdoor lifestyle exploration

Duration:

7 days - 6 nights

Greece:

Dodecanese

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+2 travellers

have booked

€675

Per person

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5.0

Sailing Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

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+112 travellers

have booked

Starting from

€920

Per person

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5.0

Dodecanese, outdoor lifestyle exploration

Duration:

7 days - 6 nights

Greece:

Dodecanese

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Arianna

has booked

€675

Per person

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4.9

Small Cyclades

Duration:

6 days - 7 nights

Greece:

Cyclades

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+12 travellers

have booked

Starting from

€890

Per person

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4.9

Paros and the fantastic Small Cyclades

Duration:

7 days - 7 nights

Greece:

Cyclades

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+27 travellers

have booked

€950

Per person

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4.9

Full sail in the blue of Ionian Greece with hostess on board

Duration:

7 days - 7 nights

Greece:

Ionian Islands

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+14 travellers

have booked

€1,050

Per person

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4.6

Cruise in the Dodecanese and off the coast of Turkey on a 17m boat with chef

Duration:

7 days - 7 nights

Greece:

Dodecanese

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+10 travellers

have booked

€1,300

Per person

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3.1

Greece Cruise in the Sporades - 2 Catamarans & 1 Sailboat

Duration:

10 days - 10 nights

Greece:

Sporades

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+9 travellers

have booked

Starting from

€1,640

Per person

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5.0

Che meraviglia navigare tra Rodi e Kos , cabine con bagno privato

Duration:

7 days - 7 nights

Greece:

Dodecanese

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+12 travellers

have booked

Starting from

€850

Per person

Why book a holiday with Sailsquare?

The world's largest marketplace for sailing holidays

The world's largest marketplace for sailing holidays

80,000 travellers have already chosen their holiday from a catalogue of 12,000 proposals in 120 destinations, worldwide.

Get onboard solo, with your family or your friends

Get onboard solo, with your family or your friends

Book a single spot, a cabin or the whole boat just for yourself, or for your friends or family.

Find out before you book who's waiting for you on board

Find out before you book who's waiting for you on board

Find out more about the skipper and travellers who have already booked the holiday, to find out more about the

Sailing holidays that suit all budgets

Sailing holidays that suit all budgets

On Sailsquare, sailing holidays are within everyone's reach. Thousands of proposals to choose from, at affordable prices.

Reviews - Yacht sailing holidays & skippered tours in Greece

1553 reviews

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Sailing Cyclades

06/16/2024

Lydie M.

-

France

Nous avons passé un merveilleux séjour à bord du voilier avec Yann en tant que skipper. Itinéraire, restaurants et visites, tout était bien organisé. Le bateau est confortable et moderne, Nous recommandons les yeux fermés !
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From Milos to Mykonos

06/15/2024

Paola R.

-

Italy

Andrea è un bravissimo skipper, conosce molto bene le Cicladi e ci ha portato in baie e paesini meravigliosi. Ci ha consentito di partecipare alle manovre e anche di timonare, dandoci spiegazioni e ordini molto chiari senza mai alzare la voce o perdere la pazienza. Lui bravissimo nelle manovre, anche nei momenti più difficili, un grande! Barca bellissima e ben organizzata, ha anche la piastra per il barbecue, ci siamo fatti una cenetta sotto le stelle con spiedini alla brace! Tornerò di sicuro con lui appena possibile!
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From Milos to Mykonos

06/14/2024

Francesca C.

-

Italy

Andrea è uno skipper molto capace e professionale, ho apprezzato molto la sua gentilezza e la pazienza con cui si è rapportato al nostro equipaggio di aspiranti velisti, creando in barca un clima sereno e rilassato. Ci ha fatto percorrere un Itinerario bellissimo, ed abbiamo navigato divertendoci da un' isola all' altra visitando Milos, Folegandros,, Ios e le Piccole Cicladi, per finire arrivando fino alla splendida Mykonos. Un' esperienza bellissima ed indimenticabile, che rifarei immediatamente e che consiglio a tutti !
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From Milos to Mykonos

06/13/2024

Alberto B.

-

Italy

Ottimo tour delle Cicladi, vele spiegate al minimo segnale di vento e via divertimento assicurato.

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Guides & tips


Greece

Ionian Islands, Cyclades Islands and Dodecanese are just some of the most beautiful destinations for a sailing or catamaran vacation in Greece
Guide to Greece by sailboat

Ionian Islands

Paxos, Zakynthos, Kefalonia and Lefkada are just some of the best destinations for a sailing or catamaran vacation in the Ionian Islands.
Guide to Ionian Islands by sailboat

Cyclades islands

Sandy beaches, small bays and blue and white villages have made the Cyclades a world-famous landscape, perfect for exploring by sailboat or catamaran.
Guide to Cyclades islands by sailboat

Greece: the most beautiful places to sail

Greece: departures by month

Other travel ideas

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