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Yacht sailing holidays & skippered tours in Dodecanese

Discover hundreds of sailing holidays in the Dodecanese Islands. Book a spot onboard and live a unique experience with a local skipper. Starting at €400 a week.

24

experiences

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5.0

SECRET DODECANESE: Astypalea and Tylos with skipper and kitchen

Duration:

6 days - 6 nights

Greece:

Dodecanese

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+4 travellers

have booked

Starting from

€750

Per person

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4.9

Fine Dodecanese to Samos with a fast-cruiser boat

Duration:

6 days - 7 nights

Greece:

Dodecanese

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+2 travellers

have booked

€930

Per person

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5.0

The Dodecanese: 10 Days, 9 Islands, A Luxurious and Fast Boat

Duration:

10 days - 10 nights

Greece:

Dodecanese

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+2 travellers

have booked

€1,341

€1,490

Per person

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5.0

From Kos to Athens via the Dodecanese, the Sporades and the Cyclades

Duration:

9 days - 10 nights

Greece:

Dodecanese

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+7 travellers

have booked

€890

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:

6 days - 7 nights

Greece:

Dodecanese

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+6 travellers

have booked

Starting from

€1,400

Per person

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5.0

SECRET DODECANESE: at full roadstead with skipper and kitchen

Duration:

6 days - 6 nights

Greece:

Dodecanese

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+8 travellers

have booked

€1,300

Per person

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5.0

SECRET DODECANESE: Patmos with skipper and kitchen

Duration:

6 days - 6 nights

Greece:

Dodecanese

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+7 travellers

have booked

€1,100

Per person

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5.0

The perfect holiday! The Dodecanese Islands

Duration:

6 days - 7 nights

Greece:

Dodecanese

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+12 travellers

have booked

Starting from

€750

Per person

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4.9

The alternative to the catamaran - All inclusive and Hostess on board

Duration:

6 days - 7 nights

Greece:

Dodecanese

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+4 travellers

have booked

€1,580

Per person

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5.0

SECRET DODECANESE: Astypalea and Anafi with skipper and kitchen

Duration:

6 days - 6 nights

Greece:

Dodecanese

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+8 travellers

have booked

€800

Per person

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5.0

SECRET DODECANESE: Kos to Rhodes with skipper and kitchen

Duration:

6 days - 6 nights

Greece:

Dodecanese

Give this experience a try!

€750

Per person

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5.0

DODECANESE SECRET: Rhodes and the Southern Islands with skipper and kitchen

Duration:

6 days - 6 nights

Greece:

Dodecanese

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+2 travellers

have booked

€750

Per person

Why book a holiday with Sailsquare?

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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 Dodecanese

168 reviews

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LAST MINUTE! - The secrets of the small Dodecanese islands between history and culture

10/8/2023

Christoph R.

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Germany

Wir sind zu zweit mit Emanuel und Annalisa eine Woche durch den Dodekanes gefahren und es war ein phantastisches Erlebnis. Die beiden haben uns so herzlich und liebevoll aufgenommen und uns die schönsten Seiten der Inseln und auch ihre nicht so bekannten Seiten gezeigt. Von kleinen Fischerdörfern über verwunschene Bergdörfer bis zu einsamen Buchten zum Übernachten war alles dabei, was das Herz begehrt. Beim Schnorcheln haben wir Tintenfische, Zackenbarsche und Skorpionfische gesehen und einmal hat uns sogar eine Seeschildkröte besucht. Emanuels Grillkünste sind der Hammer und wir haben eine schöne Mischung zwischen originalen Restaurants und an Bord Küche gehabt. Und das Segeln im Revier ist wunderschön - mit dem weißen Boot durchs tiefblaue Wasser zu fahren bleibt unvergesslich. Und die beiden haben einen prima Weg gefunden, uns behutsam ins Segelhandwerk einzuführen. Es war ein herrlicher Urlaub und fühlte sich an, wie mit guten Freunden unterwegs zu sein. Danke dafür !!
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Kufner 54, the alternative to the Catamaran - ALL INCLUSIVE

09/24/2023

paola c.

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Switzerland

Manuel e Camilla la ciliegina sulla torta di una settimana in mare all'insegna del blu del mare e del cielo. Organizzati a dovere sulla cambusa, ottima cucina salutare e gustosa, sulle norme di sicurezza garantendo sempre affidabilità e tanto relax, conoscenza di calette spettacolari, simpatia ed empatia con il gruppo. Mowgli è attrezzata davvero di ogni dettaglio utile oltre a essere spaziosa. Ho apprezzato tanto Manuel e Camilla che per me sono la dimostrazione che puoi fare una scelta di vita rivoluzionando tutto e vivere in mezzo al mare con semplicità e felicità. Grazie di cuore a voi e al gruppo per l'indimenticabile esperienza
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Kufner 54, the alternative to the Catamaran - ALL INCLUSIVE

09/13/2023

Rosie R.

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Switzerland

Vacanza meravigliosa! Abbiamo visitato posti incredibili. La barca spaziosa e attrezzata di ogni comfort. Manuele ottimo skipper, flessibile ad improvvisare anche cambi di rotta per soddisfare le esigenze di noi ospiti. Manuele e Camilla ci hanno viziati con sorprese e coccole cullinarie. Non ci hanno fatto mancare nulla e la loro compagnia è sempre stata calorosa e molto piacevole. Non puoi non amarli, con loro vivi l'essenza del viaggiare in barca a vela in piena sicurezza, la bellezza del mare, la magia di ogni luogo e il trasporto del vento. GRAZIE I simply love Mowgli ! !
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From Kos to Samos Magnificent Dodecanese

09/11/2023

Anna L.

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Italy

Se ci fossero 10 sfere le marcherei tutte perché se si dice che non esiste la perfezione beh...Manuele è l'eccezione! TOP DEI TOP grazie Manu sei grande!

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