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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.

experiences

4.9

Super!

From Samos to Kos: the best of the North Dodecanese

Duration:

7 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

Starting from

€713

€750

Per person

4.9

Super!

From Kos to Rhodes: the beautiful south Dodecanese

Duration:

7 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

Starting from

€760

€800

Per person

4.9

Super!

From Kos to Samos: the perfect Dodecanese

Duration:

7 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

Starting from

€760

€800

Per person

5.0

Super!

The enchantment of the sea: the Dodecanese islands

Duration:

7 days - 7 nights

Greece:

Dodecanese

15 travellers

Starting from

€800

Per person

5.0

Super!

Treat yourself to an unforgettable holiday. Embark with us in Kos

Duration:

7 days - 6 nights

Greece:

Dodecanese

Give this experience a try!

Starting from

€750

Per person

5.0

Super!

From the Dodecanese to the Cyclades: sailing off the beaten track!

Duration:

10 days - 10 nights

Greece:

Dodecanese

Give this experience a try!

Starting from

€800

Per person

5.0

Super!

Experience the sea at 360 degrees? embark with us in Kos

Duration:

7 days - 6 nights

Greece:

Dodecanese

Give this experience a try!

Starting from

€750

Per person

5.0

Sailing in the Northern Dodecanese from Kos to Samos

Duration:

6 days - 7 nights

Greece:

Dodecanese

14 travellers

€720

Per person

4.9

Super!

From Rhodes to Kos: the fantastic South Dodecanese

Duration:

7 days - 7 nights

Greece:

Dodecanese

6 travellers

Starting from

€800

Per person

5.0

Dodecanese Sailing Cruise: From Samos to Astypalea

Duration:

13 days - 14 nights

Greece:

Dodecanese

3 travellers

€1,200

Per person

5.0

from Samos to Kos

Duration:

6 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

€920

Per person

5.0

Unforgettable Dodecanese Islands Cruise: Rhodes to Kos

Duration:

6 days - 7 nights

Greece:

Dodecanese

Give this experience a try!

€920

Per person

Why book a holiday with Sailsquare?

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

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

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

191 reviews

SECRET DODECANESE: Astypalea and Tylos with skipper and kitchen

10/1/2024

Luca Alfonso M.

Italy

Emanuel ed Annalisa a dir poco fantastici, persone veramente squisite Bravissimi Skipper e Favolosi cuochi vacanza fantastica ed indimenticabile

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

09/16/2024

Philippe H.

Belgium

Joyeuse croisière de Rhodes à Kos, avec un équipage sympathique. Que du bonheur!

The sailing adventure of your summer - Steward on board

09/13/2024

Alessandro P.

Italy

Steffen, il capitano, e Marcel, il suo braccio destro, sono estremamente gentili e ospitali, facendovi sentire subito a vostro agio. Vi poteranno in giro per le isole del Dodecaneso, facendovi apprezzare la loro bellezza e accoglienza. Gli aperitivi al tramonto con i cocktail di Marcel sono la ciliegina sulla torta. La barca è ottimamente attrezzata (con tanto di wi-fi, macchina da caffè professionale e persino la lavatrice)! Insomma promossi a pieni voti!

The sailing adventure of your summer - Steward on board

09/7/2024

Corrado A.

Italy

Il capitano ha un'eccellente competenza tecnica che fa sentire sempre al sicuro e il primo ufficiale si dà molto da fare per gli ospiti. I due si compensano: teutonicamente diretto il primo, più empatico il secondo. Per il resto, qualcosa da "registrare" sui pasti, sulla cosiddetta pensione completa e sulla chiarezza e trasparenza comunicative al riguardo. Che, però, comparato con la bellezza d'animo e l'impegno di tutto l'equipaggio e la sua capacità di ricercare per gli ospiti chicche di magia nascoste lungo l'itinerario, non impediscono di attribuire comunque il massimo nella valutazione complessiva dell'esperienza.

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