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Whole boat with skipper yacht sailing holidays & tours in Dodecanese

Discover more than 13 opportunities to get on board a Whole boat with skipper adventure in Dodecanese. A unique experience with a local skipper, starting at €350 a week.

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5.0

Super!

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

Greece: Dodecanese

7 days - 6 nights

One departure available

August

€1,000

€900

Per person

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5.0

Super!

The enchantment of the sea: the Dodecanese islands

Greece: Dodecanese

7 days - 7 nights

One departure available

September

€750

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Rhodes to Kos

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board - Karpathos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

October

€950

Per person

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5.0

Super!

Secret Aegean with skipper and kitchen on board from Kos to Rhodes

Greece: Dodecanese

7 days - 6 nights

One departure available

September

€1,050

Per person

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5.0

Super!

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

Greece: Dodecanese

7 days - 6 nights

One departure available

August - September

€950

Per person

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5.0

7 islands in VIP formula - only 4 guests on board

Greece: Dodecanese

8 days - 8 nights

One departure available

August

€1,350

Per person

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4.6

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

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,600

Per person

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4.6

Among the Dodecanese islands on my catamaran.

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€980

Per person

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4.9

From Kalymnos to Samos Dodecanese North on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,100

Per person - min 2 pax

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4.6

From Kos to Rhodes on my catamaran

Greece: Dodecanese

7 days - 7 nights

One departure available

August - September

€980

Per person

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5.0

7 islands in VIP formula - only 4 guests on board

Greece: Dodecanese

9 days - 9 nights

One departure available

September

€1,350

€1,215

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 - Whole boat with skipper yacht sailing holidays & tours in Dodecanese

27 reviews

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Secret Aegean with skipper and kitchen on board from Kos to Rhodes

07/27/2025

Luca G.

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Italy

First experience on a sailing boat for me and my partner: wonderful! Annalisa and Emanuel are fantastic, from the management of the spaces on the boat equipped with everything necessary for all guests, to the experience during navigation up to the excellent cuisine that for them has no secrets in the preparation of different and tastefully prepared dishes every day! And every day you arrive on bays different in colors and scents, not to mention the starry skies when you stay at anchor at night! Also attentive to expenses and waste, they really know how to manage every moment of the holiday to make it unforgettable!
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From Samos to North Dodecanese Kalymnos on a magnificent 15-meter boat

07/21/2025

Markus B.

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Germany

Friendly, helpful, very competent skipper with an equally nice companion. We had a wonderful holiday! Grazie tanto a Irena e Fabio!
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Fast sailing holiday in the Aegean with gourmet cuisine

07/20/2025

Mercedes S.

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Spain

It has been a real top 10 experience! Both skippers are incredibly professional and incredible hosts You feel at home as of minute one Awesome and balanced food and very comfortable cabins Postcard and magic spots visited away from crowds Annalisa and Lorenzo are A little treasure just discovered THANK YOU in capital letters! ❤️
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Experience the sea at 360 degrees? embark with us in Kos

07/13/2025

Silvana M.

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Italy

Just returned from a wonderful week on [hidden] sailing among the northern islands of the decadonneso. Gianfranco is a professional, empathetic, sunny and fun skipper as only a true Romagna can be. Gianfranco immediately created a great team spirit by taking into account the characteristics of each crew member and creating a serene and cohesive atmosphere. I highly recommend this holiday, super location, the boat is comfortable and well maintained and Gianfranco a guarantee for a free fun and safe holiday.

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