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Sailboat yacht sailing holidays & tours in Dodecanese

Discover more than 16 opportunities to get on board a Sailboat adventure in Dodecanese. A unique experience with a local skipper, starting at €350 a week.

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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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4.9

Super!

From Rhodes to Kos: the fantastic South Dodecanese

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€880

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!

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!

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 - Rhodes to Karpathos

Greece: Dodecanese

7 days - 6 nights

One departure available

September - 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!

Sailing in the eastern Aegean, between the Dodecanese and the Cyclades!

Greece: Dodecanese

8 days - 8 nights

One departure available

September

€650

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

July

€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

2 departures available

August

€1,600

Per person

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4.9

Kalymnos Rhodes Dodecanese South on magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

August

€1,100

Per person - min 2 pax

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 - Sailboat yacht sailing holidays & tours in Dodecanese

192 reviews

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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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7 islands in VIP formula - only 4 guests on board

07/13/2025

Riccardo L.

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Italy

A Commander. He knows more than the devil and it is a pleasure to learn and confront each other. Experience that I wish to everyone!
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7 islands in VIP formula - only 4 guests on board

07/13/2025

Alessia G.

Judò is a commander who is attentive to both the crew and the boat😁. Generous and helpful in teaching. With him you travel safely. His wife Amel is a delightful and tenacious skipper helper, excellent cook and now friend not to be missed. The "Drink Team" 🤩 worked excellently, but the captain had the last word.
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Secret Aegean with skipper and kitchen on board from Kos to Rhodes

07/12/2025

Attilio A.

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Italy

Excellent welcome, well-designed itinerary, excellent on-board cuisine.

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