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Whole boat with skipper yacht sailing holidays & tours in Dodecanese

Discover more than 17 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!

The enchantment of the sea: the Dodecanese islands

Greece: Dodecanese

7 days - 7 nights

2 departures available

September

Starting from

€650

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

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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4.9

Super!

From Rhodes to Kos: the fantastic South Dodecanese

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€880

€836

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!

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

Greece: Dodecanese

7 days - 6 nights

2 departures available

July - September

Starting from

€850

€750

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

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4.9

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

Greece: Dodecanese

7 days - 7 nights

2 departures available

July - August

Starting from

€1,000

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

19 reviews

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

07/7/2025

Farida B.

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Italy

I 10 giorni in barca a vela sono stati bellissimi. Un’esperienza che mi ha riempito gli occhi e il cuore… non sarebbe stata tale se non avessi veleggiato in compagnia di bellissime persone con le quali si é creata una piacevole connessione. Ringrazio il “Super Skipper Andrea”, un professionista: competente, affidabile e generoso. Una vacanza che consiglio a chi ama il mare e la libertà!
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From Kalymnos to Samos Dodecanese North on a magnificent 15-meter boat

07/7/2025

Maddalena D.

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Italy

Una settimana bellissima, rigenerante e super positiva. Fabio e Irene ci hanno accolto su Àlisè e ci hanno fatto subito sentire a casa. La barca è bellissima, accogliente e spaziosa. Fabio è un ottimo skipper, molto disponibile e affidabile, mi sono sempre sentita al sicuro nonostante il maltemi non ci abbia mai mollato e a tratti è stato impegnativo. Irene è stata un’ottima co-skipper sia durante la navigazione che nella gestione dei pasti e della cambusa. Anche lei molto disponibile e attenta. Ottima esperienza. Grazie ancora
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From Rhodes to Kos: the fantastic South Dodecanese

07/1/2025

Patrizia F.

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Italy

Andare in barca con Alessio e Anna è stata una delizia , baie splendide , Alessio sempre molto attento a capire i posti dove fermarsi e come accontentare tutti nei limiti del possibile. Anna deliziosa e preziosa con la sua instancabile energia. Consiglio di provare !
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From Rhodes to Kos: the fantastic South Dodecanese

06/30/2025

Silvia A.

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Italy

Bellissima esperienza oltre ogni aspettativa. Lo skipper super disponibile e simpatico e i luoghi visitati di una bellezza autentica hanno reso questa vacanza ,insieme alle altre persone che erano con me , davvero indimenticabile ❤️ Grazie di cuore

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