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Sailboat yacht sailing holidays & tours in Cyclades

Discover more than 11 opportunities to get on board a Sailboat adventure in Cyclades. A unique experience with a local skipper, starting at €350 a week.

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4.9

Super!

Cyclades from Milos to Milos

Greece: Cyclades

7 days - 7 nights

One departure available

September

€800

Per person - min 2 pax

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5.0

Super!

From Mykonos to Athens by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September - October

€950

€760

Per person

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5.0

Super!

From Milos to Mykonos by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

One departure available

September

€1,000

€750

Per person

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5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

Starting from

€1,000

€750

Per person

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4.9

Super!

Sailing holiday among the wonders of the Cyclades from Athens

Greece: Cyclades

6 days - 7 nights

One departure available

September - October

€835

Per person

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4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€980

Per person

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4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

2 departures available

October

Starting from

€950

Per person

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4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

€1,161

Per person

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5.0

Sailing Odyssey in the heart of Cyclades

Greece: Cyclades

6 days - 6 nights

One departure available

September

€990

Per person

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4.0

Sailing & Diving in the Small Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,390

Per person

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5.0

Exclusive boat, you choose the route and the Cyclades islands to see!

Greece: Cyclades

7 days - 7 nights

One departure available

September

€917

Per person

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Reviews - Sailboat yacht sailing holidays & tours in Cyclades

416 reviews

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Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

09/2/2026

Rafaela C.

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IT

First experience on a sailing boat: a nice adventure with some ideas for improvement Since this is my first time on a sailing boat, the final balance is certainly positive. It was an enriching experience and the group turned out to be very pleasant, although there are some aspects that could make the trip even more comfortable and inclusive for the participants. Value of experience and galley management: The overall cost was a bit high compared to the services included. ( at the time of booking it must be specified that in addition to the initial expense there are other expenses, this has not been specified. For example.. fuel, water supply galley starter pack..... this is specified only once you have booked) Being at the first experience, we would have liked to have had extra support from the skipper or in any case from the organizational group at the time of the initial expense: a little advice to optimize the galley and avoid the superfluous (perhaps buying the rest gradually in the ports) would have been really useful. ( example once the excel has been filled in, the organizers with more experience than us can remove what seems extra to them ... instead of "scolding" each other because we did our own thing. Involvement in maneuvers: It is good to warn and know that it is an active holiday: even without any previous experience, you get involved and there is an absolute need to help the skipper during maneuvers and navigation, which makes you feel part of the crew but you need to be educated just in case. Group and fleet dynamics: Over half of the group already knew each other, and for those who struggle a little more to integrate or leave alone, this can create a small initial obstacle. To facilitate friendships, it would be great if the organization included more moments of sharing between the three boats, perhaps supporting them during the afternoon stops and not just the two evenings of sharing to really make the experience live as one big group. A trip that leaves a good memory and that I would do again, with the hope that these suggestions can help the organization to make the experience even more welcoming for future participants.

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

08/27/2026

FRANCESCO P.

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IT

Unfortunately due to Meltemi we had to totally change the initial itinerary by falling back on the Saronic islands, consequently we did not see the Cyclades at all. Apart from this inconvenience all good!
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Ios, Santorini, Anafi: the breath of the Cyclades

08/26/2026

Chiara Q.

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IT

Alessio is a very prepared, kind and helpful skipper. Wonderful and very comfortable boat, and the sea-islands of the Cyclades are a real enchantment! Beautiful experience, I recommend!

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

08/25/2026

Eleonora A.

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IT

Wonderful holiday thanks to the Skipper Massimo, extremely prepared and professional and a crew of wonderful people with whom I was lucky enough to spend unique moments. The boat was in very good condition and spacious.

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