experiences

4.8

Super!

Athens to Paros: the best of the Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August - September

€950

Per person

4.9

Super!

Fast Sailing Experience between Authentic Islands and Good Food

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

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

€1,000

Per person

4.9

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

7 departures available

June - October

Starting from

€1,080

Per person

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

Per person

4.8

Super!

From Ios to Milos, the best of the Central Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€750

Per person

5.0

Super!

Sailing Odyssey in the heart of Cyclades

Greece: Cyclades

6 days - 6 nights

One departure available

September

€1,100

€990

Per person

4.8

Super!

Milos to Paros: the best of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

July - August

€900

Per person

4.8

Super!

Luxury catamaran cruise in the Cyclades

Greece: Cyclades

7 days - 7 nights

18 departures available

June - November

Starting from

€1,000

Per person

4.9

Super!

Baie and fast sailing from Milos to Paros

Greece: Cyclades

6 days - 7 nights

One departure available

September

€890

Per person

5.0

Super!

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

Greece: Cyclades

6 days - 6 nights

One departure available

July - August

€1,050

Per person

4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

6 departures available

June - October

Starting from

€950

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 - Private yacht sailing holidays with skipper in the Cyclades

81 reviews

SHARE & SAIL - 5 days Exploring & Relaxing at the heart of Cyclades

06/6/2026

Annina P.

We had an unforgettable time in the Cyclades! Our skipper Dimitris introduced us to sailing, which was totally new for us but totally exciting and a very nice experience on the sea. It was a great mix of sailing and time on land to explore new places. We enjoyed it very much & highly recommend it:)

Sailing in the Aegean, the sea of the Gods!

06/1/2026

Viviana C.

A tour full of adventure! Andrea is very professional and with his experience he made us discover these wonderful islands, in all their beauty.

Sailing in the Aegean, the sea of the Gods!

05/31/2026

James W.

Everything about this experience was 5 star! Andrea is an incredible professional who knows how to curate the perfect tour. If given the chance, we would absolutely sail with him again!

Sailing in the Aegean, the sea of the Gods!

05/25/2026

Massimo O.

Andrea is exquisite and knows how to put you at ease. He is prepared and able to solve the various unforeseen events typical of life at sea. The variable weather prevented us from making the most of the experience at sea but the alternative proposals for shore excursions proposed by Andrea were equally exhaustive.

Customer Support

Do you need support on using the platform or for an online payment? Do you need information or is there something you don't understand? For (almost) any question, we got an answer!

Call us at

+44 20 3514 4220

Read our

Contact & Support

Can't find the perfect holiday for you?

Tell us what you are looking for and let our team find the right solution for you!