header cover
sailsquare logo

Sailboat yacht sailing holidays & tours in Greece

Discover more than 78 opportunities to get on board a Sailboat adventure in Greece. A unique experience with a local skipper, starting at €350 a week.

cover image
avatar image

5.0

Super!

Pack your suitcase and we'll take care of the rest!! Stewards on board!

Greece: Ionian Islands

7 days - 7 nights

6 departures available

August - October

Starting from

€550

Per person

cover image
avatar image

4.9

Super!

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

Greece: Ionian Islands

7 days - 7 nights

10 departures available

July - October

Starting from

€550

Per person

cover image
avatar image

4.9

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

6 departures available

July - November

Starting from

€650

€618

Per person

cover image
avatar image

4.9

Super!

Fast cruising Cicladi Occidentali

Greece: Cyclades

6 days - 7 nights

One departure available

August - September

€955

Per person

cover image
avatar image

5.0

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

7 departures available

August - October

Starting from

€1,080

Per person

cover image
avatar image

5.0

Super!

The enchantment of the sea: the Dodecanese islands

Greece: Dodecanese

7 days - 7 nights

One departure available

September

€750

Per person

cover image
avatar image

4.8

Super!

Come and discover the Saronic Islands from Poros

Greece: Saronic Islands and Athens area

6 days - 6 nights

5 departures available

July - October

Starting from

€585

€497

Per person

cover image
avatar image

4.9

Super!

From Rhodes to Kos: the fantastic South Dodecanese

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€880

Per person

cover image
avatar image

4.8

South of Lefkas between unspoiled nature, the bays of Meganisi and the myths of Ithaca

Greece: Ionian Islands

7 days - 7 nights

5 departures available

July - September

Starting from

€600

€540

Per person

cover image
avatar image

5.0

Super!

Corfu and the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

One departure available

July

€790

Per person

cover image
avatar image

4.9

Super!

Milos, Kimolos, Poliegos, Folegandros, the fantastic Western Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€870

Per person

cover image
avatar image

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

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 Greece

1662 reviews

avatar image

Crystal clear sea, relaxation, skipper and hostess on board! What more could you want?

07/14/2025

Claudia Z.

-

Italy

Seven days, one boat, a thousand emotions We spent a wonderful week on a sailing boat exploring the beauties of Corfu and the nearby islands, guided by a skipper who was truly out of the ordinary: Andrea. It is evident that he deeply loves his job – competent, professional, capable of transmitting confidence and serenity even when the weather has decided to throw a tantrum. Two days of forced stop in port could have ruined the spirit of the trip, but Andrea was able to turn everything into an opportunity to discover, learn and relax. Always ready with a kind word, interesting information or a joke at the right time, he did much more than you would expect from a skipper, including top info about the restaurants! Also on board with us was Carlo, a discreet and attentive steward, who with his caring presence made life on board even more comfortable. The boat, spacious and comfortable, was our perfect floating retreat. And Mattias, the poodle on board? A sweet cuddle that conquered everyone, including the most insensitive to hairy faces. An added value was the proximity of the boat of Andrea's brother, Alessandro: this allowed us to get to know the participants of his boat and to share very pleasant moments together, including aperitifs, laughter and chats under the stars. If I really have to find a point on which to suggest an improvement but it is a constructive personal thought: it is the kitchen. With a little more focus on variety, ingredient quality, and presentation, the experience could really level up. Because, let's face it, customers are often won over even with just a well-thought-out dish! That said, it was a holiday full of excitement, beautiful scenery and great company. We would gladly do it again and I will over-recommend it to friends at home – maybe without wind, but always with Andrea at the helm!
avatar placeholder

The alternative to the catamaran in the Sporades

07/14/2025

Pietro M.

-

Italy

The sailing experience with Manuele was magical. He is a formidable captain, attentive to everything around him, always transmitting confidence and passion in everything he does. An exceptional chef who surprises you every day with his dishes. Being able to share this experience with him was a privilege that I wish for everyone. He made me fall in love with sailing, I will definitely come back with him for more adventures.
avatar placeholder

Sailing and Hiking in the Cyclades

07/14/2025

Marco P.

-

Italy

We had a very nice holiday!
avatar image

The alternative to the catamaran in the Sporades

07/14/2025

Ginevra S.

-

Italy

This holiday aboard Mowgli was one of the best experiences of my life. It was the first time I got on a sailboat and initially I was a bit worried about not being able to sleep and not enjoy the holiday. Manuele, however, made me feel at home from the first moment, cooking excellent meals and taking care of each crew member. Manuele thought about the safety of the group at all times, taking us to coves sheltered from the strong Greek winds to ensure us a peaceful sleep and letting us explore wonderful places. Needless to say, once the holiday was over and she got off the boat, I immediately felt a very strong nostalgia! I can't wait to get back on board Mowgli.

Customer Support

nightLifeGeneralInfo

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!

search

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!

Greece: the best travel ideas

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

© 2025 Sailsquare Srl SB • All rights reserved - VAT IT07860990964