Homepage cover
logo

Log in

Sailboat yacht sailing holidays & tours in Greece

Discover more than 90 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

4.7

Marmaglia Discovery Flotilla to the Cyclades Islands in Greece

Greece: Cyclades

6 days - 7 nights

2 departures available

August

€1,290

€1,190

Per person

cover image
avatar image

4.8

Super!

Premium

Sailing paradise in Greece on a big 50 ft boat: the best local experience

Greece: Saronic Islands and Athens area

6 days - 7 nights

11 departures available

July - October

Starting from

€1,200

€1,080

Per person

cover image
avatar image

4.6

Different flotilla in Ionian Greece: nature, new friends and fun

Greece: Ionian Islands

7 days - 7 nights

One departure available

August

€1,110

€999

Per person

cover image
avatar image

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

8 departures available

August - October

Starting from

€570

Per person

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

12 departures available

August - October

Starting from

€570

Per person

cover image
avatar image

4.8

Super!

Sailing among the Islands of Ulysses. Stewardess on board

Greece: Ionian Islands

6 days - 7 nights

One departure available

August

€800

Per person

cover image
avatar image

4.8

Super!

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

14 departures available

July - November

Starting from

€700

€665

Per person

cover image
avatar image

4.8

Super!

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

Greece: Ionian Islands

7 days - 7 nights

One departure available

September

€650

€585

Per person

cover image
avatar image

5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

One departure available

July - August

€890

€680

Per person

cover image
avatar image

5.0

Super!

Saronic Gulf Cruise: Aegina, Poros, Hydra, Athens Surroundings

Greece: Saronic Islands and Athens area

6 days - 6 nights

One departure available

September

€650

Per person

cover image
avatar image

4.9

Super!

From Kos to Rhodes, the South Dodecanese on a magnificent 15-meter boat

Greece: Dodecanese

7 days - 7 nights

One departure available

July

€1,000

Per person - min 2 pax

cover image
avatar image

5.0

Super!

10-Day Cruise to the Sporades & Nature Park

Greece: Sporades

10 days - 10 nights

One departure available

August

€1,250

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 - Sailboat yacht sailing holidays & tours in Greece

1810 reviews

The most spectacular islands of the Cyclades: from Athens to Milos

07/13/2026

Marcella F.

-

IT

It was a beautiful holiday! The places visited and the sea were simply stunning. The boat was beautiful, comfortable and equipped with everything you need to spend a week relaxing. A special thanks to Alessio, our skipper: an attentive, kind person and always available to meet our requests, helping to make the experience even more enjoyable. An experience I highly recommend!
avatar image

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

07/13/2026

Sara E.

-

IT

I thought I had given myself a gift by booking a boat holiday with unknown people but the real gift was having Alessandro and Carlo as skipper and host. They were wonderful, they made me feel immediately welcomed not to mention the WONDERFUL places where they took us (and I say this as a Sardinian!) with maximum flexibility and availability for every need. A special mention for Eros, Alessandro's dog, who has remained in my heart. In short, give yourselves a great gift and set sail with them!! Fair winds :)
avatar image

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

07/13/2026

Eleonora i.

-

IT

Unforgettable experience! It was a week on a sailing boat beyond all expectations. The organization was impeccable, the itinerary allowed us to visit wonderful places and experience the sea in total relaxation. A special thanks goes to our skipper Francesco, always professional, prepared and attentive to safety, but also helpful, patient and able to create a pleasant atmosphere on board. He made us feel at ease from day one and made us discover spectacular bays and corners that we would hardly have seen on our own. The boat was comfortable and well maintained. A holiday that I will definitely carry in my heart and that I recommend to anyone who wants to experience the sea in an authentic way. If I had to do it again, I would choose this experience again without any doubt! Thank you so much for this wonderful week!

Lefkas, Kefalonia & Ithaca: 7 days of relaxation and fantastic bays

07/12/2026

maddalena d.

-

IT

Alessandro has greatly contributed to making this holiday special. He is a very good skipper, he transmits safety and reliability but above all he is an interesting, nice and fun person. Great chef... He delighted us with yummy dishes and great entertainer. I hope to be back soon on board [hidden]:) see you soon Madda and Valerio (Vittorio/vincenzo).

Customer Support

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!

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