Homepage cover
logo

Log in

Yacht sailing holidays & skippered tours in Greece

Discover more than 22 sailing holidays in Greece. Book a spot onboard and live a unique experience with a local skipper. Starting at €350 a week.

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

3 departures available

October

Starting from

€540

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

5 departures available

September - November

Starting from

€650

€618

Per person

cover image
avatar image

4.8

Super!

Greek Islands Catamaran Cruise - Saronic

Greece: Saronic Islands and Athens area

7 days - 7 nights

4 departures available

October

Starting from

€820

Per person

cover image
avatar image

4.8

Super!

Premium

Big and luxurious 60ft catamaran in Saronic Islands - best local experiences

Greece: Saronic Islands and Athens area

6 days - 7 nights

4 departures available

October

Starting from

€2,200

€1,980

Per person

cover image
avatar image

4.8

Super!

The fantastic Saronic Islands and the surroundings of Athens

Greece: Saronic Islands and Athens area

7 days - 7 nights

3 departures available

October

€750

€713

Per person

cover image
avatar image

5.0

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

Greece: Ionian Islands

7 days - 7 nights

4 departures available

October

Starting from

€520

Per person

cover image
avatar image

4.9

Super!

Sailing in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

October

Starting from

€1,080

Per person

cover image
avatar image

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

cover image
avatar image

5.0

Super!

The Saronic Islands sailing, skippered and on-board kitchen

Greece: Saronic Islands and Athens area

6 days - 6 nights

2 departures available

October

Starting from

€950

€855

Per person

cover image
avatar image
Zakynthos sailing escape - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

2 departures available

October

Starting from

€779

€701

Per person

cover image
avatar image

New

Cast off for a week at sea, a thousand ways to experience it!

Greece: Saronic Islands and Athens area

7 days - 7 nights

5 departures available

September - November

Starting from

€585

€527

Per person

cover image
avatar image
Where the blue feels like home: the Ionian islands - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

3 departures available

October

Starting from

€779

€701

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 - Yacht sailing holidays & skippered tours in Greece

1908 reviews

Sailing cruise in the Greek islands - The Saronic Islands

04/29/2026

Marc G.

-

Canada

A week on a roller coaster too windy, no more wind. Mother Nature is in charge! However our skipper was really up to the situation, Alexandre is a good captain and a good GO (nice organizer) his knowledge of the islands and the people who live there adds a lot to the fun and experience. Regarding the boat, although old, it is a very good boat but unfortunately there were several small problems that did not affect our trip, we believe that preventive maintenance could be in order. Thank you again Alexandre for your Carbonaras and the typical Greek evening. Good winds from Quebec Hélène and Marc
avatar image

Sailing in the Cyclades

04/22/2026

Miguel M.

-

Spain

Exceptional experience!! Yann is a skipper who knows the navigation area and the most suitable anchorages and ports well. In addition to being an excellent sailor, he is an endearing person who seeks the well-being of his "crew", carrying out activities on land such as hikes or visits to interesting places that give added value. His boat "[hidden]" is a sailboat of the highest level, very comfortable and designed to sail in extreme conditions and therefore absolutely safe. Yann keeps it in pristine condition and is spotlessly clean. In short, it is a highly recommended experience.
avatar image

Sailing cruise in the Greek islands - The Saronic Islands

04/15/2026

Goutham B.

-

Germany

I had a wonderful week of sailing with this team. Skipper is super cool and I enjoyed his company a lot. He was happy to customize the sailing plan according to each of our requirements and was friendly to even cook for us a few times (The pasta was delicious). Bertrand even allowed me to stay on the boat for few extra days at Aegina. However, for my bad luck, an unfriendly couple was part of the crew and they were neither willing to pay for the skipper's food, nor willing to cook which was clearly mentioned in the advertisement as the responsibility of the whole crew. Even then the skipper was cool enough to invite us all to dinner in order to build up a family feeling between the crew members. Despite all this effort, It's unfortunate to see them giving a bad review about their sailing experience here. But other than this, personally I enjoyed the whole sailing week with Bertrand and his team. I am looking forward to sail with your team in the future.

Sailing cruise in the Greek islands - The Saronic Islands

04/15/2026

Thomas S.

-

United Kingdom

The captain (Alex) asked us to lie to the police as soon as we got there about being his friends and not chartering this boat. Something about not having a charter lisence, which made us feel very uncomfortable, even though Bertrand now denys it. The toilets stank and the shower was very uncomfortable to use, but I guess thats just how boats are. It leaked when it rained and it is fairly cramped, and we left asking why we paid that price for that boat. We didn't feel like we got value for our money at all and the organiser was very rude to us when we brought up our concerns. At least the islands were nice.

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!

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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