header cover
logo

Log in

Yacht sailing holidays & skippered tours in Greece

The Greek Archipelago has over 16,000 km of coastline, with many beaches that run for kilometres, a host of secluded bays and coves, and a rich variety of wildlife. Some say the best sailing waters in the world can be found in Greece!

cover image
avatar image

4.9

Super!

Scoprire il fascino del Nord Egeo con navigazioni veloci

Greece: North Egean Islands

6 days - 7 nights

One departure available

June

€890

Per person

cover image
avatar image

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

cover image
avatar image

4.8

Corfu between bays, taverns and myths.

Greece: Ionian Islands

6 days - 7 nights

7 departures available

June - October

Starting from

€600

€540

Per person

cover image
avatar image

5.0

Ionian Greece aboard a Catamaran with Skipper/Chef

Greece: Ionian Islands

6 days - 7 nights

3 departures available

July - August

Starting from

€1,900

Per person

cover image
avatar image

4.9

Four days wandering around the Ionian Islands

Greece: Ionian Islands

4 days - 3 nights

One departure available

August

€280

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

September - October

Starting from

€779

€701

Per person

cover image
avatar image

4.9

Sailing course in the Cyclades

Greece: Cyclades

7 days - 7 nights

7 departures available

June - October

Starting from

€950

Per person

cover image
avatar image

New

A perfect August? The Ionian Islands on a sailing boat!

Greece: Ionian Islands

7 days - 7 nights

2 departures available

August

Starting from

€690

Per person

cover image
avatar image

4.4

Premium

ATHENS Paradise - Catamaran cruise with hostess FULL BOARD

Greece: Saronic Islands and Athens area

7 days - 7 nights

16 departures available

June - October

Starting from

€1,525

€1,373

Per person - min 2 pax

cover image
avatar image

4.0

Sailing and Hiking in the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

September

€1,290

€1,161

Per person

cover image
avatar image

New

Ios, Santorini, Anafi: the breath of the Cyclades

Greece: Cyclades

7 days - 7 nights

One departure available

August

€1,150

Per person

cover image
avatar image

5.0

New

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

Greece: Saronic Islands and Athens area

7 days - 7 nights

10 departures available

June - November

Starting from

€585

€527

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

1911 reviews

avatar image

Sailing in the Aegean, the sea of the Gods!

05/25/2026

Massimo O.

-

IT

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.

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

05/24/2026

Antoine A.

-

FR

Superb experience with Alex! We spent an incredible week cruising the beautiful waters of the Saronic Islands until the beginning of the Peloponnese Alex is a great guide and a very pedagogical sailing instructor (and a good cook which doesn't spoil anything, taste his pasta absolutely!!) Alex paid attention to everything and adapted to the pace and desires of each one Ideal for feeling away from it all, feeling the sensations of sailing and enjoying. We were happy to discover the bays and coves (the opportunity to swim) and in the evening stroll through the streets of the ports of stevedoring The boat is comfortable and the presence of a small shower head is a big plus compared to other boats. Above all, Alex shared with us a little bit of his life as a sailor, his stories, his personality, his readings... A big thank you and maybe see you soon! Christelle and Antoine

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

05/11/2026

Lucia K.

-

CH

Our sailing holidays around Corfu were simply exceptional. The combination of crystal-clear waters, stunning islands, and peaceful hidden bays made every single day unforgettable. The crew Andrea, Marta & Mattias was incredibly friendly, professional, and always made us feel welcome and relaxed on board. The itinerary was perfectly balanced between discovering beautiful Greek islands, enjoying time at sea, and experiencing authentic local culture. The food was another highlight — fresh, delicious, and healthy, with plenty of local specialties prepared with care. It was truly a unique and unforgettable experience that we would highly recommend to anyone looking for the perfect mix of adventure, relaxation, and comfort.

Sailing cruise in the Greek islands - The Saronic Islands

04/29/2026

Marc G.

-

CA

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

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!

Guides & tips


Greece

Ionian Islands, Cyclades Islands and Dodecanese are just some of the most beautiful destinations for a sailing or catamaran vacation in Greece
Guide to Greece by sailboat

Ionian Islands

Paxos, Zakynthos, Kefalonia and Lefkada are just some of the best destinations for a sailing or catamaran vacation in the Ionian Islands.
Guide to Ionian Islands by sailboat

Cyclades islands

Sandy beaches, small bays and blue and white villages have made the Cyclades a world-famous landscape, perfect for exploring by sailboat or catamaran.
Guide to Cyclades islands by sailboat

Greece: the most beautiful places to sail

Greece: departures by month

Other travel ideas

Let's talk Sailsquare!

HuffpostSailing todayYahoo!

Secure payments

MastercardVisaGoogle PayApple Pay

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