experiences

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

23 departures available

May - October

Starting from

€1,200

€1,080

Per person

4.8

Super!

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

Greece: Saronic Islands and Athens area

7 days - 7 nights

One departure available

October - November

€585

Per person

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

33 departures available

March - October

Starting from

€490

Per person

4.9

Super!

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

Greece: Ionian Islands

7 days - 7 nights

10 departures available

May - July

Starting from

€650

€585

Per person

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

16 departures available

June - September

Starting from

€600

€540

Per person

5.0

Super!

The Sporades Islands: A Hidden Paradise of Greece

Greece: Sporades

7 days - 7 nights

9 departures available

July - September

Starting from

€700

Per person

5.0

Super!

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

Greece: Ionian Islands

7 days - 7 nights

34 departures available

March - October

Starting from

€490

Per person

4.9

Super!

Small Cyclades

Greece: Cyclades

6 days - 7 nights

3 departures available

August

Starting from

€1,040

Per person

4.7

Sailing cruise in the Greek islands - The Saronic Islands

Greece: Saronic Islands and Athens area

7 days - 7 nights

32 departures available

April - November

Starting from

€650

€618

Per person

5.0

New

Corfu: sailing, dream bays and walks in the villages - hostess on board

Greece: Ionian Islands

6 days - 6 nights

One departure available

October

€1,200

€500

Per person

4.9

Full sail in the blue of Ionian Greece with hostess on board

Greece: Ionian Islands

7 days - 7 nights

3 departures available

August - September

Starting from

€870

Per person

4.6

Cruise in the Dodecanese and off Turkey on a 17m boat with chef

Greece: Dodecanese

7 days - 7 nights

4 departures available

July - August

Starting from

€1,400

€1,260

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

2013 reviews

The fantastic Saronic Islands and the surroundings of Athens

10/20/2026

Francesca A.

We spent a beautiful week together with Alessandro.Even if the weather was not the most clement, we were able to visit beautiful and characteristic places that we could never have discovered in any other way. In addition to the fantastic experience itself, it was Alessandro who made the difference: an experienced captain, a true master of life, with a wealth of stories to write a book about. We spent days between the sea, the wind and its stories, eating and drinking together as old friends. Thank you Ale, we will always carry you in our hearts with the hope of meeting again soon. Francesca and Davide

The fantastic Saronic Islands and the surroundings of Athens

10/20/2026

manuela c.

I had a great time on the boat with Ale, a professional, kind, helpful person who tried to please everyone (and it's not easy!) and super nice. I saw very beautiful places despite the islands being quite man-made, took nice baths in magnificent roadsteads and visited beautiful villages with even some trekking. Beautiful, solid and comfortable, the boat, suitable for any navigation, I have always felt safe. Ale also always available to cook for everyone! Experience to be done again next year in other islands. Thank you

The fantastic Saronic Islands and the surroundings of Athens

10/19/2026

ASLIHAN A.

Alessandro was the best captain one could ask for. I had to leave after two nights because of a health emergency back home. He offered me a free sailing trip im April.

Sailing in the Cyclades

10/18/2026

Tanya S.

I had a very special week with Yann sailing around the cyclades ... He is very kind , funny amazing person to be with, while being super professional , organized and knowledgeable of every little stone , port , path , view , mountain, restaurant , cafe , bar in the Cyclades !! I really thank Yann for such a beautiful holiday :)))

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!

Greece: the best travel ideas

Whole boat with skipper (80)Sailboat (70)Cooking service onboard (50)Catamaran (35)All inclusive (5)Family sailing cruises (5)

Other travel ideas

Sailboat (123)Whole boat with skipper (110)Cooking service onboard (54)Catamaran (41)Exotic destinations (31)All inclusive (29)Courses & regatta (10)Offshore (9)Family sailing cruises (5)Day trips (5)