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

11 departures available

July - October

Starting from

€1,200

€1,080

Per person

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

8 departures available

August - October

Starting from

€2,500

€2,250

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

9 departures available

July - October

Starting from

€570

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

13 departures available

July - October

Starting from

€570

Per person

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

5.0

Super!

Ionian Greece aboard a Catamaran with Skipper/Chef

Greece: Ionian Islands

6 days - 7 nights

One departure available

July - August

€1,900

Per person

4.9

Super!

Fast Sailing Experience between Authentic Islands and Good Food

Greece: Cyclades

6 days - 7 nights

One departure available

September

€835

Per person

5.0

Super!

Mykonos and the Western Cyclades by sail, with skipper and on-board kitchen

Greece: Cyclades

6 days - 6 nights

2 departures available

September

€1,000

Per person

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

4.8

Super!

Catamaran with chef in the magical sea of the Ionian Islands

Greece: Ionian Islands

6 days - 7 nights

3 departures available

August - October

Starting from

€900

Per person

Zakynthos sailing escape - hostess on board (half board)

Greece: Ionian Islands

7 days - 7 nights

3 departures available

July - October

Starting from

€779

Per person

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

€950

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 - Crewed yacht sailing holidays & tours in Greece

262 reviews

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

07/5/2026

Jacopo M.

We spent an amazing week sailing with Andrea and his team. The experience was simply perfect: the boat was immaculate, the food was excellent, and Andrea showed extraordinary care for his guests. A special mention goes to the hostess, Carol, who was absolutely fantastic in taking care of us and treating us to her wonderful dishes. Thank you too, Mattias—you are a truly special soul. If we could have given it a sixth star, we would have without hesitation. Highly recommended!

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

07/5/2026

Aymeric D.

We had a wonderful week on Andrea's boat! Andrea is a very kind, professional and attentive skipper. He drove us to fabulous places and made many suggestions, he knows the area perfectly. The breakfasts and meals prepared by the hostess Carol were very good and fresh. Thank you to her for her kindness and availability. We highly recommend this experience! And a little word for Mathias, Andrea's dog, who made us laugh ❤️ a lot

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

06/27/2026

Viviana M.

Super week!! Fantastic sea, wonderful beaches with crystal clear waters and delicious cuisine. Alessandro, skipper and Carlo, were very kind and company! My sister and I spent a relaxing and fun week together with the group who traveled with us and we made friends with. Recommended for people who love the sea, the wind in their hair and need lightness, simplicity and freedom! Thank you for this great week!

From Piraeus to Mykonos: the Aegean by sail, with skipper and on-board kitchen

06/24/2026

Cesare S.

Annalisa and Emanuel were fantastic hosts! They made us sail and cooked us excellent meals making us spend a beautiful week discovering the sea of the Cyclades and its beautiful bays, despite the Meltemi

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

Sailboat (485)Whole boat with skipper (390)Cooking service onboard (185)Catamaran (95)Sport & wellness (25)Gulet and sailing ship (25)All inclusive (20)Flotilla (10)Offshore (10)Courses & regatta (5)

Other travel ideas

Sailboat (507)Whole boat with skipper (398)Cooking service onboard (118)Catamaran (86)All inclusive (53)Exotic destinations (28)Family sailing cruises (25)Courses & regatta (25)Day trips (24)Offshore (19)