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Calendar & Prices

Greek Islands Private Sailing Holidays

Share & Sail the Greek islands, 5 days

Starts at Athens as a shared departure, Relaxing Sailing Holidays

Departs from Lavrio which is 35min drive from Athens International Airport

Join one of our Share & Sail sailing holidays, starting from Athens, as a solo or couple or small group of friends and leave with many good new friends. Swim, enjoy the Greek sun on deck, relax, taste the amazing local cuisine, explore the hidden gems of the Greek fishing villages

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15 Sep 2026 ✅

Returns on 19 Sep (5 days/4 nights)

€1080/person

30 Sep 2026 ✅

Returns on 4 Sep (5 days/4 nights)

€1080/person

18 Oct 2026 ✅

Returns on 22 Oct (5 days/4 nights)

€1080/person

28 Oct 2026 ✅

Returns on 01 Nov (5 days/4 nights)

€1080/person

21 Apr 2027 ✅

Returns on 25 Apr (5 days/4 nights)

€1080/person

26 Apr 2027 ✅

Returns on 30 Apr (5 days/4 nights)

€1080/person

11 May 2027 ✅

Returns on 15 May (5 days/4 nights)

€1080/person

21 May 2027 ✅

Returns on 25 May (5 days/4 nights)

€1080/person

06 July 2027 ✅

Returns on 10 July (5 days/4 nights)

€1080/person

31 July 2027 ✅

Returns on 04 Aug (5 days/4 nights)

€1080/person

10 Aug 2027 ✅

Returns on 14 Aug (5 days/4 nights)

€1080/person

08 Oct 2027 ✅

Returns on 12 Oct (5 days/4 nights)

€1080/person

18 Oct 2027 ✅

Returns on 22 Oct (5 days/4 nights)

€1080/person

✅ GUARANTEED TO RUN

Those are departures that will go, regardless of the number of persons booked. This means it is safe to book your flights after you receive our Booking Confirmation

Greece Catamaran Charter

Share & Sail the Greek islands, 8 days

Starts at Athens as a shared departure, Relaxing Sailing Holidays

Departs from Lavrio which is 35min drive from Athens International Airport

Set sail on one of our Share & Sail holidays, starting from Athens, whether you’re traveling solo, as a couple, or with a few friends, and return home with plenty of new friendships. Dive into the sea, soak up the Greek sun from the deck, unwind, savor delicious local dishes, and discover the charming hidden treasures of traditional Greek fishing villages.

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10 Oct 2026 ✅

Returns on 17 Oct (8 days/7 nights)

€1295/person

17 Oct 2026 ✅

Returns on 24 Oct (8 days/7 nights)

€1295/person

26 May 2027 ✅

Returns on 02 June (8 days/7 nights)

€1295/person

23 July 2027 ✅

Returns on 30 July (8 days/7 nights)

€1295/person

23 Oct 2027 ✅

Returns on 30 Oct (8 days/7 nights)

€1295/person

✅ GUARANTEED TO RUN

Those are departures that will go, regardless of the number of persons booked. This means it is safe to book your flights after you receive our Booking Confirmation

Good Life, 8days

Departs from Mykonos, a round relaxing cruise on a luxury catamaran

Departs from port of Mykonos which is a 15min taxi ride from Mykonos International Airport

Join this unprecedented shared sailing cruising on a luxury catamaran, among like-minded active people who appreciate the extra space and stability of a catamaran. Private power RIB rides to hidden bays and secret spots . Take advantage of this carefully crafted itinerary, visiting the Greek Cycladic islands. Crystal clear water, delicious food, immersing with the local community.

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8 July 2026 ✅

Returns on 14 July (7 days/6 nights)

€3600/person

8 Oct 2026 ✅

Returns on 15 Oct (8 days/7 nights)

€3600/person

16 Oct 2026 ✅

Returns on 23 Oct (8 days/7 nights)

€3600/person

17 Apr 2027 ✅

Returns on 24 Apr (8 days/7 nights)

€3600/person

25 Apr 2027 ✅

Returns on 02 May (8 days/7 nights)

€3600/person

03 May 2027 ✅

Returns on 10 May (8 days/7 nights)

€3600/person

11 May 2027 ✅

Returns on 18 May (8 days/7 nights)

€3600/person

19 May 2027 ✅

Returns on 26 May (8 days/7 nights)

€3600/person

7 Oct 2027 ✅

Returns on 14 Oct (8 days/7 nights)

€3600/person

15 Oct 2027 ✅

Returns on 22 Oct (8 days/7 nights)

€3600/person

23 Oct 2027 ✅

Returns on 30 Oct (8 days/7 nights)

€3600/person

31 Oct 2027 ✅

Returns on 07 Nov (8 days/7 nights)

€3600/person

✅ GUARANTEED TO RUN

Those are departures that will go, regardless of the number of persons booked. This means it is safe to book your flights after you receive our Booking Confirmation

Catamaran Experience

The SailwithGeorge Luxury Catamaran Experience is a high-end, downwind, one way route for extra comfort. An experience beyond the expected that exceeds the standards of the charter market. Ideal for private groups of 4-11 persons who appreciate the extra space, the extra service and would like to sail Greece in their own pace and in an uncompromised way

From April until November, departs every Saturday from Paros or every Sunday from Lavrio, Availability on request

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Happy Family

The Absolute Family Adventures are private departures, tailor-made to be ideal to families with young yachties, of any any age. Apart from sailors we are also parents ourselves so we know what it takes for an unforgettable family holiday that everyone in the family will truly equally enjoy. ‘Happy kids happy parents’ is our slogan.

From April until November, departs every Saturday from Paros or every Sunday from Lavrio, Availability on request

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Tailor Made

Tailor-made Sailing Experiences of any route & duration handcrafted by SailwithGeorge. Private departures with maximum Flexibility (in route, duration and boat type) that will match any private group of friends or family and any back to back travel arrangement. Ideal for private groups of 4-11 persons

From March until November (incl.), departs on any date, Availability on request

Learn moreOnline inquiry