37 Sailing vacations in Greece found
Luxury gulet cruise in the Aegean
5 star services while cruising the Greek Islands in luxury
From £1,035 to £1,359 8 days ex flights
Small group travel:
2021: 24 Apr, 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct
Liveaboard diving and sailing vacation in Greece
Combine a sailing and diving adventure in the Greek islands
From £677 to £788 7 days ex flights
Small group travel:
2021: 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
100 off pp, May & June departures
Learn to sail on a flotilla in Greece
Learn to sail while enjoying an exciting flotilla holiday
From £3,346 7 days ex flights
Small group travel
Sailing vacation in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From US $1,551 to US $1,741 8 days ex flights
Small group travel:
2021: 12 Jun, 26 Jun, 10 Jul, 24 Jul, 21 Aug, 18 Sep, 2 Oct
2022: 14 May, 28 May, 11 Jun, 25 Jun, 9 Jul, 23 Jul, 6 Aug, 20 Aug, 3 Sep, 17 Sep, 1 Oct
2022: 14 May, 28 May, 11 Jun, 25 Jun, 9 Jul, 23 Jul, 6 Aug, 20 Aug, 3 Sep, 17 Sep, 1 Oct
Late availability on these dates: 12 Jun, 26 Jun, 10 Jul, 24 Jul
Travel Team
If you would like some help or advice, or just want to discuss your ideas for your next trip, do give us a call.
Cyclades sailing & walking vacation in Greece
Combine a sailing & hiking adventure around the Cyclades
From £685 to £759 7 days ex flights
Small group travel:
2021: 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
100 off pp, May & June departures
Yoga and sailing retreat in Greece
-A week of relaxation and yoga while sailing the Ionian sea!
From £850 to £940 7 days ex flights
Small group travel:
2021: 30 May, 11 Jul, 25 Jul
Greece sailing vacation, Saronic coast
You don't have to be Homer to know it will be a blast!
From 525 to 799 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Sailing and biking Cyclades vacation, Greece
Self guided or guided (upon request) tour in the Cyclades
From 1,500 8 days ex flights
Small group travel:
2021: 24 Apr, 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
Greek Island cruising vacation
Discover a side of Greece riddled with myth and magic.
From US $3,900 to US $5,250US $4,095 9 days ex flights
Small group travel:
2021: 24 Jun, 8 Jul, 5 Aug, 2 Sep, 21 Oct
2022: 19 May, 23 Jun, 7 Jul, 4 Aug, 1 Sep, 20 Oct
2022: 19 May, 23 Jun, 7 Jul, 4 Aug, 1 Sep, 20 Oct
Late availability on these dates: 24 Jun, 08 Jul
Greek Islands sailing vacation, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From US $1,576 to US $1,766 8 days ex flights
Small group travel:
2021: 5 Jun, 19 Jun, 3 Jul, 17 Jul, 31 Jul, 14 Aug, 28 Aug, 11 Sep, 9 Oct
2022: 7 May, 21 May, 4 Jun, 18 Jun, 2 Jul, 16 Jul, 30 Jul, 13 Aug, 27 Aug, 10 Sep, 24 Sep
2022: 7 May, 21 May, 4 Jun, 18 Jun, 2 Jul, 16 Jul, 30 Jul, 13 Aug, 27 Aug, 10 Sep, 24 Sep
Late availability on these dates: 05 Jun, 19 Jun, 03 Jul, 17 Jul
Sailing vacation in the Aegean Sea
Uninhabited islands in a 6 person boat
From £510 to £620 7 days ex flights
Small group travel:
2021: 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
100 off pp, May & June departures
Saronic Islands sailing vacation in Greece
Sail among the beautiful islands & ports of the Saronic Gulf
From US $2,695 7 days ex flights
Small group travel:
2021: 2 Oct
Low deposit - only $250. All payments fully transferable up to 30 days before departure. More flexible options for full refunds.
Cyclades sailing holiday in Greece
There and back Again route
From 690 to 1,082 11 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Saronic Gulf small group sailing holiday in Greece
Spend a week navigating the idyllic waters of the Saronic Gulf
From US $2,249 8 days ex flights
Small group travel:
2021: 4 Sep
Travel Team
If you would like some help or advice, or just want to discuss your ideas for your next trip, do give us a call.
Sailing and walking vacation in Greek Islands
Explore mainland hikes and secret Greek Ionian beaches
From £1,170 7 days ex flights
Small group travel:
2021: 8 May, 2 Oct
Greece family sailing vacation
Sailing adventure for families or friends in Greek islands
From 3,600 to 4,800 7 days ex flights
Small group travel:
2021: 30 May, 13 Jun, 20 Jun, 25 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 10 Oct
Cyclades islands sailing vacations in Greece
A fantastic sailing adventure in the Cyclades islands!
From 1,250 to 1,415 8 days ex flights
Small group travel:
2021: 5 Jun, 10 Jul, 24 Jul, 4 Sep, 25 Sep
2022: 4 Jun, 2 Jul, 10 Sep, 8 Oct
2022: 4 Jun, 2 Jul, 10 Sep, 8 Oct
Gastronomy and sailing vacation in Greece
Explore the Greek islands and their gastronomy with a chef!
From 890 7 days ex flights
Small group travel:
2021: 23 May
Greek flotilla vacation in Lefkas
Sail around the stunning Southern Ionian
From £986 to £8,610 7 days ex flights
Tailor made:
For travel between May - October
Kefalonia Flotilla Holiday in Greece
Sail around the stunning Southern Ionian
From £986 to £8,610 7 days ex flights
Tailor made:
For travel between May - October
Ionian flotilla sailing holiday in Greece
Sail around the stunning Southern Ionian
From £986 to £8,610 7 days ex flights
Tailor made:
For travel between May - October
Bareboat sailing vacation in Corfu, Greece
Sail around beautiful Corfu
From £1,238 to £11,894 7 days ex flights
Small group travel:
2021: 24 Apr, 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct
Lefkas bareboat sailing holiday in Greece
Sail around the stunning Southern Ionian
From £986 to £8,610 7 days ex flights
Small group travel:
2021: 21 Apr, 22 Apr, 23 Apr, 24 Apr, 25 Apr, 26 Apr, 27 Apr, 28 Apr, 29 Apr, 30 Apr, 1 May, 2 May, 8 May, 9 May, 15 May, 16 May, 22 May, 23 May, 29 May, 30 May, 5 Jun, 6 Jun, 12 Jun, 13 Jun, 19 Jun, 20 Jun, 26 Jun, 27 Jun, 3 Jul, 4 Jul, 10 Jul, 11 Jul, 17 Jul, 18 Jul, 24 Jul, 25 Jul, 31 Jul, 1 Aug, 7 Aug, 8 Aug, 14 Aug, 15 Aug, 21 Aug, 22 Aug, 28 Aug, 29 Aug, 4 Sep, 5 Sep, 11 Sep, 12 Sep, 18 Sep, 19 Sep, 25 Sep, 26 Sep, 2 Oct ...
Athens bareboat sailing vacation, Greece
Sail around beautiful Athens
From £1,826 to £10,565 7 days ex flights
Small group travel:
2021: 21 Apr, 22 Apr, 23 Apr, 24 Apr, 25 Apr, 26 Apr, 27 Apr, 28 Apr, 29 Apr, 30 Apr, 1 May, 8 May, 15 May, 22 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct
Learn to sail in Lefkas Greece
Competent Crew course or Day Skipper course in Greece
From £574 to £763 7 days ex flights
Small group travel
Greece sailing vacation in Lefkas
Sail by the cabin in the stunning Southern Ionian
From £1,498 7 days ex flights
Small group travel:
2021: 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 13 Jun, 20 Jun, 27 Jun, 4 Jul, 11 Jul, 18 Jul, 25 Jul, 1 Aug, 8 Aug, 15 Aug, 22 Aug, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct
Greece sailing holiday in Dodecanese
Kos you dont have to be Homer to know it will be a blast :)
From 662 8 days ex flights
Small group travel:
2021: 16 Oct
Freediving and sailing vacation in Greece
-sail, freedive and explore the Ionian Sea
From £1,250 to £1,400 7 days ex flights
Small group travel:
2021: 9 May, 30 May, 19 Sep, 26 Sep, 17 Oct
Greece sailing vacation in Ionian Sea
Sail, explore and experience the Ionian islands in Greece
From 750 7 days ex flights
Small group travel:
2021: 13 Jun, 20 Jun
Saronic Gulf sailing vacation in Greece
An 8 day trip combines sailing & swimming in Greece
From 1,180 to 1,320 8 days ex flights
Small group travel:
2021: 22 May, 19 Jun, 3 Jul, 21 Aug, 11 Sep, 2 Oct
2022: 21 May, 18 Jun, 16 Jul, 27 Aug, 24 Sep
2022: 21 May, 18 Jun, 16 Jul, 27 Aug, 24 Sep
Get $135 off on our Sept. 11th departure and join us on board this superb sailing holiday! Explore the Greek islands beyond the ordinary way, away from the tourist masses. Island hopping, anchorage at secluded swimming spots etc are waiting for you
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