40 Sailing holidays in Greece found
Greece sailing holiday for families
Sailing trip for families/friends in Greek islands
From £580 to £750 7 days ex flights
Small group travel:
2026: 20 Sep
2027: 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
2027: 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
Greek Island Cruise
Discover Greece on this relaxing cruise around Evia
From £1,390 to £1,490 8 days ex flights
Small group travel:
2026: 6 Sep, 13 Sep, 20 Sep
2027: 20 Jun, 27 Jun, 18 Jul, 25 Jul, 29 Aug, 5 Sep, 12 Sep
2027: 20 Jun, 27 Jun, 18 Jul, 25 Jul, 29 Aug, 5 Sep, 12 Sep
Late availability on these dates: 06 Sep, 13 Sep, 20 Sep
Liveaboard diving and sailing holiday in Greece
Combine a sailing and diving adventure in the Greek islands
From £807 to £1,074 7 days ex flights
Small group travel:
2026: 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
100 off Sept and October departures
Mykonos sailing holiday for 18-35s
Island hopping and party vibes on a gulet cruise
From £689 to £859 8 days ex flights
Small group travel:
2027: 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
Contact Us
Call us for a chat about our holidays. We are happy to discuss your holiday and help in any way we can. No bots, queues or awful hold music.
01273 823 700
Call us after 10am
Calling from outside the UK
rosy@responsibletravel.com
Lefkada, Ithaca & Kefalonia family holiday
Experience fun activities and adventure with your family
From £1,250 to £1,670 14 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Yacht charter in Ionian Greek Islands
Luxury sailing in the Greek islands, blending mythical tales
From 2,550 8 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 6, maximum 10. Season runs from end of May to beginning of October.
Ionian Islands small group sailing holiday
8-day Greek odyssey exploring Zante & nearby islands
From £839 to £979 8 days ex flights
Small group travel:
2027: 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
Ionian Islands sailing and walking holiday
Sail and walk around the Ionian islands, Greece
From £946 to £1,049 7 days ex flights
Small group travel:
2026: 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct
100 off Sept and October departures
Greek Aegean Island hopping holiday
Get on board and visit ten stunning Aegean islands
From £2,730 to £3,783 8 days ex flights
Small group travel:
2027: 7 May, 21 May, 28 May, 4 Jun, 18 Jun, 25 Jun, 9 Jul, 16 Jul, 23 Jul, 6 Aug, 13 Aug, 20 Aug, 3 Sep, 17 Sep, 24 Sep
Sailing & conservation holiday in Greece
A unique wildlife & sailing adventure
From £785 to £872 7 days ex flights
Small group travel:
2026: 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Yoga and sailing retreat in Greece
A week of relaxing yoga while sailing the Ionian sea Greece!
From £950 7 days ex flights
Small group travel
Freediving and sailing holiday in Greece
Sail, freedive and explore the Ionian Sea
From £1,250 7 days ex flights
Small group travel:
2026: 18 Oct
Greece sailing holiday in Ionian Sea
Sail, explore and experience the Ionian islands in Greece
From 1,450 6 days ex flights
Small group travel
Greek Islands sailing holiday, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From £1,295£994 to £1,418 8 days ex flights
Small group travel:
2026: 15 Sep, 19 Sep, 29 Sep, 3 Oct
2027: 1 May, 11 May, 15 May, 25 May, 29 May, 8 Jun, 12 Jun, 22 Jun, 26 Jun, 6 Jul, 10 Jul, 24 Jul, 3 Aug, 17 Aug, 21 Aug, 31 Aug, 4 Sep, 14 Sep, 28 Sep, 2 Oct
2027: 1 May, 11 May, 15 May, 25 May, 29 May, 8 Jun, 12 Jun, 22 Jun, 26 Jun, 6 Jul, 10 Jul, 24 Jul, 3 Aug, 17 Aug, 21 Aug, 31 Aug, 4 Sep, 14 Sep, 28 Sep, 2 Oct
Up to £300 off selected dates.
Late availability on these dates: 15 Sep, 19 Sep, 29 Sep, 03 Oct
Late availability on these dates: 15 Sep, 19 Sep, 29 Sep, 03 Oct
Contact Us
Call us for a chat about our holidays. We are happy to discuss your holiday and help in any way we can. No bots, queues or awful hold music.
01273 823 700
Call us after 10am
Calling from outside the UK
rosy@responsibletravel.com
Cyclades Islands sailing holiday, Greece
Swim in turquoise seas & explore ancient towns
From £1,750£1,671 to £1,940£1,911 10 days ex flights
Small group travel:
2026: 13 Sep, 19 Sep, 23 Sep, 29 Sep
2027: 1 May, 11 May, 21 May, 31 May, 4 Jun, 10 Jun, 14 Jun, 20 Jun, 24 Jun, 30 Jun, 4 Jul, 10 Jul, 14 Jul, 20 Jul, 24 Jul, 30 Jul, 3 Aug, 9 Aug, 13 Aug, 19 Aug, 23 Aug, 29 Aug, 2 Sep, 8 Sep, 12 Sep, 18 Sep, 22 Sep, 28 Sep
2027: 1 May, 11 May, 21 May, 31 May, 4 Jun, 10 Jun, 14 Jun, 20 Jun, 24 Jun, 30 Jun, 4 Jul, 10 Jul, 14 Jul, 20 Jul, 24 Jul, 30 Jul, 3 Aug, 9 Aug, 13 Aug, 19 Aug, 23 Aug, 29 Aug, 2 Sep, 8 Sep, 12 Sep, 18 Sep, 22 Sep, 28 Sep
Up to £70 off selected dates.
Late availability on these dates: 13 Sep, 19 Sep, 23 Sep, 29 Sep
Late availability on these dates: 13 Sep, 19 Sep, 23 Sep, 29 Sep
Sailing holiday in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From £1,325£1,321 to £1,480£1,478 8 days ex flights
Small group travel:
2026: 12 Sep, 22 Sep, 26 Sep
2027: 4 May, 8 May, 18 May, 22 May, 1 Jun, 5 Jun, 15 Jun, 19 Jun, 29 Jun, 3 Jul, 13 Jul, 17 Jul, 27 Jul, 31 Jul, 10 Aug, 14 Aug, 24 Aug, 28 Aug, 7 Sep, 11 Sep, 21 Sep, 25 Sep, 5 Oct
2027: 4 May, 8 May, 18 May, 22 May, 1 Jun, 5 Jun, 15 Jun, 19 Jun, 29 Jun, 3 Jul, 13 Jul, 17 Jul, 27 Jul, 31 Jul, 10 Aug, 14 Aug, 24 Aug, 28 Aug, 7 Sep, 11 Sep, 21 Sep, 25 Sep, 5 Oct
Up to £40 off selected dates.
Late availability on these dates: 12 Sep, 22 Sep, 26 Sep
Late availability on these dates: 12 Sep, 22 Sep, 26 Sep
Sailing holiday in the Aegean Sea
Unique sailing adventure off the beaten track in Greece
From £690 to £870 7 days ex flights
Small group travel:
2026: 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
100 off Sept and October departures
Sailing holiday in the Ionian Sea
An unforgettable sailing adventure
From £690 to £784 7 days ex flights
Small group travel:
2026: 19 Sep
100 off Sept and October departures
Greek Islands family sailing holiday
Enjoy the beauty of the Greek islands
From £1,425 8 days ex flights
Small group travel:
2027: 30 May, 8 Aug, 15 Aug
Ionian Islands sailing holiday in Greece
Explore These Western Greek Islands on a Sailing Yacht
From £875 to £1,095 8 days ex flights
Small group travel:
2026: 6 Sep, 13 Sep, 20 Sep, 27 Sep, 4 Oct, 11 Oct, 18 Oct, 25 Oct
Greek Cyclades island hopping cruise
Greek Island Hopping, Sandy beaches and Clear azure waters
From £2,853 to £3,748 8 days ex flights
Small group travel:
2026: 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct, 23 Oct
2027: 16 Apr, 23 Apr, 30 Apr, 7 May, 14 May, 21 May, 28 May, 4 Jun, 11 Jun, 25 Jun, 2 Jul, 9 Jul, 16 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct
2027: 16 Apr, 23 Apr, 30 Apr, 7 May, 14 May, 21 May, 28 May, 4 Jun, 11 Jun, 25 Jun, 2 Jul, 9 Jul, 16 Jul, 30 Jul, 6 Aug, 13 Aug, 20 Aug, 27 Aug, 3 Sep, 10 Sep, 17 Sep, 24 Sep, 1 Oct, 8 Oct, 15 Oct
Private sailing and cycling island hopping, Greece
Self guided or guided (upon request) tour in the Cyclades
From 1,500 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Sailing and archaeology holiday in Greece
A unique sailing adventure through Greece's ancient history!
From 2,760 to 2,865 8 days ex flights
Small group travel:
2026: 19 Sep, 10 Oct
2027: 15 May, 9 Oct
2027: 15 May, 9 Oct
Saronic Greek Islands luxury charter cruise
Private yacht holiday through Greeces romantic Saronic islands
From 1,450 to 1,600 7 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 4 people. Season runs from end of May to beginning of October.
Family yacht charter sailing holiday in Greece
Luxury, private sailing for the family, with mythical tales
From 2,550 8 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 6, maximum 10. Season runs from end of May to beginning of October.
Rhodes gulet cruise in Greece
8 day Rhodes cruise around the South Dodecanessae
From 1,100 to 1,500 8 days ex flights
Small group travel:
2027: 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
Luxury Greece yacht charter in the Aegean
Sail Greeces magical islands on a luxury catamaran
From 1,500 to 1,625 7 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 4, maximum 10. Available for week long charters, Saturday to Saturday, from end of May to beginning of October.
Cyclades sailing & walking holiday in Greece
Combine a sailing & hiking adventure around the Cyclades
From £788 to £1,045 7 days ex flights
Small group travel:
2026: 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
100 off Sept and October departures
Greek myths sailing holiday, footsteps of Odysseus
Follow the sailing routes of mythical hero Odysseus
From 2,210 to 2,910 8 days ex flights
Tailor made:
This holiday can be booked by private groups of family or friends between May and October
Greece luxury yacht charter, Ionian Islands
Private luxury sailing with skipper and gourmet chef
From 19,000 7 days per yacht per week
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
