Sailing holidays in Greece
It doesn't matter whether you're lolling on a stylish varnished gulet or working the winches on a modern catamaran, when the breeze hits, there's nothing like a sailing holiday in Greece. This is a destination that's simply made for sailors. Hop between islands, test the tavernas, and moor in remote, rocky bays where you can smell the black pines on the hillside. Bliss.
33 Sailing holidays in Greece found
Greece sailing holiday for families
Sailing trip for families/friends in Greek islands
From £703 to £780 8 days ex flights
Small group travel:
2024: 22 Sep
2025: 13 Jul, 20 Jul, 3 Aug, 17 Aug, 24 Aug, 31 Aug, 7 Sep, 14 Sep
2025: 13 Jul, 20 Jul, 3 Aug, 17 Aug, 24 Aug, 31 Aug, 7 Sep, 14 Sep
Get 15% off on sailing trip 22-28th of September! Due to a cancellation we have availability for small group bookings. Departure Sunday 22nd early afternoon and return Saturday 28th morning. Start end Lefkas in Greece.
Cyclades sailing & walking holiday in Greece
Combine a sailing & hiking adventure around the Cyclades
From £785 to £872 7 days ex flights
Small group travel:
2024: 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct, 2 Nov
Greece sailing holiday in Ionian Sea
Sail, explore and experience the Ionian islands in Greece
From €1,000 6 days ex flights
Small group travel:
2024: 6 Oct, 13 Oct
Get 15% off on sailing trip 22-28th of September! Due to a cancellation we have availability for small group bookings. Departure Sunday 22nd early afternoon and return Saturday 28th morning. Start end Lefkas in Greece.
Saronic Greek Islands luxury charter cruise
Luxury sailing Greek islands, while reliving mythical tales
From €2,350 8 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 6, maximum 10. Sailing Season is from May 28 to Oct 1
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 until 6pm
Calling from outside the UK
rosy@responsibletravel.com
Greece family sailing holiday
Sailing adventure for families or friends in Greek islands
From £703 to £780 8 days ex flights
Small group travel:
2024: 22 Sep, 29 Sep
2025: 6 Jul, 13 Jul, 20 Jul, 3 Aug, 10 Aug, 17 Aug, 24 Aug, 7 Sep, 14 Sep
2025: 6 Jul, 13 Jul, 20 Jul, 3 Aug, 10 Aug, 17 Aug, 24 Aug, 7 Sep, 14 Sep
Get 15% off on sailing trip 22-28th of September! Due to a cancellation we have availability for small group bookings. Departure Sunday 22nd early afternoon and return Saturday 28th morning. Start end Lefkas in Greece.
Yoga and sailing retreat in Greece
A week of relaxing yoga while sailing the Ionian sea Greece!
From £850 to £950 7 days ex flights
Small group travel:
2024: 6 Oct
2025: 25 May, 7 Sep
2025: 25 May, 7 Sep
Freediving and sailing holiday in Greece
Sail, freedive and explore the Ionian Sea
From £1,190 7 days ex flights
Small group travel:
2024: 13 Oct
Greek Islands family sailing holiday
Enjoy the beauty of the Greek islands
From £1,149 8 days ex flights
Small group travel:
2025: 27 Jul, 3 Aug, 17 Aug, 24 Aug
Sailing holiday in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From £1,200£1,108 to £1,473 8 days ex flights
Small group travel:
2024: 8 Oct
2025: 6 May, 10 May, 20 May, 24 May, 3 Jun, 7 Jun, 17 Jun, 21 Jun, 1 Jul, 15 Jul, 19 Jul, 29 Jul, 2 Aug, 12 Aug, 16 Aug, 26 Aug, 30 Aug, 9 Sep, 13 Sep, 23 Sep, 27 Sep, 7 Oct
2026: 5 May, 9 May, 19 May, 23 May, 2 Jun, 6 Jun, 16 Jun, 20 Jun, 30 Jun, 4 Jul, 14 Jul, 18 Jul, 28 Jul, 1 Aug, 11 Aug, 15 Aug, 25 Aug, 29 Aug, 8 Sep, 12 Sep, 22 Sep, 26 Sep, 6 Oct
2025: 6 May, 10 May, 20 May, 24 May, 3 Jun, 7 Jun, 17 Jun, 21 Jun, 1 Jul, 15 Jul, 19 Jul, 29 Jul, 2 Aug, 12 Aug, 16 Aug, 26 Aug, 30 Aug, 9 Sep, 13 Sep, 23 Sep, 27 Sep, 7 Oct
2026: 5 May, 9 May, 19 May, 23 May, 2 Jun, 6 Jun, 16 Jun, 20 Jun, 30 Jun, 4 Jul, 14 Jul, 18 Jul, 28 Jul, 1 Aug, 11 Aug, 15 Aug, 25 Aug, 29 Aug, 8 Sep, 12 Sep, 22 Sep, 26 Sep, 6 Oct
Up to £90 off selected dates.
Late availability on these dates: 08 Oct
Late availability on these dates: 08 Oct
Sailing holiday in the Ionian Sea
An unforgettable sailing adventure
From £690 to £767 7 days ex flights
Small group travel:
2024: 21 Sep
Sailing holiday in the Aegean Sea
Unique sailing adventure off the beaten track in Greece
From £690 to £767 7 days ex flights
Small group travel:
2024: 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct, 2 Nov
Liveaboard diving and sailing holiday in Greece
Combine a sailing and diving adventure in the Greek islands
From £805 to £892 7 days ex flights
Small group travel:
2024: 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Greek Aegean Island hopping holiday
Get on board and visit ten stunning Aegean islands
From £2,600 to £3,609 8 days ex flights
Small group travel:
2024: 20 Sep
Greek Cyclades island hopping cruise
Greek Island Hopping, Sandy beaches and Clear azure waters
From £2,252 to £3,348 8 days ex flights
Small group travel:
2024: 20 Sep, 27 Sep, 4 Oct, 11 Oct, 18 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 until 6pm
Calling from outside the UK
rosy@responsibletravel.com
Family yacht charter sailing holiday in Greece
Private sailing with fun games, reliving mythical tales
From €2,550 8 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 6, maximum 10
Sailing & conservation holiday in Greece
A unique wildlife & sailing adventure
From £785 to £872 7 days ex flights
Small group travel:
2024: 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Greek Island Cruise
Discover Greece on this relaxing cruise around Evia
From £1,099 to £1,200 8 days ex flights
Small group travel:
2024: 22 Sep
2025: 22 Jun, 29 Jun, 6 Jul, 20 Jul, 31 Aug, 7 Sep
2025: 22 Jun, 29 Jun, 6 Jul, 20 Jul, 31 Aug, 7 Sep
Late availability on these dates: 22 Sep
Luxury Greece yacht charter in the Aegean
Luxury sailing the Aegean, while reliving mythical tales
From €2,400 8 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 6, maximum 10. Sailing Season is from May 28 to Oct 1
Yacht charter in Ionian Greek Islands
Luxury sailing in the Greek islands, reliving mythical tales
From €2,550 8 days ex flights
Tailor made:
This holiday is chartering the whole catamaran, minimum 6, maximum 10. Sailing Season is from 28th May to 1st Oct
Greek Islands sailing holiday, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From £1,342 to £1,453 8 days ex flights
Small group travel:
2024: 1 Oct
2025: 3 May, 13 May, 31 May, 10 Jun, 14 Jun, 24 Jun, 28 Jun, 8 Jul, 12 Jul, 22 Jul, 26 Jul, 5 Aug, 9 Aug, 19 Aug, 23 Aug, 2 Sep, 6 Sep, 16 Sep, 20 Sep, 30 Sep, 4 Oct
2026: 2 May, 12 May, 16 May, 26 May, 30 May, 9 Jun, 13 Jun, 23 Jun, 27 Jun, 7 Jul, 11 Jul, 21 Jul, 25 Jul, 4 Aug, 8 Aug, 18 Aug, 22 Aug, 1 Sep, 5 Sep, 15 Sep, 19 Sep, 29 Sep, 3 Oct
2025: 3 May, 13 May, 31 May, 10 Jun, 14 Jun, 24 Jun, 28 Jun, 8 Jul, 12 Jul, 22 Jul, 26 Jul, 5 Aug, 9 Aug, 19 Aug, 23 Aug, 2 Sep, 6 Sep, 16 Sep, 20 Sep, 30 Sep, 4 Oct
2026: 2 May, 12 May, 16 May, 26 May, 30 May, 9 Jun, 13 Jun, 23 Jun, 27 Jun, 7 Jul, 11 Jul, 21 Jul, 25 Jul, 4 Aug, 8 Aug, 18 Aug, 22 Aug, 1 Sep, 5 Sep, 15 Sep, 19 Sep, 29 Sep, 3 Oct
Late availability on these dates: 01 Oct
Sailing adventure in the Cyclades, Greece
Explore The Aegean Islands On a Skippered, Sailing Yacht
From £795 to £945 8 days ex flights
Small group travel:
2024: 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Ionian Islands sailing holiday in Greece
Explore These Western Greek Islands on a Sailing Yacht
From £795 to £945 8 days ex flights
Small group travel:
2024: 22 Sep, 6 Oct
Ionian Islands sailing and walking holiday
Sail and walk around the Ionian islands, Greece
From £890 to £990 7 days ex flights
Small group travel:
2024: 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct, 26 Oct
Small ship sail powered Greek Island cruise
-Sail on a beautiful ship around the Greek Islands
From £4,402 to £4,650 8 days ex flights
Small group travel:
2024: 21 Sep, 28 Sep, 5 Oct
Sailing and archaeology holiday in Greece
A unique sailing adventure through Greece's ancient history!
From €2,600 to €2,680 8 days ex flights
Small group travel:
2024: 12 Oct
2025: 10 May, 11 Oct
2025: 10 May, 11 Oct
Saronic Islands sailing holiday in Greece
Sail among the beautiful islands & ports of the Saronic Gulf
From US $4,295 8 days ex flights
Small group travel:
2025: 3 May
Cyclades islands sailing holidays in Greece
A fantastic sailing adventure in the Cyclades islands!
From €2,300 to €2,520 8 days ex flights
Small group travel:
2024: 21 Sep
2025: 7 Jun, 5 Jul, 6 Sep, 20 Sep
2025: 7 Jun, 5 Jul, 6 Sep, 20 Sep
Gastronomy and sailing holiday in Greece
Explore the Greek islands and their gastronomy with a chef!
From €970 7 days ex flights
Small group travel
Saronic Gulf sailing holiday in Greece
An 8 day trip combines sailing & swimming in Greece
From €2,180 to €2,520 8 days ex flights
Small group travel:
2024: 5 Oct
2025: 17 May, 21 Jun, 2 Aug, 13 Sep, 4 Oct
2025: 17 May, 21 Jun, 2 Aug, 13 Sep, 4 Oct
Rhodes sailing holiday in Greece
Aegean sea island hopping and sailing school
From €2,000 8 days ex flights
Tailor made:
Sailing during Greek summer in the Aegean Sea
