41 Sailing vacations 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:
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
Sailing adventure in the Cyclades, Greece
Explore The Aegean Islands On a Skippered, Sailing Yacht
From £930 to £1,095 8 days ex flights
Small group travel:
2026: 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct
Greek Island Cruise
Discover Greece on this relaxing cruise around Evia
From US $1,970US $1,580 to US $1,970 8 days ex flights
Small group travel:
2027: 20 Jun, 27 Jun, 18 Jul, 25 Jul, 29 Aug, 5 Sep, 12 Sep
Mykonos sailing vacation 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 vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
Liveaboard diving and sailing vacation 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: 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Yoga and sailing retreat in Greece
A week of relaxing yoga while sailing the Ionian sea Greece!
From £950 to £1,100 7 days ex flights
Small group travel:
2027: 16 May, 30 May, 6 Jun
Sailing vacation in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From US $2,085US $1,890 to US $2,397 8 days ex flights
Small group travel:
2026: 6 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
2028: 2 May, 6 May, 16 May, 20 May, 30 May, 3 Jun, 13 Jun, 17 Jun, 27 Jun, 1 Jul, 11 Jul, 15 Jul, 25 Jul, 29 Jul, 8 Aug, 12 Aug, 22 Aug, 26 Aug, 5 Sep, 9 Sep, 19 Sep, 23 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
2028: 2 May, 6 May, 16 May, 20 May, 30 May, 3 Jun, 13 Jun, 17 Jun, 27 Jun, 1 Jul, 11 Jul, 15 Jul, 25 Jul, 29 Jul, 8 Aug, 12 Aug, 22 Aug, 26 Aug, 5 Sep, 9 Sep, 19 Sep, 23 Sep
Late availability on these dates: 06 Oct
Greek Islands sailing vacation, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From US $1,995US $1,813 to US $2,212 8 days ex flights
Small group travel:
2026: 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
2028: 29 Apr, 9 May, 13 May, 23 May, 27 May, 6 Jun, 10 Jun, 20 Jun, 24 Jun, 4 Jul, 8 Jul, 18 Jul, 22 Jul, 1 Aug, 5 Aug, 15 Aug, 19 Aug, 29 Aug, 2 Sep, 12 Sep, 16 Sep, 26 Sep
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
2028: 29 Apr, 9 May, 13 May, 23 May, 27 May, 6 Jun, 10 Jun, 20 Jun, 24 Jun, 4 Jul, 8 Jul, 18 Jul, 22 Jul, 1 Aug, 5 Aug, 15 Aug, 19 Aug, 29 Aug, 2 Sep, 12 Sep, 16 Sep, 26 Sep
Late availability on these dates: 03 Oct
Sailing vacation in the Aegean Sea
Uninhabited islands in a 6 person boat
From £690 to £870 7 days ex flights
Small group travel:
2026: 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Ionian Islands small group sailing vacation
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
Lefkada, Ithaca & Kefalonia family vacation
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
Ionian Islands sailing and walking vacation
Sail and walk around the Ionian islands, Greece
From £946 to £1,049 7 days ex flights
Small group travel:
2026: 26 Sep, 3 Oct, 10 Oct, 17 Oct
Greek Aegean Island hopping vacation
Get on board and visit ten stunning Aegean islands
From US $2,890 to US $4,390 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
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.
Contact Us
Call us for a chat about our vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
Sailing & conservation vacation 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
Freediving and sailing vacation in Greece
Sail, freedive and explore the Ionian Sea
From £1,250 7 days ex flights
Small group travel:
2026: 18 Oct
Greek Islands family sailing vacation
Enjoy the beauty of the Greek islands
From US $1,970US $1,580 8 days ex flights
Small group travel:
2027: 30 May, 8 Aug, 15 Aug
Cyclades Islands sailing vacation, Greece
Swim in turquoise seas & explore ancient towns
From US $2,755US $2,471 to US $3,104 10 days ex flights
Small group travel:
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
2028: 29 Apr, 9 May, 19 May, 23 May, 29 May, 2 Jun, 8 Jun, 12 Jun, 18 Jun, 22 Jun, 28 Jun, 2 Jul, 8 Jul, 12 Jul, 18 Jul, 22 Jul, 28 Jul, 1 Aug, 7 Aug, 11 Aug, 17 Aug, 21 Aug, 27 Aug, 31 Aug, 6 Sep, 10 Sep ...
2028: 29 Apr, 9 May, 19 May, 23 May, 29 May, 2 Jun, 8 Jun, 12 Jun, 18 Jun, 22 Jun, 28 Jun, 2 Jul, 8 Jul, 12 Jul, 18 Jul, 22 Jul, 28 Jul, 1 Aug, 7 Aug, 11 Aug, 17 Aug, 21 Aug, 27 Aug, 31 Aug, 6 Sep, 10 Sep ...
Sailing vacation in the Ionian Sea
An unforgettable sailing adventure
From £690 to £784 7 days ex flights
Small group travel
Saronic Greek Islands luxury charter cruise
Private sailing 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.
Greek Cyclades island hopping cruise
Greek Island Hopping, Sandy beaches and Clear azure waters
From US $3,090 to US $4,690 8 days ex flights
Small group travel:
2026: 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
Sailing and archaeology vacation in Greece
A unique sailing adventure through Greece's ancient history!
From 2,760 to 2,800 8 days ex flights
Small group travel:
2026: 10 Oct
2027: 15 May, 9 Oct
2027: 15 May, 9 Oct
Family yacht charter sailing vacation 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.
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
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
Cyclades sailing & walking vacation in Greece
Combine a sailing & hiking adventure around the Cyclades
From £788 to £1,045 7 days ex flights
Small group travel:
2026: 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Greece small group sailing vacation in the Saronic Gulf
Sail Greece slowly, discover islands, flavours, friendships
From US $3,995 to US $5,795 8 days ex flights
Small group travel:
2027: 15 May
Greek myths sailing vacation, 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
All inclusive sailing vacation in Greece
Crewed sailing holiday in Greece's beautiful Ionian islands
From 1,500 to 2,800 8 days ex flights
Small group travel:
2027: 10 May, 17 May, 24 May, 31 May, 7 Jun, 14 Jun, 21 Jun, 28 Jun, 5 Jul, 12 Jul, 19 Jul, 26 Jul, 2 Aug, 9 Aug, 16 Aug, 23 Aug, 30 Aug, 6 Sep, 13 Sep, 20 Sep, 27 Sep
