49 Mediterranean sailing vacations found
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: 17 Oct, 24 Oct
Turquoise Coast luxury gulet cruise, Turkey
Luxury gulet cruise along Turkey's southern coast
From £1,395 to £1,915 8 days ex flights
Small group travel:
2027: 22 May, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 4 Sep, 11 Sep, 18 Sep
Sailing in Croatia
A multi-activity adventure sailing cruise in Croatia
From 580 4 days ex flights
Small group travel:
2026: 12 Oct, 13 Oct, 16 Oct, 17 Oct
Sardinia and Corsica private yacht charter
Private luxury sailing in Sardinia and Corsica
From 18,500 to 20,000 7 days per yacht per week
Tailor made:
Season for sailings is June to 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.
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rosy@responsibletravel.com
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
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: 17 Oct, 24 Oct, 31 Oct
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: 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
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 $2,202 to US $2,572US $2,397 8 days ex flights
Small group travel:
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, 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
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
Greek Islands sailing vacation, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From US $2,112 to US $2,462US $2,272 8 days ex flights
Small group travel:
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
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
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: 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
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: 17 Oct
Sardinia and Corsica wellness sailing vacation
Luxury wellness sailing adventure in Sardinia and Corsica
From 3,300 7 days ex flights
Small group travel
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
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
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 $1,970 8 days ex flights
Small group travel:
2027: 30 May, 8 Aug, 15 Aug
Amalfi Coast sailing vacation, Italy
Gorgeous beaches, ancient ruins & sumptuous fresh seafood
From US $3,481 to US $3,756 7 days ex flights
Small group travel:
2027: 15 May, 22 May, 29 May, 5 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
2028: 13 May, 20 May, 27 May, 3 Jun, 10 Jun, 17 Jun, 24 Jun, 1 Jul, 8 Jul, 15 Jul, 22 Jul, 29 Jul, 5 Aug, 12 Aug, 19 Aug, 26 Aug, 2 Sep, 9 Sep, 16 Sep, 23 Sep, 30 Sep
2028: 13 May, 20 May, 27 May, 3 Jun, 10 Jun, 17 Jun, 24 Jun, 1 Jul, 8 Jul, 15 Jul, 22 Jul, 29 Jul, 5 Aug, 12 Aug, 19 Aug, 26 Aug, 2 Sep, 9 Sep, 16 Sep, 23 Sep, 30 Sep
Cyclades Islands sailing vacation, Greece
Swim in turquoise seas & explore ancient towns
From US $2,884 to US $3,359US $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
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
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.
Dubrovnik to Hvar sailing vacation
Active sailing adventure around Croatia
From 990 5 days ex flights
Small group travel
Croatia sailing vacation, Dubrovnik to Split
Experience the old-world charm of Croatia
From US $2,257 to US $2,777US $2,557 8 days ex flights
Small group travel:
2027: 8 May, 15 May, 22 May, 12 Jun, 19 Jun, 10 Jul, 17 Jul, 31 Jul, 7 Aug, 21 Aug, 28 Aug, 4 Sep, 18 Sep, 25 Sep, 9 Oct, 16 Oct
2028: 6 May, 13 May, 20 May, 27 May, 10 Jun, 17 Jun, 1 Jul, 8 Jul, 15 Jul, 29 Jul, 5 Aug, 19 Aug, 26 Aug, 2 Sep, 16 Sep, 23 Sep, 7 Oct, 14 Oct
2028: 6 May, 13 May, 20 May, 27 May, 10 Jun, 17 Jun, 1 Jul, 8 Jul, 15 Jul, 29 Jul, 5 Aug, 19 Aug, 26 Aug, 2 Sep, 16 Sep, 23 Sep, 7 Oct, 14 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: 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
Sardinia (shell)
Crewed catamaran holiday in Sardinia's La Maddalena islands
From 2,200 to 2,925 8 days ex flights
Small group travel:
2027: 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep
Sicily luxury sailing vacation
Private luxury yacht charter with skipper and chef
From 19,000 8 days per yacht per week
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
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
