50 Mediterranean sailing vacations found
Sailing in Croatia
A multi-activity adventure sailing cruise in Croatia
From 580 to 790 4 days ex flights
Small group travel:
2026: 11 Aug, 14 Aug, 15 Aug, 17 Aug, 18 Aug, 21 Aug, 22 Aug, 24 Aug, 25 Aug, 28 Aug, 29 Aug, 31 Aug, 1 Sep, 4 Sep, 5 Sep, 7 Sep, 8 Sep, 11 Sep, 12 Sep, 14 Sep, 15 Sep, 18 Sep, 19 Sep, 21 Sep, 22 Sep, 25 Sep, 26 Sep, 27 Sep, 28 Sep, 29 Sep, 2 Oct, 3 Oct, 5 Oct, 6 Oct, 9 Oct, 10 Oct, 12 Oct, 13 Oct, 16 Oct, 17 Oct
Turquoise Coast luxury gulet cruise, Turkey
Luxury gulet cruise along Turkey's southern coast
From £1,392 to £1,915 8 days ex flights
Small group travel:
2026: 5 Sep, 12 Sep, 19 Sep
2027: 22 May, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 4 Sep, 11 Sep, 18 Sep
2027: 22 May, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 4 Sep, 11 Sep, 18 Sep
Dubrovnik to Hvar sailing vacation
Active sailing adventure around Croatia
From 990 5 days ex flights
Small group travel:
2026: 14 Aug, 14 Sep
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.
1-866-821-6866
Call toll free
Calling from outside the USA
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:
2026: 30 Aug, 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
£400 off a whole boat charter Sun 30 August to Sat 5 September for your family or friends (up to 6 people). Now available due to a last minute cancellation. Discount refers to whole charter booking and not per person.
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: 15 Aug, 22 Aug, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Ionian Islands sailing vacation in Greece
Explore These Western Greek Islands on a Sailing Yacht
From £875 to £1,095 8 days ex flights
Small group travel:
2026: 16 Aug, 23 Aug, 30 Aug, 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 US $3,090 to US $4,690 8 days ex flights
Small group travel:
2026: 14 Aug, 21 Aug, 28 Aug, 4 Sep, 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
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
Sailing vacation in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From US $1,970US $1,621 to US $2,315US $2,307 8 days ex flights
Small group travel:
2026: 15 Aug, 25 Aug, 29 Aug, 8 Sep, 12 Sep, 22 Sep, 26 Sep, 6 Oct
2027: 4 May, 8 May, 18 May, 22 May, 1 Jun, 5 Jun, 15 Jun, 19 Jun, 29 Jun, 3 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, 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 US $330 off selected dates.
Late availability on these dates: 15 Aug, 25 Aug, 29 Aug, 08 Sep, 12 Sep, 22 Sep, 26 Sep, 06 Oct
Late availability on these dates: 15 Aug, 25 Aug, 29 Aug, 08 Sep, 12 Sep, 22 Sep, 26 Sep, 06 Oct
Greek Islands sailing vacation, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From US $1,780US $1,507 to US $2,250US $2,212 8 days ex flights
Small group travel:
2026: 18 Aug, 22 Aug, 1 Sep, 5 Sep, 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 US $470 off selected dates.
Late availability on these dates: 18 Aug, 22 Aug, 01 Sep, 05 Sep, 15 Sep, 19 Sep, 29 Sep, 03 Oct
Late availability on these dates: 18 Aug, 22 Aug, 01 Sep, 05 Sep, 15 Sep, 19 Sep, 29 Sep, 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: 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
£100 off Sept & Oct departures
Ionian Islands small group sailing vacation
8-day Greek odyssey exploring Zante & nearby islands
From £739 to £1,099£979 8 days ex flights
Small group travel:
2026: 17 Oct
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
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
Late availability on these dates: 17 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: 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 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
Sardinia and Corsica wellness sailing vacation
Luxury wellness sailing adventure in Sardinia and Corsica
From 3,300 7 days ex flights
Small group travel:
2026: 5 Sep
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:
2026: 4 Sep
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
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.
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 to US $2,090 8 days ex flights
Small group travel:
2026: 16 Aug
2027: 30 May, 8 Aug, 15 Aug
2027: 30 May, 8 Aug, 15 Aug
Late availability on these dates: 16 Aug
Cyclades Islands sailing vacation, Greece
Swim in turquoise seas & explore ancient towns
From US $2,435US $2,199 to US $3,019 10 days ex flights
Small group travel:
2026: 20 Aug, 24 Aug, 30 Aug, 3 Sep, 9 Sep, 13 Sep, 19 Sep, 23 Sep, 29 Sep
2027: 1 May, 11 May, 21 May, 25 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, 25 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 US $330 off selected dates.
Late availability on these dates: 20 Aug, 24 Aug, 30 Aug, 03 Sep, 09 Sep, 13 Sep, 19 Sep, 23 Sep, 29 Sep
Late availability on these dates: 20 Aug, 24 Aug, 30 Aug, 03 Sep, 09 Sep, 13 Sep, 19 Sep, 23 Sep, 29 Sep
Amalfi Coast sailing vacation, Italy
Gorgeous beaches, ancient ruins & sumptuous fresh seafood
From US $2,915US $2,292 to US $3,651 7 days ex flights
Small group travel:
2026: 15 Aug, 22 Aug, 29 Aug, 5 Sep, 12 Sep, 3 Oct
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
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
Up to US $700 off selected dates.
Late availability on these dates: 15 Aug, 22 Aug, 29 Aug, 05 Sep, 12 Sep, 03 Oct
Late availability on these dates: 15 Aug, 22 Aug, 29 Aug, 05 Sep, 12 Sep, 03 Oct
Sailing vacation in the Ionian Sea
An unforgettable sailing adventure
From £690 to £784 7 days ex flights
Small group travel:
2026: 22 Aug, 5 Sep, 19 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
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.
Croatia sailing vacation, Dubrovnik to Split
Experience the old-world charm of Croatia
From US $1,870US $1,647 to US $2,422 8 days ex flights
Small group travel:
2026: 22 Aug, 29 Aug, 19 Sep, 10 Oct
2027: 8 May, 15 May, 22 May, 12 Jun, 19 Jun, 3 Jul, 10 Jul, 17 Jul, 31 Jul, 7 Aug, 21 Aug, 28 Aug, 4 Sep, 18 Sep, 25 Sep, 9 Oct, 16 Oct
2027: 8 May, 15 May, 22 May, 12 Jun, 19 Jun, 3 Jul, 10 Jul, 17 Jul, 31 Jul, 7 Aug, 21 Aug, 28 Aug, 4 Sep, 18 Sep, 25 Sep, 9 Oct, 16 Oct
Up to US $320 off selected dates.
Late availability on these dates: 22 Aug, 29 Aug, 19 Sep, 10 Oct
Late availability on these dates: 22 Aug, 29 Aug, 19 Sep, 10 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: 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
£100 off Sept & Oct departures
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
Huge last minute deal for August! 500 euro discount for private groups booking the yacht for our Odysseus adventure. Discount applies to the entire group. For trips until 6th September 2026
Sardinia (shell)
Crewed catamaran holiday in Sardinia's La Maddalena islands
From 2,285 to 2,835 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
