96 Sailing holidays found
Greece sailing holiday for families
Sailing trip for families/friends in Greek islands
From £710 to £790 8 days ex flights
Small group travel:
2026: 13 Jul, 20 Jul, 2 Aug, 9 Aug, 6 Sep
Sailing in Croatia
A multi-activity adventure sailing cruise in Croatia
From €680 to €890 5 days ex flights
Small group travel:
2026: 3 Apr, 4 Apr, 6 Apr, 7 Apr, 10 Apr, 11 Apr, 13 Apr, 14 Apr, 17 Apr, 18 Apr, 20 Apr, 21 Apr, 24 Apr, 25 Apr, 27 Apr, 28 Apr, 1 May, 2 May, 4 May, 5 May, 8 May, 9 May, 11 May, 12 May, 15 May, 16 May, 18 May, 19 May, 22 May, 23 May, 25 May, 26 May, 29 May, 30 May, 1 Jun, 2 Jun, 5 Jun, 6 Jun, 8 Jun, 9 Jun, 12 Jun, 13 Jun, 15 Jun, 16 Jun, 19 Jun, 20 Jun, 22 Jun, 23 Jun, 26 Jun, 27 Jun, 29 Jun, 30 Jun, 3 Jul, 4 Jul, 6 Jul, 7 Jul ...
Arctic sailing voyages, North Spitsbergen
Spitsbergen tall-ship wildlife and natural history sailing
From €3,540 to €4,990 8 days ex flights
Small group travel:
2026: 1 May, 29 May, 5 Jun, 25 Jun, 5 Jul
Maldives holidays, Dhoni cruise
Cruise the atolls' unspoilt tropical islands
From £1,475 to £2,095£2,045 8 days ex flights
Small group travel:
2026: 11 Jan, 18 Jan, 25 Jan, 8 Feb, 22 Feb, 8 Mar, 22 Mar, 29 Mar, 5 Apr, 19 Apr, 26 Apr, 3 May, 9 Aug, 23 Aug, 20 Sep, 4 Oct, 11 Oct, 18 Oct, 25 Oct, 1 Nov, 8 Nov, 15 Nov, 22 Nov, 29 Nov, 6 Dec, 13 Dec, 20 Dec, 27 Dec
Late availability on these dates: 11 Jan, 18 Jan, 25 Jan, 08 Feb, 22 Feb, 08 Mar, 22 Mar
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
Greek Island Cruise
Discover Greece on this relaxing cruise around Evia
From £1,365 to £1,465 8 days ex flights
Small group travel:
2026: 21 Jun, 5 Jul, 12 Jul, 19 Jul, 26 Jul, 9 Aug, 6 Sep, 13 Sep, 20 Sep
Turquoise Coast luxury gulet cruise, Turkey
Luxury gulet cruise along Turkey's southern coast
From £1,218 to £1,914 8 days ex flights
Small group travel:
2026: 2 May, 23 May, 13 Jun, 20 Jun, 27 Jun, 4 Jul, 5 Sep, 12 Sep, 19 Sep
Oban to Stornoway sailing holiday, Scotland
Join the Adventure as we sail the Western Isles of Scotland
From £2,495 10 days ex flights
Small group travel:
2026: 20 Jun
Stornoway to Wick sailing holiday, Scotland
Join leg 2 of our full NC500 sailing tour
From £2,495 10 days ex flights
Small group travel:
2026: 2 Jul
Wick to Oban sailing holiday, Scotland
Join leg 3 of our full NC500 sailing tour
From £2,495 10 days ex flights
Small group travel:
2026: 14 Jul
Sail the North Coast 500, Scotland
Adventure sailing around the north coast of Scotland
From £6,495 27 days ex flights
Small group travel:
2026: 20 Jun
Croatia sailing holiday from Split
Relaxing, hands-on sailing with a world leading skipper
From £2,495 7 days ex flights
Small group travel:
2026: 22 Aug, 29 Aug
2027: 21 Aug, 28 Aug
2027: 21 Aug, 28 Aug
Whale watching sailing holiday, Norway
Sailing Norwegian Fjords Whale Watching & Northern Lights
From €1,900 5 days ex flights
Small group travel:
2025: 20 Dec
2026: 2 Jan, 3 Jan, 9 Jan, 10 Jan, 16 Jan, 17 Jan, 23 Jan, 24 Jan, 30 Jan, 31 Jan, 7 Nov, 14 Nov, 21 Nov, 28 Nov, 5 Dec, 12 Dec, 19 Dec
2026: 2 Jan, 3 Jan, 9 Jan, 10 Jan, 16 Jan, 17 Jan, 23 Jan, 24 Jan, 30 Jan, 31 Jan, 7 Nov, 14 Nov, 21 Nov, 28 Nov, 5 Dec, 12 Dec, 19 Dec
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.
Skye and the Small Isles sailing holiday
Sail Scotland's Small Isles and visit spectacular Skye
From £1,600 to £2,960 9 days ex flights
Small group travel:
2026: 5 May, 10 May, 30 Jul, 18 Aug, 26 Aug, 29 Aug, 9 Sep, 13 Sep, 16 Sep
2027: 29 Apr, 10 May, 15 May, 14 Jun, 30 Jul, 14 Aug, 18 Aug, 26 Aug, 8 Sep, 9 Sep, 13 Sep
2027: 29 Apr, 10 May, 15 May, 14 Jun, 30 Jul, 14 Aug, 18 Aug, 26 Aug, 8 Sep, 9 Sep, 13 Sep
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
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: 2 May, 9 May, 16 May, 23 May, 30 May, 6 Jun, 13 Jun, 20 Jun, 27 Jun, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct
Whisky and wildlife sailing holiday in Scotland
Malt Whisky and Wildlife Cruise to Mull, Jura and Islay
From £2,100 to £2,180 11 days ex flights
Small group travel:
2026: 12 May
2027: 12 May
2027: 12 May
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: 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, 31 Oct
Lisbon to Madeira sailing holiday
A 600m ocean passage, mile making and night sailing
From €2,499 10 days ex flights
Small group travel:
2026: 24 Jan
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: 6 Jun, 13 Jun, 20 Jun, 27 Jun, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct
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:
2026: 15 May, 22 May, 29 May, 5 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 4 Sep
Early bird discount. 10% is for all the summer 2026 cruises. Book by 31st January 2026.
Maldives private gulet cruise holiday
Cruise the Maldives island paradise by Turkish Gulet
From US $13,999 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Greece family sailing holiday
Sailing adventure for families or friends in Greek islands
From £710 to £790 8 days ex flights
Small group travel:
2026: 13 Jul, 20 Jul, 2 Aug, 9 Aug, 6 Sep
Yoga and sailing retreat in Greece
A week of relaxing yoga while sailing the Ionian sea Greece!
From £950 to £1,050 7 days ex flights
Small group travel:
2026: 24 May, 17 Jun
Freediving and sailing holiday in Greece
Sail, freedive and explore the Ionian Sea
From £1,250 to £1,450 7 days ex flights
Small group travel:
2026: 21 Jun, 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:
2026: 26 Jun
Greenland sailing cruise and northern lights
The world's longest fjord & spectacular Aurora Borealis
From £6,695 12 days ex flights
Small group travel:
2026: 7 Sep, 16 Sep
Greek Islands family sailing holiday
Enjoy the beauty of the Greek islands
From £1,365 8 days ex flights
Small group travel:
2026: 2 Aug, 16 Aug, 23 Aug
Sailing holiday in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From £1,336 to £1,516£1,411 8 days ex flights
Small group travel:
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, 22 Sep, 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
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
Amalfi Coast sailing holiday, Italy
Gorgeous beaches, ancient ruins & sumptuous fresh seafood
From £2,163 to £2,268 8 days ex flights
Small group travel:
2026: 16 May, 23 May, 6 Jun, 13 Jun, 20 Jun, 27 Jun, 4 Jul, 11 Jul, 25 Jul, 1 Aug, 8 Aug, 15 Aug, 22 Aug, 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct
2027: 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
2027: 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
Greek Islands sailing holiday, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From £1,306 to £1,556£1,381 8 days ex flights
Small group travel:
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, 4 Aug, 8 Aug, 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, 7 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, 7 Aug, 17 Aug, 21 Aug, 31 Aug, 4 Sep, 14 Sep, 28 Sep, 2 Oct
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