Sailing holidays
Whether you are looking to learn to sail, lie on deck and let someone do the work, or just enjoy sailing as a means of getting from one aquatically alluring A to an even more beautiful B, sailing holidays are all about going with the flow. Amalfi or Adriatic, Channel or Cyclades, sailing holidays take you island hopping, wildlife watching, scuba diving. Or indeed, just plain sailing.
95 Sailing holidays found
Sailing in Croatia
A multi-activity adventure sailing cruise in Croatia
From €580 to €750 4 days ex flights
Small group travel:
2024: 17 Sep, 19 Sep, 21 Sep, 23 Sep, 24 Sep, 26 Sep, 28 Sep, 29 Sep, 30 Sep, 1 Oct, 2 Oct, 3 Oct, 5 Oct, 6 Oct, 7 Oct, 8 Oct, 9 Oct, 10 Oct
Late availability on our popular sailing holiday for late August, September and October 2024 departures - enquire now!
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.
Arctic sailing voyages, North Spitsbergen
Spitsbergen tall-ship wildlife and natural history sailing
From €4,790 8 days ex flights
Small group travel:
2025: 8 Jun, 18 Jun, 28 Jun
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
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
Maldives private gulet cruise holiday
Cruise the Maldives island paradise by Turkish Gulet
From US $11,850 to US $34,000 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
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.
Dubrovnik to Hvar sailing holiday
Active sailing adventure around Croatian Islands
From €820 5 days ex flights
Small group travel:
2024: 12 Oct
Turquoise Coast luxury gulet cruise, Turkey
Luxury gulet cruise along Turkey's southern coast,Bodrum to Gocek
From £1,189 to £1,625 8 days ex flights
Small group travel:
2024: 21 Sep
Skye and the Small Isles sailing holiday
Sail Scotland's Small Isles and visit spectacular Skye
From £1,560 to £2,880 9 days ex flights
Small group travel:
2025: 30 Apr, 4 May, 10 May, 20 May, 15 Jun, 18 Aug, 19 Aug, 22 Aug, 5 Sep, 9 Sep
2026: 30 Apr, 5 May, 10 May, 14 Jun, 30 Jul, 14 Aug, 18 Aug, 26 Aug, 29 Aug, 9 Sep, 13 Sep, 16 Sep
2026: 30 Apr, 5 May, 10 May, 14 Jun, 30 Jul, 14 Aug, 18 Aug, 26 Aug, 29 Aug, 9 Sep, 13 Sep, 16 Sep
Whisky and wildlife sailing holiday in Scotland
Malt Whisky and Wildlife Cruise to Mull, Jura and Islay
From £2,100 11 days ex flights
Small group travel:
2026: 12 May
Wildlife sailing holiday in Scotland
Extraordinary wildlife above and below the waves
From £975 to £1,960 6 days ex flights
Small group travel:
2024: 19 Sep, 25 Sep
2025: 22 Apr, 10 May, 20 May, 15 Jun, 25 Jun, 13 Jul, 31 Jul, 10 Aug, 19 Aug, 7 Sep, 23 Sep
2025: 22 Apr, 10 May, 20 May, 15 Jun, 25 Jun, 13 Jul, 31 Jul, 10 Aug, 19 Aug, 7 Sep, 23 Sep
Croatia sailing holiday from Split
Relaxing, hands-on sailing with world leading skipper
From £2,495 7 days ex flights
Small group travel:
2025: 23 Aug, 30 Aug
Turkey wellness sailing holiday
Luxury wellness sailing adventure in Göcek, Turkey
From €2,250 8 days ex flights
Small group travel
Sardinia and Corsica wellness sailing holiday
Luxury wellness sailing adventure in Sardinia and Corsica
From €2,200 8 days ex flights
Small group travel
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
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
St Lucia & the Grenadines sailing holiday
Soak up the unique charms of these Caribbean islands
From £2,699 12 days ex flights
Small group travel
Scotland to England sailing course
Enhance your skills with expert guidance
From £899 6 days ex flights
Small group travel
Lofoten Islands sailing holiday, Norway
Jaw-dropping scenery, pristine beaches, and northern lights
From £2,699 12 days ex flights
Small group travel
Sailing holiday in Scotland, Greater Clyde
Sailing and outdoor activities with local seafood in Argyll
From £600 6 days ex flights
Small group travel
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
Arctic sailing voyages, around Spitsbergen
Spitsbergen tall-ship wildlife and natural history sailing
From €6,389 15 days ex flights
Small group travel
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
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.
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
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
Amalfi Coast sailing holiday, Italy
Gorgeous beaches, ancient ruins & sumptuous fresh seafood
From £2,180£2,032 8 days ex flights
Small group travel:
2024: 28 Sep
Up to £140 off selected dates.
Late availability on these dates: 28 Sep
Late availability on these dates: 28 Sep
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
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