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, Caribbean or Cyclades, sailing holidays take you island hopping, wildlife watching, scuba diving. Or indeed, just plain sailing.
82 Sailing holidays found
Sailing in Croatia
A multi-activity adventure sailing cruise in Croatia
From €580 4 days ex flights
Small group travel:
2022: 1 Oct, 2 Oct, 4 Oct, 5 Oct, 6 Oct, 8 Oct, 9 Oct, 10 Oct, 11 Oct, 12 Oct, 13 Oct, 15 Oct
Luxury gulet cruise in the Aegean 2023
5 star services while cruising the Greek Islands in luxury
From £1,250 8 days ex flights
Small group travel:
2023: 27 May, 2 Sep
Liveaboard diving and sailing holiday in Greece
Combine a sailing and diving adventure in the Greek islands
From £719 to £799 7 days ex flights
Small group travel:
2022: 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct
Yoga and sailing retreat in Greece
-A week of relaxation and yoga while sailing the Ionian sea!
From £850 to £950 7 days ex flights
Small group travel:
2023: 28 May, 25 Jun
Travel Team
If you would like some help or advice, or just want to discuss your ideas for your next trip, do give us a call.
Dubrovnik to Hvar sailing holiday
Active sailing adventure around Croatian Islands
From €920 5 days ex flights
Small group travel
Sailing holiday in Greece, Mykonos to Santorini
The boat, the beach and inviting Greek villages
From £1,281 to £1,381 8 days ex flights
Small group travel:
2023: 13 May, 16 May, 27 May, 8 Jun, 10 Jun, 24 Jun, 2 Jul, 8 Jul, 22 Jul, 25 Jul, 5 Aug, 17 Aug, 19 Aug, 2 Sep, 10 Sep, 16 Sep, 30 Sep, 3 Oct
Greek Islands sailing holiday, Santorini to Mykonos
Sapphire waters, whitewashed villages & history laden ruins
From £1,281 to £1,381 8 days ex flights
Small group travel:
2023: 6 May, 9 May, 20 May, 1 Jun, 3 Jun, 25 Jun, 1 Jul, 15 Jul, 18 Jul, 29 Jul, 10 Aug, 12 Aug, 26 Aug, 9 Sep, 23 Sep, 26 Sep
Arctic sailing voyages, North Spitsbergen
Spitsbergen tall-ship wildlife and natural history sailing
From €2,790 8 days ex flights
Small group travel:
2023: 15 May, 22 May, 29 May, 8 Jun, 18 Jun, 28 Jun, 8 Jul
Tall ship sailing holiday, Bay of Biscay
Explore bay of Biscay by tall ship
From €490 to €750 5 days ex flights
Small group travel
Sailing and cycling Cyclades holiday, Greece
Self guided or guided (upon request) tour in the Cyclades
From €1,500 8 days ex flights
Small group travel:
2022: 1 Oct, 8 Oct, 15 Oct
Skye and the Small Isles sailing holiday
Sail Scotland's Small Isles and visit spectacular Skye
From £1,520 to £2,480 9 days ex flights
Small group travel:
2023: 8 May, 20 Jul, 16 Aug, 23 Aug, 4 Sep, 5 Sep
2024: 16 Apr, 14 May, 19 May, 17 Jun, 3 Aug, 20 Aug, 22 Aug, 7 Sep
2024: 16 Apr, 14 May, 19 May, 17 Jun, 3 Aug, 20 Aug, 22 Aug, 7 Sep
Seychelles 7 day sailing cruise
Cruise the Seychelles on a beautiful wooden sailing ship
From £1,332 7 days ex flights
Small group travel
Sailing holiday in the Aegean Sea
Unique sailing adventure off the beaten track in Greece
From £502 to £613 7 days ex flights
Small group travel:
2022: 1 Oct, 8 Oct, 15 Oct, 22 Oct, 29 Oct
Greek Island cruising holiday
Discover a side of Greece riddled with myth and magic.
From £2,705 to £3,580£2,780 9 days ex flights
Small group travel:
2023: 18 May, 22 Jun, 20 Jul, 3 Aug, 17 Aug, 21 Sep
Travel Team
If you would like some help or advice, or just want to discuss your ideas for your next trip, do give us a call.
Cyclades sailing & walking holiday in Greece
Combine a sailing & hiking adventure around the Cyclades
From £712 to £791 7 days ex flights
Small group travel:
2022: 2 Oct, 9 Oct, 16 Oct, 23 Oct, 30 Oct
Whisky and wildlife sailing holiday in Scotland
Malt Whisky and Wildlife Cruise to Mull, Jura and Islay
From £1,520 11 days ex flights
Small group travel:
2023: 28 Jul
2024: 29 May
2024: 29 May
Whale watching in Norway, sailing cruise
Whale watching, king crab safari and Midnight sun in Varanger
From NKr14,900 6 days ex flights
Small group travel
Tall ship sailing holiday in Northern Spain
Adventure sailing in Spain on a historic ship
From €620 to €840 7 days ex flights
Small group travel:
2022: 1 Oct, 10 Oct, 17 Oct
Greater Clyde sailing holiday, Scotland
Sailing and outdoor activities with local seafood in Argyll
From £750 6 days ex flights
Small group travel
Egypt cruise holiday, Aqaba to Tel Aviv
Discover Israel,Egypt and Jordan with an expert Egyptologist
From €1,650 to €2,700 8 days ex flights
Small group travel:
2022: 11 Dec, 25 Dec
2023: 8 Jan, 22 Jan, 5 Feb, 19 Feb, 5 Mar, 19 Mar
2023: 8 Jan, 22 Jan, 5 Feb, 19 Feb, 5 Mar, 19 Mar
10% off cruise fare for honeymoon couples, free cabin upgrade upon availability, Candle-lit dinner on board, free massage for two at the Jade Spas (selected ships) & A Bubbly Welcome Honeymoon treatment in your cabin
Greece sailing holiday for families
Sailing trip for families/friends in Greek islands
From €4,250 8 days ex flights
Small group travel
Spain tall ship sailing holiday, Spanish speaking
Practice Spanish while sailing on a historic wooden ship
From €650 6 days ex flights
Small group travel
Egypt, Jordan & Suez Canal small ship cruise
Gods, Kings & Pharaohs, while crossing the Suez Canal!
From €1,650 to €2,700 8 days ex flights
Small group travel:
2022: 18 Dec
2023: 1 Jan, 15 Jan, 29 Jan, 12 Feb, 26 Feb, 12 Mar, 26 Mar
2023: 1 Jan, 15 Jan, 29 Jan, 12 Feb, 26 Feb, 12 Mar, 26 Mar
10% off cruise fare for honeymoon couples, free cabin upgrade upon availability, Candle-lit dinner on board, free massage for two at the Jade Spas (selected ships) & A Bubbly Welcome Honeymoon treatment in your cabin
Istria and Northern Adriatic sailing adventure, Croatia
Multi-activity sailing holiday around Croatian islands
From €1,540 5 days ex flights
Tailor made:
This trip can be booked from April to October
Small group sailing in Saronic Greek Islands
Luxury sailing in the Greek islands with mythical adventures
From €2,800 8 days ex flights
Small group travel:
2023: 8 Jul
Greek Aegean Island hopping holiday
Get on board and visit ten stunning Aegean islands
From €2,400 to €3,650 8 days ex flights
Small group travel
10% off cruise fare for honeymoon couples, free cabin upgrade upon availability, Candle-lit dinner on board, free massage for two at the Jade Spas (selected ships) & A Bubbly Welcome Honeymoon treatment in your cabin
Tall ship festival, Bilbao to San Sebastian
3 day Pasaia Maritime Festival
From €960 to €1,350 8 days ex flights
Small group travel
Greek Cyclades island hopping cruise
Greek Island Hopping, Sandy beaches and Clear azure waters
From €2,070 to €3,450 8 days ex flights
Small group travel:
2022: 7 Oct, 14 Oct, 21 Oct
10% off cruise fare for honeymoon couples, free cabin upgrade upon availability, Candle-lit dinner on board, free massage for two at the Jade Spas (selected ships) & A Bubbly Welcome Honeymoon treatment in your cabin
Arctic sailing voyages, around Spitsbergen
Spitsbergen tall-ship wildlife and natural history sailing
From €5,640 15 days ex flights
Small group travel:
2023: 18 Jul
Luxury sailing holiday in the Aegean
Luxury sailing the Aegean, while reliving mythical tales
From €2,340 to €2,940 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
