Sailing holidays in Scotland

Visit Scotland under sail and you could find yourself gliding alongside big wildlife. You might be in the remote, far north of the British Isles, but you won't be alone: there are seals, whales and dolphins. When you book sailing holidays in Scotland, you'll discover the islands aren't as isolated as you'd think. Follow old Viking routes from Norway, cross to Ireland, or go down into England on a bonny boating adventure.

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Skye and the Small Isles sailing holiday

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
Wildlife sailing holiday in Scotland

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
Whisky and wildlife sailing holiday in Scotland

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
Sailing holiday in Scotland, Greater Clyde

Sailing holiday in Scotland, Greater Clyde

Sailing and outdoor activities with local seafood in Argyll
From £600 6 days ex flights
Small group travel
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Calling from outside the UK
Scotland to England sailing course

Scotland to England sailing course

Enhance your skills with expert guidance
From £899 6 days ex flights
Small group travel
Iceland to Scotland sailing holiday, via Faroe Islands

Iceland to Scotland sailing holiday, via Faroe Islands

Extraordinary voyage through the North Atlantic's untamed beauty
From £2,799 12 days ex flights
Small group travel
St Kilda & Hebridean Islands sailing holiday

St Kilda & Hebridean Islands sailing holiday

Adventure sailing in Scotland's Outer Hebrides and St Kilda
From £2,199 12 days ex flights
Small group travel: 2025: 26 May
Scotland and Orkney Islands sailing holiday

Scotland and Orkney Islands sailing holiday

Explore the east coast of Scotland & Orkney Islands
From €1,485 9 days ex flights
Small group travel
Scottish Islands sailing holiday

Scottish Islands sailing holiday

Explore the Orkneys, Fair Isle and the Shetland islands
From €1,165 8 days ex flights
Small group travel
North Atlantic sailing holiday, Scotland to Faroe Islands

North Atlantic sailing holiday, Scotland to Faroe Islands

Sail the captivating beauty of the North Atlantic
From £2,499 12 days ex flights
Small group travel
Scotland to Faroe Islands sailing holiday

Scotland to Faroe Islands sailing holiday

Untamed, rugged and remote
From £2,299 12 days ex flights
Small group travel
Scotland private charter sailing holidays

Scotland private charter sailing holidays

Private Charter a small ship around the Scottish Islands
From £7,500 to £15,000 7 days ex flights
Tailor made: This trip can be tailor made throughout the year to suit your requirements
    Photo credits: [Page banner: Krisjanis Mezulis] [Railway holidays : Jack Anstey] [Small ship cruises : pxhere] [Watching wildlife: eric niven] [Types of holidays : Petr Meissner] [Where to go in Scotland : Nathan Anderson]