Our Sailing holidays & tours
You don’t need to have salty sea dog credentials to go on a sailing holiday. Trips come in all shapes, styles and sizes, from short breaks cruising the Amalfi coast, to hands-on wildlife watching off Scotland’s islands. Whether you want sunshine, snorkelling and relaxation or hoisting sails and scaling sea cliffs, we’ve a holiday to suit. Our sailing holidays are run by captains and crew who care deeply about their local areas – whether they’re provisioning from local businesses, participating in beach cleans in their off-season, or helping conservation organisations with their dolphin counts. By going by small sailing boat, rather than large cruise ship, you can explore communities without overwhelming them and spread money to shallower bays and more remote villages.
Our top Sailing holidays
Sailing in Croatia
From
€580 to €790
4 days
ex flights
A multi-activity adventure sailing cruise in Croatia
Small group2026: 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
Greece sailing holiday for families
From
£580 to £750
7 days
ex flights
Sailing trip for families/friends in Greek islands
Small group2026: 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
Arctic sailing voyages, North Spitsbergen
From
€3790 to €5350
8 days
ex flights
Spitsbergen tall-ship wildlife and natural history sailing
Small group2027: 7 May, 14 May, 14 Jun, 24 Jun, 4 Jul
Sail the North Coast 500, Scotland
From
£2495
27 days
ex flights
Adventure sailing around the north coast of Scotland
Small group2027: 19 Jun
Greek Island Cruise
From
£1390 to £1490
8 days
ex flights
Discover Greece on this relaxing cruise around Evia
Small group2026: 6 Sep, 13 Sep, 20 Sep, 2027: 20 Jun, 27 Jun, 18 Jul, 25 Jul, 29 Aug, 5 Sep, 12 Sep
Turquoise Coast luxury gulet cruise, Turkey
From
£1392 to £1915
8 days
ex flights
Luxury gulet cruise along Turkey's southern coast
Small group2026: 5 Sep, 12 Sep, 19 Sep, 2027: 22 May, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 4 Sep, 11 Sep, 18 Sep
Wick to Oban sailing holiday, Scotland
From
£2995
10 days
ex flights
Join leg 3 of our full NC500 sailing tour
Small group2027: 14 Jul
Oban to Stornoway sailing holiday, Scotland
From
£2995
10 days
ex flights
Join the adventure as we sail the Western Isles of Scotland
Small group
Sardinia and Corsica wellness sailing holiday
From
€3300
7 days
ex flights
Luxury wellness sailing adventure in Sardinia and Corsica
Small group2026: 5 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
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Sailing holiday highlights
What are sailing holidays like?
Sailing holidays vary widely with the seas and seasons but share some common themes. Trips tend to run for a week or more, although short breaks of four nights sailing are possible in southern Europe and in Scotland and Norway. Typically, you’ll sail for three to four hours daily, dropping anchor for a swim, snorkel, or dive, or to explore quiet harbour towns, hike to a hilltop or cycle a coastal path. Breakfast and lunch are often served on board, unless you’re heading way off the charts, in which case full board catering is the norm, with fresh fish caught off the boat. There’s often an itinerary, but it’s a loose one. If dolphins are frolicking around the prow, lunch may get pushed back. If the wind is whipping up choppy seas, the skipper may choose a different route. But this is where the similarities between sailing holidays end. Each offers something unique, in terms of location, style and experience.
Leisurely sailing holidays
The opportunity to relax on deck, cool off in crystal clear waters and relax on deck some more is the top offer of Greece, Italy, Turkey and Croatia sailing trips. Come in the summer and you can dodge the crowds clustered on the resort beaches, sailing to quiet bays and escaping back to your vessel each night. Meals are prepared for you in the day (you’ll eat on shore at local restaurants in the evenings) and the crew sail the ship, too, so you won’t be called upon to read the charts or hoist the sails (although you’re welcome to help if you like). There will always be the option to kayak or snorkel, jump on the paddleboard or have a swim around the boat at anchor at your lunch stop. Once you’ve docked, you can explore island ports or potter round pretty churches.
Active sailing holidays
Some sailing trips are two-for-the-price-of-one in style, offering a specific activity alongside sailing. Go to the Ionian Islands in Greece to sail and hike, or combine sailing with yoga or even freediving, or slip over to the Cyclades to scuba dive. On some sailing trips, the sailing itself is the activity, with guests invited to be involved in the whole adventure; navigating, steering, hoisting sails and preparing meals for their fellow ship mates and crew. You may also fish from the boat for supper or, in Scotland, gather in lobster pots, too.
We also sell more extreme offshore sailing holidays, where you’ll be undertaking crossings of open water for multiple days at a time. These passage-making trips give you valuable experience and more nautical miles under your belt. In Europe this might include sailing in challenging areas like the Bay of Biscay, the North Sea or around the Canaries. In the Caribbean, look to St Lucia, the Grenadines and Antigua. For an even more extreme adventure, you can even cross the Atlantic.
We also sell more extreme offshore sailing holidays, where you’ll be undertaking crossings of open water for multiple days at a time. These passage-making trips give you valuable experience and more nautical miles under your belt. In Europe this might include sailing in challenging areas like the Bay of Biscay, the North Sea or around the Canaries. In the Caribbean, look to St Lucia, the Grenadines and Antigua. For an even more extreme adventure, you can even cross the Atlantic.
Wildlife watching as you sail
There’s no better place to observe marine life than from a boat, and some sailing adventures make wildlife watching their focus. In Scotland, wildlife sailing holidays bring you closer to the west coast’s seals, cetaceans and seabirds, and you’ll report any sightings to research and conservation programmes. You can cruise around the Maldives in a dhoni, for the opportunity to snorkel with manta rays, or go deep into Spitsbergen’s fjords to see polar bears, walruses and reindeer. In the Ligurian Sea in Italy you can participate in conservation research into whale and dolphin populations on a six-day cruise, or head to the Cyclades in Greece in the company of a wildlife guide and see dolphins, seals and sea turtles in the water, and falcons and eagles soaring above, too.
Trips with a twist
Some sailing holidays (in Croatia, for example) include land-based accommodation with daytime excursions to islands – perfect if you want a little space in which to spread out and sleep but you still love to explore by sea. It’s also possible to find fully participatory trips, requiring you to shop for provisions, sail, cook and clear up. These are great for building camaraderie and tend to be cheaper, too.
Trips that take children are available, too, there’s usually a minimum age limit of around seven, or you can book out the entire yacht. Scotland is a great destination for family sailing holidays, with a chance to learn about sailing, spot wildlife, kayak and explore on land, and if you can only get away during school holidays, it’s cooler here than southern Europe.
Trips that take children are available, too, there’s usually a minimum age limit of around seven, or you can book out the entire yacht. Scotland is a great destination for family sailing holidays, with a chance to learn about sailing, spot wildlife, kayak and explore on land, and if you can only get away during school holidays, it’s cooler here than southern Europe.
Our Sailing holidays reviews
4.6
363Sailing holidays reviews
Daniel Ling02 Aug 2026
One of the best holidays we’ve had and we’ll definitely be doing it again. We had the most amazing time and our captain Panos was truly brilliant.read more
Eve Brewster26 Jul 2026
It was fantastic- we would recommend without hesitation. We are a family of four with two teenage boys and we all had an amazing time.read more
Jo Boothroyd26 Jul 2026
We especially loved mooring overnight in a quieter beach and having great food in a restaurant there. Our teenagers loved the swimming, paddle boarding and snorkelling.read more
Leina Bryson20 Jul 2026
Absolutely gorgeous waters of the Adriatic Sea...Excellent.read more

