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

Greece sailing holiday for families

From £710 to £790
8 days ex flights
Sailing trip for families/friends in Greek islands
Small group2026: 13 Jul, 20 Jul, 2 Aug, 9 Aug, 6 Sep

Sailing in Croatia

From €680 to €890
5 days ex flights
A multi-activity adventure sailing cruise in Croatia
Small group2026: 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

From €3540 to €4990
8 days ex flights
Spitsbergen tall-ship wildlife and natural history sailing
Small group2026: 1 May, 29 May, 5 Jun, 25 Jun, 5 Jul

Wick to Oban sailing holiday, Scotland

From £2495
10 days ex flights
Join leg 3 of our full NC500 sailing tour
Small group2026: 14 Jul

Stornoway to Wick sailing holiday, Scotland

From £2495
10 days ex flights
Join leg 2 of our full NC500 sailing tour
Small group2026: 2 Jul

Maldives holidays, Dhoni cruise

From £1475 to £2095
8 days ex flights
Cruise the atolls' unspoilt tropical islands
Small group2026: 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

Greek Island Cruise

From £1365 to £1465
8 days ex flights
Discover Greece on this relaxing cruise around Evia
Small group2026: 21 Jun, 5 Jul, 12 Jul, 19 Jul, 26 Jul, 9 Aug, 6 Sep, 13 Sep, 20 Sep

Oban to Stornoway sailing holiday, Scotland

From £2495
10 days ex flights
Join the Adventure as we sail the Western Isles of Scotland
Small group2026: 20 Jun

Croatia sailing holiday from Split

From £2495
7 days ex flights
Relaxing, hands-on sailing with a world leading skipper
Small group2026: 22 Aug, 29 Aug, 2027: 21 Aug, 28 Aug
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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.

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.

Our Sailing holidays reviews

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Elaine Darran07 Nov 2025
An amazing holiday. Would definitely recommend. I’m 65 female sharing the experience with my 39 year old son. I was looking forward to the spectacular scenery and any whales or northern lights would be a bonus. We were lucky to see both, with whales in abundance.read more
Laurie Dunn18 Oct 2025
Fantastic - by far the highlight of our trip to Greece.read more
Heike Oberg02 Oct 2025
Once in a lifetime experience.read more
Julie connor28 Sep 2025
We had a fabulous holiday, couldn’t fault it. Great boat, crew, chef and fellow holiday companions. Will definitely do another boat trip, maybe in Croatia.read more
Written by Joanna Simmons
Photo credits: [Page banner: Markos Mant] [What are sailing holidays like?: Hu Chen] [Active sailing holidays: Getty Images / Unsplash+] [Wildlife watching as you sail: Annie Spratt]