Our Mediterranean sailing holidays

Experience the Med’s best beaches and exclusive moorings without another soul in sight. Our Mediterranean sailing holidays are a memorable way to relax on the coasts of some of the most beautiful parts of Europe. Spend your days sailing from cove to cove, jumping in for a swim whenever you’re so inclined, looking for turtles off the bow and eating, sunbathing and dozing on deck. From Croatia’s islands to the Greek Cyclades, the Aegean to the Adriatic, sailing in the Mediterranean gives you time to relax both on land and at sea. Let sunshine and a sea breeze orchestrate the holiday of a lifetime.

Our top Mediterranean sailing holidays

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 ...

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

Turquoise Coast luxury gulet cruise, Turkey

From £1218 to £1914
8 days ex flights
Luxury gulet cruise along Turkey's southern coast
Small group2026: 2 May, 23 May, 13 Jun, 20 Jun, 27 Jun, 4 Jul, 5 Sep, 12 Sep, 19 Sep

Yacht charter in Ionian Greek Islands

From €2550
8 days ex flights
Luxury sailing in the Greek islands, blending mythical tales

Liveaboard diving and sailing holiday in Greece

From £807 to £1074
7 days ex flights
Combine a sailing and diving adventure in the Greek islands
Small group2026: 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, 31 Oct

Greece family sailing holiday

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

Greek Aegean Island hopping holiday

From £2730 to £3783
8 days ex flights
Get on board and visit ten stunning Aegean islands
Small group2026: 15 May, 22 May, 29 May, 5 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 4 Sep

Greek Islands family sailing holiday

From £1365
8 days ex flights
Enjoy the beauty of the Greek islands
Small group2026: 2 Aug, 16 Aug, 23 Aug

Sailing holiday in Greece, Mykonos to Santorini

From £1336 to £1516
8 days ex flights
The boat, the beach and inviting Greek villages
Small group2026: 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, 22 Sep, 6 Oct, 2027: 4 May, 8 May, 18 May, 22 May, 1 Jun, 5 Jun, 15 Jun, 19 Jun, 29 Jun, 3 Jul, 13 Jul, 17 Jul, 27 Jul, 31 Jul, 10 Aug, 14 Aug, 24 Aug, 28 Aug, 7 Sep, 11 Sep, 21 Sep, 25 Sep, 5 Oct
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Highlights of our Mediterranean sailing holidays

Taking part or taking a break?

If you fancy a whole boat, a whole bay, or maybe even a whole island to yourself then we offer tailor made sailing trips. Charter a boat for you and your friends – it comes with a handy crew, of course. Alternatively, if you want to make friends and meet people, we also offer small group trips where you can bag your berth on board with just six or eight passengers. Want to learn the ropes? We offer participatory sailing trips where you become part of a crew, learn how to sail and helm the boat – great if you want a hands-on experience on board. Alternatively, choose to let the crew do the sailing, leaving you strictly on dolphin-spotting duty.

Greek island hopping

If there’s one country that’s made for sailing, it’s Greece, with its thousands of islands and long-established boating scene. Greece’s island groups make for interesting destinations – beaches, headlands and secret coves come thick and fast between the waves and you can head ashore for coastal walks or make a beeline for the nearest taverna to the port. Head to the Ionian for your first taste of life under sail, for calm waters and beautifully green islands. Alternatively, try the Cyclades to explore the shores of Santorini, Mykonos and Naxos without running into too many crowds.

Italy, Croatia & Turkey

From Sardinia to Turkey’s Turquoise Coast, our sailing holidays explore the Med from all sides and within all seas – sail into the Mediterranean’s Adriatic arm around Croatia, where the gorgeous Dalmatian Coast is the perfect place for island hopping and stopping at traditional konobas (eateries) along the way. Alternatively, head to Italy, where the Amalfi Coast plunges into the Tyrrhenian Sea and explore this scenic shoreline without running into its famous crowds of tourists at every turn.

Family sailing holidays

Up for a swashbuckling good time? Watching your kids gain their sea legs, grow in confidence in the water and even learn to man the helm for themselves is one of the pleasures of our family sailing holidays. Share the boat by booking into a couple of berths and join a couple of other like-minded families. A catamaran (twin-hulled boat) will give you and your family more space above and below deck. Alternatively, charter the whole boat for yourself – it comes with a crew – and that way you and your kids get to dictate the swimming spots (and who has to walk the plank).

Our Mediterranean sailing holidays reviews

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Laurie Dunn18 Oct 2025
Fantastic - by far the highlight of our trip to Greece.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
Cicelia Potgieter04 Sep 2025
It was one of the highlights of my life. Sotiris, our skipper, was very knowledgeable and experiences and created the perfect itinerary. If I have to pick a favourite it will have to be the very charming Ano Koufanisi.read more
James Denton24 Aug 2025
Brilliant and our skipper Ileas was amazing, so tuned into what we wanted each day and great fun.read more
Written by Eloise Barker
Photo credits: [Page banner: Karla Car]