Our Mediterranean sailing vacations

Experience the Med’s best beaches and exclusive moorings without another soul in sight. Our Mediterranean sailing vacations 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 vacation of a lifetime.

Our top Mediterranean sailing vacations

Turquoise Coast luxury gulet cruise, Turkey

From £1395 to £1915
8 days ex flights
Luxury gulet cruise along Turkey's southern coast
Small group2026: 19 Sep, 2027: 22 May, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 4 Sep, 11 Sep, 18 Sep

Greece sailing vacation for families

From £580 to £750
7 days ex flights
Sailing trip for families/friends in Greek islands
Small group2026: 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

Sailing adventure in the Cyclades, Greece

From £930 to £1095
8 days ex flights
Explore The Aegean Islands On a Skippered, Sailing Yacht
Small group2026: 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct

Sailing in Croatia

From 580 to750
4 days ex flights
A multi-activity adventure sailing cruise in Croatia
Small group2026: 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

Dubrovnik to Hvar sailing vacation

From 990
5 days ex flights
Active sailing adventure around Croatia

Sardinia and Corsica private yacht charter

From 18500 to20000
7 days per yacht per week
Private luxury sailing in Sardinia and Corsica

Liveaboard diving and sailing vacation in Greece

From £807 to £1074
7 days ex flights
Combine a sailing and diving adventure in the Greek islands
Small group2026: 19 Sep, 26 Sep, 3 Oct, 10 Oct, 17 Oct, 24 Oct, 31 Oct

Sardinia and Corsica wellness sailing vacation

From 3300
7 days ex flights
Luxury wellness sailing adventure in Sardinia and Corsica
Small group

Greek Islands family sailing vacation

From US $1580
8 days ex flights
Enjoy the beauty of the Greek islands
Small group2027: 30 May, 8 Aug, 15 Aug
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Highlights of our Mediterranean sailing vacations

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 vacations 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 vacations

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 vacations. 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 vacations reviews

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Stephanie Escalas29 Aug 2026
10/10 best vacation ever. Discovering the boating life, changing every day. 5 stars.read more
Ellen Craig29 Aug 2026
Another fantastic week with the host company! Everyone enjoyed and it was the perfect blend of relaxation, exploration and plenty of swimming! Particular thanks to skipper Elias for being so thoughtful and ensuring we all had a truly wonderful vacation. We’ll be back!read more
Joanna Burton16 Aug 2026
Swimming in the most beautiful turquoise waterread more
Duncan Morley11 Aug 2026
A week on a yacht around the South Ionian islands was amazing, stopping for swimming and snorkelling, and visiting a different port each night.read more
Written by Eloise Barker
Photo credits: [Page banner: Karla Car] [Greece: Mirna Dalic]