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 trips
Small group
Turquoise Coast luxury gulet cruise, Turkey
From
£1395 to £1915
8 days
ex flights
Luxury gulet cruise along Turkey's southern coast
Small group2027: 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 group2027: 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 group
Sardinia and Corsica private yacht charter
From
€18500 to €20000
7 days
per yacht per week
Private luxury sailing in Sardinia and Corsica
Tailor made
Sailing vacation in the Ionian Sea
From
£690 to £784
7 days
ex flights
An unforgettable sailing adventure
Small group2027: 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep
Freediving and sailing vacation in Greece
From
£1800
7 days
ex flights
Sail, freedive and explore the Ionian Sea
Small group2027: 23 May, 26 Sep, 17 Oct
Ionian Islands small group sailing vacation
From
£839 to £979
8 days
ex flights
8-day Greek odyssey exploring Zante & nearby islands
Small group2027: 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct
Ionian Islands sailing and walking vacation
From
£946 to £1049
7 days
ex flights
Sail and walk around the Ionian islands, Greece
Small group2027: 1 May, 8 May, 15 May, 22 May, 29 May, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct
Contact Us
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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).
Latest reviews
4.7
286Mediterranean sailing vacations reviews
Lisa Rolle09 Oct 2026
Having a small number of passengers on the vessel was brilliant. Jake, the skipper, could not have done more to make sure our needs and expectations were metread more
Jody Mahoney03 Oct 2026
A wonderful way to get out and see the Greek islands!read more
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
See all our Mediterranean sailing vacations
