Your Very Own Sailing Holiday Voyage of Discovery
Sailing over shimmering waters to destinations steeped in history and natural beauty—what more could you ask for in a boating holiday? From iconic ancient landmarks to pristine white sand beaches against an azure sea, charming villages brimming with culture and unforgettable culinary experiences, the Mediterranean has it all.
With such a diverse range of travel options, the Mediterranean caters to every sailing enthusiast. While Italy, Greece, and Croatia are perennial favorites, there’s so much more to explore in the Balearic Islands, Turkey, Malta, Montenegro, and the South of France. All of these stunning destinations are featured in our comprehensive guide to Mediterranean yacht charters.
Taking the Work out of a Mediterranean Charter
With so many incredible destinations to choose from, selecting a charter boat in the Mediterranean can feel overwhelming. To ensure smooth sailing, it’s essential to work with an experienced and reputable boat operator. With over 30 years in the charter business, we’ve built a network of only the best operators—trusted partners who will provide exceptional care for you, our client. We’ll match you with the ideal yacht from a top operator, taking into account your budget, comfort preferences, and sailing experience.
Our team has spent considerable time sailing throughout the Mediterranean, personally reviewing boats and their management. This hands-on experience extends to the destinations themselves, offering us invaluable insights that we’re eager to share.
Experienced sailors will find bareboat sailing and boat handling straightforward in the Mediterranean. For those who prefer extra relaxation, adding a skipper is always an option. The skipper assumes responsibility for the boat and ensures you reach your desired destinations safely and on time.
Alternatively, you can opt for a fully-crewed yacht, complete with both a cook and skipper for the ultimate relaxation experience. Even seasoned sailors often choose a crew, which we select carefully in consultation with our operators. Your crew will handle all the details while also serving as local guides, sharing recommendations for must-see spots and activities along the way. They’ll help you immerse yourself in the culture and lifestyle of the places you visit.
When you enlist our help to organize your Mediterranean sailing charter (or one anywhere else), our services come at no extra cost to you.
Are one-way sailing charters a good option in the Mediterranean?
One-way sailing charters can be a fantastic option in the Mediterranean Continue reading...
Can Sail Connections match prices I see on other charter websites for the Mediterranean?
Should I choose a bareboat, skippered, or fully crewed charter in the Mediterranean?
Choosing between a bareboat, skippered or fully crewed charter depends on several things Continue reading...
What are some less well known Mediterranean sailing destinations worth exploring?
Beyond the waters of Greece, Croatia etc., the Med offers a host of hidden gems Continue reading...
Is the Mediterranean suitable for families taking their first sailing holiday?
Yes, the Med is one of the best places for a family-friendly sailing holiday Continue reading...
What are the differences between catamaran and monohull for Mediterranean sailing?
The choice comes down to what kind of sailing experience you’re after Continue reading...
Can you help plan my Mediterranean sailing holiday itinerary?
Absolutely. We're here to make your Mediterranean sailing holiday seamless Continue reading...
Which Mediterranean destinations are most popular for charter sailing holidays?
The Mediterranean is a dream sailing destination Continue reading...
How much does a sailing holiday in the Mediterranean cost?
The cost of a sailing holiday in the Mediterranean can vary widely Continue reading...
Do I need a licence to charter a yacht in the Mediterranean?
Yes, if you're planning a bareboat charter (where you skipper the yacht yourself) Continue reading...
With so many Mediterranean sailing holiday destinations to consider, where do I begin?
It’s true—the Mediterranean is packed with incredible sailing options Continue reading...
What are your favourite Mediterranean sailing spots?
When it comes to sailing in the Mediterranean, we're totally sold! Continue reading...
How far in advance should I book a charter boat in the Mediterranean?
For the Mediterranean It’s best to book 6 to 12 months in advance. Continue reading...
When is the sailing season in the Mediterranean?
The Mediterranean sailing season generally runs from April to October Continue reading...
The Best Mediterranean Charter Sailing Destinations
For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter ...
Latest Blog Posts
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Getting to Vava'u, Tonga for your Sailing Holiday (2025)
Your 2025 guide to getting to Tonga—international flights, Fiji to Vava‘u direct service, domestic Saab 340B airlink from Tongatapu and ferry option via Haʻapai.
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Why a Lot of Itinerary Advice Misses the Mark for Sailing Holidays
Learn why many bareboat sailing itineraries found online can be misleading, and how first-hand advice makes all the difference.
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Modern Consumer Tech on Sailing Charter: do we really need it?
When thinking about a sailing holiday, it’s natural to wonder whether to bring our modern gadgets along for the ride - or leave them behind entirely. Technology is so deeply woven into the fabric of our daily routines. So should we pack our tablets and smartphones or is a sailing charter the perfect opportunity to fully disconnect and reset?
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Gulet vs. Catamaran: which is the Best Charter Boat for you?
Planning a sailing holiday in the Mediterranean is a dream come true for many, with its crystal-clear waters, historic ports, and sun-soaked islands. Once you’ve chosen your destination, there’s still a crucial decision to make: should you charter a classic Turkish gulet or opt for a modern catamaran?
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Chartering with a Crew: the Options and all the Advantages
A sailboat charter that includes a paid crew can mean different things: a crewed bareboat with your party joined by freelance skipper and sometimes cook; a boat that must have a skipper included, and the full-service charter with permanent, professional crew attached.
The Sail Connections Guarantee
One contact - every option - advice you can trust.
- Matching any competitive offer
- Sourcing boats with discounts available
- Personalising our proposal just for you
- Qualifying the operator as well as the boat
- Advising without bias based on 25+ years of experience
- We do more than just book yachts!
We will match any discount website offer on charter boat price, and still provide our customary high level of service.
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