Sail the Mediterranean

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.

For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter ...

Latest Blog Posts

  • Exciting Times for Discovering New Zealand by Sail

    Exciting Times for Discovering New Zealand by Sail

    Determined to make use of my time during the covid pandemic lockdown, Robert Cross set out to build himself a boat. The result is the Elliott 11.5 tourer ‘Denim’, launched October 2024 and now available for charter in the Bay of Islands, New Zealand

  • Modern Consumer Tech on Sailing Charter: do we really need it?

    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?

  • Gulet vs. Catamaran: which is the Best Charter Boat for you?

    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? Both offer unique experiences, so let’s dive into a comparison to help you make an informed choice for your group’s holiday.

  • Chartering with a Crew: the Options and all the Advantages

    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.

  • Sailing charter versus resort stay: comparing the costs

    Sailing charter versus resort stay: comparing the costs

    A sailing holiday frequently combines with a land-based resort stay. How many nights aboard charter boat and how many nights onshore, or foregoing one or the other due to cost, is often a discussion point. So we did an exercise on the price comparisons between boat and resort. The cost benefits of a sailing holiday are clear

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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The Essential Guide to Sailing Holiday Charters

The Sail Connections Essential Guide to Bareboat and Crewed Sailing Holiday Charters is packed full of useful tips for getting the most out of your next boat charter. And it is FREE to download.

Download Guide

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For a personal proposal structured to meet your needs, with advice on all aspects of your sailing charter.