How To Charter a Yacht: Ultimate Sailing Holiday Guide

Rob Melotti tells us how, when, and where to plan your dream sailing holiday.

You might have a picture in your head of what your ideal charter sailing holiday looks and feels like, but how do you go about booking and arranging it and what are the pitfalls to avoid? Perhaps you have never set foot on board a yacht before and need a total introduction to the mechanics of getting ‘out there’ from here?

Modern yacht charter holidays are hugely popular and growing in all kinds of new ways. Companies are constantly experimenting with new destinations, updated itineraries and interesting packages, but if you spend a bit of time browsing the options, the big classic themes come up again and again as if reminding you that it need not be complicated: nice weather and simple navigation on a clean, comfortable boat is, quite simply, a recipe for a gorgeous getaway. 

If you are a charter first timer or newcomer to sailing, it pays to narrow down the search by understanding your own requirements, such as who you are travelling with, and the type of holiday you, your family/group of friends want. You’ll also need to consider experience particularly if you are planning on a group holiday because it is important that it is suitable for all levels. But if in doubt, follow the crowd and remember: it’s a holiday in the sun that the best companies just can’t wait for you to experience, because they know that once you’ve been… you’ll be back for more. You can’t go too far wrong.

Types of Charter… Which is Best For You?

Bareboat charter means you hire the entire boat and have the freedom to sail anywhere without restrictions. However, in most countries, the skipper must have the required relevant qualifications, which the company will explain to you depending on what the local regulations are.

Skippered charter, as the name suggests, is where the yacht you charter comes complete with a skipper, relieving you of the responsibility for navigating or sailing.

Crewed charter means the yacht comes with both a skipper and a crew/hostess cook, arguably offering the ultimate in luxury and relaxation.

Flotilla charter is where you and your party hire your own boat but sail in the company of other yachts under constant supervision. An experienced and qualified flotilla leader will organise your itinerary and help you make the most of this social and relaxing holiday. If you don’t have the relevant qualifications or experience to take charge of the yacht though, you’ll still need to hire a skipper.

Stay and Sail holidays offer the opportunity to combine a beach-club or waterside holiday experience, with a period aboard a charter yacht, be it flotilla, crewed, skippered or bareboat. This often takes the form of one week ashore and one week afloat.

‘By the Cabin’ charter means you hire a cabin on board, and it’s a popular option, particularly as an individual, if you want to just turn up and go sailing.

Where to Go?

For UK sailors, the Mediterranean is the ideal charter holiday destination. The Greek islands in summer have very little tide, plenty of lively, safe, deep-water ports, thousands of empty beaches to anchor off for lunch and long afternoons, reliable wind, hot sun and reasonable prices. The Adriatic Sea coast of Croatia and the former Yugoslavian countries is also a popular cruising location and often considered slightly less busy at the height of the summer season.

For European winter holidays in the sun, look no further than the Caribbean: with direct flights from London to Antigua, Bahamas or St Lucia and dozens of other even better charter bases just a short inter-island flight further on. Check out the Grenadines, the Virgin Islands (British and US) and Grenada for starters.

With a growing interest in exotic and far-flung locations, it’s not surprising that many charter companies now have bases in places like Thailand, the Seychelles, Australia and Tahiti. Also, if you are looking for a bareboat charter, you’ll find many boat charter agents such as the Globe Sailor can find you a boat virtually anywhere in the world.

But it’s not all about travelling to the other side of the world, the UK is also becoming a popular choice with companies like Sunsail now running summer flotillas. Also check out Scandinavia, and what northern France has to offer, or the Atlantic islands such as the Canary Islands, Azores and Cape Verde.

How Much Does a Charter Holiday Cost?

Prices vary widely depending on the type of charter you choose, time of year, and what’s included in the package, but relatively speaking, a charter holiday is comparable to the cost of renting a villa. To give you an idea, I searched one site from the directory and found half a dozen options for chartering a six-berth yacht in the Greek Ionian in early May 2025 for under 1300Euro for seven nights (not including flights). The same search in Thailand revealed two yachts under 2000Euros. If you want to employ a professional skipper you will be looking at adding approximately 150 Euros a day.

Peak season (June, July and August) prices rise considerably (around 40 per cent), and you must remember that most companies offer holiday packages without flights or food included. When budgeting for your holiday therefore, it’s imperative to check these details and find out exactly what the package includes.

Which Company?

There are a lot of companies to choose from, so the more research you can do, the better. It won’t take too many searches to start appreciating the best prices, but look at the small print to figure out what is and isn’t included. Many companies have seasonal offers, or early booking discounts, which are well worth watching out for.

The large global players like Dream Yacht Worldwide, The Moorings, or Sunsail don’t offer boats absolutely everywhere at all times of the year, which is a reminder that seasons do matter – even in the tropics – and that quality assurance and peace of mind for charterers is more than just a box ticking exercise. Expertise and longevity on the water really counts for something. But don’t ignore the independent family businesses such as Sailing Holidays or Sail Ionian that are hugely popular with a loyal ‘return customers’ base. Location specialists operate in a competitive market, so the offers are well put together and the staff are often keen to share their passion and experiences of the area with their customers to give the holiday another dimension.

While there has always been an uptake of specialist-style holidays, this sector is on the increase. For hard-core racers who want to compete at some of the glitziest regattas in the world for example, there has never been more opportunity or choice. As well as companies who specialise, you’ll also find a growing number of private skippered bespoke charters. Same goes for classic yacht or tall ship holidays. Now if you want to sail to remote parts of the world on an historic ship, there is plenty of choice and great opportunities.

Web aggregators/yacht agency network companies such as PlainSailing, Helm yt, the GlobeSailor, latesail.com, sailchecker.com, and boatbookings.com specialise in finding the best last-minute deals for bareboat charters. Basically, they do the searching according to your requirements and can also offer extras such as a pro skipper and/or crew, and tuition.

Do You Need Any Prior Sailing Experience?

No, not at all. There is no requirement to have prior sailing experience to go on a charter holiday but, if you are keen to give it a go, it’s the ideal opportunity to learn a new sport.

If you are already a seasoned sailor but want to improve your skill or gain some valuable experience, then sailing in a group on a flotilla, under supervision of a qualified instructor, is highly recommended. Another popular option if you are keen to improve your skill further is to sign up for a course to qualify as a yacht skipper.

To help match your experience to the right holiday options, we suggest that beginners, and improvers without a skipper qualification, should choose from – Flotilla (with skipper), Crewed, or By the Cabin charters.

Qualifications Required as a Skipper

Richard Falk – RYA Training Manager – sums up what’s needed

Flotilla

While you do not need to be hugely experienced to take a flotilla holiday, someone on board needs to be comfortable handling the boat and have basic sailing skills. These may be obtained through prior experience or alternately through familiarisation courses offered by most flotilla companies.

It is becoming more common for local authorities to be requiring a qualification even for flotilla sailing, however, this does vary from location to location and the company you are sailing with will be able to provide you with relevant requirements for the area in which you will be sailing.

Bareboat

In most countries outside of Europe the RYA Day Skipper qualification or above is recognised and accepted as evidence of an individual’s competence to skipper a boat for the purpose of a bareboat charter. However, within Europe more and more port authorities are requiring charterers to hold what is known as an ICC (International Certificate of Competence).

This can be applied for through the RYA on the basis of already holding an RYA issued course completion certificate of RYA Day Skipper or above. Alternatively, sailors with plenty of experience but no qualification can undertake an ICC direct assessment through an RYA-recognised training centre. RYA qualifications are widely recognised, having been around for more than 50 years. For the avoidance of doubt over what qualifications you need, particularly following Brexit which has seen some changes to what individual countries require, it is always wise to seek advice from the company from which you are chartering. This should be done well before your charter, so you have time to meet the requirements.

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