Long lazy days sailing around the crystal clear waters of the Mediterranean with the sun on your back and the wind in your hair. Tying up each night in small fishing villages and chatting to the locals, sampling seafood that was caught only a few hours ago and washing it down with a few ice cold beers before being rocked to sleep by the gentle motion of the waves. Sounds like a dream, right? Something attainable only by the rich and famous? Well, it’s not! Gather a few mates together and prepare for the holiday of a lifetime…

As someone with no yachting experience up until a couple of years ago, I had always assumed that sailing holidays were off the agenda until a friend ended up working for a yacht charter company in the Ionian Greek Islands. He never stopped talking about those few months, to the point where a couple of years ago we had to book a sailing holiday there just to shut him up. It was an absolutely incredible experience — there really is no other way to describe it — and surprisingly affordable. With four or five other willing crew members the charter costs can drop below US$150 a day per person, which covers the yacht, flights to and from the UK and (obviously) accommodation.  Once you are there, food and drink is cheap, plentiful and uniformly excellent.

Types of trip

Depending on the amount of sailing experience that your party has and where you are based, there are three main types of trip that you can choose from. If you are looking for a shore-based holiday with a few sailing lessons and other water sports, resort-style holidays are available at several locations throughout the Mediterranean and around the world.

If you have minimal previous time on the water but wish to spend a week or two sailing, there are a number of options available.  You can do either accredited or unaccredited courses before you charter a yacht by yourself, and many companies also offer the ability to hire a skipper for some or all of your time on the water. Flotillas are also a popular choice for groups with a small amount of experience; this is where several yachts travel in a loose convoy under the direction of a ‘lead crew’ who will assist with mooring and casting off and provide hints and guidance each day.

If you can find a couple of friends who have reasonable sailing skills (the exact requirements vary by charter company and location), the ultimate trip is a bareboat charter. For a week or longer, you and a few friends have your very own vessel. Where you go and what you do each day is entirely up to you, and you can decide where to moor each night based on whether you want to party, explore the area, meet the locals or whatever you wish. The yachts are usually designed especially for chartering, with large fridges, stereo systems, plenty of navigational aids (GPS etc) and generally more creature comforts than you might expect, particularly on the larger vessels.

Where to stop

One of the many great things about sailing in the Ionian is that distances are short and there are plenty of places to anchor up for the night or even longer. The island of Ithaca, for example, has a number of great harbours to base yourself for a couple of days — for the classical history buffs this was reputedly the home of Odysseus and has enough ancient ruins, monasteries, beaches and views to justify spending plenty of time ashore exploring on foot or by scooter. Of course if the day is a little too hot to be out adventuring in the sun, there’s always a friendly taverna owner nearby happy to serve you a cold drink instead. The wine is somewhat hit or miss, but the local and imported beers and spirits are guaranteed to hit the spot.

What to look for

With so many different locations and charter companies available, it can be hard to know which option to choose. Once you have decided which part of the world you’d like to travel to, key things to look for are inclusions (insurance, fuel and water, transfers to and from the marina and the like) and most importantly, the age and amenities of the available yachts. Charter yachts tend to have a pretty hard life, so any vessel over five years old should be viewed with suspicion. Our charter was with Sunsail based out of Vounaki marina, and the well-maintained yacht and facilities made for a hassle-free trip — so much so, in fact, that we used them again for a similar trip in Australia the following year.

Hot sun, blue skies, warm seas, great food and drink, wonderful people and oozing with history – a sailing holiday in the Ionian truly is an experience like no other.

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This article was written by Dave

Born and raised in the South Island of New Zealand, Dave started travelling over a decade ago and hasn't quite figured how to stop yet. His degree in Political Science and History was the perfect preparation for a career in IT, which has given him the freedom to work around the world and enough internet access to book his next plane ticket. Dave isn't quite sure what he wants to do when he grows up but suspects it may involve sun, beer and a large body of water.