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Forget Flying: How I’m Planning a Dream Private Yacht Sailing Trip Around the Greek Islands

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Updated: 8th March 2020


At the end of last summer, I found myself torn. I had a week booked on the Greek Island of Corfu with my best friends from school, which clashed with a work opportunity to sail around the Portuguese Azores islands on a private yacht charter – while the latter was a dream trip for me, time with my friends was always going to be the winner. Happily, we spent the week drinking Ouzo, visiting picturesque beaches, munching on Feta and laughing constantly. In summary, it was a dream trip of its own!

But it got me thinking: How awesome would it be to go island hopping around some of the best islands to visit with my best friends and explore more of the country? One of my friends is an ex-croupier on a cruise sheep, and my other is a chief steward on a luxury yacht, so although it seemed we had some of the skills needed to embark on such an adventure, my research on Click and Boat quickly taught me that if you didn’t want to learn to sail but still wanted to charter your own yacht, there were many options with a skipper included. The bonus as well as the prices weren’t quite as heart-wrenching as you would expect.

So, quickly, it became another dream of ours to start planning an island-hopping adventure together. First, we considered 10 days in Croatia before looking into yacht charters in Greece because we all love the Greek islands. We decided planning a multi-island Greece trip would be incredible. Still, to be honest, we are all slightly restless souls who like to explore as much as possible on holiday. Even when I packed myself off to Kos the year before for my ‘sun, sand and nothing else’ beach holiday, I ended up hopping on some island trips to nearby islands like Nisyros, one of my favourite islands in the world. There are so many beautiful smaller islands across Greece that the appeal of setting sail and exploring by boat is undeniable.

Why does a private yacht charter appeal to me?

There are other reasons that a private sailing trip appealed to me, though. Firstly, I’m trying to reduce the amount of flying I do, as while much of my job is tied to flying, it’s the elephant in the room everyone in this industry needs to acknowledge. With solar panels starting to appear on boats and entirely wind-powered operations, sailing is undoubtedly kinder to the environment than taking multiple flights to hop around Greece, often involving connecting flights in key hubs.

Secondly, while the idea of a cruise had once appealed to me, and I’ll admit I did enjoy my cruise around the Baltic Sea a few years back, I liked that because it was lots of little city breaks tied together, visiting the likes of St Petersburg without needing a visa, or having a day exploring Tallinn works in my mind, when I want an island holiday, I want to relax and go at a slower pace, not defined by an 8-hour limit on ports. Also, as it turned out, cruising isn’t exactly great for the environment.

More recently, of course, Coronavirus has exposed some of the downfalls of having 5,000 people together on a ship, eating together, confined together – and the idea of being in quarantine on a mega-ship makes me shudder, so small, private, Greek yacht charters also navigate that option.

Being on the water is my favourite thing; the ocean is my happy place – and living on the beaches of Portugal, whenever I go away for a while, I start to get sad and miss it, so even if big ship cruising is out, my heart was still set on setting sail – something I had tried my hand at in Antigua and really enjoyed, even if I was slow on the uptake!

So, we decided to all start saving and are hoping next year we will make our big Greek yacht charter dream a reality – but then the question is where to go, and just how possible and affordable was this dream of ours?

How does a private yacht charter work, and how much does it cost?

After an introductory email from Click and Boat, I realised that peer-to-peer boat rentals are a thing. It shouldn’t come as a surprise really, with the growth of Airbnb and the likes, and last year I even discovered a similar website for small planes and short flying trips – crazy what the internet has given us access to eh.

So we started looking through the yacht charter in Greece options, and while we assumed perhaps our budget was going to dash our dreams, we quickly found that there were plenty of options that actually weren’t so expensive.

The base price of the charter is often for just the boat, and those prices can range hugely depending on the size, the number of bedrooms, and the age of the ship. In Greece, the costs to charter the boat seemed more favourable to the likes of the Azores or Caribbean destinations, which is why we decided to stick with our original designation plan.

On top of that, you need to factor in the fuel. There are plenty of handy calculators online to help you do this, but in all honesty, as I quickly found out, it’s really not that easy to work out – certainly not as simple as with a car. As such, the simplest way is a thoughtful and helpful conversation with the boat owner when you are making your enquiries; they can help out on the pricing as they know the consumption better.

Additionally, if no one in your party is a qualified captain or has the relevant license, you’re going to need to bring a skipper on board, which can be booked with the boat. The cost of this is around $169/€150 per day on average it appears, but remember that will mean one less bedroom for you to use, so keep that in mind when making the selection. Additionally, the kitty for food and stuff on board, for any skipper or additional crew, will usually be coming from your funds, too.

So, if we take this example:
Here is a sailboat, based in Corfu for $189/€167 a day with three cabins and sleeping up to six people (one cabin is going to the skipper)

Let’s look at the costs of making this happen for a week:
Boat hire for seven days: $1323 / €1169
Skipper for seven days: $1470 / €1330
Cleaning fee: $110 / €100
Insurance: $470 / €420

This brings the total for the week to $3373 or €3019. Split between four it’s just $843 or €754 per person.

Then, in addition, you’ll have your expenses on top such as food, personal insurance, any mooring fees if needed, and o course, a sizeable deposit. And the fuel, don’t forget the fuel costs!

Costs can be reduced considerably if you are crewing it yourself, so perhaps now is the time for me to make some sailing friends!

The benefits of a private yacht charter

Comparing these prices to the likes of G Adventures sailing trips in Greece, they are on par or slightly cheaper for the boat, the skipper, and the basic fees – but not the fuel. The big bonus, though, is you are on a private trip, with complete control, rather than signing up for an organised tour with others on a route that is pre-determined.

One of the main draws to me towards this trip, apart from the copious wine we drank from ceramic jugs while we planned it, was the freedom of being out on the open seas. To be honest, that was the thing I loved about the cruise so much, the heading off, looking out at the uninterrupted ocean, and feeling like an explorer – until I turned around and realised my floating mini-city was not expedition-like at all.

The main benefits of a private yacht charter in Greece is the freedom, the control of picking our own route, of not having to rush off if you final a place you really love, and not having to be on someone else route or clock.

Which sailing route are we planning in Greece

The routes I have looked at have varied over time, and while I’ve been to Athens before, Corfu a couple of times, and Kos and Nisyros in the Dodecanese islands, I’d like to go somewhere completely new.

Thus, my current attention is on the Cyclades islands, though I’m not yet sure whether to go for the Northern Cyclades, where beautiful spots such as Syros, where one of my dear friends hails from, and the popular gay-friendly destination of Mykonos awaits or the Southern Cyclades, most famed for Santorini, although I’d be wanting to hunt out the smaller hidden gems on my Greece yacht charter.

The big thing I’ve learnt on this planning mission so far, though, is to pick the route before you start picking the boat. As it is now blindingly obvious to me and a naive mistake at first, finding a sailboat as close to where you want to start and finish (a loop is most sensible with costs on a private trip) will dictate how much you spend.

Going through the website and looking at the different options available, you’ll also find plenty of boat owners making suggestions of possible routes and itineraries on their listing page based on different numbers of days and what is close by their home port. This has given me a whole other level of inspiration to plan from, as I’ve found out about islands I’ve never heard of before.

Right now, we are considering a slightly larger boat, so we can sail for maybe two weeks and split the costs between more people, either way after we cancelled out on our big 30th birthday trip all together a couple of years back, I’m full steam ahead on making sure this dream adventure goes ahead!

This article is about an adventure already in the works, and I’m grateful to Click & Boat for partnering with me on this content – stay tuned to see how our sailing experience actually turns out.

9 replies
  1. Laurel Christine says:

    Sorry, you missed out on that trip to the Azores but so glad you get to spend time with friends in Corfu. It sounds like a dream. I also didn’t even realize that peer to peer boat rentals was a thing but now it makes total sense and seems like a great way to reduce flying while having an amazing time exploring the Greek Islands.
    Laurel Christine ([email protected])

  2. Mark Robinson says:

    Good luck on your planning endeavors! An excellent idea to cruise around the Greek islands on a sailboat – could not think of any better way to spend a vacation. Who knew borrowing a yacht or sailboat could be mostly reasonably priced!

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