Early spring in a bay on Meganisi island, south Ionian Sea, and a single boat moors in the harbour. The vessel is sleek, almost 50 feet from bows to stern, shaped like a missile with its streamlined hull. It shimmers silver as iced ouzo. Its swaying mast protrudes as a lonely beacon. Cobalt blue of the bay, indigo hues of the dawning sky. Morning sun behind a silhouette hillside. On the far side of the bay, a cloud clings fixedly to the hilltop, a mile or so distant, the sails of the village windmill barely visible. It’s early dawn. On the quayside of the tranquil bay a fisherman is sitting beside nets. He is crouching forward, elbows on his knees. His shirt is unbuttoned, and his chest exposed to his waist. He wears a denim sailor cap and ragged-old shorts. The cadaver of an octopus flops forlorn on an upturned pale. He uses one hand to grasp a tentacle of the invertebrate, then chops it in a skilled flurry, using the razor hunting knife in his other hand to carve up the meat into chunks. It looks like he is crafting the octopus into a jigsaw. A dozen or so white houses, each facing to the sun-dappled Ionian sea. This is Sportachori: more hamlet than a village. The houses have sloping roofs of clay, moss or thatch, with unkempt bundles of sea-bird’s nests sitting upon the chimneys. Most are shrouded with Bougainvillea branches only budding before the floral summer display arrives. The Maistro – the prevalent wind that blows from the North West – begins to breathe upon Meganisi, and it brings welcome relief to stifled homes, propels village boats many miles distant to bountiful fishing waters, and brings the fisherman’s catch safely home.

This is a typical Greek Island scene you can only experience on a flotilla holiday. You don’t need to know how to sail to join one, here’s how my family of land lubbers got on on our first flotilla holiday.

Flotilla Sailing In The Greek Islands

Greek Islands Flotilla SailingIn the early summer of 2014, my family (my wife, myself, my 14-year-old daughter and my 12-year-old son) took the plunge and decided to take a two-week flotilla sailing holiday around the Greek Islands of the South Ionian Sea. We weren’t sailors as none of us could sail, three of us had never even stepped on a yacht. We just loved the sea, the sun, all that the Greek islands have to offer and, crucially, we all shared lust for adventure.

No experience (or Skill) Required

You may well ask “Don’t I need to know how to sail and have a skipper’s certificate to go on a flotilla holiday?”.  Well the answer is no, not at all. Personally, I’d had just a handful of basic dinghy sailing lessons on the River Deben in Suffolk. As a family we’d also used the small Hobbycat (a basic catamaran boat designed especially for beginners) out on the bay a couple of times whilst on holiday in the Caribbean. But that was all the experience we had. None of us was day skippers, nor even qualified as competent crew. My wife and kids had never stepped on a full-sized yacht before, never mind crewed one, and I’d only spent half a day aboard one of the Global Challenge yachts during a corporate event in the Isle of Man a few years prior.

We did however do some research. We learnt a few basic knots, a bowline and some fender knots, with the help of the excellent Animated Knots website. I also purchased a couple of books about the basics if sailing, such as the sometimes slightly off-putting nautical terminology, and the basic manoeuvrings of the boat. There were also several good videos on YouTube, including the great flotilla specific videos posted by Sailing Holidays and the slightly more technical one on mooring techniques. Armed with only this basic background knowledge, we manage to successfully sail a 33-foot yacht for two weeks, with no crashes, no capsizes and generally not too much trouble.

What Y0u Should Expect

Expect abundant sun, sea, lots of laughs and, maybe, a few stubbed toes. Add to those lasting new friendships, fantastic home-cooked traditional Greek food, varied scenery that changes every day, the best frontline sea view accommodation you could ever imagine and, of course, an amazing sense of achievement. This is what you can expect from a flotilla holiday.

Every day is different from the one before, every evening you’re in a different harbour and eating at a different taverna. Each morning you wake to different sea views in achingly pretty tiny Greek fishing villages. Every journey between ports of call brings opportunities to find increasingly stunning and even more secluded swim spots.  Of course, as each day passes you develop new skills in sailing and navigating, and the bond between your family members grows stronger and fonder.

We booked our flotilla with the excellent Sailing Holidays who were extremely helpful from the very beginning. They helped us choose the right yacht for our needs, reassuring us that our lack of experience wouldn’t matter and even persuading us to book for two weeks instead of one as we originally planned, citing that “after seven days you’re really only just starting to get the hang of it and it would be a shame to go home at that point”.

We went for a 10.35m long Beneteau 331 boat which is an ideal family and beginners boat, though, by the time you’re reading this post, it’s probably a little outdated and replaced with something similar but more modern. We didn’t want anything too big for our first time, but I also didn’t want something so small it would be cramped for the four of us. 

Greek Island Flotilla Sailing

The Beneteau was essentially a luxurious and more spacious camper van, but on the water and with a sail (well two actually). There was a small but ample galley (kitchen sink, hob, grill, dining table), a shower room, and three cabins – one a double and then two with twin bunks. To be honest, other than when sleeping or using the radio, we spent very little time below deck. 

Not all flotilla companies allow complete beginners to hire boats, but Sailing Holidays were fine with this. Their boats are specially adapted to ensure they are easy to sail with “furling” sails that are easy to let out or draw in by just pulling the relevant colour coded line (also known as a rope to land-lubbers).

On arrival, we were ferried by coach to the starting port at the bay of Sivota on the island of Lefkas. We were shown to our boat which was named “Cordelia” and, just to emphasise the bond you’ll develop with your boat, I later named the family business after her (Cordelia Technologies). The flotilla’s engineer, Muzz, came aboard and literally showed us the ropes. He gave us a briefing on how to start the engine, prepare for sailing and what to do when we arrived in port. We then met up with the other crews and the rest of the lead crew for our first briefing, then had the evening to unpack, have a lovely dinner and explore the boat.

The briefings took place each morning, usually over coffee and croissants in a local cafe. We were shown a map of our route and any hazards such as shallow water or hidden rocks that were to be avoided. The skipper talked us through how we would moor at the destination port and roughly where he would be standing to guide us home, and then the Hostie gave us suggestions on nice swim spots en route, or picturesque bays where we could anchor for lunch.

A Helping Hand

The real benefit of a flotilla holiday is the variety of staying in a different picturesque Greek fishing village almost every night, always with a stunning, but unique sea view. Often the ports you stop at are off the beaten track as they’re not easily accessible by road and so are very quiet and calm, and have kept their tradition and cultures. You also build up a strong rapport with your fellow sailors, sharing stories of your experiences over a glass or two of local wine at the end of each day. But if you prefer to keep yourself to yourself, then that’s perfectly possible too. 

Navigating between ports couldn’t be easier. After the briefings, the first task is to enter the destination into the boat’s sat nav system. This then gives you a clear course to follow so it’s impossible to get lost.

We were surprised that, when out on the water, it wasn’t just a case of following the lead boat from port to port like an obedient row of rubber ducks. You leave port when you want to and the lead boat stays behind until the crew are sure all of the flotilla boats are on their way without any hitches. They then power directly to the destination harbour so they are there to help you moor when you arrive. In some cases, we would arrive at the destination before the lead boat, in which case we’d circle for a while just outside port, or maybe find a convenient place to drop anchor and go for a swim. 

Once out on the sea we were free to explore bays and coves en route or do a bit of sport sailing (or practicing the basics in our case) out in the open water. This was a great way to learn to sail on what was mostly calm and deserted open water. Each yacht also had a radio on a set channel, so that we could always talk to the lead boat or the other flotilla boats if we need help or advice – “is the beer cold at the taverna” being the most common one, “how can I be sure I emptied the sanitary tanks properly” being another (the answer being “look for the bubbles trailing behind the boat!”), followed by the shout we were all hoping for – dolphins had been spotted ahead.

Why Sailing Is A Great Holiday

During the holiday you will build a strong rapport with your fellow sailors, sharing stories of your nautical experiences over a glass or two of local wine at the end of each day. But if you prefer to keep yourself to yourself, then that’s perfectly possible too.  On a couple of the stops, the Hostie organised games such as dinghy racing, a beach barbecue and a cocktail evening, but all of these are optional if you prefer to be alone.

All of the boats had Diesel engines and if we’d wanted to it was entirely feasible to motor the whole time. However, that would mean we would have missed out on the thrill of silently coasting along under sail. Initially, my wife and daughter were a little nervous and insisted we left the engine idling in neutral even when sailing, as they were worried in case it wouldn’t restart (even if that had happened the lead crew and help was only a radio call away). After a few days, our confidence built, and before too long we were tacking (changing direction with the wind) like pros, well-improving amateurs anyway. Having the motor meant that inexperienced sailors like ourselves could sail into the wind (that is, when it’s easiest to do so) and then use the motor when needing to sail directly with the wind (which would normally mean zig-zagging (tacking) and slow progress to your destination). We also motored in and out of harbours, so don’t worry about having to tack in tight spots, there’s nothing to hit when you’re out at sea so you can experiment to your heart’s content.

One of the days was a “free sail” day when we could pick our own destination, sail to it, stay overnight and then make our own way to the next port when the whole flotilla would meet up again. You even had the option to just anchor in a remote bay, eat on board and just enjoy a night of pure solitude. The lead crew would radio the harbour master in your chosen port so he expects your arrival and can be ready to help you moor the boat. We chose the lovely tiny bay of Sportachori on Meganissi and as promised the harbour master was waving cheerily to us as we arrived in the bay, ready to guide us safely into the harbour. He also took our dinner reservation as he also owned the only taverna in the village which was right on the quayside.

As mentioned, each flotilla has its lead boat, which is crewed by a skipper, an engineer and a “hostie”. The skipper gives the daily briefings and guides you into your mooring spot at the end of the day. The trick is to not get overconfident and just do what he says. It’s easy to ignore him standing on the quay, signalling manically with his hands. Often he appears to be telling you to vastly over-steer, but he is experienced in each of the harbours and knows exactly how to read the currents and winds, and sure enough, when we diligently followed his commands, we’d glide gently into our mooring berth. 

Casting off (leaving port) and mooring (essentially, parking up) are great for family time. Each member of our crew had a specific job to do – get the fenders ready, throw the mooring lines to the skipper, steer the boat, lower the anchor etc. After a while, it worked like clockwork and we even rotated the roles so everyone had a chance to skipper the boat into port.

The lead boat also has a mechanic. Ours was the affable Muzz who worked tirelessly for what often seemed twenty-four hours a day, ensuring the ten or so boats were in shipshape. There was also “Cookie” our hostie, who is basically the fixer, calling ahead to book you into a mooring slot in the various ports, reserving tables at tavernas, organising the group events, buying food and drink for the group beach picnic and helping nurse the few cuts and bruises.

On our final night Cookie organised a farewell party where much food, drink and merriment was had by all. At the end of the evening, we were surprised and humbled to be voted the “most improved” and awarded a “zeroes to heroes” certificate (to be fair we’d started out with so little skill and experience that improvement wasn’t that difficult a task!). In all seriousness, we’d improved as sailors, simply by listening to the Skipper and doing exactly what he asked us to, trying to relax and just by having a go. One of the most rewarding parts of the holiday was our arrival in the port of Nidri on Lefkada. During the briefing, we’d been warned that it was quite a tricky stern-to (reverse parking) mooring onto a flimsy wooden jetty with quite strong crosswinds and against the tide. As it happened, we glided in like professionals with the lead skipper standing on the jetty, arms behind his back letting us get on with it. It was a real joint sense of achievement, especially considering that as we readied the boat for the evening, other more professional sailors, struggled to moor often taking several attempts.

Life Onboard

In terms of comfort onboard, with hindsight, I’d have gone for a slightly longer (38 or even 40 footer) and slightly newer boat, as the better, modern designs have improved comfort and space on deck and down below. Talking to our lead boat skipper suggested that a larger boat is no harder to sail, if you can sail a 33 footer, you can sail a 40 footer, we were told.

The cabins (bedrooms) are a little cramped and can get hot at night, but you spend most of the time on decks or ashore. You’ll also be so tired after a day at sea followed by a large Greek meal and several drinks, that you’ll hardly notice the heat after a couple of nights and sleep like a baby, with the gentle movement of the boat rocking you to the land of nod.

We ate onshore at the traditional tavernas in each port and ate only lunch on the boat, which usually consisted of deliciously salty local feta cheeses with ripe tomatoes and olive oil, the juiciest of peaches, fresh warm bread and melt-in-the-mouth slices of cured hams. Oh, and not forgetting those amazing giant ring doughnuts that were freshly baked at the village bakeries each morning. The food and water were readily available from the small supermarkets in each port. Onboard there is a fridge that is turned off when the motor is off in port or when under the power of sail, in order to preserve the battery. We learned to keep the fridge and its contents cold by placing a couple of frozen bottles of water inside, which you can drink cold at the end of the day. In some ports, you could hire an electric cable that gave power to your boat overnight, but we never bothered with this.

There’s a perfectly adequate toilet (the head) down below, but it was important to remember to flush out the tank when out at sea and not in port! We did have a problem where we were pulling the wrong lever for the first few days and draining much of our freshwater into the sea instead of the waste, we wondered why there were no bubbles in the water! We tended to pay a couple of Euros to enjoy a hot, power shower onshore at one of the many tavernas that cater to the visiting flotillas. My daughter washed her hair off the back of the boat using the outdoor shower. After a few days, you’ll get into the swing of things and forget about being so clean and perfectly presented all the time, sporting just the best ever tan you’ve had, your swimming costume and sunglasses the whole time.

For those with smaller children, you can request deck nets to be installed. These prevent small people from falling overboard. There are also life-vests on board.

Should I Go Ahead And Book?

Yes. Go on, give it a try. You’ll learn new skills, get a fantastic tan, see and explore beaches, bays and villages none of your friends will have even heard of, and best of all, meet a whole group of new like-minded friends. Trust me, we did it, so anyone can do it, it’s a once in a lifetime experience (unless you get addicted and it becomes your life!). In future years, when the kids are all grown up, it will be something you’ll reminisce about fondly over Sunday lunches and barbeques.

Make it Happen

I booked directly with Sailing Holidays, initially through their website ( I also had a very useful phone call with them where they helped ensure we reserved the correct yacht and answered any questions or concerns I had.

A one-week early or late season flotilla starts at £525 per person including flights from several UK airports and transport from the airport to your boat. The two-week South Ionian flotilla I went on starts at £625 per person. There are reduction for children. We paid £50 to have a skipper on board with us on the first day.


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After travelling internationally on business for multiple decades, I have decided to take early retirement. I am now fulfilling two dreams. To travel more slowly and to write my own thriller novels.

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