For one week this Summer, we were the captains of our own Greek adventure. With none of the usual household chores and without so much as opening my laptop, we simply enjoyed quality time together — and a generous stretch of Ionian blue. Welcome to the charming pleasures of a flotilla sailing holiday — courtesy of Sail Ionian, an independent family-run company operating out of Vliho Bay, Lefkada.

Without being complacent, we were looking forward to some hopefully easy sailing in friendly winds, short hops between islands, and a sun that rarely clocks off. Most of our training had been in somewhat less inviting conditions off the west coast of Scotland, but this would hopefully have put us in good stead for anything unexpected.

The idea of sailing in a group — in convoy, but with the freedom to roam and support on hand — offered the perfect blend of independence and reassurance.

What is a flotilla holiday?

A flotilla is a small fleet of boats — usually no more than ten — loosely travelling the same route. Each evening, everyone gathers at the same port or anchorage, but by day, you’re free to sail, explore, meander, race, or pause as you wish. Some companies offer a social programme each evening, whilst others — like Sail Ionian — do not, allowing you to mix with others as much or as little as you like.

Support comes in the form of a lead crew who guide, advise, and occasionally step in when you’re struggling to moor. It’s camaraderie with a light touch. Guidance without intrusion. And our expert flotilla support team included skipper Maria (who went by the radio name of Rodney for some reason!), Ervin, and Nick — all calm under pressure, and always appearing precisely when needed, like nautical genies.

What’s required to sail a yacht?

In Greece, at least one person on board needs an ICC (International Certificate of Competence) or an RYA Day Skipper qualification. A second adult must be at least at the level of ‘Competent Crew’ — essentially someone who knows their port from their starboard and won’t tie themselves to the boom during a gybe.

To become an RYA Day Skipper, there’s a theory and practical component — with at least 40 hours of study recommended for the theory, whilst the practical element is a 5-day course (but assumes a degree of prior experience, such as the 5-day RYA Competent Crew course). Once you have the RYA Day Skipper qualification, you can get ICC certification but this is not currently required for Greece – just the Day Skipper will suffice.

We were a mixed party of ten adults across two families — four qualified Day Skippers of differing expertise in our family and six enthusiastic novices in the other. We had initially looked at chartering two yachts but regulations would not have allowed us to regularly chop and change the personnel on each both, so we instead opted for one boat to accommodate us all.

This made for an ideal balance of experience and fresh-eyed wonder, with enough skill to sail independently but no shortage of awe for what we were about to experience.

Our yacht

Our floating home for the week was Te Anau, a Bavaria 46 Style yacht, which Sail Ionian keeps in immaculate condition.

She boasts in-mast furling, a self-tacking genoa, bow thruster, generator, and that rare Aegean luxury — air conditioning. The cockpit was spacious, shaded by a bimini, and the saloon was equally generous.

Te Anau sleeps ten people – up to four with an en suite in the bow, two en suite rooms either side of the aft, and a saloon that can accommodate another two or three. Of course, with ten of us on board, it was cosy – but we knew that would be the case and were prepared for it… it’s a good job we get along well. As the week progressed, several of us preferred to sleep under the stars on deck as that tended to be lovely and cool.

There was a lovely welcome basket that greeted us on arrival, too.

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Our route

Our route was to take us around the South Ionian, calling at a variety of different islands, with the exact itinerary evovling as the week went on, depending on the weather conditions. Here’s where our journey took us:

Day 1: Vliho Bay, Lefkada to Vathy, Meganisi

Sail Ionian doesn’t dilly-dally. After a welcome briefing and yacht handover by Chris, we were off the dock and motoring through the Vliho strait by late afternoon. The sea was gentle, our spirits high, and we were looking forward to the adventure that lay ahead.

We cut east between Skorpios and Sparti — Skorpios once owned by the Onassis family, now shrouded in billionaire mystery. Our destination: Vathy on Meganisi, where a table awaited us at Karnagio, a beachside taverna draped in bougainvillaea and charm. A few of us paddleboarded after dinner, because… why not? When in Greece…

Day 2: Vathy, Meganisi to Sivota, Lefkada

The morning involved the moving of fenders and a little parking practice before setting off again. Between Meganisi and Lefkada, we caught a fleeting glimpse of dolphins — too quick for the camera, but enough to put big smiles on our faces.

We dropped anchor at Mikros Gialos for a swim and snorkel, before continuing to Sivota, where we moored outside Taverna Ionion. Our waiter there was quite a character and even posed for a selfie with our group, told us a tale or two, and served us the catch of the day — red snapper and dorada, simply grilled, perfectly flaky.

Day 3: Sivota, Lefkada to Fiskardo, Kefalonia

The wind was in our favour. We sailed — actually sailed — most of the passage at around 4-5 knots, a kind of unhurried pace that makes you realise time on the water flows differently.

Fiskardo is no secret — a pastel-painted harbour where superyachts jostle with charter boats and the scent of jasmine competes with espresso. We made landfall early to secure a space and took the tender to Foki Beach, where we explored a once-mined limestone cave with tunnels that extend over 100 metres deep.

Dinner that night was a curveball, recommended by our support crew: Lord Falcon, a lovely Thai restaurant tucked away in one of Fiskardo’s back streets.

Day 4: Fiskardo, Kefalonia to Vathy, Ithaca

There are many Vathys in Greece, and today we visited another: the one on Ithaca, fabled home of Odysseus and proud bearer of one of the deepest natural harbours in the Ionian. (The name ‘Vathy’ comes from the Greek word “βαθύς” (vathýs), meaning “deep” — an apt description for the sheltering harbours that bear its name.)

We stopped first at Filiatro Beach — turquoise, crystalline, postcard-perfect — and spent an hour swimming, lounging, and paddleboarding. That night, securely anchored, we skipped the taverna and cooked aboard Te Anau . A dinner with the stars as our ceiling.

Day 5: Vathy, Ithaca to Kalamos, Kalamos Island

After a morning stroll, we sailed ownard toward Atokos Island, a dramatic hunk of rock with aquamarine waters — and pigs.

Yes, pigs. With different theories abounding as to why they’re there, from shipwrecks to a source of food, they’ve become unlikely icons. But if you should visit, please remember these are feral animals and don’t pick them up as we saw one child attempt… the piglet’s mother did not seem so happy!

Later, we reached Kalamos, where we wandered to Alogoborós beach, the most wonderful secluded cove which we enjoyed to ourselves.

Dinner was at George’s taverna, a local favourite with the most delicious chicken souvlaki.

Day 6: Kalamos, Kalamos Island to Palairos, mainland Greece

A number of us — myself included — had been running each day. This morning’s challenge: a 180m climb to the church of Agios Georgios before breakfast at George’s. Built in 1886, this lone basilica offered sweeping views and, perhaps, a little cardio-induced clarity.

After a day on the boat, having stopped for a swim in a lovely bay just east of Mytikas, we anchored off Palairos, took the tender ashore, and found a bar with cold refreshments and a pool table. We enjoyed dinner on board at sunset.

Day 7: Palairos, mainland Greece to Vathy, Meganisi

With storms in the forecast and our flotilla return imminent, we decided to head back to Vathy, Meganisi, returning to a familiar bay where we knew the taverna. But before that, we anchored at Pachara Bay, cooled off with a swim and messed around on the paddleboards either side of an on-board lunch.

Day 8: Vathy, Meganisi to Vliho Bay, Lefkada

A short, quiet morning motor brought us full circle. The Ionian sun had shone all week and we were now a little more tanned, a little saltier, and entirely smitten.

We packed our things, disembarked Te Anau and had a late breakfast at Vliho Yacht Club, before our respective families said our farewells, but not without promising to do a similar adventure together next year. Our holidays were not as we each had a few days left – us in Greece still, and the other family returning to the United States via Italy.

The final verdict

Often when people think of luxury yachting holidays, they might think of silver trays and white gloves. This wasn’t like that all – it was something better. It was informal, magical, mildly chaotic (there were ten of us on board after all), and utterly joyful. And the luxury came in the form of time together, endless laughter and a truly memorable experience.

We took selfies with pigs. We ate red snapper that was caught just hours earlier. We somehow managed to cram eight days of being on the boat into a seven-day florilla. And the flotilla set-up gave us freedom with a safety net. Adventure with guidance. Independence without isolation.

Would we do it again? Absolutely. Though next time, we might keep a tally of how many times we said, “This is the life”.

Disclosure: This post is sponsored by Sail Ionian. Our trip was sponsored by AEGEAN Airlines.

Paul Johnson

Paul Johnson is Editor of A Luxury Travel Blog and has worked in the travel industry for more than 30 years. He is Winner of the Innovations in Travel ‘Best Travel Influencer’ Award from WIRED magazine. In addition to other awards, the blog has also been voted “one of the world’s best travel blogs” and “best for luxury” by The Telegraph.

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