A boat only has to float. You aren’t flying an F16. Once you are underway in good weather sailing can seem simple. All you need do, once the sails are up and trimmed to the wind, is sit and gently helm.

That’s how it was for us, three freshly qualified skippers beating through deep blue water along the Ionian coast — friends in our early thirties with a chartered boat and no one else on board.

Tom, Charlie and I had all mucked about on boats for a decade, serving as incompetent crew for my father on sailing trips around the Mediterranean. But we hadn’t learnt much at all, other than how to lie down with a book in hand while occasionally pulling in a line or letting out a sail. We thought it about time we became more capable, to enjoy the freedom of the seas for ourselves.

Man steering a sailboat in Greece.

Harry Lambert learned to sail around the Greek islands

When you land at Preveza, on the Greek mainland, you land on historic terrain, though you wouldn’t know it. It’s where Marc Anthony gathered his men shortly before his decisive clash with Octavian for control of the Roman empire. They fought in the nearby sea, Cleopatra escaping with her fleet after Anthony’s defeat, the republic in ruins.

Although there are plenty of places to achieve the day skipper qualification in the UK, we had come to this area for a week in the spring to complete it in advance of our summer holiday. We chose Sail Ionian, a family-run business based in Vlicho, a spectacular bay on Lefkada, the one island in the Ionian connected to the Greek mainland by a long causeway.

We had stepped aboard tentatively on hearing that our instructor for the week was ex-military, imagining long days scrubbing decks and being ordered to wake at 0600 hours. But Craig Thornley turned out to be more of an intense wanderer who had gone from not knowing how to sail to being an instructor in five months, a feat he’d also accomplished as a skier. We had toured the inland sea, getting to know a number of places to which we now planned to return. Craig later told us he knew he could pass us within the first hour of meeting us; a show of confidence that wasn’t entirely warranted, as our return trip would prove.

Sailboat sailing in a Greek bay.

Harry and his friends chartered a Bavaria C42 boat

12 of the best beach holidays in May

Before setting out to sea, we ate that first night at Pavlos, a hillside taverna a ten-minute taxi ride from Vlicho that was pleasantly busy and served delicious cuts of chicken and pork from an open grill (mains from £13; lefkadaopen.gr), then slept onboard our Bavaria C42, moored in Vlicho harbour.

We set out the next day as a trio, bolting across the bay for a drink before sunset in Palairos, a gentle west-facing village, where we had two more friends to meet who had signed up as crew under our nominal command. Out at sea alone for the first time, we were free at last. All the Mediterranean lay in wait. We would go wherever the wind took us, with plans to alight on the nearby island of Ithaca within a day or two.

Leaving Vlicho was stress-free; we had simply motored out into open water. The difficulties come when you have to go in or out of a bay, or the weather turns, or night falls. You only truly discover who is able to command a boat when you get into the narrow marinas. That’s when someone has to execute sharp turns in a fibreglass can three times the length of a car, one that is always moving, has no brakes and that must not, under any circumstances, hit anything.

Despite that, life at sea has been made much easier by the invention of an essential on-board machine: the AIS, or automatic identification system. First made mandatory on large commercial vessels in 2002 it allow ships to view marine traffic in their area and to be seen by that traffic. This live digital dashboard — a Google Maps for water — is only meant to supplement the careful study of a paper chart. In practice it supplants it, showing shallow water, marinas, safe anchorages and no-go areas. In small bays you use it to navigate between other yachts; at sea it alerts you to potential collisions with 400m tankers; and at night it will help you to discover the owner of the searingly lit superyacht anchored off shore.

Our C42 came with two other modern inventions: a self-furling mainsail and a self-tacking jib. The main — which rolled into the mast, rather than falling down along the boom — was a welcome difference from our training boat. The jib initially seemed like it would make sailing too easy. In training we had tacked like mechanics in a pit; one of us steering the boat through the wind, another releasing the windward sheet and a third pulling in the leeward line, tightening the jib to its new angle. That synchronous dance was no longer necessary.

Palairos beach in Greece with thatched umbrellas and mountains in the background.

The beach at Palairos

GETTY IMAGES

Plenty else would be, we would soon find, and it didn’t take long to realise how much we didn’t know. On the second day we chased a strong wind down the mainland coast, where a few sun-drenched homes dotted a shoreline of otherwise unbroken shrubs. We found the wind, which pushed us obligingly along the coast, and then began to push us onto it. We didn’t yet know that we were being overpowered; we had too much sail up to turn our boat away from a dawning encounter with jagged rock. We revved the engine, attempting to drive the boat out to sea like a car, but horsepower can’t beat wind. You have to sail, as we eventually realised, reefing our sails to control them.

We anchored that night off Kastos, a thin spit of an island with two neighbouring tavernas — one for fish, the other for meat — and a good bar, El.a Café (£8; no website).

A day later, now a party of six having collected my girlfriend in Agios Nikitas on Lefkada, I insisted we cross late in the day to Ithaca, the mythological home of Odysseus. Inaccessible other than by boat, the island lacks some of the characteristics described by Homer — it isn’t the westernmost island in the Ionian, as described, for a start — but it is as captivating as anywhere in Greece. Tourism hasn’t overtaken its population of 2,800. If you have the time, the best way to explore the island is by moped, available for rent in the two main towns, Vathy and Kioni.

Interior of a sailboat, showing the galley, seating, and stairs to the cabins.

Inside a C42 boat, which can sleep up to eight people

MICHAEL HARTZ PHOTOGRAPHY

We sailed fast for Kioni, catching the reliable wind that blows through the channel between the islands, hitting 8.7 knots (10mph) — quite fast for our type of boat. But I’d set out on a voyage for madmen, having pulled rank as the one who had procured the boat, upending the normal system of majority rule on board.

The first warning came as we reached the shore. Kioni was ringed by large hills and faced northeast, which meant the sun was setting faster than we had planned for. We were out of direct light by the time we reached the bay, which was packed. It was the middle of August.

16 of the best quiet Greek islands

We had expected to find a kindly mariner who would see us in, but we had come to an unmanned port that was pretty much full. We found a solitary slot on the edge of town. We would have to approach stern-to, backing into the space as you would park a car. You stop a boat by dropping anchor; in 10m of water, you drop at least 50m of chain. But that only stops you going back once it bites; you still need to hold steady if you are near to any other boats. We’d need to run stern lines ashore, wrapping them around rocks to create tension.

What we hadn’t realised is that we needed to do that before backing into place. We reversed in and promptly drifted into the boat on our starboard side, a line of fenders sparing us from impact. We retreated to the middle of the bay, night having now fallen. Two of the crew took our dinghy ashore, rowing in as we had no time for them to affix the outboard motor, stored on board. When they told seasoned skippers in Kioni’s restaurants of our plight, they said we should go to Vathy, an hour away.

Sailboat deck and harbor view in Greece.

Harry and his friends hit 8.7 knots (10mph)

MICHAEL HARTZ PHOTOGRAPHY

We made one last attempt to stay, dropping half our anchor chain into Kioni’s narrow channel, until the owner of a nearby boat asked what would happen if the wind changed. Before we could answer he did so himself. “You’ll hit me,” he said drily.

And so we made for Vathy, heading into the black of the night, the AIS giving us the confidence to move. The wind that carried us to Kioni had, by luck, died away, so we motored down the coast under a starlit sky, arriving at last to find plenty of water shallow enough for us to anchor in. We came to rest in a ring of light from the shore and even though it was a quarter to twelve, we had a fine meal of the day’s catch, roast potatoes, Greek salads, saganaki and tzatziki at a wind-beaten taverna, Porto (mains from £12; portovathy-thassos.gr). This was the magic of having our own boat — we could always sail away and find somewhere new.

Two days later we rendezvoused with my father, who was staying on Lefkada for a week. He expected us to arrive by car, but we called him from the boat, telling him to look out towards the bay. Did he see the yacht with its sails up? We were on it, we told him. “Blimey,” he said, “do you have any idea what you’re doing?” By then, at the end of the week, we could say we just about did.
Harry Lambert was a guest of Sail Ionian, which has seven nights’ charter for eight from £1,430. Six-night day skipper course from £1,170pp, including accommodation onboard, plus £265pp for the accompanying Royal Yachting Association theory course (sailionian.com). Fly to Preveza

Three more sailing trips

By Katie Bowman

Learn to sail: Portsmouth, UK

Women learning to sail on a sailboat.

Sail the Solent with Sunsail

Sunsail’s schools are some of the best in the business, offering internationally recognised Royal Yachting Association (RYA) qualifications at both UK and overseas destinations. If you want to get the certificate under your belt and worry about the holiday later consider Portsmouth, sailing the Solent. Options run from a two-day beginner course through to competent crew (essential if you want to work on yachts yourself, à la Below Deck) to the week-long yachtmaster.
Details Two-day RYA start yachting course from £299pp including two nights’ accommodation, breakfast and lunch on board (sunsail.com)

First charter when qualified: Croatia and Montenegro

Sailboats moored in a harbor.

Joining a Seafarer flotilla is a social way to sail

MICHAEL HARTZ PHOTOGRAPHY

So, you’ve got your qualifications but it’s your first trip sailing solo? Joining a flotilla is a great option, since you’ll sail alongside other boats and it offers the chance to socialise and compare notes each evening. Seafarer runs week-long trips from May to October, in and out of Dubrovnik, ticking off Mljet and Korcula in Croatia and as far south as Budva in Montenegro. Yachts are three-cabin: big enough for a family holiday.
Details Seven nights’ self-catering for six from £1,839, including accommodation, a tank of fuel and crew assistance (seafarersailing.co.uk). Fly to Dubrovnik

Sailing with a skipper: a gulet in Turkey

Sailboat anchored in a calm bay in Turkey.

Nautilus Yachting’s Turkish gulets sleep up to 22 guests

GETTY IMAGES

With one and two-week charters sailing out of the gorgeous coastal hubs Bodrum, Gocek and Marmaris, Nautilus Yachting are the folks to call if you’ve always wanted to experience a Turkish gulet. The beautiful traditional wooden sailing boats are fully crewed with an experienced captain and chef, so you can be as hands-on as you wish. Captains are happy to show passengers the ropes and dictate routes, so it’s your show if that’s what you want. Gulets sleep 8-22 people and often include windsurfers, kayaks, canoes, kneeboards, water-skis, wakeboards and inflatables, as well as snorkelling and fishing equipment.
Details Seven nights’ gulet-only for eight from £9,100 including crew assistance (nautilusyachting.com). Fly to Bodrum

Become a subscriber and, along with unlimited digital access to The Times and The Sunday Times, you can enjoy a collection of travel offers and competitions curated by our trusted travel partners, especially for Times+ members

Sign up for the travel newsletter and follow us on Instagram and X