How to spend a week sailing around Greece’s Ioanian islands

“Ready to tack?” a voice shouts. Before I can ask what that means, the sails flicker and the entire boat suddenly tilts sideways. Dishes and bowls of fruit crash against each other inside the cabin. I grab hold of the railing and laugh nervously, but the smiles on my crewmates’ faces reassure me that this is a good manoeuvre. Moments later, we catch the wind and we’re off. Apostolis Tsiokos, our tanned,silver-haired skipper, is humming along to We Are Sailing by Rod Stewart.

The 52ft monohull yacht, Neifinn, can accommodate up to 11 crew members but, this week, there’s only three of us on board: me, Apostolis and Loïc, a passenger from France. We’re just one boat of the 11-strong flotilla — a convoy of nine other monohulls and a catamaran, with sailors from around the UK, Germany and the US, as well as a lead boat helmed by Sunsail’s local team. We all met yesterday on the island of Lefkada (sometimes known as Lefkas), which sits in the Ionian Sea just off the west coast of Greece. It has deep connections to Homer’s epic poem The Odyssey — German archaeologist Wilhelm Dörpfeld believed modern Lefkada was Odysseus’s ancient Ithaca. Today, the island draws visitors to its many interesting historical sites, and to its golden bays for windsurfing and other watersports.

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“The Ionian Sea is a paradise,” says Apostolis in a slow, baritone voice. “It has a lot of islands, beautiful beaches, welcoming ports, quiet places… I like this job and meeting different people from all over the world.” The 60-year-old Lefkada native spent most of his adult years teaching PE and worked as a skipper during the school holidays. When he retired from teaching he continued skippering, and now has clients that book with him time and time again.

Sailing south from Lefkada towards the smaller island of Meganisi, the gentle wind blows us and we glide effortlessly along the calm, silky surface of the water. En route, we pass the small, private island of Skorpios, which is notable for being the spot where Jackie Kennedy married Aristotle Onassis in 1968. Transformed from barren to verdant by the Greek shipping tycoon, it’s still known as ‘Onassis Island’ nearly 50 years after his death.

Meganisi, positioned southeast of Lefkada, is renowned for its sea caves, including Papanikolis Cave, a rumoured hiding place of the eponymous submarine during the Second World War. Eager to experience this history for ourselves, we anchor Neifinn near the grotto and climb into the tender boat (dinghy). As we row closer towards the shadowed cave, the temperature plummets and the cool stillness envelopes us. The sound of the waves lapping against rocks echoes through the enormous cavern. White-washed crags, stained with red algae, peak out just above the surface of the water. We sit quietly for a few minutes to absorb the calm before heading back to the yacht. As we sail away to our stop for the night, Meganisi’s Vathi Harbour, the jagged, grey cliffs and the intensely blue water swiftly conceal their secret hiding place once again.

Before following our flotilla from Vathi to the island of Kastos the next morning, the lead boat announces over the radio that we’re going to have a regatta — but the lack of wind makes for a relatively slow race. We bob around a little and that dreaded seasick feeling washes over me. I pause to remember what I’d spoken about with Dee Caffari — an MBE and record-breaker for sailing around the world nonstop three times — who’s part of our flotilla. Before we set off on our voyage, she advised me: “Actively engaging in the activity really helps. If you have something to focus on, like driving or looking at the horizon or the sails, you don’t have time to think about feeling sick.”

Apostolis ushers me to the helm to pilot the boat. He instructs me to keep my eye on a specific part of the jagged mountain top in the distance and guide the boat towards it. He smiles and nods approvingly as I drive. The seasickness fades away and I take pride in my new entry-level sailing skills.

As we approach Kastos, a stone windmill-turned-taverna stands alone on the hill to the left of the bay. On arrival, I find mountain goats and cats to be the main inhabitants, bar a small number of permanent residents who run the shops and tavernas. A family of goats trot nonchalantly through the town square as I walk by. When I make my way up the hill towards to the restaurant, another goat watches me weave around the tiny, prickly cactuses dotted on the pebble path. We sit for dinner by the water at Taverna Belos, joined by other crew members from the flotilla, and admire the boats swaying softly in the tiny harbour. I devour a plate of saganaki (pan-seared cheese) and a huge portion of fried calamari. The rest of the menu is full of Greek favourites such as pork souvlaki, kolokythokeftedes (fried courgette balls), lamb chops and aubergine salad.

A few hours of relaxed sailing from Kastos brings us to the town of Kioni on the island of Ithaca — just off the northeast coast of Kefalonia. “The three most important sailing tips are: drink water, drink coffee and smoke cigarettes,” Apostolis chuckles, as he releases a cloud of pungent vape. “After the first coffee, my mind starts to work, but before this… nothing.” I nod in agreement as I sip my freddo cappuccino. Loïc and I decide to hike into the quiet hills to search for Kioni’s prominent lighthouses. The punishing afternoon heat gets to us before we find them, so we begin the trek back to the boat. En route, an elderly lady observes us from her porch and her face lights up when we greet her. Smiling, she offers us a coffee. We thank her but persevere with our journey — we’re being treated to a hearty, slow-roasted lamb kleftiko dinner at Calypso restaurant later.

The next day, anchored just off the beach of Mikros Gialos in southeastern Lefkada, I dangle my feet in the cool water as I sit on the back of the boat. Apostolis breezes towards me — clutching slightly stale bread in one hand, his e-cigarette in the other. I break up the offering and drop a piece in the water. This must be the favourite meal of wrasses — a breed of shiny, bright blue fish often found in these waters. The entire school darts to each piece I toss, their stripes glinting in the sun.

(Why you should go beach-hopping by boat around Paxos, Greece.)

Later, we dock in the busy port of Sivota, a village on the southern coast of Lefkada. It’s dotted with boutique shops, cafes with fridges full of gelato and tavernas touting cold beers. Tonight, we’re expecting a full moon and Apostolis knows the perfect place to watch it. As in every port, he’s greeted almost like a celebrity, shaking hands with all who cross our path — he seems to know everyone, and everyone knows him. We head to Stavros Taverna, overlooking the harbour where we’re welcomed warmly by the elderly owner Stavros, who keeps a watchful eye on his guests and their needs. I sample a range of delicious starters recommended by Apostolis, followed by some squid ink risotto and a moussaka.

“People think a sailing holiday is all sailing, 12 hours a day, but actually, it’s more like moving your hotel room to a different location” Dee explains at dinner. “You can snorkel, swim, bike, discover the village, eat great food. You explore more of the destination in an enjoyable way and go to places that other travellers may not get to go to.”

Her words echo in my mind as we stop at a secret beach before beginning our journey back towards Lefkada. There’s not another soul in sight. The turquoise water glistens in the sun as it gently rolls onto the shore. We have the whole white sand beach to ourselves.

“Sailors are smart, quiet people,” says Apostolis. “We might look lazy, but we’re always watching: the wind, the sails, what’s on the horizon,” he trails off, raising the sails for our final day of sailing.

“Slowly, slowly,” he directs an eager Loïc. “We have time. We’re never in a hurry.” I’d raised the anchor earlier, feeling fulfilled, like I was slowly getting the hang of sailing. I can feel the wind pick up and I know what’s coming next. I’m prepared this time — like the maids in Mary Poppins taking hold of all the valuables before the admiral fires his cannon. I grab hold of the loose items within arm’s reach and stand poised, ready to tack.