Where the winds take you

A year ago, Ben and I were about to embark on a journey back to the Greek Islands, revisiting some of the places we discovered together in 2006 – when we met.

Our skipper from the sailing trip in ’06, Patrick, would be at the helm again. We’d get to see new places, we’d make new friends, and we’d celebrate a decade since we first met on the pier in Santorini.

This is about where the winds take you…

There’s something rather magical about going where the wind takes you, quite literally. The cares and stresses of everyday life ebb away, and the present becomes everything. Briny air, inky blue swells, and a wind that carries you and your fellow sailors to the next port. It’s freeing.

Seven people, one yacht, five Greek islands and one incredible week.

Group pic - sailing trip

Day One

We meet with eager faces at the port of Vlychada on the southern coast of Santorini. The marina is abuzz with energy as dozens of people chatter loudly and mill about between the dock and their vessels, a mixture of pleasure craft and fishing boats. The weather is a perfect 28°C with a warm breeze and only a few clouds in the vibrant blue sky.

Our Skipper, Patrick, shows us to our boat, the Argo, and we take turns to climb aboard and explore below deck, unpacking what we can into cubbies and stowing our luggage. The Argo will be our home for the next week. I take off my watch and stash it away, because I won’t need it today. Time moves differently when you’re on a boat.

Our boat

We are seven, including Patrick, our ages ranging from mid-30s to mid-50s. We are across industries and continents in our everyday lives, but for the next week we will be the Argonauts, as dubbed by our Irish boatmate almost as soon as she is aboard. Both her laugh and instant camaraderie are infectious.

Tonight, we will anchor just off Akrotiri on Santorini, as the winds will be more favourable for our sail up to Ios in the morning. None of us mind. The view is beautiful and we enjoy swimming off the boat in the deep Oxford blue water. Colours, particularly of the water, will be important to the Argonauts, because every day we sail, the Aegean will reveal its vast palette and we will discover that the waters off each island are distinctive.

We watch the sunset over the island, and then break into two groups for a short ride to shore on the tender. I’m in the first group and we pull up at a restaurant where the tables are surrounded by water on three sides. A tall waiter sees us coming and hurries to help us ashore, a task that sounds simpler than it was, with the water line 3-feet below him. Patrick returns to the Argo while four of us get settled and devour the menu with our eyes.

When the others join us, we order practically one of everything and chat amiably over fresh seafood, deep red and delicious tomatoes, and tangy dips with crusty bread. We drink table wine, which is surprisingly drinkable. We don’t finish everything on the table, but we are full and when the sun completely disappears, we make our way back to the Argo. It takes only a few minutes to get used to the gentle rocking as we drift asleep.


Day Two

Sailing through the caldera offers a magnificent view not just of Santorini, but also of Thirasia, the island sitting opposite, and the ever-evolving Palea Kameni which is situated in the caldera’s centre and was site to the cluster’s most recent eruption in 1950. Looking up at Fira and the other towns that cling to the rock faces, you can’t help wondering how they stay there and what feats of engineering got them built in the first place. It’s stunning.

We moor for lunch in a cove just off Thirasia with a perfect view of Oia, the town perched on Santorini’s northernmost point. The water here is cooler than off Akrotiri, but after a simple lunch of tomatoes, bread, tzatziki and cheese, we swim off the boat until we’re called back aboard by our Skipper. For the first time, we will be solely under sail as we begin our trip north to Ios.

Patrick gives orders to his crew of civilians with the ease of someone who has done this many, many times before. With his guidance and good humour we make ourselves useful, raising the sails and setting course for the port of Ios. Once underway, he directs several of us to sit on the windward side of the boat. It will make us sail faster and is also a better spot for those of us with seasickness. Some of us – me included – do not have our sea legs yet.

The undulating sea is mesmerising and the seasickness does recede as we talk about nothing and everything. We will find that we form friendships quickly with so much concentrated time to get to know each other. Every once in a while, as we change tack, there is a burst of energy as we’re all given something important to do.

Ios emerges in front of us through a low haze, and before long we can make out the brilliant white of a church standing guard at the entrance of the port. As we get closer to our destination, we erupt into action as we make ready to dock. The port is crowded, but we ease into a berth between a luxury yacht and another sailboat, its Italian skipper lending a helpful hand as we secure our moorings. I am fascinated by the easy camaraderie of the two skippers despite being strangers and not speaking each other’s language.

Docked in Ios

Ios is bustling. It reminds me of Fira, only the crowd here seems to be mostly of twenty-somethings. We’re here for dinner, then to sleep the night and we will be off after breakfast. In the interim, we must shop for the following four meals, and will be on water rations until we reach another serviced port in two nights’ time. Patrick’s promise of a spectacular and secluded spot to spend our third night has us intrigued.

Dinner that night is close to where we have docked – we can see the Argo from our seats – and we order cheap, traditional food. Once again we don’t clear our plates, because it is so plentiful. Ios is alive. Children play loudly nearby as we eat, adults laugh and toast each other, and there is a thrum of energy. At a time when I would typically be asleep, it seems like Ios is just getting started. After dinner, we seek out the ice cream parlour and wait in a long, but fast-moving line. The ice cream is excellent and more reminiscent of gelato.

I wonder at being able to sleep aboard a boat docked in such a busy marina, but lull of the rocking sends me off peacefully.

Day Three

The supermarket is busy, extremely busy. The narrow aisles are crowded with goods and tourists. We have a long list and four of us are navigating with two trolleys. We need four meals, snacks, bottled water and drinks – wine and beer. One of us knows a bit about Greek wine and is scouring the wine aisle for some good picks. We check out having spent far less than we’re all used to spending in our respective home countries, and the frenzy of the market will prove a vast contrast to the second half of our day.

We are heading towards a secluded bay on the island of Dhespotiko, a spot Patrick found on his last trip. The sail is shorter than yesterday’s and I find that I am acclimating to the rhythms of the Aegean and finding my sea legs.

As promised, the hidden bay is incredibly beautiful. The island rises sharply from the water on either side of the narrow bay and is covered in reddish rocks and tufts of green. We anchor just off a small sandy beach and are the only boat in sight. The water is clear and we can see to the sandy depths. One of us, David, is a diver and he gears up to set our moorings below the water. The rest of us swim or prep for dinner.


It takes a few runs with the tender to ferry all of us, along with the fixings and tools for a BBQ, across to the beach. Tonight, we will eat by moonlight, a selection of meat, seafood and vegetables grilled under the stars. The warm water laps at the tiny shore and we mix cocktails of spirits and juice, sipping from plastic cups as we watch the sun go down. The food is incredible, as is the reflection of the moonlight on the small bay. We laugh and talk and poke sticks into the fire. Late at night, Patrick ferries us back to the boat for a very quiet night’s sleep.

Day Four

We are in no hurry to leave the unnamed bay the next morning, all of us wanting to get the most out of this unique location. Some of us swim, others set off to climb the giant hill that overlooks the beach. Even from only half-way up the vantage points will produce some incredible photos. The Argo is a long white sliver in an arrow head of vibrant blue, both cupped by rugged red earth. After following a goat track back down the hillside, I leave my camera, shoes and clothes in the tender and swim back to the boat from shore. It is exhilarating being in this water. I want to stay all day.


Eventually, it is time to leave and we say goodbye to what our Irish boatmate has now dubbed Artemis Bay, in honour of the moon goddess who provided such great lighting for our beach party the night before. Our next stop is the port of Vathi on Sifnos.

Again we sail with only the power of the wind, four of us taking our places on the windward side. I love this spot on the side of the boat, watching each swell approach. Some of the swells break against the hull and send a wave of cool water over us as we laugh and squeal like children at a water park. We arrive at Vathi salt-crusted, sun-warmed and eager for dinner at the waterside restaurant that Patrick has suggested.

We anchor in the middle of the bay surrounded by calm water, and even though there are a couple dozen other boats, it is peaceful here, a nice contrast to the vibrancy of Ios. Two tender rides from the Argo and we are all onshore. The water laps at a narrow shoreline as we walk – sometimes in the water – around the bay to a lovely restaurant under the trees. It has a perfect view of the setting sun.

We order from across the menu a wide selection of Greek specialities – lamb, octopus, squid, stuffed vegetables, tzatziki and olives. We are particularly impressed with the wine selection, and the first bottle of Assyrtiko is so delicious we order a second bottle almost straight away. Around us, families – many of them Greek – enjoy the serene setting, delicious food, and warm evening breeze. Under the table, I cheekily feed a ginger cat who has hungry kittens in a nearby tree. It’s a lazy, enjoyable meal. We walk even more slowly back to the tender, full from our feast and ready for bed.



Day Five

It will just be a short jaunt today, around the coast of Sifnos to Kamares. Kamares is a larger port than Vathi, with a wide sandy beach of golden, glittery sand and whitewashed buildings that climb up the hillside from the water. We moor in the middle of the bay and Patrick ferries us to shore on the tender for a day of exploring. Not knowing our destination, we follow Patrick onto the local bus where a few Euros each will get us across the island to Platys Gialos.


Sifnos is just beautiful. The roads to Platys Gialos are winding, and the bus rises to the top of hills and dips into the valleys. There are homes, farms, small towns and windmills – some working, some decorative. We share the crowded bus with travellers and locals, and at each stop the passengers manoeuvre up and down the aisle trying to get off or find a seat. I hear “excuse me” in many languages.

When we emerge from the bus the sun is high in the sky and warm on our faces. Collectively, we are parched and hungry. Fortunately, and I am guessing this is by Patrick’s design, we are across from a row of restaurants that back onto the beach. We choose the closest one and from our table we can almost dip our toes in the sand. The beach, unlike Vathi the night before, is brimming with people, mostly Greek families. This is a popular travel destination for Greeks, especially those from the mainland. Our waitress is delightful and the menu offers an array of fresh vegetables and seafood. I cannot resist the fried anchovies, so don’t. They are delicious.

There is a laziness to the afternoon, and we eat leisurely before heading back to the bus stop to catch a bus in the other direction. There is another stop on our itinerary before we will go back to the boat and get changed for dinner. Patrick promises us there will even be time for a swim later that afternoon.

Two busses get us to Kastro, a fortress town perched high on a hill and with views on all sides. We walk the perimeter of the town, Patrick in the lead, and see Roman-built walls too old to fathom, amongst the whitewash and bougainvillea. Stray cats gaze at us lazily from vantage points. As we round a corner, we see a tiny white church balanced on an outcrop of rock far below us and just above the sea line. Waves crash close by, and we can just make out the path that leads to it from the town.


The tour is quick, as it is not a large town, and we await the next bus – more than an hour away – at the Dolci Café. It overlooks farms that dot the valley, and the cocktail list is impressive. So is our waiter, who is rightfully arrogant about speaking five languages fluently, and an entertaining conversationalist. The cocktails are excellent and the time passes quickly.

Two more busses deposit us back in Kamare and Patrick is right, he has left us enough time to swim before changing for dinner. The water is warmer here than anywhere we have swum before and we can see a nearly-full moon rising over the hills before the sun even sets.

Dinner that night is in Apollonas, a gorgeous town in the heart of Sifnos. It is reminiscent of Mykonos, with whitewashed buildings and cobbled pathways leading off the main square in a tangle of walkways and alleys. Families, couples, groups of friends, travellers and local alike, fill the town with an intoxicating energy. The shopfronts boast beautiful wares from artisans and jewellers, and clothes in flowing fabrics and vibrant colours.

The choice of bars, cafes and restaurants is overwhelming, and thankfully we have a reservation where we will sit on a terrace overlooking the excitement. The wine is great, the food is fantastic and collectively, we never seem to run out of things to talk about. We will split up after dinner, some of us to shop, others to grab a drink at a local bar. Late that night we meet back at Kamare to ferry to the boat. It has been our busiest day, and it has been exquisite.


Day Six

A day of sailing to Kythnos where we will moor in a beautiful cove surrounded by jagged rocks and caves called Ormos Kolona. It is a popular spot, but the beauty of sailing is that even with neighbouring boats – big and small – the cove is peaceful and the atmosphere friendly. The water here is so clear we can see straight to the bottom, and several of us swim to shore to indulge in the natural hot springs.

We commute via tender to the only restaurant in the area, a lively place where you can meet your fellow travellers and even dance, if you feel like it. The moon is full now and hovers over the cove, with long milky fingers stretched across the water. It is our last night together and we enjoy a nightcap when we arrive back at the boat after dinner.



Day Seven

To Athens. It is a long day of sailing, but we are well and truly seafarers now, deftly moving about the boat executing the Skipper’s orders. We sail via Cape Sounion, the southernmost tip of mainland Greece where the Temple of Poseidon reigns from on high. It’s a perfect spot to stop for lunch sheltered from the strong winds that have carried us back from the islands.


As we get closer to Athens, civilisation emerges in small increments, and soon enough we are sailing past the long beach and apartments blocks of Glyfada. Athens spills out across the valley in front of us, climbing part way up the surrounding hills. Soon we can make out the Acropolis and Mount Lycabettus. The marina that welcomes us is the busiest place we have seen in a week.


We dock, we pack and chat, and when it is time to say goodbye, it feels like we are leaving family. There are hugs and promises of emails and photo-sharing to come. As my partner and I climb into the cab that will take us to the airport, I feel contented. It was an incredible week of exploration, relaxation, adventures and just being. Wonderful.


With thanks to Ben Reierson for some of these images.