Sailing in the Mediterranean

Follow a group of artists and explorers from around the globe as they sail through the cities, towns, and islands of Greece.

February 8, 2017
in Sail

Last year, photographer Magdalena Wosinska sent us a proposal that we simply couldn’t pass up. She had planned a trip with a group of her closest friends – artists and explorers from every corner of the globe – and was preparing to set sail through the cities, towns, and islands of Greece with a boutique travel group called The Sailing Collective.

Read about their Odyssey in the words of adventurer, entrepreneur, and outdoorsman Stefan Wigand below.

It’s finally the day. After working with Magda and the team at Sperry, our crew was prepared to set off on an odyssey through the Mediterranean waters of Greece – an adventure that was merely a seed of an idea not long before.

With the help of The Sailing Collective, a bespoke charter sailing company, we had gathered a motley crew of individuals from different walks of life and countries – but with a common spirit of adventure and lust for life. On August 15th, we would set out to sail through the islands of Greece.

Arriving in Athens, our crew was connected by only one common factor: Magdalena Wosinska, a photographer who has traveled the globe and made friends everywhere she goes. Aboard The Sailing Collective’s Jeanneau 54’ sailing vessel, Magda had gathered intrepid souls that held onto the same bug that she did: a deeply-rooted desire to travel and to live well with no boundaries.

Among our crew was Strath Rabbidge, an Australian deep sea diver; Axel Gothenburg, drum master and future captain; Kelly Steffy, a self-learned botanist and boat mermaid; Hamilton Trimm, a master of the exotic diet and boat chef; Alexys Oliver, our boat mother and jokester; Dan Dealy, backflip expert and video camera wizard; and myself: Stefan Wigand, the crew’s first mate and dish washing zen monk.

Captained by Dayyan Armstrong, a New England-born sailor with salt in his veins, we found ourselves in the capable hands of the very founder and owner of The Sailing Collective. Rising beyond the norm of most bespoke travel companies, Armstrong sets himself apart from others by specializing in bringing together folks from all over and getting them out on the water in epic locations. His crew had an indescribable and magnificent way of taking the sport of sailing and transforming it into a much deeper experience; through eating, chilling, and exploring, a group of strangers quickly turned into family.


Setting sail, we quickly learned that there are two major winds in the Greek islands. These very same winds are those that have myths written about them in old books. One wind comes in from the North, another from the South. Originally planning to head South to the distant island of Mythos, we were forced to change course at the outset of our voyage. The winds had shifted, and with that our plans shifted too.

Heading West towards the Sardonic islands, we set off for Agina. As you sail around the horn of mainland Greece, your trip through time begins as you look atop the hill and see the temple of Poseidon standing tall and proud looking over his grand creation the sea.

The shift in the wind may have changed our plans, but we were blessed with 40 nautical miles of smooth sailing, where we started to develop our sea legs. Most on the boat were novice sailors, so we began with the basics. Bow. Stern. Port. Starboard. Captain Dayyan proved to be a hands-on teacher. We started winching and slacking lines as we set a smooth course downwind towards Agina.


We arrived shortly after noon in a quaint fishing village with a small marina. There was no room for us at port, so we dropped anchor just outside and prepared for the evening winds. And thus, our first lesson in anchoring begins.

We drop out 10m, 20m, 30m, 40m… hold. We wait, and wait, and wait until the moment when the boat stops moving and the chain tightens. We thought we were all set, but then, our Captain shouts, “Nope, do it again!” As a skilled sailor, he explained that the seabed didn’t have great hold.

Finally, our anchor caught solid ground, and not long after, the crew jumped in the water, ready to embrace the emerald blue sea around us. This was an activity that we would repeat over and over again through out the trip.

The next day, we awoke to a calm sea, drank our coffee, and headed off toward our next destination: Poros. The day is open for adventure, and with two small islands ahead of us, we decide to see if either is worthy of exploration.


As we approached the island, we discovered the most beautiful cove you could imagine and docked alongside another boat – they too had discovered this small slice of heaven on earth. Without a thought, we plunged straight into the water for our requisite daily swim.

This was followed by an arduous hike up a cypress-covered mountain, where we discovered an incredible view once at the top.

After a quick scramble down the mountain, we board the Jeanneau to find our next desination; but what had started as a beautiful sunny day next turned to dense fog. And through that fog, there it was: Poros.


As we approached the entrance of Poros, we hit a solid jibe – the wind is strong and we are moving well. A few of us are in the main cabin of the boat, when suddenly from above the Captain yells “hold on!” We are hit with a squall that has come up over the mountain. After recovering from the first gust of wind, we all jump to our posts and prepare to take on Zeus as he blows his mighty breath upon our sails. We hold our line with a mighty heal for 10-15 minutes and manage to make our way through, the wind giggling at our backs.

As we motor in, we see the faces of other sailors that had just felt the same winds we did.; the experienced sailors with sadistic smiles of enjoyment and the inexperienced sailors trembling from their encounter with mother nature. By the end of that day, we were a unit and had earned our sea legs. With smiles on our faces and blood pumping through our veins, we slept hard and well.

The next day we circumnavigated the corridor in lighter winds, discovering a little island protected by an uninhabited cove. We throw down anchor in the afternoon and settle for the night..


From afar, Hydra is surrounded by mountains and tucked in a perfect little cove hidden away from the eye. As we sail closer, we start to see this village and its beautiful buildings. Arriving early, we tie down to a boat that is tied to the seawall and gear up as we head to land.

Once ashore, some of the crew heads off on solo adventures while the rest of us gravitate to the water to swim. The sea is crystal clear, and we dive deep to find a galaxy of underwater critters swimming beneath us. At this point in the trip, we feel as if we are turning into fish, finding more comfort in water than on land.

The spot we head to is an underwater playground, with myriad caves and spots to explore. Dan “Danger” Dealy scopes out the perfect rock to jump from and promptly says, “Grab the cameras – I’m jumping off.” After we check the depth, Dan turns, squats, and lunges backwards before laying out a perfect sprawled backflip. The maneuver was a perfect 10.

We gather the crew later in the day for a meal at a local spot, then make our way back to the boat to fall asleep in our floating village with dreams of what tomorrow’s adventures will bring.


Leaving Hydra after a magical day and evening, we all promise to make our way back to this magical island someday. We hardly make our way out of the harbor before we find ourselves again throwing down anchor amongst the islands. With perfect skies, we venture toward a small outcropping of rocks teeming with life. This memory of us swimming amongst the rocks will stick with me for a long time to come. All of us have begun to believe that we could quit everything and continue this for the rest of our lives…

Thank you to Madgalena for pulling this crew together, to Captain Dayyan and The Sailing Collective for keeping our sails and bellies full, and to Sperry for giving us the opportunity to escape from reality for these seven days at sea in the Sperry 7 Seas.


To photographer Magdalena Wosinska for inviting us along, and to The Sailing Collective for hosting the crew as they sailed through the Greek Isles and explored in the Sperry 7 Seas.


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