Feelings of awe-inspiring exuberance were in the air when my friends Spencer, Anna and Aaron and my brother Tyler walked through the door of the Zeus hostel in Athens, Greece. While the five of us have spent a lot of time adventuring together, the expedition we were about to embark upon was certain to be the most unfamiliar and ambitious to date.
Six months earlier we had been living together in Lake Tahoe, California, for the ski season, fantasizing about the idea of sailing around the Greek Islands to climb rocks and explore new places. At the time, our combined sailing experience was minimal—none of us had ever skippered a boat for more than a daysail. Nonetheless, we sat around the kitchen table in our winter cabin and came up with a plan to make the trip happen the following summer.
As it came closer to our departure date, we had completed the prerequisite sailing classes, arranged a bareboat charter and figured out how to get ourselves to Greece. Shortly thereafter, we moved onto our new home, Hellenic Sky, a 44ft Bavaria sailboat, and looked forward to six weeks of exploring the Aegean Sea.
Sailways, our charter company, perhaps sensing our inexperience, offered to provide a local skipper for the first two days of our voyage, and welcoming a friendly Athenian local named Fiori to show us the ropes was no problem for us. In fact, Fiori proved invaluable in helping us get acquainted with this unfamiliar environment: teaching us how to use our navigation tools and showing us the nuances of the sailboat, and most importantly, how to identify a good spot to drop anchor.
We spent our first night anchored in a small bay at the Temple of Poseidon. The magic started taking hold as we jumped off the boat into the clear waters as the sun faded from the horizon. As the sun set, we swam to shore and climbed the steps to the ancient temple, ate dinner under the stars and went to bed in a mixed state—part blissful satisfaction—part exhaustion, a feeling we would experience often during our trip.
While we were sad to see Fiori leave when he boarded a ferry on Kithnos two days later, we were also thrilled as our newfound responsibility began to sink in. We felt confident we could manage our boat, but also knew a number of lessons undoubtedly lay ahead—and indeed, over the next few days every event seemed like a momentous occasion. Raising our sails required focus, pulling up the anchor was a five-person job, and each trip in and out of a new harbor was planned and discussed in detail.
From Kithnos we sailed to Rinea and then to the island of Mykonos. With its elegant beachside storefronts and iconic windmills overlooking the downtown area, Mykonos flawlessly blended ancient beauty with an eclectic crowd of fine dining tourists and young people there for the party.
We heard rumors of a surf beach on the other side of nearby Kolympithra and decided to check it out. Unfortunately, the fierce wind and swells made this impossible. In addition to learning how to sail, we were also new to climbing and eager to explore the Greek rock formations. Tyler arranged climbing lessons with a local named Manthos, who in addition to teaching us some of the fundamentals of outdoor climbing, explained the story of Exomburgo Castle, which stands at the island’s highest point.
While many things went smoothly for most of our charter, our passage from Tinos to Patmos did not. Despite Fiori’s cautioning message, we left Tinos harbor at dawn and spent 13 hours getting slammed by 8ft waves on the port beam.
Although we were miserably seasick the entire way, we also made it to Patmos with a newfound respect for the power of the sea. Every morning thereafter we diligently checked the forecast and planned our movements based on the sea and weather conditions, rather than our own partialities.
After spending a couple of days recuperating on Patmos, we sailed to the small island of Nisos Archangelos, where we anchored in a small cove and slept in hammocks on deck as we stared up at the Milky Way. As most sailors know, experiencing the immeasurable freedom and euphoria in having a self-contained home in a remote part of the world with people you love, is measureless. That night under the stars, we felt that enchantment collectively as we drifted to sleep.
Unfortunately, the next morning our engine died as soon as we were underway, and the charter company arranged for some local fishermen to tow us to the island of Telendos, directly across a narrow channel from Kalymnos, where we grabbed a mooring.With its endless cliffs and a culture that celebrated the natural beauty of the islands, we found Kalymnos to be a climber’s paradise and spent 10 days exploring before sailing on toward Santorini.
By now, although we were still learning, our crossings were getting progressively smoother and we were feeling more confident. As we approached Santorini and rounded its northern tip, we were awe-struck by the dramatic red cliffs that thrust up from the sea’s surface. The natural beauty of Santorini was only matched by the architectural elegance of Oia, which overlooks the sea from atop the steep cliffs. With classic Mediterranean white adobe flowing together seamlessly with the landscape, it’s no surprise that every picture taken in Oia is postcard-worthy.
From Oia, we sailed to the southern side of the island, where we anchored at Parisa beach, took our dinghy in, and ate and hung out at the casual beachside cafes, where we were able to climb on some nearby cliffs. As evening approached on our second day there, a wave of inspiration came over us and we decided to attempt a night sail to the nearby island of Los. Often when we embark on these kinds of trips, we are perfectly content sitting on a beach, reading a book. However, there are also those moments, like this one, when the hunger strikes and before we know it we are jumping into high gear. In this case, we got to Los at approximately 0200 hours, just in time to dance for the rest of the night. As we were nearing the end of our trip, this proved to be a great opportunity to celebrate before motoring back to Poseidon’s Temp and finally returning to Athens.
When we chose to embark on our sailing adventure, it was always about more than seeing new places and experiencing different cultures and atmospheres. Before I ever set foot on a sailboat I sensed that sailing awakens a feeling of personal empowerment, freedom and well-being, both individually and for those you’re with. Not only did we learn how to work as a team on this charter, we also learned how to work with the wind and the sea, an experience that was powerful, rewarding and humbling. It has also inspired me to continue to push my limits in the future and hopefully inspire other adventurers to do the same.
Ian Drogin is a passionate outdoor enthusiast and world traveler who loves to ski, backpack, surf, and now climb and sail
Photo courtesy of Ian Drogin