We thought hard before deciding on whether to take a sailing vacation or follow the beaten path of selecting a single destination and eventually trying to find attractions and activities in close proximity that would embellish our holiday experience. We were intrigued by Greece as a destination; it had been on our bucket list for a while now, knowing about the numerous islands and islets, the vastness of its history and culture, and the hearty goodness of Mediterranean food and Greek hospitality. There are numerous routes, including several options for island hopping from Athens. Comfort and privacy were at the top of the list. The typical sailing yacht option infers hard work on the skipper’s part and small quarters, so we eventually explored the alternatives and came across cruise liner options.

Our holiday plunge was surreal, as the choice for a cruise sailing trip by a leading boutique cruise line never came to our minds. Taking an 8-day tour of Classical Greece, we present the five learned and most irrefutable reasons to set sail around Greece.

Fabulous Weather

Greece is a climatic paradise, enjoying ambient and warm temperatures that dominate largely between April to October, meaning that there are usually excellent, if not highly favourable, conditions for sailing or cruising. The seas are generally calm, and if you avoid the windy period of August, which is the meltemi (strong North wind) season, this strongly increases your chances for the smoothest sailing ever! As part of the tour, we travelled at different hours of the day and night, yet the journeys were as tranquil as ever; some legs of our tour had to be done during the night while we were asleep; we departed for our first point of call, island Delos, during the first evening, (as we did with our transfer to Crete on the third day) and after sleeping like babies on board, there is something extraordinary about waking up from a carefree sleep, to be greeted by the golden shores of an island, in the middle of the Mediterranean.

Multiple Destinations

Consider a generic single destination holiday; you must meticulously select your destination whilst juggling between the factors of location, the choice of accommodation venue, and available attractions and activities for you to do once you arrive there. By deciding to sail or cruise, you are opening your vacation experience horizon, as these usually include at least a generous handful of destinations. When setting sail, you can explore the true identity of each destination as you visit areas that, in many cases, are not accessible by any other means. Our 8-day tour included eight destinations, with ample time for stops to swim or explore the location particulars: demure Delos, cosmopolitan Mykonos, majestic Santorini, wealthy Crete, the hidden gem Kythira, the historical Monemvasia, the old city of Nafplio, and quaint Spetses.

Now someone would argue that eight destinations in 8 days seem tiring, yes? Far from it. Consider this simple fact: you have only packed your suitcase once, you are primarily dressed in beach wear for the entirety of your holiday, and you can never suffer from boredom. If you select your cruise liner correctly, you will not lift one finger in visiting all these amazing places, which we would, in other circumstances, need a three-week holiday, with a lot more effort on my part, to see all these amazing locations.

Sense of Freedom

There is something about waking up in the middle of the great big blue or being sent off into sleep by the lullaby of the rocking sea. The light sea breeze gently brushed our hair in the mornings while soaking in the sun. You can literally skip the morning caffeine fix and dive straight into the crisp, clear waters only instants after waking up. During all times, the marine landscape in Greece is enchanting; the breakfast view is incredible as your ground is a living body of water, with multiple shades of blue spanning from azure, turquoise and cyan. During the hours when the sun is high in the sky, the light reflects the depths of the sea, and you can see directly at the bottom of the sea if you are in relatively shallow water. At sunset, you do not want to be anywhere else as nature takes its paintbrush and creates a visual masterpiece of pink, orange and purple hues across the evening dusky sky.

Worry-free

The phrase ‘hassle-free vacations’ carries significant weight in our agenda, and we believe a multitude share this inclination. No hassle means limiting factors that eat away your precious holiday time without value. This includes having to decide on daily itineraries that could be subject to change and mess up your schedule, making choices on where to eat and potentially taking risks and ending up in very touristic places, which we resent, having to wait for queues in general not only with regards to your meals but also considering the alternative transport methods by air or commercial ferries and the waiting and carrying that is involved. Our fave part is you only need to pack and unpack once!

Salient privacy

Picking a cruise as a holiday type means you are getting a private service to a great extent. The combination of being at sea while maintaining comfortable quarters makes up what we like to call salient privacy. However, chartering a smaller yacht type guarantees absolute privacy due to its size and charter options (usually available for exclusive use). Salient privacy on board a cruiser is perhaps the best of both worlds, as you enjoy your own private cabin with a sea view (of course!) for as long as you like, and if you are feeling more social, you are free to roam around the rest of the interior or exterior public areas at your will, interact with people and meet some new faces.