Taking vacations is a part of self-care that all-to-often gets neglected in the hustle and bustle of our busy daily lives.

Those of you who know me well know of my love for Greece… and memories of my trips there are never far from my mind. I’m going to share some of those memories with you to get you in the mood for planning your next getaway…wherever that may be. Make sure you get and take all of your vacation time…you deserve it!

I spent my last holiday on a private 49′ sailing yacht, and the experience was truly one of ultimate relaxation, adventure and glorious views! While we may be in the midst of winter, now is the perfect time to start planning YOUR trip to Greece.

Though we (meaning four of my dear friends and our illustrious Skipper, Yannis) had done this trip before sailing the islands of the Cyclades, this last year we sailed the chain of Greek islands known as the Dodecanese. We boarded our yacht on the island of Kos and headed north toward Patmos, stopping along the way at a number of incredibly charming island ports and bays, always in search of something I consider a necessity of life… phenomenal turquoise water. Needless to say, we were not disappointed.

Most of the tiny islands we visited you would not know by name, so I won’t bother with the details, but suffice it to say WOW! Each island seemed more spectacular than the last.

We followed a similar routine most days; we’d start with breakfast on board in the morning, then set sail for several hours. Around noon or so we’d moor in a beautiful cove or small port, enjoy a light lunch and lounge on deck. This was followed by reading, swimming or snorkeling in the glorious turquoise water, listening to music and chatting the afternoon away. Around five or six we would sail to another part of whatever island we were visiting and find the spot where we’d spend the night. After laying anchor and enjoying a beautiful sunset, we’d get ready for dinner.

Most evenings we’d head to a local taverna (often right on the beach) where we would partake of the most incredible local fare… fresh feta, dolmas, calamari, mashed fava beans with olive oil and onions, salad, lots and lots of tzatziki, local wine and the list goes on… Afterward we would head back to the boat for cards or music and visiting followed by some of the most glorious sleep I have had in a loooong time.

For those of you who have already expressed an interest in arranging a similar vacation (this would be a perfect trip for families), OR for those of you whose curiosity has now been piqued, you will want to note that there are two critical components to the magic behind an expedition such as this… the first being the company from whom we chartered the yacht and the second being our beyond incredible skipper, Yannis Kastropoulos.

Our boat was chartered through a company called Blue Aegean Yachting (info@bay.gr / phone +30 2310324378) and we have used them for both of our trips. They came highly recommended by a Greek associate of one of my friends on the trip, and the referral came from a native Greek family who had experience with them and their fine reputation.

Our skipper, well, we were privileged to have met him on our first trip by chance, and because of both his professionalism and who he is as a human being, we have maintained our friendship with him over the last six years. As a result, we were all willing to work around HIS schedule to ensure that he was our skipper on this trip as well. Fortunately for us, the stars aligned and Yannis was free when we were. To quote one of my compatriots, we would sail with him anywhere!

As is often the case with many Europeans Yannis speaks three languages (and is working on a fourth). He is so well versed in music and film that we often had trouble keeping up. He is entertaining, has a delicious sense of humor, but most importantly, we feel safe in his hands as that is always his main priority.

The combination of traveling with dear friends in such an amazing setting would have made for a spectacular trip in and of itself… but Yannis made the experience all the more beautiful with his wonderful presence and the aura of caring and safety that come so naturally to him. If you are going to seriously pursue this adventure, Yannis Kastropoulos is your man; we cannot recommend him highly enough and you will be so glad you made the connection.


Below are some pictures of our adventure. Please enjoy. And if you would like Yan’s contact information, I would be delighted to pass it on to you. Happy sailing!

Photos by BIS Creative Director, Liz DeMarco