Best Tips and Itinerary for a Private Yacht Cruise in the Greek Islands

A highlight of my 2015 travel itinerary was my planned trip to sail in the Greek islands.

I placed this on my calendar after receiving an invite from the owners of a new travel startup. I met the owners of Mar-A-Mar Travel at a travel conference and learned that the company specializes in fitness-oriented sailings in the Cyclades in Greece. This group of islands in the Aegean Sea always seemed so fascinating to me, and the idea of getting to island hop and play in the waters and on land fit perfectly with how I like to travel.

Little did I know just how much fun I would have (check out my video showing all the activities and a tour of the boat). I was a bit unsure about how I would react to being on such a small vessel for an extended period of time, in the open waters that can get choppy. Would I get seasick? That was a definite concern. I was going to be out of my comfort zone a bit on this one.

Let me tell you: Strangers become fast friends when you squeeze together in a 50-foot sailing yacht.

Our yacht for the voyage. It sleeps six to eight people in cozy quarters down below deck.

You have no choice but to get to know one another when you share such tight quarters on the high seas.

And when your voyage takes you through the incredible Greek islands on a summer cruise, these friends can become like a family. This happened for me on my trip with Mar-A-Mar Travel. The nine days spent playing and exploring rank among my best travel experiences to date.

Laughter and storytelling over shared meals. Attacking new adventures each day in a new place to explore — like swimming in a bay or hiking into cave-filled hills. We even spent an afternoon frolicking with dolphins.

I had never been on a sailing yacht, but I think I quickly took to the lifestyle that requires little beyond a swimsuit, sunscreen, a good hat and an adventurous spirit.

Of course, DO NOT forget your camera! Also, I did not get seasick. We had mostly calm seas, and the day it was a little bit rough, I was able to hold on tight and keep my stomach in check.

I met up with Mar-A-Mar Travel co-owner Sherman Pencescu in Mykonos to join the boat. It would be seven of us for about a week before co-owner Sandra Schmitt would come onboard with another guest. I overlapped two sailings during my time with Mar-A-Mar.

In Mykonos, I met skipper Fiori Dobi, a young, gregarious and expert sailor, who despite being in his mid-20s, has been sailing the Greek isles for the better part of a decade. Dobi knows nearly every square mile of the region and hunted out special spots for us to explore — secluded bays to swim in, caves, hot springs, hills and hikes. He set the itinerary for the voyage.

Winds and weather often dictate when and where you can sail in the Greek islands, so you have to be flexible and expect that any outlined itinerary or schedule is merely a suggestion. Things can easily change, but this won't affect your fun. Mar-A-Mar works with its passengers to find out what they like to do and where they might want to explore. I'll sum up how my time in the Greek isles sailing for more than a week went. Just imagine yourself following along, then consider how you might like to experience your first sailing trip. The journey can be yours, almost however you want it!

Day 1 in Mykonos

In Mykonos, right before sunset. When the sun goes down, things really heat up in Myknonos.

We spent the night at port, waiting for winds to calm before setting sail the next morning. Sherman and I walked to town from the pier, about a 20-minute stroll along the coastline. Mykonos is a crazy maze of tiny alleyways filled with restaurants, clubs and boutiques. Things get started late there, and after we had dinner and a couple stops for beers, we were ready to head back to the yacht. But it seemed like things were just getting started for most residents and other visitors. And this was about 11 p.m.!

I settled into my cabin, which is below deck and cozy but not cramped and with efficient storage space integrated into the design, for my first night's sleep onboard. (I'm 6-foot-4, so I moved cautiously the whole time I was onboard but still bumped my head almost daily.)

The next day, I got up, went for a run and swim at a nearby Agios Stefanos beach and then we set sail for Syros.

Day 2: Rineia and Syros

Now, that's a good Greek lunch. We often ate onboard the boat during our time playing in a bay (limanaki).

Our first stop along the way, was at a swimming spot in a bay off Rineia. Two hours into my first sailing trip, and I was already hooked! The waters are amazing, warm and blue and shimmering in the sunlight, during September.

In my mind, I already was making plans to get Colleen out here with me next year.

Mar-A-Mar offers snorkeling equipment to borrow during your trip, and I used it occasionally. But I generally loved just diving off the side of the yacht or the gangway that can be extended to create a diving board. Fiori, our skipper, also thrills at rigging the ropes and masts to make rope swings to propel over the water for dramatic splashdowns.

After swimming, we had our first meal onboard — lunch. Mar-A-Mar Travel provides a light healthy breakfast (think croissants or yogurt) for passengers. The rest of the meals will be enjoyed onboard (everyone chips in for groceries) or shoreside at a restaurant. You might mix in a few of these meals together as a group, or you can decide to go off on your own, depending on your mood or plans.

After our lunch, we sailed of for a few hours to reach Syros. This was how the trip would go. A day of sailing and enjoying the waters before pulling into a harbor or bay in late afternoon to anchor or tie up for the night. We would explore the town, enjoy authentic Greek meals and cool beers, and I would find a deeper passion for the beauty of this way of life and the historic Greek towns I was experiencing for the first time.

Nighttime on Syros, in the town of Ermoupoli.

In Syros, we took a bus from the pier to the town of Ermoupoli, the capital of the island. We wandered stone streets that were filled with shops and restaurants, with Fiori leading us the way to a fantastic restaurant and our family-style dinner enjoyed outdoors in the warm evening air, of course.

The next morning, before sailing, Sherman and I rose early for a run into the hills to go to a beach he wanted to show me. Running past farms into the hills, we arrived at the resort area and noted that just a few others were up enjoying the waters. We spent about 50 minutes working out at the beach and swimming before running back to the marina. What a perfect way to get my day started.

I was starting to find my groove.

Day 3: Kythnos

Wouldn’t you love to try this rope swing?

We pulled up to an enclosed and quiet bay on the island of Kythnos. We would anchor here overnight, and we had plenty of time to play. This spot features a beach with a natural hot springs tub and a hill to hike. We also did our first rope swinging from the boat.

Day 4: Serifos

The sun is starting to set as we arrive to the main town on Serifos.

Sherman joins me climbing the steep steps to explore the main village on Serifos.

The opening in the hillside is called Cave of the Cyclops.

After a playing in the waters some more at Kythnos in the morning, it was on to Serifos. We anchored in a bay on the quiet side of the island of Serifos away from the main town and took a cab over to explore and pick up groceries. The small whitewashed village is very pretty, and we climbed through the hillside village to explore the church that overlooks the shops, restaurants and marina. The next morning, from our spot at Megalo Livadi, Sherman and I went for a swim to shore and then a hike into the mining tunnel before scrambling up a hillside to inspect the "Cave of the Cyclops."

Day 5: Poros

On the way, we enjoyed an escort of about 30 or so dolphins who joined. This was an amazing surprise. The waters were calm all day for our sailing time in the sun, and the dolphins capped off a perfect day on our voyage to Poros (see video).

High above Poros. A view to the marina from the neighborhood streets high above the town.

The Poros clock tower, built in 1927, serves as a landmark for the island.

Poros has a busy marina and a lot to do on the well-developed island. It is located just across from mainland Greece and features hiking trails, beautiful beaches, historic churches and more. We rented bikes for $8 for the day and toured half the island, with stops at Russian Bay beach for lunch and beers, then at Monastery Beach for a late afternoon swim. Much needed after the hilly pedaling needed to get there.

Day 6: Athens

On the way to Athens, we stopped twice at small harbors (bays or limanakis in Greek) to go swimming and rope swinging and snorkeling. One of our stops was at Moni, an incredibly beautiful place (but also very busy). You get the idea of how this trip went by now, huh? We broke up our sailing time with plenty of fun and the much-needed lunch breaks, of course.

In Athens, we spent the night and welcomed Sandra and a new Mar-A-Mar guest onboard while saying goodbye to the previous group.

Day 7: Back to Poros

Russian Bay beach is a gorgeous spot to swim. Many boats pull up during the day, but we found the beach itself not too crowded. Beers and food are inexpensive, too.

Departing Athens, we stopped at Aegina for — you guessed it — swim and snorkel time in the bay.

Then, it was back to Poros, which fast became one of my favorite places. I had found a good running route through town and a track nearby right next to a beach. So, I could get in a morning workout and a quick swim to start my day. I was amazed at how secluded these places can be, and I was pleased to find my own little slices of paradise.

Day 8: Hydra

The awesome sight of arriving at Hydra's marina.

We left Poros for Hydra, which would be my final Greek island on my trip.

Hydra is another unique and gorgeous village. There are no private vehicles on the island. Only rubbish trucks are allowed. No motorcycles, either. So people get around on foot or by horse, donkey or mule on the extremely steep stone streets that rapidly ascend into the hillside from the marina.

Hydra is filled with all sorts of shops and restaurants, as well as a museum and the historic Cathedral of Hydra, located right in the heart of the marina.

We had an extended stay in Hydra, arriving early afternoon. This allowed me to enjoy lunch, sunset cocktails, dinner and gelato dessert with my new friends before I would have to say goodbye the next morning.

Sunset on Hydra is a popular time to gather for cocktails and relaxing before dinner.

It was an incredible trip with Mar-A-Mar Travel. And now that I have the sailing bug, I am telling all my friends and family that we have to get together for this type of trip as soon as possible. Intrigued? Book your own trip with Mar-A-Mar Travel.

Thanks for reading,

JR