Last updated: 10:47 AM ET, Mon November 30 2015

Island Hopping: The Joy of Sailing in Greece

Destination & Tourism | John Roberts | November 30, 2015

Island Hopping: The Joy of Sailing in Greece

PHOTO: The clock tower rises over the marina on Hydra, Greece. (photo by John Roberts)

Imagine long, relaxing days on clear blue waters under sunny skies, with no appointments to keep and your next destination wherever you, your fellow passengers and the skipper decide.

My voyage on a 50-foot yacht sailing in the Greek isles delivered all I had anticipated — and more.

As a long-time cruiser (you know, the big ships), I knew climbing aboard a sailboat for the first time to traverse the open waters of the Aegean Sea would represent something altogether foreign to me. I was fairly certain I would have to deal with a bout or two of seasickness.

But the weather cooperated, the seas were pleasant, I did not get sick and the trip was an epic delight. I traveled with Mar-A-Mar Travel, a company that charters yachts in Greece and hosts passengers for customized sailing experiences.

I sought to tackle a full range of fitness-based adventures, activities that help me explore the natural beauty of the Greek islands and their surrounding waters. Stuff that leaves me exhausted but satisfied, knowing I had gotten the most out of the day and destination.

My journey started when I joined the yacht in port at Mykonos. The famed Cycladic winds kept us there overnight, which gave me a perfect chance to venture into town for a dinner outside in the warm air and settle into the late-night vibe of Greek life in the summer.

I munched on the first of what would be many Greek salads and skewers of grilled chicken over the course of my 10-day trip, tipped back a couple cold beers and strolled the maze of narrow, winding alleys carved into the tidy complex of white-washed shops and residences stacked neatly onto one another.

Back at the boat, I settled into the tight confines. At 6-foot-4, the below-deck quarters that can sleep six to eight people deliver at least one daily bump to my noggin. While sailing, you become part of a family that forms along the way. Work on the ropes, prepare meals and dine together, share stories, play in the waters of the bay. You get the idea. It's not luxurious, but it's definitely rich in fun and camaraderie.

Each day, we would chart a course for our activities and ultimate new destination where we would overnight. On the island of Kythnos, we slept on the boat in a bay, where we could swim ashore to reach the beach or go hiking up a hill. We even found a natural hot tub and immersed ourselves into waters heated by springs.

During one afternoon on the voyage, the boat sailed alongside a large pod of dolphins. The playful escorts raced along our bow in groups of up to 10 at a time, creating an understandable buzz onboard as we raced for our cameras to capture the amazing close encounter.

We also visited Hydra, Poros, Syros and Serifos — all amazing in their own ways, with friendly residents and fabulous food and historic sites to discover.

Daily activities included jogging, swimming, snorkeling, hiking and biking. Like fishing? You can do that, too. At night, we would watch stunning sunsets, stroll through the towns on the islands for a little shopping or to seek out our next tasty family-style meal or a good bar to sip a beer and savor the atmosphere under the bright moon and stars.

As travelers, it's nice to step outside our comfort zones in a bid to add fresh experiences. A sailing trip in Greece gives you a chance to set your own pace and collaborate on the type of experience you are going to have each day.

The best part of this trip is that while the number of interesting islands, historical venues and natural beauty seems infinite, prices are reasonable in Greece. I found food, drinks, shopping and activities to be incredibly affordable.

And the memories priceless.

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