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Cruising the Greek Islands

Santorini

The appeal of small ships

It’s safe to say I’ve never really been a cruise person, but 10 days cruising the Greek islands changed that point of view.

Sailing effortlessly from one colorful port to the next, visiting islands big and small, touring charming Cycladic villages, intriguing archaeological sites and sleepy out-of-the-way beaches, I suddenly realized the value, ease and possibility that comes with touring this way.

There is a certain delight in waking up in a new location each morning, the sun rising outside your cabin window to illuminate all the colors and sights of a new port. There’s also a comforting feeling each night as you drift off to sleep, knowing that the chore of traveling to a new destination will be taking place while you rest.

With thousands of islands large and small spread over only a few hundred miles, Greece is uniquely suited to island-hopping.

And touring the Greek islands via a small ship allows you to visit a long list of destinations in a compressed period of time. In some cases, you can tour one island in the morning and enjoy dinner on another that evening—without feeling rushed. Trying to coordinate visits to this many islands on your own would be logistically daunting, to say the least.

Halfway through my recent trip, I started thinking about Jackie Kennedy and her days sailing amid the Greek islands while being romanced by Aristotle Onassis. Suddenly this mode of travel took on a whole new meaning and historically glamorous appeal.

Syros

Island hopping

For my recent journey, I sailed with Celestyal Cruises, a Greece-based company. With small ships, Celeystal is able to access tinier harbors that the large cruise ships cannot — a feature that sets the company apart and allows its cruises to include charming, less frequented ports of call.

My island hopping was divided between two different cruise itineraries — one that focused on the iconic Aegean islands: Mykonos, Santorini, Patmos, Crete and Rhodes and a second that highlighted smaller, more idyllic ports and lesser-known islands like Samos, Milos, Syros, Kos and Ios.

I also appreciated the fascinating variety of pre-arranged, hassle-free excursions on each island. There were options for those interested in scenery, culture, fine dining or merely beach hopping, or a little bit of all of the above.

When touring the island of Kos for instance, the excursions included visiting local, family-run wineries and honey makers; spending the day lounging on remote, pristine beaches or touring the intriguing archaeological ruins of Askleipion, which date to around 400 B.C. Often, there were simply too many tempting choices to squeeze into a single day’s visit.

There was a similar variety of choices on Ios — including whiling away the day on the pristine Maganari Beach, touring the pre-historic ruins of Skarkos, and meandering through the charming Chora village, where picturesque white cube houses and narrow stone streets cling to a steep hillside and offer dramatic views of the bay below.

On Mykonos, I enjoyed dinner in an incredibly quaint and charming beachfront restaurant in Ornos that I probably would not have found were it not for the cruise company. The small community offered a quiet, idyllic place to dine and escape thecrowds of Mykonos Town. A smattering of kids played in the water a few hundred yards from my open-air table. Sailboats bobbed quietly in the cove before me, and lights from the houses cascading down the nearby hillside twinkled, as the sun slipped beneath the horizon.

Kos

Traveling with Relaxation and Comfort

After a long day exploring archaeological ruins or wandering down the winding, cobblestone streets of the many small villages we visited, I was ready for a little rest and relaxation.

Back on the ship I found the perfect antidote in the spa, where each afternoon I pampered myself as we sailed from port to port — choosing a facial one day, a pedicure, foot and leg massage the next. I also enjoyed lounging on the poolside deck as we cruised through the impossibly blue waters of the Aegean, observing the island scenery as we sailed.

And because I did not have to waste time packing and unpacking each day, I was able to focus more time on just relaxing, digging into a good book, or reading about our next destination. During our sailing time, Celestyal also showcased Greek culture with language lessons, dancing classes and mythology quizzes.

Celestyal Cruises Olympia

A trip I won’t soon forget

Visiting the Greek islands is easily a bucket list trip. The islands have long had a special glamour, mystique and allure associated with only a select group of other destinations. There’s a reason Jackie O, as she later came to be known, came back again and again.

And cruising from one island to the next, not worrying for a moment about how you will get from place to place, makes the experience all that much more pleasant. Instead of being distracted by any of the hassles of travel, I was free to focus on the many pleasures of vacationing in this fabulous part of the world.

What’s more, I took my trip amid the height of the Greek financial crisis. While news headlines around the world projected gloom and doom, and a descent into chaos for the country, the islands remained as they ever were: a quiet sanctuary from the cares of the world.

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