Are you dreaming of Greek Island sailing? Do you want to dip your toes into the deep blue waters of the Aegean or feel the warm Mediterranean breeze on your face as you sail into an island harbor ringed by whitewashed houses?

The Greek Islands are a popular cruising destination with an overwhelming number of choices in terms of ships and itineraries. Would you prefer a large ship because of all the wonderful amenities or a smaller yacht for its quieter ambiance?

On my recent Greek Island sailing on Running On Waves, I think I had the best of both worlds. 

About Running On Waves

Arriving at the Island of Syros: Greek Island Sailing

Arriving at the Island of Syros

Running On Waves is a one-of-a-kind barquentine sailing ship experience that you will not find anywhere else in the Greek Islands. A barquentine is a specific category of tall sailing ship, with the most famous one being Sir Ernest Shackleton’s ship Endurance which was crushed by ice in the Antarctic seas in 1917.

The possibility of encountering sea ice in the Aegean is so remote that there is no need for concern on a luxury Greek Island sailing. However, Running on Waves is a completely modern ship. She was built in 2011 and has all the current technological advantages expected in a cruise ship today, but with her sails fully furled and blowing in the wind, she offers the classic romantic image of days gone by. 

At 210 feet in length, this beautiful tall ship strikes a perfect balance between being small enough to offer an intimate setting, yet large enough to provide the luxury experience that many cruisers are looking for. On my cruise, there were 28 passengers representing 10 nationalities, served by 20 crew. Half the crew ran the ship while the other half were on the “hotel” side that managed and took care of passengers’ needs.

Life aboard the ship

Comfy, shaded outdoor seating

Comfy, shaded outdoor seating

The front-facing crew was expertly led by Hotel Director Robert and Cruise Director Claudia. Despite the international clientele, they succeeded in providing a personalized experience to each guest. They truly cared about making this Greek Island sailing the best possible experience for each person on board and it was this authentic and caring interaction that raised the bar from an excellent cruise to an exceptionally memorable one.

For a small ship, the accommodations were quite comfortable. The cabin choices on Running On Waves vary from spacious deluxe cabins on the Main Deck to more basic but comfy cabins on the Tween Deck. All cabins include bathrooms with showers, a mini-fridge, satellite TV, AC or heat as needed, and portholes or windows. No dark, inside cabins here. I was also pleased to have free WiFi.

Food is an important part of any cruise, and here, Running On Waves did not disappoint either. There were plenty of choices at each meal to suit all international tastes with lots of fresh and local ingredients.

A colorful and delicious dinner on Running on Waves on a Greek Island sailing

A colorful and delicious dinner on Running on Waves

I loved the fresh-squeezed orange juice each morning along with the freshly baked, crispy croissant. Lunches and dinners always had plenty of salad choices as well as fresh fruit along with the meat and seafood entrées. My favorite choice for dinners though was the special pasta dish that Hotel Director Robert prepared each night. 

Plenty to see and do 

A shady place to relax at the Ocean Bar

A shady place to relax at the Ocean Bar

Running On Waves offers charter cruises as well as unique itineraries throughout the Greek Islands. With each sailing, they try to strike a balance between the famous “must-see” destinations and some lesser-visited spots. My cruise included stops at the iconic islands of Mykonos and Santorini, as well as the islands of Syros Patmos, and Kos which I enjoyed exploring even more because they were less crowded.

The UNESCO listed fortification on Patmos

The UNESCO listed fortification on Patmos

Another advantage of being on a cruise with only a few passengers is the ability of the crew to adapt activities to the guest’s interests. Cruise Director Claudia quickly set up private guided tours for our group at a few of our island stops once she identified that there was an interest. 

There are plenty of outdoor spaces to relax on board the ship, including lounge chairs and a hot tub on the Sun Deck, and an outdoor bar offering drinks any time of the day. For those not wanting to be in the sun all day, there are also plenty of comfy options in the shade where you can sit and read a book or just let the gentle rocking of the boat lull you into an afternoon snooze.

The sundeck with its Jacuzzi on Running on Waves

The sundeck with its Jacuzzi on Running on Waves

My Greek Island sailing: The bottom line

The Greek Islands are a special destination, and a sailing cruise to see them for the first time was a dream come true for me. But what made this cruise even more special was being on a luxury ship where for a week, everyone knew my name, and I was welcomed like family and treated like an honored guest. 

Watching the sun set over Santorini

Watching the sun set over Santorini

What’s appealing to the over-50 luxury traveler? 

  • The personalized attention that you get when you are cruising with only a few dozen other passengers
  • A quiet and serene cruise experience without crowds
  • The unique itineraries that a small ship can take
  • Cruising on a unique, one-of-a-kind sailing ship

Take note

  • Because this is a smaller ship, rough waters will be felt more easily. For those prone to seasickness, bring appropriate medication.
  • Good mobility is necessary as the stairs connecting the decks are steep. There are no elevators.
  • Closet and storage space is limited so don’t overpack.

Disclosure: The author’s cruise was hosted by Running on Waves but any opinions expressed in this post are her own.

All photo credits: Rosemarie Palmer


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