Release Your Inner Jackie O On A Luxury Sailing Holiday in Greece

Experience the best sailing holiday in Greece with the beautiful Running On Waves tall ship.

a luxury sailing holiday in Greece with Running On Waves ship

Last Updated on 08/04/22 by Rose Palmer

This story was recognized by the North American Travel Journalists Association with a Silver award in the Cruise category in the 2021 annual media travel awards competition .
“All I ask is a tall ship and a star to steer her by”  John Masefield

There wasn’t just one star, but rather, a pantheon of constellations blanketing the sky as the last rays of the setting sun disappeared over the horizon. To the east, a slim crescent moon was slowly rising out of the sea with the same grace as the goddess of love in Botticelli’s painting. A slight breeze and the gentle back and forth rocking informed me that our ship was under way. My dream Greece sailing tour had started.

I think I must have been a mariner in a previous life because I am inexplicable drawn to boating vacations. There is something about looking out over a vast expanse of blue while feeling the swaying rhythm of a boat that brings on a sense of peace that I don’t feel anywhere else.

I have been on a number of wonderful cruises, but my greatest wish was sailing around the Greek islands on a tall ship. The beautiful Running on Waves fulfilled that dream, and then some.

A One Of A Kind Luxury Sailing Holiday in Greece

My first view of Running On Waves
My first view of Running On Waves

She is a one of a kind modern sailing vessel designed and built out of love by a multi national team and was completed in 2011. I am not a tall ship expert, but I am told that her design is that of a traditional barquentine which means she has three masts with the front one being square rigged and the others fore and aft rigged.

When the captain and crew let out all the sails, I got a sense of what that meant, though how the crew knew what to do with the forest of ropes is beyond me.

Just a small amount of the rope rigging on the Running On Waves

There is no doubt that Running On Waves is a sailor’s dream  boat, but she is also a passenger vessel designed to provide an intimate luxury experience to those looking for a different type of Greece sailing vacation.

With a maximum capacity of 40 guests (though our cruise only had 28) and served by 20 crew this is more like being on a private yacht than a cruise. However, with a length of 210 feet, she is big enough to offer the variety of amenities that one would find on much larger ships.

Running On Waves docked at the island of Syros
Running On Waves docked at the island of Syros

The cabins

To accommodate its passengers, Running On Waves has cabins that are roughly the size of what you would find on larger ocean going vessels. There are 5 premium cabins on the Main Deck which measure 150-215 square feet; three of these have king sized beds.

Stairway leading down to the Tween Deck

There are an additional 13 cabins on the Tween Deck that measure 118-129 square feet. You can choose from cabins with king sized beds, twin beds or bunk beds. Many of the cabins can accommodate three people with an additional Pullman berth.

All the cabins have en suite bathrooms with showers and modern amenities, a mini fridge, a safe, TV with satellite channels, air conditioning and heat as needed, and portholes or windows. The ship also provides free internet which was more than adequate for staying connected to family and friends each day.

the bathroom in my cabin

I had cabin 23 on the Tween Deck with twin beds for myself and my traveling companion. Though closet space was tight for two women, there was additional storage under the beds and we also used the Pullman berth as a handy storage area for our clothes. The cabin also had plenty of convenient outlets for charging electronic devices.

My cabin on Running on Waves

For the minimal amount of time that I spent in the cabin (sleeping, showering and changing), the amount of space was quite adequate for me.

The public spaces

When I wasn’t exploring one of our ports of call, I was enjoying one of the many comfortable public spaces on the boat. The front half of the top Sun Deck had lots of deck chairs for those wishing to work on their tans, as well as a refreshing jacuzzi. I just liked laying on the deck chairs here and looking up at the web of rigging, trying to figure out how it all worked.

The Sun Deck on Running On Waves
The Sun Deck on Running On Waves

On the aft part of the Sun Deck there was a large, shaded area with a comfy couch (good for afternoon napping) and more chairs. In the mornings, this area was also used for yoga sessions.

Shaded seating area on the aft portion of the Sun Deck

The Ocean Bar on the Main Deck was another outdoor area where guests liked to congregate and get a refreshing drink any time of day. On the aft end of this deck there was more shaded seating with comfortable sofas.

The Ocean Bar
The Ocean Bar
More comfy seating on the aft end of the Main Deck

The Main Deck is also where the elegant indoor dining room was located. This space was the heartbeat of the ship – it’s where all the passengers gathered together to eat, drink and socialize.

The elegant dining room on Running On Waves
The elegant dining room on Running On Waves

Exceptional food

Cruising has become synonymous with good food and lots of it. The beauty of a small ship cruise is that the chef can focus on producing quality rather than quantity. And on Running on Waves the menu used a variety of locally sourced, fresh ingredients which raised the bar even higher.

Meals were served buffet style with plenty of choices for all tastes and dietary requirements. There was always fresh fruit, fresh veggies and choices of salads, crispy breads, a delicious selection of cheeses (my favorite), a couple of choices of protein that always included a seafood option and a delectable desert. The last evening’s dinner of local lobster tails and beef fillet was especially memorable.

Drink options were equally varied and started with a welcome aboard champagne reception. Breakfast always included freshly squeezed orange juice and the best cappuccinos made in a copper espresso machine that was as much a work of art as a means of providing caffeine. Premium alcoholic beverages were also available (any time of day) for an extra fee.

A cruise for all nationalities and ages

It was during the meals that I got to know and connect with my fellow cruisers. I like to travel because it gives me the opportunity to get to know people from other parts of the world. It may seem counterintuitive, but on this small ship cruise in Greece I met a greater diversity of travelers than I have on much larger ships.

A few of the guests enjoying a beautiful sunset while anchored at the island of Santorini

Though our group only numbered 28, we were a global community representing 10 nationalities and four continents. The participant ages were equally diverse ranging from their 20’s to their 70’s. And while English was the primary means of communication, the conversations around the tables included German, Spanish, Portuguese, French and Italian.

Exceptional service

The ship’s crew added an additional level of cultural uniqueness. They hailed from the Ukraine, Russia, the Philippines, Germany and Austria. The one thing they all shared though was the desire to provide an exceptional sailing holiday, not always an easy task with such a diverse group of clientele.

Half of the crew worked behind the scenes, sailing, cooking and in general, keeping everything running so smoothly that it all looked effortless (though I am sure it was not).

It was always such a pleasure to be greeted by the crew when we came back on board after a day of touring the islands

The front facing staff were led by Hotel Director Robert and Cruise Director Claudia. Coming from over 20 years experience running large luxury cruise ships, the couple apply their expertise to insure a perfect Greek island sail experience for each individual on the ship – again, not a straightforward task with so many different nationalities, ages and expectations.

Robert and Claudia set the tone that took the cruise from unique to extraordinary. They were always friendly, positive, and engaged genuinely with every passenger in a way that was authentic and open. They both made themselves easily accessible to all the guests and were intimately involved in ensuring a positive guest experience for every person, every day. They provided that personal touch which is not possible on a larger cruise ship.

Hotel Director Robert and Cruise Director Claudia

Robert handled the complex logistics of sleeping, feeding, and caring for his passengers. In fact, it was not uncommon to see him in port each morning, supplementing the ship’s pantry with additional fresh local goodies. He is a talented and passionate cook as well, and I quickly started to look forward to his daily pasta specialties at dinner every night.

Robert making one of his daily pasta specials for dinner

Claudia guided us every day through the various sightseeing options at the ports of call and helped us to stay on time with the ship’s schedule. She also set up fantastic private tours for our group at three of the island stops which really made it much easier to see all the sights, especially in the summer heat.

Following Claudia’s and Robert’s example, the rest of the staff that I interacted with were equally eager to please. One of the most fun aspects were the “magic” blue bells which were placed at various spots around the ship. When I pushed the button on the bell, it lit up and within a few minutes, one of the wait staff magically appeared so I could request a drink or snack. I wish I could have one of these bells at home, but I don’t think it would work as well.

It was this high level of personalized service that made this cruise truly memorable and that took it to a level of luxury that would not have been possible on a large cruise ship.

Each day our friendly crew took us back and forth on the tenders

Unique itineraries

Though she is a relatively large sailing ship, Running On Waves has a shallow draft. This means she can easily get into ports where larger cruise ships can’t go. This allows for itineraries that combine the popular “must see” islands like Mykonos and Santorini, with the less visited island jewels in the Aegean.

sunset at the Mykonos windmills
Sunset at the Mykonos windmills with Running On Waves in the distance

My Greek Island hopping cruise included a sampling of ports from west to east and back again. We stopped at the islands of Syros, Delos, Mykonos, Patmos, Kos, Santorini, and Milos. (Read all the details in my post Cruising In Style to the Most Beautiful Islands in Greece).

Classic view of Santorini

Delos is a small, sacred island that is normally visited as a day trip from Mykonos. However, our ship could easily anchor off the coast of Delos which allowed us to see this popular UNESCO site in the early morning before the majority of the crowds arrived.

The UNESCO listed island of Delos
The UNESCO listed island of Delos

Each Running On Waves cruise itinerary is unique which means you could sail numerous times on this beautiful ship and do something different on each sailing excursion. For groups or families, the whole boat is also available for charter with custom itineraries. They also offer special “last minute” crossing cruises as they reposition from one location to another, which adds another lever of unique itineraries.

Other activities

For those that did not choose to spend time in port, Running On Waves also offered other activities. At the back of the boat, a hydraulic ramp allowed for easy access to swimming or water sports like kayaking and wind surfing. I found that a quick, cooling dip in the Aegean was an ideal way to cool off after a hot day of sightseeing.

One of the fun activities, at least for those with a head for heights, was the opportunity to climb the mast to the first crow’s nest. Since I don’t do well with heights, I didn’t do this, but it was interesting to watch others as they made the climb. The activity was completely safe as the guests were tied down and also had a crew member spotting them as they climbed the rope ladder.

Indoors, there were also plenty of board games available and a large screen in the dining room turned the space into a cinema. Cruise director Claudia gauges the group’s personality and puts together distractions and entertainment as needed. Our group was fairly sedate and we were content to just chat or relax on deck during our free time.

A beauty that turns heads

Since our itinerary had to follow a timeline which required being in ports of call at specific times, we motored for the majority of the cruise. However, for a little while when the conditions were right, the captain and crew unfurled the sails, and we could tour around her in the tender and appreciate her beauty when she was “fully dressed”.

There is no doubt that Running On Waves drew attention in every port she was in, even without her sails full. More than once, I caught people taking photos or selfies with her in the background.

Parked next to the large cruise ships that towered over her, Running On Waves looked like the intimate bespoke experience that she is. With all the individualized personal attention I received, I have no doubt that she is one of the best Greek island small ship cruises out there.

Running On Waves at sunset in Mykonos
Running On Waves at sunset in Mykonos

Sadly, all too soon my weeklong floating holiday in Greece came to an end. I had very high expectations for this experience and this dream cruise exceeded all of them. For one week I was spoiled and pampered and had the chance to feel just a little bit like Jackie O yachting the Greek islands.

My travel bucket list keeps getting longer so a true test for me on how much I loved a trip is whether I would take the time to do it again. In this case, another Running On Waves luxury small ship cruise in the Greek islands is most definitely high up on my travel list.

Running On Waves at night
Running On Waves looks just as pretty at night as she does during the day

Please note that my cruise was hosted by Running On Waves. All the content and opinions expressed in this post are my own.


Other Greece stories you may enjoy:

Discover the best islands in Greece: Cruising in Style to the Most Beautiful Islands in Greece

Two days on the island of Hydra: My Lovely Two Days on Hydra Island

Best historic sites on the island of Kos: A History Lover’s Guide to One Day in Kos, Greece

Review of a Ruby Princess Cruise through the Panama Canal: Living Like Royalty on a Princess Cruise – A Ruby Princess Review With Photos

A luxury barge cruise on the Burgundy Canal in France: My France Canal Cruise – Quiet Luxury in the French Countryside

A luxury barge cruise on the Briare Canal in the Loire Valley in France: An Intimate Loire Valley Barge Cruise on the Renaissance with European Waterways

Thanks for visiting.



Pin this!

Sharing my experience of the best luxury sailing cruise in the Greek islandsDiscover how to best experience the Greek Islands on a luxury sailing cruiseHow to have the best luxury small group cruise in the Greek Islands