Island Windjammers Greek Isles Cruise
By Alison Abbott
My first introduction to Greece took place during my college years. Imagine getting course credit for one month of cultural study in the Greek isles. Yes, my father said the same thing!
There were quirky cruises involved, but they were in the form of ferries, complete with farm animals on board, no luxury windjammer in site. I was young, adventurous, a bit naïve but nonetheless ready to drink in the cultural cocktail of such a warm and welcoming environment.
Working with a backpacker’s budget, I can still taste my first meal: an omelet dripping with feta and loaded with fresh cuts of fragrant dill. Thick, creamy yogurt sweetened with thyme honey from the hills and pistachios greener than any culinary nut to pass my lips.
Combined with my love of the sea, it’s no wonder I was seduced by Greece so many years ago.
Fast forward and the call of the Aegean was again at my door. This time as an invitation to sail on an Island Windjammers ship in the waters of the Dodecanese isles.
Can you guess my response?
For anyone with a love of Greek mythology and eco-friendly sailing you couldn’t ask for a better pairing.
A windjammer is one of the best ways to explore the many shades of cerulean waters found in this part of the world, slow travel in the very best sense of the word.
Alison aboard the Lyra near Telendos. * Photo: Alison Abbott
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Mythology Everywhere on an Island Windjammers Greek Isles Cruise
Olympic gods, goddesses and titans. We would visit the sites of their narratives.
Leros was the favorite hunting spot of Artemis. Kos was home to Hippocrates and Asclepius, the god of healing.
The Asclepius temple. * Photo: Alison Abbott
Poseidon carved off a piece of Kos and tossed it like a Frisbee during a battle.
The resulting island of Nisyros is still an active volcano that rumbles with the sound of its prisoner, Polyvotis trapped beneath.
The Nisyros caldera. * Photo: Alison Abbott
This is just a sampling of our journey where the weather, sun and tides determine the day’s program. Leaving from and returning to Kos, this 10-night small-ship cruise gives plenty of time for luxurious comfort in a relaxed setting. Recharge, refresh and dig deep into the land of the original storytellers.
Are you ready to come aboard?
The Dodecanese Isles
There are over 6,000 islands and islets in Greece. A mere 227 are inhabited. The Dodecanese islands, an enchanting archipelago nestled in the southeastern Aegean Sea, boast a mesmerizing blend of history, culture and natural beauty.
Compromising 12 major islands and numerous smaller islets, this sun-kissed paradise invites travelers to explore its diverse landscapes and immerse themselves in a rich heritage.
Map lovers will marvel at the proximity to coastal Türkiye.
The Dodecanese Islands (in purple). * Image: Shutterstock
Eco-friendly Sailing & Cruising
Traveling under wind-powered sail is an environmentally positive way to explore. Although a motor is available for arriving at destinations when the winds are not favorable, Lyra really comes alive and glides through the water when her sails are full.
Mate Stefanos working on a sail. * Photo: Alison Abbott
Every attempt is made to provision the boat with local produce, beer and wine. Island markets are visited, as are local fishmongers.
Chef Despina displayed such enthusiasm when she discovered some delicious fresh mussels in one of the ports. Traditional flavors and dishes were present at each meal.
Connecting with local villagers at their cafes and as guides and drivers was a priority for the cruise, a responsible means for keeping dollars sustainable in the local economy.
Our Island Windjammer Lyra
After an overnight on the island of Kos, we headed to the marina to board our home for the next 10 days, the gleaming sailboat Lyra. Docked in the main marina, she stood out as a stunning vessel amongst the other yachts and ferries.
Author Alison Abbott boarding the Lyra in Kos. * Photo: Alison Abbott
Details on the Ship
Windjammers are a classic way to explore the Aegean. A modern windjammer usually refers to a tall, multiple masted sailboat used for cruising.
Island Windjammers is owned by a small group of investors who began offering casual, island sailings in the Caribbean in 2009. They’ve got two ships year-round in the Caribbean — the 10-passenger Diamant and the 26-passenger Vela.
This year, Island Windjammers expanded to the Greek Isles, positioning the 8-passenger Lyra there for the 2024 and 2025 summer seasons.
The two-masted Lyra anchored off Kalymnos. * Photo: Alison Abbott
Lyra was built in 1984 and refitted in 2017. She is 98’ long with a beam 23’8”. Throughout the boat is a gleaming nautical décor with classic blue accents. Activity on the boat takes place on three different levels.
The upper deck has a covered area with two banquettes for lounging. This is where we spent most of our time, watched the sun set, had cocktails and relaxed during the sailing.
The open aft area has room for comfortable deck chairs and plenty of space for cushions should you like to stretch, do some yoga or sunbathe. Captain Markos spent most of his time navigating the boat from this level.
The aft deck area of Lyra. * Photo: Alison Abbott
Down a short flight of stairs is an interior salon with couches on each side and panoramic windows exposing a bird’s eye view of our journey. The bridge is centered in the space where the captain can steer in inclement weather.
On each end of this salon is an additional set of stairs. Aft are the four staterooms. Down a spiral six stairs at the other end is a combined lower lounge and dining room where most of the meals are served. Beyond this room is the galley and crew’s living quarters.
Spiral stair case to the lower lounge. * Photo: Alison Abbott
The lower lounge of Lyra. * Photo: Alison Abbott
Staterooms and Suites on Lyra
There are four staterooms aft on the lower deck of Lyra. Sagitta and Cygnus are the luxurious larger suites featuring king beds, ensuite bathrooms, portholes, plenty of storage and air-conditioning.
Additionally, Orion and Aquila the other two staterooms feature queen beds, storage, portholes, a/c and ensuite bathrooms. These two staterooms have an ingenious shower system with two swinging glass doors that hook together to form a shower inside the bathroom. The design keeps guests from soaking the entire bathroom when showering, a big plus in my books.
After viewing all of the rooms, I felt the larger suites were a much better value for the trip. The additional space, full closet and separate shower are roomy bonuses which some guests will surely appreciate.
Having access to both sides of the bed (which the Sagitta and Cygnus cabins offer) is important for anyone with flexibility issues or using the bathroom during the night hours.
VIDEO: Alison shows us around her cozy cabin, Aquila, below.
https://youtube.com/shorts/tWqTm-wDrn4?feature=share
Lyra’s Wonderful Crew
Lyra’s crew of five wear many hats and cover different roles on board. To watch them in action is to observe a well-oiled machine. Between jockeying for marina space, the expert setting of the sails, preparing and serving food and beverage, and handling of the guests’ little idiosyncrasies, we could not have asked for more.
Lyra’s great crew of five. * Photo: Alison Abbott
We had several medical mishaps during the sailing (one passenger hit their hand in a fluky way on deck and needed stitches in port, while another developed a sinus infection), and it was reassuring to see the knowledge, kindness and supplies on hand to handle emergencies. Through it all, the crew’s smiles and joyful personalities shined through.
The guests and crew of Lyra. * Photo: Alison Abbott
Food and Beverage Aboard Lyra
Our sailing included three meals a day and snacks whenever the mood struck.
One of the couples (who was on their ninth sailing with Island Windjammers) brought a chalkboard to display the daily offerings, a fun addition! We all eagerly awaited its display throughout our sail.
Healthy delicious meals made with local ingredients. * Photo: Alison Abbott
Breakfast had a hearty serving of some type of egg, a bread offering and yogurt with nuts and rich honey along with juices and coffee. Sadly, I didn’t discover until the end of our trip that there is also cappuccino and espresso on board!
Lunch always included a fresh green salad and a main course ranging from drunk mussels or stuffed cabbage to local fish and chicken. And of course wine…all of it from small vineyards and delightful.
Fresh salad aboard Lyra. * Photo: Alison Abbott
Chef Despina shared traditional dishes at both lunch and dinner, but the fare was heartier at the end of the day. Salad from the garden of a café owner in Leipsoi couldn’t have been any fresher. Moussaka, lahanontolmades (stuffed cabbage) and cauliflower steaks were delicious.
A delicious charcuterie platter included local cheese, meats, olives and jam. * Photo: Alison Abbott
Octopus was served in a variety of appetizing ways. Desert made an appearance whenever we could find the room, and I loved that the focus was on time-honored flavors and healthy options.
Our Orthodox Easter lunch on board. * Photo: Alison Abbott
My Highlights of Island Windjammers’ Dodecanese Islands Itinerary
One of the advantages of sailing with Lyra is the ship’s ability to visit islands which larger cruise ships cannot.
These lesser-known destinations listed as possible itinerary stops were:
- Kos
- Leros
- Arki
- Patmos
- Leipsoi
- Kalymnos
- Levitha
- Kea
- Falos
- Tilos
- Nisyros
Because of wind and weather conditions, we were able to visit six of these 11 islands on our itinerary.
The Deal with Shore Excursions
For any passengers who’d like a guide or transport in port (which costs extra), the captain happily arranged it ahead of time so the guides would be waiting when we arrived. My husband and I chose not to use a guide as we typically prefer to wander on our own and be independent. In fact, all six passengers felt this way as we were all active types. We wanted to hike and walk after a morning sail (where there is lots of sitting and relaxing) rather than get into a van for more sitting.
There was an opportunity to get off Lyra every day and some of the islands were small enough to just cover on foot. The crew gave us directions on hikes and most times we were always able to see Lyra from the shore. Some of these islands only had one main road, there was never a fear of getting lost.
For Nisyros we did ask the crew to help us hire a car and driver to take us to the famous caldera; it cost $50 per couple for about four hours.
Below are some port standouts on our Island Windjammers Greek Isles cruise:
Leros
With a population of 8,500, this island is very inviting. The harbor of Panteli is a traditional fishing village with a picturesque beach lined with palapa umbrellas and inviting cafes. Houses are built in the Italian architectural style.
Lyra in harbor at Leros. * Photo: Alison Abbott
Above Panteli, we hiked to the Byzantine castle of Panagia. Along the route are traditional windmills which have been revitalized into self-catering accommodations for two. At night, the lit castle made a perfect backdrop for a tasty dinner.
Dessert against the backdrop of the Byzantine castle of Pangia. * Photo: Alison Abbott
Nisyros
Nisyros is a dormant, but still active volcano and the youngest in Greece, formed a mere 160,000 years ago. Having previously been to Santorini, I was anxious to compare notes.
After a challenging docking experience because of high winds, we took a van first to the charming town of Nikia, all whitewashed and gearing up for the summer season.
Pretty Nikia. * Photo: Alison Abbott
Then on to Emporeio which is home to the Castle of Pantoniki with a birds eye view of the caldera, stopping at a thermal cave along the way.
The big event was hiking down the caldera. The otherworldly landscape gave the impression we were on the set of a Dune movie. Different layers of every earth tone you could imagine formed circles around the cavity. Steam came through several portals. The crater, called Stefanos, is one of the largest of its kind in the world and a truly worthy destination.
A visit to the Nisyros caldera. * Photo: Alison Abbott
Kalymnos/Telendos
I first heard of Kalymnos watching a rock-climbing movie on a return flight from Egypt. It was fascinating to see how this island had revitalized its tourism sector by promoting the caves, vertical walls and crags as an adventure destination. When I saw the island on the itinerary, I was so excited to see it in person.
We anchored off a small island called Telendos. Little did I know that this rocky outcropping was part of Kalymnos until the 6th century when an earthquake collapsed the land bridge connecting the two. The climbing caves I was so curious about were right above us!
Pretty Telendos. * Photo: Alison Abbott
Although the were no climbers on the rock face during our visit, we were able to hike around the car-free island and have a fantastic lunch of fresh seafood in a harbor café. The chef insisted we try the Kalymniko garidaki (fried baby shrimps only found in this region). One eats them whole, skin, legs and head, as they are way too tiny to peel. I didn’t have high hopes, but color me a convert! They were delicious and addictive. Our table devoured them like popcorn!
Kalymniko garidaki (fried baby shrimps only found in this region). * Photo: Alison Abbott
As we ended our meal, a group of German climbers shuffled into the café, clearly challenged from the morning’s activity. I only wish we could have seen them in action.
Each of the islands we visited presented an opportunity to take the tender to shore, hike and explore. Some were natural settings with lovely landscapes and others were historical sites with relics and adjacent museums. It was a nice balance of isolated locations and cultural opportunities.
Motoring or sailing between islands usually took place after breakfast and we were always anchored or on a dock for the night.
Tendering to shore. * Photo: Alison Abbott
What’s Included on an Island Windjammers Greek Isles Cruise
The all-inclusive price covers:
- Breakfast, lunch and dinner.
- Drinks including water, juice, soda, beer and wine are complementary (guests are welcome to bring additional spirits on board if they have a preferred drink, which our host was more than happy to mix).
- Daily cabin service.
- Use of snorkel gear for the cruise.
- Captain and crew are experienced with the destinations and happy to give overviews of island highlights and recommendations for cafes if you’d like to have a meal off the boat.
And what’s not included:
- Optional tours with a driver or guide in local ports of call (which you arrange with crew). These are very reasonably priced and further support the local economy.
- Entry to any sites or museums is not included.
- Hard liquor, but it may be brought on board.
- Tips for the crew must be paid by credit card. No cash is accepted.
- Transfers to and from the boat.
Captain Markos introduced us to the owner of the charming Dilaila cafe and wine from his vineyard was served on Lyra. * Photo: Alison Abbott
Additional Travel Before and After a Dodecanese Islands Cruise
Athens is a great arrival city for additional connections before and after this cruise. One of the couples in our group spent five days in Istanbul. The other spent pre-cruise time in Rhodes and post in Athens. Flights and ferries from Kos allow for many options.
My husband and I were on a tighter schedule and flew from Boston to Athens (am arrival) and then on to Kos that same afternoon. The Athens airport is small and easy to navigate. Once arriving in Kos, I highly recommend a stay at the Kos Aktis Art Hotel. Centrally located, all of the rooms have a dreamy view of the Aegean, the perfect antidote to jet lag! The restaurant is good, again right on the water and a bountiful buffet breakfast is included with the room. We had 24 hours to explore Kos City, but there is much more to do on the island if you have the time.
On our return, we spent one night in Athens, arriving just after noon at our hotel. We had both spent time in Athens before and because of time constraints, spent the day enjoying leisure time walking in the city.
Full Charters of an Island Windjammers Greek Isles Cruise
Lyra can be privately chartered for families or a group of friends. Solo travelers can book a cabin for a supplemental fee.
Weather Details for the Greek Isles
- According to U.S. News and World Report, one European country ranks above all others with a record 300 sunny days a year — Greece took the top spot for No.1 pleasant climate.
- While the weather in the Greek islands is a bit more wind dependent, skies in the Dodecanese Islands are usually sunny.
- We traveled at the end of April and had one night of rain.
- Temperatures in May /June range from 62° to 83°F, July/August 73° to 88°F, and September/October 63° to 82°F .
VIDEO: As seen below, Alison experienced sunny but windy conditions on her late April cruise aboard Lyra, perfect for sailing & anyone with sea legs!
Things to Know Before You Go
- Island Windjammers’ 6- and 10-night Greek Isles cruises in 2025 and 2026 will be offered from May thru October.
- For the 2024 season, passengers will fly in and out of Kos Island airport, usually via Athens. Ferry passage is also available if you happen to be visiting other islands before or after your cruise. NOTE: 2025 & 2026 itineraries will all depart from near Athens).
- Consider the dates for your travel. Early season cruises have less crowds, but many of the small cafes and shops are not yet open. Water is still cold for swimming. High season July-August will be much more crowded. Fall season the waters are still sun kissed from the summer sun and many of the tourists have departed.
- Consider the type of accommodations you would like onboard before settling on a date and make sure they are available on Lyra.
- Sea sickness is real, and with high winds, the boat heels, pitches and rocks. If you have any doubts, bring the medication so you’ll have the option to take it.
- Shoes. No shoes are allowed on the ship. This is barefoot cruising. You might want to bring socks to pad around the decks. Leave the heels at home. Cobblestone or rough streets are the norm and a pair of shoes with good support and traction are essential for hiking and climbing the hills and stairs. Water shoes are a must for swimming on the rocky coastline.
- Definitely pack a hat with a neck tie for sun and wind protection. Likewise for layers of clothing.
- Stairs are required to access the different levels of Lyra. Climbing mobility getting in and out of the beds in both the Orion and Aquila staterooms requires some flexibility.
- There is intermittent Wifi on board.
Don’t forget to pack hats! Here, Alison and her husband Neil. * Photo: Alison Abbott
I Really Enjoyed the Lyra & Recommend It
It was such an intimate experience and felt like a private yacht. We were lucky that everyone got along well and the crew was delightful.
On a yacht larger than our 8-passenger Lyra, it would be a completely different experience. Summer will be so different as well from our April cruise — it will be hotter (too hot?) and swimming and water sports would be an option.
Interested in This Island Windjammers Greek Isles Cruise?
Fares start at $6,750 per person for 10-night Greek Isles’ cruises for the 2024/2025 /2026 seasons (and $4,050 per person for six nighters in 2025/2026). Note, starting next year, Lyra will offer both six- and 10-night Greek Isles cruises, which will all sail round-trip from near Athens (at the port of Lavrio) not Kos. Check the Island Windjammers website for occasional specials and prices going forward.
Although this was my first cruise with Island Windjammers, the company has built a tight knit community of repeat guests that speaks highly of how much cruisers enjoy the experience.
For more information on this Island Windjammers Greek Isles cruise or their Caribbean offerings, visit their website.
RELATED: A first timer falls for Islands Windjammers’ brand of Caribbean cruising.
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HEIDI SARNA
