Island Hopping in the Dodecanese

Some of us are lucky enough to have flexible jobs in that we can work from anywhere, which makes travelling anytime of the year more possible, and Summer is a great time to travel. And I don’t mean our Summer, I mean European Summer.

Last Summer two of our great friends were married in Greece. The plan was to meet in Bodrum, on the Turkish side and travel by Gullet around the Aegean Sea for 10 days.

Now picture this, 36 people who have never met before (bar a few interconnections and who all have extremely strong personalities) aboard a Gullet called the Love Boat. 36 of the bride and grooms favourite people all in one place – how amazing!

The Love Boat

All 36 drinking eager soon-to-be buddies met at a central location donning our sailor jerry outfits, but what’s a Grewe family holiday without a bit of drama. As we board the boat, Henry, the best man gets knocked out by a cable and its pulley that snapped, and rushed off to hospital. Two hours later dazed Henry arrives back and off we go. Being the first cruise of the Summer season, the crew were a tad bit rusty, but hey, that’s why almost everyone on the boat, came from working with Amy and Ollie…on a boat! Good planning Mr & Mrs Cann.

On night number one we docked in the harbour of Kos, one of Greece’s Dodecanese islands, known for its abundant sandy beaches and rich Greek and Roman landmarks. Many of these landmarks we discovered the following day as we explored the town for the hen party, which began on the Foinikes (Palm trees) lined streets that housed the medieval bridge. A creative and clever way to see the island.

Kos & Hen Party

This is what we discovered:

  • The Asklepion, the holistic medical centre of ancient physician Hippocrates that was built in the 4th century and is accessed by a grand stairway. The landmark sits on four enormous terraces, the lowest of which has the foundations of the patients’ rooms.
  • Hippocrates Plane Tree, the tree where Hippocrates himself would teach his students and is now over 2500 years old.
  • Ancient Agora, which is near the port which contains ruins of previous buildings, warehouses and houses.
  • Small family owned restaurants with the most welcoming nature and delicious cuisine.
  • That the boys cycled around the entire island wine tasting and stopping for drinks en route to meet us at a bar at end of day.

We cruised along the waters to find the quaint Pserimos, a small Greek island in the Dodecanese chain, lying between Kalymnos and Kos. It is part of the municipality of Kalymnos, and has a reported population of 80. In season, hundreds dock in the bay and make use of the few rooms to rent, the tavernas and the long stretch of beach with golden sands and limpid waters.


Leros, probably an island you haven’t heard of before is where Mussolini’s former military barracks held political prisoners during Greece’s military dictatorship and soon became notorious mental hospitals that are now refugee camps and are closed to tourists. After arriving, we took a short swim to shore, where we hired scooters to navigate through the beautiful, cobbled, narrow streets and discover the picturesque island.

Manolis & his son at Manolis Tastes

The central attraction however is Lipsi, were the wedding of our dear friends took place. Lipsi is a beautiful island of the Dodecanese located between Patmos (which we decided to skip) and Leros. Thanks to its small size, lack of mass tourism and long distance from Athens, Lipsi has emerged as a peaceful destination and home of award winning chef Manolis Hiras who I got to know in more detail as I assisted with the organising of the wedding. Manolis has overseen the transformation of one of Lipsi’s most historic buildings and turned it into the most beautiful restaurant, Manolis Tastes. He was recently selected to join the Chef Club of Greece (only the best are invited to this esteemed organisation). From loaning us his vehicle and helping us with the wedding, to his wife conducting a wine tasting for us at well-known small producing Lipsi Winery and the reception at his restaurant – he is truly a trustworthy and honourable Greek man. Upon our departure, he gifted me a bottle of Aposperitis, a sweet red wine made from sundried grapes of the rare Greek variety Fokiano. It has won Top Gold in 2016 and 2017 and at the beginning of this year was awarded one of the Top 20 Greek Wines of 2018.

Mr and Mrs Cann Wedding

To end off a great experience we explored Kalymnos, a charming fishing village that stands out for its amazing rocky landscape. We took quad bikes and scooters on what felt like an extremely long trip around the island, with many of us running out of petrol to view the breath taking landscape and medieval castles unique to Dodecanese. We also stumbled across the Agios Sabba Monastery, where many had to be quietly reminded that it was a monastery, and overlooked the entire city to generate some beautiful scenic shots. Along the shore we also found an array of vendors selling natural sea sponges, which have specific significance to the Kalymnos culture.  


What I loved about this trip was that we did not go to the commercialized islands such as Mykonos, Santorini or Crete, we discovered the small and underrated islands whose sites, attractions, history, beaches, culture and local charm make them the most memorable.

What must also be noted is the friendships (and even ‘loveships’) that were made between 36 strangers. One would’ve thought that 36 strong personalities in a confined space over a period of 10 days would’ve seen fireworks. But no. We did see fireworks however, but not the kind I am referring to.  


Morning tea & coffee as we try recollect the night before

Leave a Reply

Your email address will not be published. Required fields are marked *