The Dodecanese islands, almost within hailing distance of Anatolia, are the furthest island group from the Greek mainland. Each island has its own charm and characteristic landmarks, ranging historically from the times of Byzantine and Ottoman rule to the Italian era and contemporary Greece. Our 12-day cycling tour of the Dodecanese features seven days on a privately chartered gulet, which will not only provide us with comfortable accommodations and freshly prepared meals, but will also allow us to explore the beautifully carved coastlines of the islands we visit, and enjoy leisurely stops in impressive bays with crystal-clear water. Cycle along quiet roads on hilly terrain and explore 9 different islands. Attractions include the wonderful medieval enclave of Rhodes Old Town; the gorgeous ensemble of Neoclassical mansions that surrounds the harbor on Sými; the grandiose temple-sanatorium of Asklepion on Kos; the rugged landscapes of Kálymnos; the cave and monastery on Pátmos, where St John had his vision of the Apocalypse…and many more.
admission to all the sites visited together (The Palace of the Grand Master on Rhodes, the Archaeological Museum of Rhodes, the Asclypeion on Kos, the Monastery of St. John on Patmos and the Heraion of Samos) and the usual.
We work hard to maintain consistency across all of our tours, but some trips have unique differences. Here are some things to keep in mind about this tour.
Itineraries can change depending on weather conditions, coast guard restrictions, tour logistics and our captain's discretion.
Our boat is a traditional wooden sailing gulet that has been equipped with a motor. Although the boat has masts and sails, we depend on the engine to improve speed and assure the itinerary can be met. Motor-less sailing will be determined at the captain's discretion.
Highlights: Neratzia Castle and the old town of Kos, test ride – Board the Boat
Welcome to the island of Kos! We’ll meet this afternoon to fit and test bikes before boarding our private motorized sailing gulet and home for the next seven days. Dinner together on board.
The June 1, 2024 group will gather at our luxurious seafront hotel for the first night.
This morning we cruise to Kalymnos for our ride. The views are spectacular – it’s no wonder Kalymnos is rated a must-visit Greek island – so stop often to admire the scenery. Our lunch stop after a short but stout hill climb is worth the effort. Find time to visit the wonderful Archaeological and Nautical museums this afternoon. Dinner together on board.
Highlights: Visit to the island’s Volcano, Paleokastro Castle, the picture-perfect village of Nikia
The island of Nisyros is one of Greece’s more active but less known volcanoes. The last eruption of Nisyros in 1887 left a moonscape with colorful craters and very active fumaroles. Later this morning, enjoy a refreshment in one of the most photogenic squares on the Dodecanese before sitting down to an authentic lunch on the island’s most famous balcony. Dinner together in the village square of Mandraki tonight.
Highlights: Leisurely lunch and swim in a secluded bay, exploration ride on Halki, pastel -colored neoclassical architecture
Whatever Halki lacks in size, it makes up for in landscapes and colors. Brightly colored 19th Century houses – many of them lovingly restored – line the port of Emporios. Their ceramic-tiled roofs and wooden windows will charm you before you even step off the boat. Our ride today is short enough to allow you to enjoy the afternoon in this colorful town.
Highlights: Rhodes’ natural beauty, Ancient and Medieval monuments, afternoon walking tour
Traveling from Halki to Rhodes will feel like leaping between two different worlds. Our ride will lead us away from the coast, providing the opportunity to explore authentic villages and the island’s natural beauty. This afternoon we’ll take a walking tour to learn about the island’s complex, multi-faceted history. Rhodes’ ancient and medieval monuments, the legacy of the Colossus of Rhodes and the Crusades will tell the story of an island prized by all.
Highlights: The Monastery of Archangel Michael, the pictureque settlements of Gialos and Chorio
The magic of the small island of Symi is revealed from the moment we enter the elegant harbor in Yialos. We will pedal to Panormitis Bay, on the island’s southern tip, where Symi’s most visited attraction is located. We will return in time to witness the afternoon light that highlights the beauty of Chora’s pastel-colored neoclassical houses dating back to the island’s glorious past.
Highlights: Sanctuary of the God of Medicine, cypress forest, the tree of Hippocrates
Today we head back to Kos and will enjoy exploring the island on our bikes. Our route will allow you to connect several attractions including the famous ancient site of Asklepieion, the attractive villages of Lagoudi, Pyli, and Mastichari and the tree under which Hippocrates is said to have taught his pupils! Dinner together on board.
The May 18, 2024 group will spend the last night at the Kos Divine Hotel & Suites and enjoy a sumptuous dinner on land.
Highlights: Italian rationalist architecture, War Museum, the Medieval Castle of Pandeli
You’ll be intrigued when we arrive at the port town of Lakki on Leros, thinking you’ve traveled back in time to 1930’s Italy. During the Italian occupation this entire town was built in typically Italian rationalist style, which resembles art deco. After a week on board our yacht, we are on land tonight and our hotel perfectly situated to explore town or hit the beach.
Highlights: Monastery of St. John, the Cave of the Apocalypse, explore the alleys of Chora
The small island of Patmos is most renowned for being where St. John’s vision and writing of the Bible’s Book of Revelations took place. Today, along with its spiritual significance, the island boasts unique beauty with its sheer cliffs, volcanic soil and beautifully preserved villages, including the island’s capital, Chora, a UNESCO World Heritage site. We will have a day full of scenic cycling and memorable cultural visits.
Highlights: The Heraion, Samos Wine Museum and our seaside retreat
Famous for its sweet wine, Samos is also historically significant. It was the legendary birthplace of Hera, and the sprawling ruins of her ancient sanctuary, the Heraion — which we will visit on our ride today, are impressive. Don’t miss the opportunity to visit the spectacular Archaeological Museum, with its colossal statue of a Kouros dating to the 6th Century BC.
Highlights: Spectacular coastal views, authentic villages of Samos and the town of Karlovasi
Our last ride might be the most impressive of the whole tour. We will ride through lush forests and beautifully kept villages with breathtaking panoramic views of the turquoise water below. Our destination is Karlovasi, a flourishing tannery and tobacco manufacturing center in the early 1900s. We will have time to explore the many magnificent neoclassical mansions from that period as well as the remains of the large stone-built factories at the “Ormos” seaside. Dinner tonight will be a special conclusion to our island hopping adventure.
Surcharge: $300 for 6 to 8 day tours; $375 for 9 to 15-day tours
Frame : Alloy with carbon fork
Type : E-Road
Arrival & departure
All 2024 departures except June 1:
June 1 2024 departure only:
Meeting time on Day 1
2 p.m.
2 p.m.
Meeting place
Boat dock at Limenas Ko Harbor You won't miss the bikes and our boat.
Starting hotel Kos Aktis
Early arrival
If you are planning to arrive a day or two early, you are free to book any hotel and arrangement of your choice. See hotel recommendations in walking distance to the boat dock. You may wish to ask for a late check-out by 2 PM.
If you wish to book extra nights at the tour starting hotel listed above, we will be happy to assist. You are of course free to stay at any hotel of your choice pre-tour (see a link to recommendations on the left).
Note: As you are planning, remember that the hotels listed in our itineraries are our primary hotels and are – in rare cases – subject to change. Before you make arrangements, check with us if your tour departure is guaranteed. If your tour departure is out further than 6 months, please also check with us as there might be slight changes to the itinerary.
Airport: We recommend flying into the Kos Ippokratis Airport (KGS).
The rides were challenging and rewarding and the scenery was beautiful. The wildflowers were in full bloom and beautiful. The meals and wines were a delight. We also had a great group to be with.
Cliff M., Knockville, TN – May 2023
Bike and Boat: Cycling Greece’s Dodecanese Islands Plus! Samos