Greek Island Hoping Cycling Tour (11 days)

Greek Island Hoping Cycling Tour (11 days)

During this 12-day cycling holiday you will follow the lead of your guide who will be riding along with you across four beautiful cycling islands in the southeast of Greece: Rhodes, Kos, Leros and Patmos, with a stop-over on Kalymnos.

While cycling you will become familiar with these islands of the Colossus and the Asclepeion, the crusaders and the sponge fishermen; islands with both Italian and Turkish influences. You will balance pleasant cycling tours with cultural heritage excursions and boating trips on azure blue waters. The unknown Leros is the surprise of this cycling holiday: a green jewel. Patmos is a photogenic island full of monasteries and chapels. The trip will be kept as light as possible. You will cycle along the coastal regions and only occasionally encounter a real incline.


  • Accommodation in hotels, 2-person room with shower or bath, and lavatory
  • Breakfast (all) and dinners (5)
  • Baggage transport
  • Accompanying tour guide (English-speaking)
  • Comprehensive route directions
  • Dutch agent and technical support
  • Ferry tickets
  • Bike

Not Included:

  • International airfare to and from the destination, please contact us for the best available prices from your home city.
  • Travel Insurance is not included, but available, please contact us for the best options for your family.
  • Meals and drinks not mentioned in the itinerary below.
  • Tours not mentioned in the itinerary below.
  • Gratuities (optional).
  • Entrance fees

Day 1:  Arrival in Rhodes You will be picked up from the airport and brought to your hotel. We have used Kalavarda as our cycling village on Rhodes for ten years now. You will stay at Hotel Vouras, 900m from the sea. If you are arriving in the morning, there is an afternoon walking tour of Kalavarda, including a visit to the beach. Because Hotel Vouras is a small hotel, we might possibly book you into Hotel Meliton in Theologos.

Day 2:  Kalavarda, daytrip, up to 39 km Today you will visit one of the most important sites of Kalavarda: the ancient city of Kameiros. You can stroll around here through the labyrinthine streets, beautifully located on a plateau with views to the sea. Before or after having lunch at a seaside (fish) restaurant, you will explore a totally uninhabited and unadulterated stretch of coastline. After a ride of around 20km you will get to see the Chalki and its neighbouring islands. Depending on your preference, the final destination of this daytrip will be either the fishing harbour of Kameiros Skala (34km) or the castle ruins of Kritinia (39km).

Day 3:  Kalavarda – Rhodes City, 38 or 44 km. This stage, leading to Rhodes City, follows a trajectory that runs largely through the island’s interior. The butterfly valley Petaloudes can be found here as well as beautiful villages such as Theologos and Maritsa. Pastida is a large village and a very suitable place to stop for lunch. A particularly wooded route will bring you to the only unavoidable incline of the day, which will lead you into Rhodes City through the back door. After climbing a hill scattered with ancient ruins you will make your descent to the harbour.  At the end of the afternoon you will take the boat to Kos.

Day 4:  Kos – Mastichari 28 km. Today starts with some sightseeing in the capital of Kos, which is well worth a visit. Ruins from ancient times snake through the city. Mosques remind us of the island’s Turkish period and other buildings betray the many years of Italian influence. After sightseeing you will get back on your bike for the stage to Mastichari, one of the smallest and most intimate seaside resorts on Kos.

Day 5:  Mastichari, Plaka round trip, from 29 km Today you will discover a beautiful part of central Kos. You will visit Andimachia, with its restored windmill and Plaka, a forest in a ravine where semi-wild peacocks roam freely. The basic route of 29km can be extended if desired, with a visit to Magic Beach, for example, the first in a series of wonderful beaches on the south coast (5km extra) or to the castle of Andimachia, a gigantic complex perched on a hilltop (7km extra).

Day 6:  Boat to Kalymnos, boat to Leros The boat to Kalymnos usually departs at 9am from the pier opposite your hotel. By 10am you will already be in Pothia, the capital of Kalymnos and the epicentre of the sponge fishing industry, even though the fishermen now travel far for their catch. The time and place of departure of the boat to Leros will determine whether there is time to cycle around a little on Kalymnos. It is most probable that the boat will depart in the afternoon at some point from Myrties, 10km from Pothia. If desired you can still make a round trip to Myrties and back, following the coast. The road is a ribbon of oleanders amid a fascinating rock landscape. On Leros it’s a short but steep climb to your hotel, which has a great location with a view of the harbour and a castle.

Day 7:  Leros, round trip of the island, 29 km During this cycling tour you will visit both the remote church of Maria of the Crabs in Xirokampos and the little church on the micro-island of Agios Isidoros. This trip will allow you to see all the beautiful bays of the amoeba-shaped island. In Lakki there are many beautiful buildings from the Italian period.

Day 8:  Boat to Patmos The expected time of departure of the boat to Patmos is around noon. It is one or two hours sailing. It is a spectacular arrival in Patmos, the monastery fortress towering above the white, sugar-cube houses of Chora. The rest of the day is free. In the morning on Leros you could still cycle or walk to the castle. Once on Patmos you can cycle to a remote bay and enjoy a beautiful beach.

Day 9:  Patmos, island tour, 33 km The daytrip on Patmos consists of two parts: in the morning you will climb to Chora, a maze of alleys around the monastery fortress, with a chapel on every street corner. Three restored windmills make the picturesque scenery complete. During the descent you will pass through the resort of Grivos with Petra beach, dominated by an immense boulder-shaped rock. In the afternoon you will cycle to the north with its remote beaches.

Day 10:  Boat to Rhodes The boat, a swift catamaran, will leave at approximately 1.30pm and you will be back on Rhodes at 6.30pm. On the way you will again encounter Leros, Kalymnos and Kos, and also Symi, where you will dock in the especially photogenic harbour.

Day 11:  Rhodes City, rest day Use your rest day in Rhodes to get a closer look at this magnificent historical city. You can do this with a city walking tour that will not only take you to the highlights (such as the knight’s castle, the well-restored mosques and the Turkish bathhouse, the squares and the city gates) but also to the back streets and even the double city walls where you will find an unexpected oasis of quiet. The rich history of Rhodes goes back to the time of the crusades.

Day 12:  Rhodes, departure after breakfast


Prices starting from:

$2,413.95 Canadian per person, based on double occupancy

Above pricing includes taxes where stated. In Canada, GST/HST included. Country taxes that must be paid locally are not included.  Prices listed were correct at time of publication.  Prices can change to reflect exchange rate changes. Custom World Vacations reserves the right to amend prices at any time without prior notice.  All vacations are subject to availability.


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