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Dodecanese

The Dodecanese island group in southern Greece is perfect for beautiful cycling tours. Sun is guaranteed, and the west wind ensures mild temperatures. The landscape is surprisingly green, and the sea is as blue as in the postcards. After starting on Rhodes, the cycling tours also visit Kos, Leros, and Patmos. » read more about Dodecanese

  • Island hopping on Rhodes, Kos, Leros, and Patmos
  • Butterfly Valley Petalóudes (June–September)
  • Ruins of Ancient Temples and Theaters

Greek Super Quartet

In Greek, Dodekanesos means "twelve islands." In reality, this island group in southeastern Greece counts 163 islands. This cycling tour covers three of them; the 15-day version even visits four. The villages on Rhodes, Kos, Leros, and Patmos offer charming labyrinthine alleys, and in the quiet harbors, fishing boats gently bob against the quay. Distinctive fishermen mend their nets while the scent of moussaka blends with that of fresh fish from the tavernas behind them. Here, days slip by in peaceful serenity. Cycling across the islands, you’ll often encounter architectural remnants left behind by the Romans, Greeks, Ottomans, and Venetians.

Cycling and sailing

You begin on Rhodes, with two loop rides—including visits to the beautiful villages of Platánia and Apóllona. Then you sail to Kos, where you can enjoy two round trips on the island and additional routes on nearby Kalymnos or Nisyros. Finally, you spend two days on Leros before returning to Rhodes. You’ll have one last day to explore Rhodes Town or take a trip to picturesque Symi.

Marmari BeachMarmari Beach

A Knightly Feat

UNESCO has taken the fortified old town of Rhodes under its wing. During this holiday, you’ll have a full day to stroll along the ancient city walls, built by the Knights of St. John around 1309. They built so well that it wasn’t until 1521 that the Turks managed to conquer the city — even though the island lies within sight of the Turkish coast. Rhodes Town is a true masterpiece of medieval fortification and rightfully listed as a UNESCO World Heritage Site. A city walk takes you past all the highlights: the Palace of the Grand Master, the Street of the Knights, city gates, squares, churches, mosques, and the synagogue. Our tip: don’t miss the hidden alleyways and their peaceful corners.

Mediterranean Kos

Visit Kos Town and you’ll be pleasantly surprised. Greeks, Romans, Ottomans, and Italians all left their architectural marks. Nowhere else in Greece will you find such an Oriental flair. A robust knight’s castle stands next to an Ottoman mosque, while Greek temples neighbor Roman patrician houses. You’ll stroll through medieval alleys and suddenly come upon neoclassical Italian buildings. In the early 20th century, the Italians also planted hundreds of palm trees, giving Kos Town its distinctly Mediterranean and exotic atmosphere.

KosKos

Pilgrimage to Patmos

When the evangelist John was exiled from the city of Ephesus to the island of Patmos in 95 AD, the Romans thought they had silenced him. Surely his preaching would end quickly on the sparsely populated island. Well, they were wrong. It was there that he wrote the final book of the Bible: the Apocalypse. A thousand years later, the Monastery of the Apocalypse was built in his honor — a fortress-like monastery resembling a crusader castle. This, in turn, attracted many pilgrims. Alongside Rome and Jerusalem, Patmos has therefore been a prominent destination on the pilgrimage map for centuries.

When are you going to take this trip?

Dodecanese

Prices and dates

Routes

The Dodecanese island group in southern Greece is perfect for beautiful cycling tours. Sunshine is guaranteed here, and the pleasant western wind ensures mild temperatures. The landscape is surprisingly green, and the sea is truly as blue as in the pictures. After starting on Rhodes, the cycling tours also take you to Kos, Leros, and Patmos. Each island has its own character, well worth discovering, and they all share the welcoming Greek atmosphere.

Dodecanese

Cycling Routes 11-Day Tour on Rhodes, Kos and Leros (Three-Island Tour)

Day 5 - Pláka (29 to 61 km), Pylí (33 km), or a visit to Kalymnos or Nisyros

Cycling Routes 15-day Tour on Rhodes, Kos, Leros, and Patmos (Four-Island Tour)

TIP
You can turn the 11-day tour into a 12-day tour by adding an extra overnight stay in Mastichari. This allows you to enjoy additional cycling tours. The program will then shift by one day. To do this, simply book an extra night in Mastichari during the tour under the extensions.

Details

Included in the 11-day tour (three-island tour)

  • 10 nights accommodation including 2 half board nights (day 2 and 10 ) and 8 nights bed and breakfast
  • Luggage transport (except for 300 m in Mastichari from the hotel to the boat)
  • Airport-hotel transfer and return
  • Maps and navigation app for your smartphone (GPS tracks for your own GPS device on request)


Included in the 15-day tour (four-island tour)

  • 10 nights accommodation including 2 half board nights (day 2 and 14 ) and 12 nights bed and breakfast
  • Luggage transport (except for 300 m in Mastichari from the hotel to the boat)
  • Airport-hotel transfer and return
  • Maps and navigation app for your smartphone (GPS tracks for your own GPS device on request)

Excluded

  • Ferry: Rhodes-Kos-Leros-Patmos-Rhodes approx. €150 (rate September 2025)
  • Mastichari-Kalymnos return approx. €16
  • Kardamena-Nisyros return approx. €30
  • Return flight Rhodes: we can tailor-make the flight reservation for you
  • Travel insurance
  • Tourist tax
  • Rental bikes
  • Entrance fees, transfers, etc. that are not listed under “including”

  • Rental bike (24 gears, excl. bike insurance):
    11-day tour: € 45- p.p.
    15-day tour: € 55,- p.p.
  • E-bike (excl. bike insurance): 
    11-day tour: € 80,- p.p.
    15-day tour: € 90,- p.p.
  • When booking a rental bike/E-bike, we ask for your height so that we can provide a suitable bike.
  • Bicycle Insurance: You can take out a separate bicycle insurance with Happy Cycling Holidays. A travel insurance often does not cover bicycle damage and/or theft.
  • Read more about rental bikes, helmets and insurances

  • Extension during the trip: you can extend your stay in any stopover town with bed and breakfast. Please inform us when booking.
  • Island order: due to ferry schedules, the order of the islands may change; the number of nights on each island will remain the same.

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Dodecanese

Soroni Beach
Soroni Beach
Rhodes town
Rhodes town
Kalymnos
Kalymnos

Prices and dates

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