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Cycling Holidays in Greece
Greece · 6 retreats
Compare 6 cycling holidays in Greece. Expert-reviewed retreats with real photos, itineraries and verified availability.
- Cyclades Island-Hopping by Bike: Kea, Kythnos, Syros, Paros and Serifos
- Laconia by Bike: Sparta to Monemvasia Self-Guided Cycling Holiday
- Messinia Coast by Bike: Self-Guided Cycling Holiday from Kalamata
- Western Crete by Bike: Omalos Plateau, Elafonissi and Chania
- Eastern Crete by Bike: Heraklion to Rethymno via Knossos and Phaistos
- Ionian Islands Boat & Bike: Guided Island-Hopping from Corfu
Greece makes a natural home for a cycling holiday, with island roads, mountain plateaus, quiet coastlines and ancient sites never far from the saddle. The six programmes on this page cover four distinct corners of the country: the Ionian Islands, Crete, the Cyclades and the Peloponnese. Most run for eight days, and most are self-guided, so you ride at your own pace with the route planned for you.
If you would like to combine cycling with the sea, two trips are built around island-hopping. In the Ionian Islands you live aboard a crewed motor yacht, the Panagiota, starting and ending in Corfu, with a guided ride each day before sailing on to the next island. In the Cyclades you ride a different island each day, from Kea, Kythnos and Syros to Paros and Serifos, taking the ferry between them, starting at Lavrio port near Athens and finishing at Piraeus.
Crete has two options. Western Crete takes you from Chania up to the Omalos plateau, with the choice of riding down to Palaiochora on the south coast, and includes Elafonissi along the way. Eastern Crete begins in Heraklion with Knossos on your first riding day, continuing via Agios Nikolaos, Ierapetra and Phaistos to Rethymno.
On the mainland, the Messinia coast route from Kalamata mixes easy coastal riding with a few hillier stretches, past beaches, castles and seaside towns, while the Laconia route runs from Sparta to the medieval castle-town of Monemvasia, pairing Byzantine and ancient history with quiet beaches and fishing villages.
Frequently asked questions
How long are cycling holidays in Greece?
Most programmes on this page run for eight days. That includes the Ionian Islands boat-and-bike trip, the Cyclades island-hopping route and both Peloponnese holidays in Messinia and Laconia.
Are these cycling holidays guided or self-guided?
Most are self-guided, so you follow a planned route and ride at your own pace. The exception is the Ionian Islands boat-and-bike holiday, where each day's ride is led by an English-speaking guide.
Where in Greece do these cycling holidays take place?
The programmes cover the Ionian Islands from Corfu, the Cyclades, western and eastern Crete, and two regions of the Peloponnese: Messinia in the south-west and Laconia in the south-east.
Can I combine cycling with island-hopping?
Yes, two programmes are designed around it. In the Ionian Islands you sail between islands on a crewed motor yacht, and in the Cyclades you ride a different island each day before taking the ferry on to Kea, Kythnos, Syros, Paros or Serifos.
Where do I stay on the Ionian Islands boat-and-bike holiday?
You live aboard a crewed motor yacht, the Panagiota, and sleep on board throughout. The yacht starts and ends in Corfu, sailing to a new island after each day's ride.
Where do the trips start and finish?
It depends on the programme. The Ionian trip starts and ends in Corfu, the Cyclades route runs from Lavrio port near Athens to Piraeus, Western Crete begins in Chania, Eastern Crete starts in Heraklion and finishes in Rethymno, Messinia is based around Kalamata, and Laconia runs from Sparta to Monemvasia.
Is there a route with gentler riding?
The Messinia coast holiday from Kalamata is described as mainly easy coastal riding, with a few hillier stretches along the way. It mixes cycling with beaches, castles and seaside towns.
Can I see historical sites on a Greek cycling holiday?
Several routes are built around history. Eastern Crete takes in Knossos on the first riding day and Phaistos later on, while the Laconia route combines Byzantine and ancient history between Sparta and the medieval castle-town of Monemvasia.