Cycling in the Cyclades

A typical cycling vacation is around eight days, during which you can expect to cover about 30km a day on mostly low-traffic roads, so it’s nice and relaxed – though remember the Cyclades are definitely not flat. On some islands there will be a choice of routes open to you, so you can make the day’s ride a bit longer, or more challenging if you wish. If you’re riding as part of a small group there’s nothing to say you can’t split into two and reconvene at a taverna or the port.

Since you almost certainly won’t want to take your own bike with you, cycling vacations include the hire of suitable, high-quality road bikes with panniers and locks. E-bikes are available too and worth considering if you want to zip up those hilly sections. But while you’ll encounter the odd calf-stretching incline here and there, routes are carefully chosen so that anyone in reasonable fitness should be able to ride them with little difficulty. You ought to be familiar with basic bike maintenance such as how to fix a flat tyre, but if not then full training, as well as spare inner tubes, can be provided.

Small group cycling tours (which can be either guided or self-guided) will often use private sail boats to get from island to island, so the skipper can wait for a while if you’re stopping for a quick refresher before the final downhill to the port. On tailor made trips you will usually be taking public ferries between islands. As well as sailing schedules and tickets you’ll be provided with route notes, GPS maps, and 24-hour support should you need it. You’ll be encouraged to stick to marked trails throughout, as heading off-road can potentially damage delicate environmental habitats.

At the end of every afternoon a small, often family-run hotel will be waiting to welcome you for the night. Your hosts will have copious recommendations for restaurants to dive into Greek cuisine. Meaning that, between sleeps and eats, your cycling vacation spreads tourism income across the islands like hummus spread on pita bread.

The Cyclades are served by a handful of ferry companies and the schedules, though subject to weather and the occasional strike, are generally reliable. During spring (March to May) and autumn (October and November) you should expect ferry services to be reduced, while they get very busy over Greek Orthodox Easter when many Greeks return for family celebrations. Boats are comfortable, with plenty of seating available and larger vessels, such as modern catamarans, will have food and drink for sale too.

If you’ll be getting around by ferry then our partners ensure you have an up-to-date schedule of sailings to ensure you get to each port on time. There are a few hubs, such as Syros, Paros and Naxos, while the mainland port Piraeus, near Athens, serves most of the Cyclades.

The Aegean Sea is generally quite calm, and of course the distances between islands are quite short. But keep in mind that rough crossings do happen occasionally – the Meltemi winds blow throughout the summer, peaking in July and August, and can create choppy waves in the open sea.

When you’re cycling the Cyclades as part of a small group then you’ll likely be traveling between islands on a private boat with a local skipper. Often a group of family or friends will hire the boat for themselves in which case itineraries can be tailored to their abilities and interests.

You’ll sleep in double cabins (solo travelers will be accommodated with someone of the same sex, but single supplements may be available). Typically a boat will have just eight berths but there are also larger vessels where you’ll have private bathrooms, the option of an above deck cabin, and a crew of four including a cycling guide.

Expect to be sailing for around four hours a day, during which you can sunbathe on deck, admire the scenery (look out for dolphins) or even help the skipper out with the sailing if you fancy learning the ropes.