Sailing and cycling Cyclades holiday, Greece

“Discover the beauty of the Cyclades, and the joys of island hopping, with this self guided sailing and cycling holiday. Wake up and ride on a different island every day!”


Cyclades | Self-guided cycling | Lavria | Kea | Syros | Ermoupoli | Paros windmills | Sifnos | Apollonia | Kythnos | Serifos | Chora | Merichas |

Description of Sailing and cycling Cyclades holiday, Greece

This eight-day, self guided cycling and sailing holiday in the Cyclades is the perfect antidote to those that feel Greece has gotten too busy, or that they’ve seen all there is to see. It allows for a more immersive form of travel in local culture and environment, while at the same time creating strong bonds with your fellow travellers in a small group – each boat has only eight berths.

Over the course of a week, departing from Lavrio, your route will take you to six of the more than 200 Cyclades islands: Kea, Syros, Paros, Sifnos, Kthynos and Serifos, always moving yet at a blissfully unhurried pace. Each day’s cycling covers around 30km, though on several islands there is the option to take a longer route if preferred, while boat travel averages around four hours a day during which you can relax and sunbathe, or take a few lessons in sailing from your captain! In addition, this trip of course includes comprehensive maps, 24-hour support should you need it, and convenient luggage transfers between accommodations so you can travel light.

Sifnos, midway through the trip, is sure to be a highlight, with its hundreds of churches and monasteries, traditional white houses and delicious cuisine. Followers of Greek mythology, meanwhile, will love the chance to cycle around Serifos, said to be the birthplace of Perseus and where the Cyclops lived in a cave. The ride up to the hilltop capital, Chora, is one of the steepest inclines of the trip, but more than worth the extra effort. And don't miss your photo of the world-famous windmills of Paros.

Enjoy the gorgeous beaches, bobbing on the deep blue Aegean, and dining on traditional Greek gastronomy every evening as you take a very special holiday in the Cyclades with a group that are sure to become fast friends by the end of the trip.

Hello. If you'd like to chat about this holiday or need help finding one we're very happy to help. Rosy & team.

01273 823 700

Check dates

For departure dates contact us on 01273 823 700

Responsible tourism

Responsible tourism: Sailing and cycling Cyclades holiday, Greece


A Sustainable Holiday
We believe in sustainable and responsible tourism, and we are committed to have the lowest possible environmental impact. As this is a sailing and biking trip, carbon emission are minimal as we use the power of wind and the power of legs. We try to minimise the impact of our boat on the marine environment by using the motor as little as possible, mainly just to enter and leave the port, of course as long as the weather allows us to. On top of that, we inform our guests not to litter, to recycle on possible and general to follow responsible travel guide lines. To help offset the carbon emissions we also donate 10 euros per client which is shared between forestry commissions in the Peloponnese for reforestation after the deadly fires of 2007. We also as a company, gather plastic caps and donated them to a local club that helps children with special needs by buying them special trolleys.


By employing only local guides and using only regional services we provide a form of tourism that benefits the community. The visitor also benefits by being able to come closer to authentic local cultures and traditions due to our unique local knowledge. We think tourism should be about respect and benefit to the local inhabitants and that responsible travellers will get more out of their holiday by giving a little bit back to the special places and people that they meet. But the most important thing for us, is that your presence here gives us a strong negotiation card for pressing the local authorities for the development of our area, such us constructing cycling streets, increase the local recycling program, improve social buildings etc. In this sailing trip the skipper will be local, thus he will have very good knowledge of the area. Also, all of our employees in the office are locals.

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