Renting a sailboat and sailing in the Cyclades

Hi everyone, our friend is a real Captain with experience—last time we rented in the Balearics and it was amazing. This year, we’d like to rent a sailboat for a week in May or September to sail around the Cyclades. I have a few questions, starting with the wind. 1/ Does it really blow very hard during these periods? Some crew members aren’t exactly seasoned sailors. 2/ Is it better to rent from Athens or one of the Cycladic islands from a cost and time-management perspective? We only have a week. 3/ Which are the most beautiful and wild or least crowded islands, and where should we start? 4/ Do you know of a good sailboat rental agency?

Thanks a million for your answers—I hope some fellow sailors will chime in too!

Hi there, I’ll start by saying I don’t sail myself, but I can answer three points for you.

First point: the wind does blow very strongly in June or September. Depending on the captain’s experience, sailboats might leave the next day or stay docked for a day or two based on the forecast. Second point: from what I’ve gathered talking to some sailors, most rent out of Athens even for just a week. Third point: opinions vary. What I can tell you is that two islands close to each other—Sifnos and Serifos—are less touristy.

Catherine