Depending on which region you would like to sail, there are many sailing routes. Especially in larger groups of islands like Cyclades, there can be countless combinations. However, regardless of any reason you might choose a place or route, weather and sea conditions are the critical factors for any final decision to a safe trip.
In bareboat charters, it is strongly recommended for the licensed people that will operate the boat to ask for advice from their Trip-to-Sail representative and check on the Greek Waters Pilot regularly before and during the trip.
On the other hand, in skippered charters we highly recommend keeping open mind and always have your captain informed of what you are interested in experiencing and he will do the rest!