The first question every new charterer asks is "do I need a licence?" — and the answer (only for bareboat; a captain solves everything) usually arrives with relief. But the licence question hides the better one: what kind of week do you actually want?
Bareboat means freedom and responsibility in equal measure. You choose when to leave, where to anchor, whether that dark cloud matters. It also means you do the 6 a.m. anchor check when the wind shifts, you plan water and fuel, and you take the stern-to mooring in a crosswind with an audience of taverna guests. For crews who sail regularly, that's precisely the joy of it.
Skippered changes the arithmetic. A good skipper is not a chauffeur — think of them as local knowledge with a wheel: they know which bay is sheltered from tonight's wind, which konoba is worth the detour, and they'll happily teach anyone aboard who wants to learn. You surrender one cabin and roughly €180–220 a day; you gain sleep, safety margin and, oddly, freedom — nobody spends the holiday being responsible.
Our honest rule of thumb: if your crew includes two people who have each skippered a comparable boat in the last two years, go bareboat. Otherwise take the skipper for the first charter — and expect to go bareboat the year after. Either way, the boat, the bays and the swimming are exactly the same.