I've been on half a dozen flotilla holidays. In fact I learnt to sail a yacht on a flotilla holiday having done a level 2 on a dayboat. That made me the most experienced sailor on our boat! Since then I've gone on to become a keen yachtie, doing the Fastnet last year.



The Ionian is a popular starting place, having lots of green islands fairly close together so you have short travelling distances and can spend lots of time anchored up in bays having lunch and swimming off the boat - an important part of the experience for the non-committed sailors. The winds are generally pretty light, picking up a little in the afternoon to a F3/4 though you may well get a few more windy afternoons (up to a F5).



Turkey is a bit windier, depending on exactly where. Turkey is also less developed but is largely sailing along the coast without the islands. Croatia is also very popular, with more sophisticated destinations. I'd avoid the Cyclades as they can get very windy. Similarly the Dodecanese. The Saronic gulf of Greece is another possible introductory place.



I'd advise going in late May or June whereever you go. Later on it gets busier, hotter, less green and you tend to get more flat calms. Sleeping in a fibreglass tub in mid August can be uncomfortable in the Med.



Most of the modern yachts are very easy to sail. In fact too easy and a bit boring for keen sailors. In-mast furling mains are becoming the norm. The poor sailing performance can result in a lot of motoring if the wind is light. This is unlikely to bother the non-sailors who are usually happy to have the sails put away to stop them getting in the way of the sun.



I'd forget taking windsurfers. They get in the way on a boat and you'll probably only use them a couple of times at most.



Companies? Sunsail are fine but pricey. Neilson are good. Sailing Holidays are OK.



The flotilla experience has its bonuses - company with other families etc. - but there are some downsides. The route is usually planned beforehand to avoid clashes with other flotillas: you don't want 30 boats all turning up in a small village harbour. So you end up sailing upwind when you could be on a nice fast reach to another island. Some companies overdo the "you're all on holiday so we're going to get you pissed all the time" (stand up Sailing Holidays). Of course you might love this.



And of course you all arrive at the same little harbour at the same time, putting instant demands on all the facilities. Consequently I think that the best solution is to try to arrange a couple of boatloads of friends on a bareboat holiday. You obviously need some experience for this.