Head south! That's the mantra you should follow for early season sailing. Very early on you should also consider that even in some southerly areas, e.g. Sicily and the Ionian Islands, tavernas and restaraunts will still be shut. The best areas to sail are the Saronic Islands and Gocek and Fethiye where things do open early.
It is still early season in May, so heading south to Turkey and Greece is a safe bet. Further areas are beginning to open to those listed for April however, so the choice is wider. The Cyclades Islands, Ionian Islands, Marmaris and Bodrum all become open for business. Sicily is also worth a good look later in May.
June really is the first full month where weather is reliable in all our sailing destinations. Many argue that June is the best month for sailing anywhere in the Med, as the weather is lovely, the crowds haven't arrived, there are no kids around, everything has started to kick into gear and holiday costs tend to be cheaper.
July is peak summer, so everywhere is going to have fantastic hot weather. Considerations should be with the extremes - remember the Cyclades become very windy this time of year so perhaps avoid. Also bear in mind that Turkey does get incredibly hot, so if you are susceptible to overheating then perhaps head north.
Peak summer with hot dry days throughout the Med. Look out for extremely hot weather in Greece and Turkey, with Turkey into the 40s. Croatia is slightly cooler (low-mid 30s) so great for kids and those not keen on being oven roasted. Look out for extremely strong winds in the Cyclades Islands - we recommend avoiding.
A lovely month for sailing and our personal favourite here at Seamaster Yachting. The kids have cleared off home after the holidays, the weather is great and the seas are warm. Perhaps only the Cyclades are still not recommended due to high winds. Later in September, Croatia may start having the odd rough day as well.
October is getting to be late season so we end up with the old mantra again of head south! Generally speaking, Turkey and Greece will remain the warmest and driest for the longest. We would avoid Croatia and recommend the Cyclades Islands as the winds there die down and open up some fantastic sailing.