Originally Posted by akallabeth
I had hoped to do any initial bareboat chartering is a limited sailing region - the Northern Sporades islands are close to my wife's home in Greece and are all within site of each other for the most part. We've also considered BVI etc., but that would be for another season, but may indeed be where we decide to do this. Chartering a skipper may also be in the plan.
Welcome to Sailnet! I like your handle too! Lots of good advice on this thread, with which I mostly agree (particularly the point that education is helpful, but there's no substitute for experience). I did just want to make one additional point:
I don't know what time of year you hope to do your chartering in the Greek isles, but just be aware that during the summer months you can encounter some very challenging conditions there. Beginning in June, the Meltemi begins to blow, and it builds stronger during July and August, then gradually diminishes in September-October. You probably realize that the Meltemi is a strong, consistent northeast wind that blows in the Aegean during the summer months, especially in the Sporades and Cyclades. Beaufort Force 5-7 wind and sea state are typical, which can make for exciting but challenging sailing. So I'm not sure it's the place I would recommend that a novice charterer go for practice. Keep that in mind as you work your way up.
Sailing is a great past-time, take it slow and you can look forward to a lifetime of enjoyment from it. Best of luck to you!!