Join Date: Mar 2007
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That's a lot of territory that you plan to cover. There's so much to see along the way, would you consider a somewhat less ambitious itinerary?
My general suggestion would be to skip Tunisia on your eastbound leg and leave it for the return trip (assuming you are going to sail back westbound out of the Med to the Atlantic again). If you end your sailing season in Tunisia, you will still have a long slog to Greece next year. And it's hard to cover Greece and the Ionian coast of Turkey in one season -- so you'll want to be strategically pre-positioned when you begin that leg.
My suggestion would be to winter-over somewhere on mainland Italy or Croatia, or even Greece itself. If you winter-over on an island (like Elba, Sicily, Malta, etc) you will have a lot of additional travel logistics as you come and go from the boat. If that doesn't bother you, Elba and Malta are usually recommended. Elba probably isn't far enough along the itinerary, though.
If you stick to mainland southern europe, I'd suggest pushing through the Straits of Messina, rounding the heal of Italy and looking for a good spot in the Adriatic, in the vicinity of Brindisi or along the Dalmatian coast (Tomas, a SailNet member, lives thereabouts and might have a good suggestion for you), or even jump across from Italy to Greece.
The nice thing about Italy is that it's centrally located in southern europe, with easy access by train or auto to France, Germany, Switzerland, etc, if those countries are on your winter travel plans. On the downside, it's probably pricier than Croatia.
Send us a trip report, eh?