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Jsailor said:
A little bit of of a trek but Consider Croatia. I sailed from Dubrovnik to Split several weeks ago and hit 4 or 5 islands along the way. Nice sailing and friendly folks that (most) speak English.

If you're lucky! Practice your German (presuming you dont speak Croatian). I love Croatia biut be aware that the climate is definitely no where near Caribbean. We literally experienced four seasons In a day (including snow) in early September, I truly want to return to this beautiful area, but it is NOT an easy alternative to anywhere in the Caribbean. Also you need specific sailing qualifications or else you need a 'captain'.