Yeah it would definitely be a cold journey down, but if you want to ride for the sake of riding, go for it!
I would avoid Istanbul because traffic will shave a good day off your trip. The road over to Cannakale is much nicer anyway, and the ferry is quite short.
The ferry from Italy would be nice too, but it would add quite a bit of time to your already short journey. Just rip straight down on the route you already planned out if you want to spend some quality time with your friend in Fethiye.
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