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Depends if you're motorwaying down and back or backroads...
If motorway I'd probably go for big ADV (GS or Super Tenéré maybe) or Sport Tourer (perhaps some BMW thing?)...
If backroads a super naked type like the aforementioned 990SMT would be great or maybe even a Tuono?
Nahguavkire-
More back roads, possibly some easier TET sections if possible. I'm hoping to test ride some ADV style bikes over the next few months. I have short legs so want to make sure they are for me. 990SMT is right up my street and so is this https://www.facebook.com/marketplace/item/614254500841287/
For some reason I keep gravitating to older bikes, obviously want to make my life harder.
Haggis
2500 mile round trip down to Italy, what bike would you get if you had a 5k budget? I was down in Umbria/Tuscany and was shocked at how bad the roads are, I will never complain about Wiltshire again.