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Croatia to Italy last week in September through October (Bernina Express?)

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Hi, planning to leave from the US the last week in September and going to Croatia for at least that week (Dubrovnik then…. ?) and then onto Italy (was going to do NW Italy, (Cinque Terre, Siena…) but heard weather might wreak havoc in Cinque Terre in October, so now I'm worried.
We have 16 nights. There are 5 of us.
The only for sure thing so far is basically Croatia, then somewhere else, most likely Northern Italy (and now the Bernina Express IMO IME is begging for attention and I don't know if it's worth it for this trip or save it for another time…. Not sure if all parties are interested in Venice, as maybe 2 of the 5 have been there done that..
We are interested in hiking (mild to moderate), touring of ruins, doing just a bit of relaxing by the sea or cafes watching passerby with a glass of wine perhaps.
We enjoy architecture, exploring quaint little towns and alleyways, would love hillside towns along the coast (a big reason we are going to Croatia) and maybe some wine tasting, as at least one of the group has expressed a hope for this. She had suggested Tuscany for this. I had wanted to see Siena. I understand Siena is in tuscany…
I would like to know if a day of pleasure boating might be possible on this trip. Is it possible to rent a boat so that we might enjoy an easy, pleasant scenic boat ride somewhere? It'd be a nice activity and would add variety.
Would it be warm enough for this?
Should we be mindful of the weather in NW Italy in October and avoid Cinque Terre and maybe go instead to Venuto, Friuli-Venezia-Giulia as weather won't be a problem at this time of year as someone suggested?
Are we way too late right now to even THINK of finding lodging in Cinque Terre for October?
The Bernina Express IMO IME from Milan to St Moritz looks beautiful, and I don't know if it's do-able at all on this trip or not… should we just maybe do Croatia and the train, and get off and hike and sightsee along the way? To be honest, there's so much to research that we haven't gotten into researching this option much yet, not sure how easy it'd be to get there and how many nights we'd need between Croatia and Italy or for the Bernina 'excursion'.
Any advice would be much appreciated.
I'd like to keep this as stress free as possible, so I was thinking the minimum number of nights in any one place should be no less than three, and perhaps it should be something like 5 nights in one place, 6 nights somewhere in the middle, and 5 nights at the end. We've done that before and found it to be very do-able.
I could really use your help. It's difficult to get an itinerary that pleases all of us, with weather we can count on (we all hope for warmish, not too cool. I understand October is getting there…), and easy navigating from place to place.
Thank you very much

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