We will be celebrating a major anniversary Sept. 2018 and we have done incredibly adventurous trips in the past that have been farther afield (Myanmar, Rwanda, Manchu Picchu, Australia/New Zealand/Tasmania, Tahiti, Figi, Indonesia). Last anniversary trip was Croatia. I was thinking romantic on this trip since I want to see Venice and have only skied in northern Italy. Thoughts are flying into Milan and continuing to Lake Como, Venice, Florence, Cinque Terra, and definitely wine country such as Barbaresco (husband's fav). We are very active travelers so want to hike, possibly bike (even a city bike tour), but also like culture, art and food. Any ideas of a good itinerary or is there a city in the area that we should visit versus the well known destinations. We love going off the grid and finding the unique -- my husband is planning to drive most of the trip unless train travel makes sense. Thanks for any input or recommendations you can provide. If there is a destination beyond Italy that you feel is very romantic but active, don't hesitate to chime in.
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If you stick to the listed destinations (too many for 14 days IMO), you won't be going "off the grid" and having a car would be more of a burden than a help in getting around. Only Piemonte really requires a car to reach and explore. It's also the destination most likely to provide exposure to less-crowded sights and to activities like hiking and biking. FWIW, I don't find city bike tours very satisfying, and most of your destinations aren't conducive to them.
Whether alternative towns in the same general area as the main cities would satisfy you depends on how much time you'd still want to spend in the main cities which would therefore necessitate lots of commuting back and forth.
FYI, September is still very much high season in the places mentioned, and it's all wine country of one appellation or another.