14 days, recommendations

I'd like to know more.

Do you have a particular time of year in mind? How flexible are you with dates? Have you been to other European destinations in the past? Do you speak Italian? Have you driven in Italy? Are you comfortable with a small car? Manual transmission? When you say "splurging for a great experience" do you mean an evening, a day, or the whole trip? Do you want long stays in a few places or a series of short (2-3 nights) in more places? What do you want to do with your time besides interacting with locals? Art? History? Scenery? Hiking?

Airbnb may not suit you. It's been my rather limited experience that you'll have little or no interaction with most hosts, unless you find a situation where you have a host who lives on the property and rents out bedrooms in a house or large apartment. I've only stayed in 3 like that and found all of them through private recommendations. Two of them were in Italy - in Salerno and Venice.

I suggest that you consider the Dolomites. We just spent 3 nights in Ortisei, and discovered that was not nearly enough time to explore the region. Planning for a future return trip there is already in the works. As Chani mentioned, knowing the time of year as well as more specific details for your trip will help fellow travelers offer suggestions.

Thank you for the replies.
We are flexible on the travel dates and even time of year for travel.

I have been to Italy and Portugal but that is all. I am very comfortable driving in Italy and with a small car and manual transmission. Both of these trips were in late May/early June. We were thinking around that time frame but there is nothing holding us to it. We would prefer to avoid July/August due to crowds.

As for lodging I don’t mind not interacting with the hosts of our accommodation but would prefer to avoid a large hotel situation. We enjoy conversations with people from the area rather than an isolated location.

Unfortunately I do not speak Italian. During my last trip we learned enough to be polite and respectful and relied on Google Translate for the rest.

Splurging is relative I know. My thoughts - if there was a great place to stay in a recommended location but it was considered pricier compared to most, please suggest. A wonderful restaurant, experience, beautiful area, etc. We were thinking around combination of occasional cooking as well as out to eat depending on location.

The Dolomites could be great. This was an area I looked into for my last trip.

I am not opposed to relocating once or twice but would prefer a base location with travel rather than packing up and moving every few days.

As for our time in areas: love nature, hiking/walking, love art and music. Happy to shop/explore small stores and markets, wineries, farms, villages. We enjoy seeing different architecture and learning about an area. Not a huge fan of long lines or really crowded areas just to briefly walk by something and say we’ve seen it.

Best recommendation for now is to peruse a website or book and see what stands out. There is nowhere in the country that you could not find what you are looking for, so it’s really too broad a question.
Many say they want to avoid crowds, but when it comes down to it, they still want to see the famous things—nothing wrong with that!—so you need to collectively decide if you will actually nix Rome, Florence, Venice, etc. I can assure you you can have a great trip other way.