Hi all. My wife and I are planning an extended trip (38 days) with our two 6 year olds in Italy from late November through all of December.

I realize it is not the best time of year to travel, but we wanted to pick a time that avoids the traditional tourist season so that we could attempt to immerse ourselves in the local culture. Although we do plan to go to some of the traditional tourist locations, our primary goal is to spend time trying to experience what “normal life” would be like living there full time.

We are entertaining a permanent move to Italy in the coming year, and this trip is designed as sort of a trial run to see if we can handle the culture change. We want to explore the various regions to narrow down the actual area that we would want to call home when the time comes. So, unlike a typical tourist trip we want to spend time in smaller, quieter areas.

From afar, we are very attracted to the Tuscany lifestyle and envision if we move to Italy of owning a farmhouse with some livestock, close to a small town (20,000 to 150,000 people), a place where a slower pace is celebrated and people are inviting of foreigners.

Thinking about the trip, ideally we would pick 4-5 different locales spending 5-10 days in each that have close proximity to a village, but also are a short car ride to the various ‘traditional’ tourist sites in that region. With our 6 year olds in tow, we can’t do too many of the traditional tourist activities, but rather are looking for kid friendly activities. In fact, if the towns have playgrounds or places for the kiddos to burn some energy where local children frequent, this would be an added perk.

In a perfect world, we would rent a farmhouse or outbuilding on someone’s property that have children of their own. Being able to talk to them about moving there and watch the kids interact would be an added perk. Ideally we want a kitchen, since we want to take a stab at shopping and cooking to see how difficult (or easy) it will be to survive there.

Would love some recommendations of cities to see, places to stay, but more importantly cities that are particularly friendly to foreigners (with children). Also, if you have suggestions of actual people to rent from it would be appreciated.

We are a little nervous about being there in December with the colder weather for the kids, but if the weather was particularly bad we would just stay in on those days, again … simulating normal life for us if we were to ultimately move there.

Some other details … We are planning on renting a car for the trip, although it sounds like getting around in some places may be difficult. In places we stay for longer periods, having internet access is really important. Our Italian at this point is VERY rough, although we are working on it every day.

Grazie mille … As we start digging into this undertaking, we are feeling quite overwhelmed. I REALLY appreciate any suggestions you can provide.