Sharing Italy 2026

Dear Family & Friends,

An amazing new endeavor is in the works and we invite you to join us. Many of you know that we have spent more than 10 years visiting Italy learning about the culture, food, people, architecture, history and language of this magnificent country. The only missing piece for us has been the opportunity to share the experience with so many we love and enjoy.

In 2026, we look forward to renting a couple of spectacular places: near water in August

and in our beloved Tuscany  in September. Similar to how we traveled to Italy on first trip together.

If you have always wanted to visit Italy and experience a completely different way of life, now is your chance.

We will be sharing specifics  and locations as we get closer to travel dates. If you prefer to travel over with us, we will be booking our own flights out of Chicago to accommodate those who wish to do so.

Our goal is to be there for 2 months to give everyone interested a chance to choose a time frame that works for their schedules. The time period you stay is up to you. For perspective on the cost - our goal is to keep a month long trip to around $5,000.00 including air and lodging. In our experience you can expect to pay around $1000 for economy airfares. Yes, there are better fares out there but usually the travel times or layovers are less than desirable. The more who join us the greater the savings to the entire group on our residence.

You book your flights (Pisa is the closest airport but Florence & Rome are also available) and we’ll have the place to stay , recommendations, transportation to and from the airport (unless you prefer your own vehicle), introduce you to how we live as the locals do, cooking and dining out, day trips to various towns in the region. There is no pressure to restrict yourself to our plans and schedules but if you want to you are welcome.

We are an ideal option for those who don’t want the restrictions of a bus tour schedule that includes costly and crowded tourist attractions, restaurants and lodging.

If you prefer to have a more authentic experience when you travel we’ll be a good fit. We’re also ideal for those who don’t speak Italian or are intimidated to drive in Italy (with good reason!) We prefer to stay and sleep in a more tranquil, quiet location and visit nearby locales where the action is happening so our time at home is relaxing.

How we spend our days:

Living like locals- Visiting public gardens, beaches, produce markets, wineries ,vineyards, olive groves, medieval churches and towns.

For Foodies: cooking classes can be arranged, local farmers markets, visiting Restaurants and cafes, & picnics

Eden Enthusiasts: A special focus on the garden- local flower farms and gardens along with botanical

and historic gardens in Italy. Floral related classes can be arranged. Perfume making course.

Sewists: Tailor made for those who enjoy and wish to learn more about needle arts, sewing & tailoring. Visits to fabric mills and fabric/trim shops. Classes can be arranged.

In the Garage- car and motorcycle enthusiasts will enjoy riding and viewing Italian designed vehicles, car museums and for those who don’t mind paying a premium an ultimate rare car experience can be coordinated starting in April 2027.

The Daily Grind:

A focus on famous & local brews (coffee & tea) and delicious pastries

The Artful Life: view art of local and renowned artisans, craftsmen and women, museum and galleries

Healthy Habits: bicycle rides, walking or hiking, swimming, yoga & more.

If you have an affinity with any of the above, please let us know and we will be sure to include these types of activities during your stay. For those who prefer to take each day as it comes you are welcome to stay back, relax and bask in the beauty of nature in our tranquil home away from home.

If you’re interested in joining us in Summer/Fall 2026 or learning more, please contact Deborah at (815) 271-2573 or via email at yourfriends@italylittlebylittle.com.  You will be added to the wait list and reserving a trip will happen on a first come first serve basis based on availability of accommodations. You will receive more information as we do. Destinations, lodging and airfare will all be considered with respect to the overall experience and cost. If you’re working with a budget we can work together to help make your trip memorable.