Retiring in Tuscany: How Road Scholar Sally R. Made Her Dream a Reality

How It All Began 

Sally is no stranger to doing new and different things. “I am a serial retiree,” she explains. “I worked for American Airlines for 20 years at the airports, and then I retired and went to law school when I was 42. I worked for the federal government for 11 years, and then I worked in private practice for seven years and then I retired.” 

Her initial travels to Italy quickly became another exciting adventure. “Every day was a look at a different place, or a cooking class with Gianluca as the chef. And it was wonderful, hands on, with delicious food. We went shopping in the market, picking out the very fresh foods that we then brought back and cooked. My friend and I came back with many sets of meals and recipes, and we were cooking for our friends for weeks.” 

It was this culture that made a lasting impression on Sally. “I remember so distinctly,” she describes. “We were sitting at the ‘bars,’ or coffee shops basically, and I’m looking around. And I’m seeing young families pushing their babies in strollers, and I’m seeing the grandparents walking hand in hand. I’m seeing the teenagers flirting with each other on the road, and I was like, ‘Oh my gosh, people live here!’ And of course my friends were saying, ‘Yes, Sally, people live here.’ But I was like, ‘No, people live here.’” 

The Turning Point 

Returning home from that Road Scholar adventure, Sally began to realize how much she had been affected by it. “I came back to work and the managing attorney came into my office one day and said, ‘Sally, let me know when you’re back.’ And I said, ‘What do you mean?’ He said, ‘No, your body’s here, but you’re not back yet. Tell me when you’re back.’ And so I realized that it had stuck in me.” 

Sally continued her learning experience by diving into the Italian language. “I started taking Italian classes in Nashville, where I was, and then I signed up with an Italian language school here in Lucca and came back the following year. And in 2021 I came back and took classes at a different school and again met more people. Every time I came I wanted to stay longer — every time I left I would find myself weeping as the plane took off. 

“So I kept coming back and spending more time, and I learned about the limitations of how long I could stay. Then the last time I was here vacationing, in 2023, I found myself thinking, ‘What kind of visa can I get? Can I move?’ The second-to-last day I was here, a friend of a friend’s daughter had an apartment she was looking to rent, and it fell in my lap. So how could I not make the move?” 

Making the Move 

It may sound like a simple trajectory, but Sally explains that the process was not totally linear. “It’s funny because people think I just decided, ‘Oh, I’m going to move to Italy!’ But it was a five-year process,” she says.  

In order to make the move, Sally went through logistical processes and hurdles, including securing permits and visas. "Doing all that and paying your bills and exchanging currency are necessary. And you have to know some Italian.” 

Sally also has a big piece of advice for others considering a major move like hers. “I needed to have that support system,” Sally says. “If you’re thinking of going someplace, spend time there. There are so many communities, and you have to get to know the people there. Take your time, don’t get upset, and have a good support system and roll with it.” 

Living in Lucca 

Sally finds living in Lucca has lots to offer. “There’s always something going on,” she says. “The week I was there with Road Scholar, there was a paper exposition with giant sculptures made of paper, and little opera arias being sung in the piazza in the middle of the afternoon. Tonight, I’m going to a concert and a three-course dinner afterwards, and yesterday I played mahjong with a group of women that I play with once a week. I also have a group that has game nights once a month. You could literally do something every night.” 

Sally stays connected with the instructors from her Road Scholar program, too. She has run into her Group Leader, Christina, on the street and her cooking instructor Gianluca in the piazza, and each time they greet her by name. Sally had the opportunity to catch up with them when she stopped in on a lesson with the latest group of Road Scholars exploring Italy. 

Now a local, Sally has lots of advice for anyone planning their own exploration of Italy. “I would say, if someone is considering coming, go ahead and invest in an expert to show you around, at least initially,” she says. “And there are lots of Facebook groups that can give you good ideas. The trains are wonderful — you don’t really need to rent a car if you don’t choose to. Lastly, I would say to anyone who’s coming to visit Tuscany, don’t rush. The whole point of Italy is to go slowly, savor it.” 

As for homesickness, Sally admits it can be hard to not be able to travel to see her friends easily, and living in vastly different time zones can make coordinating phone calls difficult. But she also has a great appreciation for the city of Lucca and its culture and atmosphere, which she says cheers her up quickly. “If you get sad, it’s easy to take a walk and not be sad again,” she says. “You know, it’s just really an amazing place. I love it.” 

Looking Back 

Sally has also given back through contributions to Road Scholar’s Annual Fund. “I loved what it did for me, and while it’s not expensive, it can be out of reach for some people. I don’t want that to be the reason they’re held back.” 

For Sally, Road Scholar was influential in her love of Italy and her eventual move. “I’ve been to Italy before, and it was all very nice. But the Road Scholar program — it was the people, the place, and it’s an amazing program that they put together. I worked in the airline industry for 20 years and I traveled all over, and this was the best program I have ever been on. 

“It was almost a fluke that I took the Road Scholar program, and it changed everything.”