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Leading Women’s Tours in Tuscany in Midlife: Lisa’s Story

Published on 03/22/2015

Lisa’s profile picWhen Lisa visited Italy at 56, she didn’t want to leave; so she quit her job, sold most of her belongings, and moved to Florence three months later. Tell us a little about your life before your next act? I was born, raised, and educated in Salt Lake City and didn’t live outside of Utah until after I married. We lived in California, Colorado, and Texas while raising our two children. I had a 32-year career in fitness, as an instructor and personal trainer.   When did you start to think about charting a new direction for yourself in midlife?

Lisa with her daughter, Lauren

Lisa with her daughter, Lauren

My “aha” moment was just that. In 2012, at the end of a fabulous vacation in Italy with my daughter, I made the decision to move there. It was early morning, and we were waiting over espressos for the taxi that would take us to the airport; I didn’t want to leave. Divorced for 8 years, kids grown up, I knew in my heart that there was something in Italy I needed to explore. Three months later, at the age of 56, I moved to Florence. I had sold my home, my car, and 90% of my possessions to finance this move. I didn’t know a single person here or a single word of Italian.   What is your next act? I am the co-founder, with Sarah Walton, of Better Way to Italy, a boutique, luxury tour company that brings small groups of women to Tuscany. There are so many women who want to travel but don’t have anyone to go with them. Our tours speak to that need. Tuscany seems to hold a special magic for women, much of which has been documented in books and movies. There is nothing I enjoy more than seeing women relax into the beauty of this country and find their own feeling of joy here. Sarah and I give classes geared to women on courage, passion, and intuition. We keep the groups small and they become very cohesive very quickly.

There is nothing I enjoy more than seeing women relax into the beauty of this country and find their own feeling of joy here.

Currently, we offer two Signature Tours, Tuscany with the emphasis on either Chianti or Cinque Terre. We spend 5 nights based in Florence and 2 nights in Cortona. All in all, we visit 7 towns. We are currently expanding our tours to include Rome, Venice, and the Amalfi Coast.

Signature Tour, spring 2014

Signature Tour, spring 2014

Our philosophy is that all a woman has to do to travel with us is pack her bag. We have everything covered, so she can relax and enjoy an experience that will exceed her expectations. It’s luxury, but friendly and always well organized. Our price is inclusive of absolutely everything (right down to a guide’s gratuity) with the exception of airfare and a few meals.

Sarah and Lisa

Sarah and Lisa

Sarah is in New York, and I am in Italy. We think this is a big plus for our business. She handles the interaction with clients in the US, and I create the tours here. My living here is the biggest difference that we offer. I will ensure that our guests see Tuscany through an insider’s eyes.

Every day I am in awe of what I see and experience.

Mostly, however, my next act has been about finding my way on my own in a foreign country. It’s been challenging, and so rewarding to navigate through this experience. Often, people will ask me if I am living my dream, and my answer is no. I never knew enough about life in Italy to dream this! Every day I am in awe of what I see and experience.   Why did you choose this next act?   I have a fundamental belief that life is supposed to be joyful, and the life I had been living in Salt Lake City was no longer that for me. I knew I needed a change. I thought the option for change would probably come about in a new relationship, or possibly a new career, but I had never thought about living in a new country! I think it is the lifestyle and culture in Italy that felt so good to me. I still find it so joyous. There is a sense of timelessness to Italy; the pace is slower, the emotions are always on the surface. Italians understand the rhythm of life and what really matters: Dinners take 3 hours…and that’s how it should be. Family, art, and beauty are all priorities here. I recognized that quality of life initially, and I love it still.

Shopping at Mercato Centrale in Florence

Shopping at Mercato Centrale in Florence

I know I was blessed in choosing Florence. There is a large expat community here, almost entirely made of women. Because we are all fairly new to Italy, we reach out to each other and have built a tremendous network for socializing. I also have Italian friends that I have made along the way, and for that I am very grateful. Having an Italian become your friend is not necessarily easy, but they are so generous once you are. Florence is a walking city, so I walk instead of going to the gym these days. I love just taking off and not really knowing where I am headed. I love the museums and markets and I also adore going to the small hill towns of Tuscany. I will get up early and wander the narrow streets while the trucks are bringing in the produce to the markets, and the town is just waking up. I love standing at the bar for a caffe with the locals. What keeps me here is the exquisite thrill of life so outside of what I normally had experienced. Learning, just for the sake of learning, has been such a joy to me. I have learned about art and architecture, writers and history, and all types of subjects that I never even knew I was interested in. I have toured the countryside and castles and hiked along the Italian Riviera to my heart’s content. And, of course, I’ve enjoyed the food and wine of this region, which spoils one for any other. I have had experiences I never thought could be mine, and now my business is to share those with the women who travel with us.

 Learning, just for the sake of learning, has been such a joy to me.

How hard was it to take the plunge? How did you prepare? My timing was such that I had just a few months to prepare for such a large change. All of my energy went into selling my possessions and moving from Salt Lake City. Reality didn’t hit until I was on the other side of the Atlantic! Behind me were a house that had sold in 6 weeks, a storage unit that held the few earthly possessions I couldn’t part with, fitness students who had cheered me on, lifelong friends, and my son and daughter. The first year I lived in Italy, I didn’t do any kind of work. I took some Italian culture and language classes and allowed myself time to acclimate to this new adventure. Every day was different; I gave myself permission to just explore. It was scary to trust that I would be ok financially, but I lived very small, and I wanted to give myself that time. Taking the plunge to create a new business with Sarah Walton was very challenging. Like any new business owner, we worked 7 days a week to get Better Way to Italy off the ground and wondered if it would really succeed.

Lisa and Sarah in Florence

Lisa and Sarah in Florence

How supportive were your family and friends? Having been born and raised in Utah, I had a large circle of lifelong friends, students, and clients, who were very surprised at my decision. Most were fairly supportive but some were downright dream-squashers. They pointed out things like I didn’t speak Italian and I didn’t know a single person there. They wanted to know where I would spend Thanksgiving, and what my children thought.

I have a fundamental belief that life is supposed to be joyful.

There were a few people, however, who totally embraced my choice to go. I could see it in their eyes. Most of them were older, all of them women. They knew how small the window of time could be for us to act on a dream. One woman sent a bracelet to me with the inscription “Woman of Courage.” I still wear it every day. The only people who had a say in my choice were my two children, who were 27 and 30 at the time. They were, and still are, my biggest supporters. My daughter told me that she had never seen me as happy as I had been with her in Italy. My kids knew it would mean that I would miss birthdays and Sunday dinners with them, but they both told me that I had given them everything as they were growing up, and that now it was my turn. I give them a lot of credit for being so unselfish and so mature. We Skype several times a week, thankfully; we still share our lives together, just in a different way.

Ponte Vecchio, Florence

Ponte Vecchio, Florence

What challenges did you encounter? Nothing in my first 50 years would have had me thinking about, or preparing for, life in a foreign country! The challenges of living in a new country, by myself, were many and daily. The language barrier, cultural differences, and just the fact that I was all alone, so far away from what was familiar, was equally exciting and terrifying! I learned to speak Italian, but certainly not fluently. Day-to-day in the markets, traveling by train, in a trattoria, I do fine. I call my level of Italian, “functional.” Italians who work in the center of Florence, where most tourists go, will speak English. But, outside of that, and certainly in the smaller towns of Tuscany, most don’t speak English. Italian is only spoken in Italy, so it seems that when I try to speak, even a little, Italians immediately warm up to me.

Every day life in Florence at the Sant'Ambrogio Market

Everyday life in Florence at the Sant’Ambrogio Market

The Italians have seen many expats come and go through the years, and they tend to not be really friendly until you prove yourself a bit. Once they knew I was here to stay and was speaking some Italian, they warmed up. It’s different than the US type of friendliness and, by understanding that, I have gained many friends here, whom I treasure.

Italians understand the rhythm of life and what really matters.

There are many people I miss in the US, of course, and I am American so that culture is a part of me. Still, I have found a lovely balance between both countries, and both cultures, and they weave into my soul equally. I usually go to the US once or twice a year for a couple of weeks. It always takes me a few days in either country to get back into the groove.

Lisa with her son, Justin

Lisa with her son, Justin

After 3 years of back and forth between the two countries, my kids know now how hard it is for me to leave them after I have been in the US, and we switch roles for the last few days. I get teary and vulnerable, and they tell me how proud they are of me. I have had some girlfriends visit here, and my son works in Europe a couple of times each year, so that’s a bonus. When you have an apartment in Italy, people do like to visit! Better Way to Italy required me to develop skills I had never used before. I was designing tours, planning itineraries and marketing our business. Sarah is a brilliant business partner, and also my dear friend, and she was doing the same hard work; it helped enormously to be sharing our vision. There were times when I would feel overwhelmed, and the processes, just to live here, would seem to be too difficult. But I am stubborn, and I knew that I wanted to be here and to share my experiences with other women. Sarah and I felt we had a product we believed in and could deliver on, and we just wanted the opportunity to present it.

 I am stronger and more courageous than I thought I was.

What did you learn about yourself through this process? Being alone has been a real adjustment for me and I have learned so much about myself in doing so. I will never know how much of what I learned was from being in Italy, living alone, or just growing older and wiser. The process has taught me that I am stronger and more courageous than I thought I was. I have learned that taking risks can produce wonderful results and that standing on my own two feet is very rewarding. I have learned to be independent of what others may think. To know oneself is the journey of life, I think, and I have come to know and understand myself deeply.

Lisa enjoying a meal with her Signature Tour participants, spring 2014

Lisa enjoying a meal with her Signature Tour participants, spring 2014

What is your advice to women seeking to reinvent themselves in midlife? Take calculated risks! All that you have poured into others along the way, now give to yourself. Trust your instincts, believe in your own strength, and follow your passion. If you don’t know what your passion is, find something that brings you joy, and pursue that. When one woman acts courageously, it gives permission for others to do the same. I think midlife is a fascinating time for women to be fully creative, less critical, and embrace who they really are.

 When one woman acts courageously, it gives permission for others to do the same.

What advice do you have for those interested in pursuing your path? Do it! Even if you choose to be an expat for just 3 months, try it. Traveling and living in another culture provides an education that can never be duplicated elsewhere. Physical possessions weigh us down at midlife—choose some fabulous experiences instead!

Lisa with guide Stefano

Lisa with guide Stefano

Befriend locals. It’s been important to me to have Italians, in addition to other expats, as friends. When it comes to renting an apartment, finding a good trattoria, or dealing with bureaucracy, there is nothing like having a friend who is a local and a native speaker to help out. Choose your business partner carefully. Sarah was my children’s babysitter so I have known her since she was 12 years old, and she is like family. Because we had that relationship, we easily trusted each other and had a similar vision of what we wanted for this company. We Skype every day to split up tasks and responsibilities. Choosing a business partner is like choosing a life partner—very important, and I have a great one!

I think midlife is a fascinating time for women to be fully creative, less critical, and embrace who they really are.

What resources do you recommend? If you are thinking of trying life as an expat, read blogs of those who are actually living in the country of your choice. They provide a wealth of information and often a more honest view of what day to day life is really like. I follow Georgette Jupe at https://girlinflorence.com/ and Nardia Plumridge at www.lostinflorence. They are women in the know when it comes to Florence and I read their blogs long before I knew them as friends. I didn’t even read the book or see the movie, Under the Tuscan Sun, until after I had moved here. It was filmed in Cortona, my favorite hill town in Tuscany, so I have enjoyed watching it many times now. I loved Jennifer Criswell’s book, At Least You’re in Tuscany as it so reflects what it is like for an expat to move into Italian life. And Jen is a good friend now, so it is a fun read for me. In movies, when I see the gorgeous Chianti hills or the beautiful coastline of Amalfi, it looks surreal. But I know it’s not. It truly is that beautiful. And when I am experiencing those places for myself, I often think, whose life is this? Oh yes, mine! Most countries have expat sites that answer questions and offer assistance. Read those but trust your instincts too. There are so many language programs available both online, classes and private tutors. Try some out and see what works the best for your type of learning.

 Physical possessions weigh us down at midlife—choose some fabulous experiences instead!

What’s next for you? Do you think you have another next act in your future? The business is really taking off, so I believe Italy will always be a big part of my life. I don’t look too far into the future but, for now, Italy is where my joy is. I have learned that this chapter of life is full of surprises. There is such incredible freedom at this age; if you embrace that, there is always another adventure just around the corner. The immediate future for me is continuing to share Tuscany, and Italy, with other women. I also write for the Huffington Post about my experiences in Italy and am currently working on a memoir reflecting on my journey. Writing requires a great deal of discipline and reflection; I am anxious to finish my book and to get it published. And, I am open now, after a decade of being single, to another partner in life. It would be great to fall in love again. It’s a risk, for sure, but I am all about taking those!   UPDATE!! 

In 2015, Better Way to Italy was dissolved, and Lisa Condie launched her new company, Find Yourself In Tuscany. Under her direction, the top priority for Lisa is still providing tours for groups of women. Women will see, first hand, why this region holds Lisa’s heart! Sharing classes on passion and courage while being surrounded by the stunning beauty of Tuscany is a magical combination! Tours run in the spring and fall months and fill quickly.

Lisa also provides customized itineraries for travelers and organizes all aspects of retreat planning in the Tuscany area.

Currently, Lisa is writing a memoir of her first three years in Italy.





HeleneTStelian Musing
I’m Hélène Stelian, the Midlife Mentor with a passion for facilitating personal development in women 40+. Through my THRIVE Courses, I help introspective, curious, action-oriented women 40+ deepen their journeys of self-discovery and growth—and create their next chapter with courage and intention.



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  1. Donna

    Congratulations on your life and your choice. I recently visited Florence for 3 months and immediately felt like I belonged there. You are very brave and I congratulate you for living your life to the fullest!!!!

  2. A Cook Not Mad (Nat)

    Congratulations! We have often thought of moving to Italy but can’t fathom all the bureaucracy and hoops you must have to go through.

  3. Lisa Condie

    Thank you for the kind words! Yes, the red tape of living legally in Italy is a bit overwhelming, but I am finished now for a year! Lisa

  4. Jane Johnson

    Lisa- I loved your story especially while sitting in the frigid cold of Chicago in March! I did something similar in my twenties when I sold everything and bought a one way ticket to Japan! I ended up living there for almost 3 years and it changed my life. What a “next chapter” to do it later in life! Why not!? Best wishes for your continued adventure!

  5. Margaretha (Equine Guided MD)

    What an absolutely splendid idea, Lisa, running tours to Italy for small groups of women, and how rewarding it must be! I live in France, if you ever decide to expand your business to our country please let me know, I am sure it would be as successful here.


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