How to: Quit Your Job and Go to Italy

Our Florence apartment is on the upper floor.

What a difference a week can make! The sun is shining a bit today, we have groceries in the cupboard, I got our bus passes, we found a play group, and we even found a church. Doug has made friends with our smack-talking butchers.

Today I want to start answering your questions about the choices we made and how we got here, in case you were considering making a similar move.

Assuming that you’d want to go to a different country, of course. Wondering how to flush the toilet and riding around the city on a bus because you can’t remember the name of your bus stop isn’t automatically everyone’s idea of fun.

And it’s not like one day I just said, “Hey Doug, how about you quit your job?” and then, “Let’s go live in Italy!”

Well, actually, that is kind of what happened, but we had two factors that helped us to make this decision in both a spontaneous and responsible way, not like in the movies how “a bird pooped on me, so I bought a Tuscan fixer-upper.”

This wasn’t the first time we tried to stay in Florence. A few years ago, early in our marriage, we found a small fifth-floor walk-up apartment in the Oltrarno we could rent for six weeks. (It’s the yellow one on the roof in the next picture.) We had recently paid off all our debt, and we were working on building our savings. We didn’t feel comfortable enough however for both of us to take a six-weeks leave from work, and the combination of paying the expenses on our current apartment and to stay in Italy felt like more than we could afford.

We decided not to go, we stayed home and added to our savings, a couple of years later we had kids, and I forgot all about it.

I forgot about it until the year that Doug turned forty years old. On his birthday I realized that he had worked for twenty-five years, and I thought it would be a good idea for Doug to take a year off from working sixty-hour weeks, spend some time with the family, and think about what he will work on for the next twenty-five years. This could be a sabbatical year, and with no job constraints, we could live anywhere.

This time we had two factors working in our favor: good timing and position. By timing I mean the circumstances and situations that we don’t have any control over. By position I’m talking about the choices and decisions that we have made so far. Also, even though the trip seems random, I’m seeing how God is unfolding a purpose to our being here in an exciting way.

I feel like it’s important to mention that I had no worries about Doug leaving his job. In his previous line of work he regularly received job offers, and even if he didn’t work for someone else, we often thought up new business ideas he could do on his own. His job also wasn’t our only source of income. He directs our stock trades and investments, so we have some money coming in from investments, and I also make a little side income from freelance writing. (In case you’re curious, he already has a job possibility lined up for when our trip here is over.)

When I share ideas at Small Notebook for having a simplified and organized home, one of my personal motivations is having the freedom in flexibility. Even without plans to go overseas, I liked being flexible enough to go somewhere if the opportunity ever arose.

This is the path that I follow on my walk, pushing the baby in the stroller. Can you see the Duomo on the other side of the river?

To make a trip like this, I saw that we had good timing and position, and so I grabbed the opportunity while I could.

For good timing:

  • Our family is all in good health.
  • Our extended family is in good health.
  • Our apartment lease ended, so we could move without obligations and put our stuff in storage.
  • My parents let us live with them for a month while we transitioned from our old apartment before we came here, which was immensely helpful.
  • Our kids are not school-age yet, which helps to make things simpler.

For good position:

  • We are debt free with savings (additional savings than what we set aside for a house and retirement).
  • Because we have lived in rented apartments, we don’t own a lot of furniture and stuff.
  • Since we paid cash for both cars, we don’t have a car payment. We sold one car that we had racked up the miles on and stored the other.
  • We don’t have pets to take care of.
  • We have some income apart from full-time employment.

To take care of the first questions that came to mind, here is how we managed to find an apartment, arranged for passports and looked into visas, and obtained health insurance:

1. Renting an apartment overseas:

We searched for furnished rentals on sites like Craigslist, Home Away, VRBO, IHA, and Sabbatical Homes. Though the listed rates for weekly rentals are usually high, we contacted owners directly and asked what their discounted rates would be for a long-term stay. Since we are making this trip during the spring instead of the summer, prices are less and there are more choices. We didn’t need to move any household goods, so we transferred our stuff to a storage unit.

2. Passports and visas:

We needed our passports renewed and new ones for the kids. Visas are complicated, and I spent an entire day just learning about the process. With our US passports we could travel in Italy (and any other country in the Schengen agreement) for up to 90 days without a visa, but we would need one for a longer trip. Because of Doug’s new job offer, we decided to limit our trip to 89 days and avoid visas.

3. Health insurance:

After our employer group health coverage ended, I bought short-term health insurance for while we lived in the states and international health insurance for our time overseas. Both are coverage for accidents and illness. They have deductibles, exclusions, and no preventive care, so they cost less than the full coverage we had before. Before our full coverage ended I made sure to catch us up on doctor appointments, and I got new glasses. That’s good advice for anyone who is going on a long-term trip or not: stay current on your health care; don’t assume you will always have your good health insurance available.

Tying up loose ends took much more time than I expected. I dealt with a lot of paperwork. We also spent a lot of time shopping before the trip, buying things like shoes for the kids and other things we anticipated needing in the following months, while we had the selection I wanted and the currency exchange rate was in our favor.

Over the next few months I’m looking forward to enjoying the fruits of the work that we did in advance, and I’m also practicing my Italian.

Because right now it sounds like “Ciao, y’all.”

About Rachel

I write about practical tips that will help you simplify at home. Connect with me on Pinterest and Twitter.


  1. It seems like you got settles in just fine! I’m so happy for you :)

    Your apartment looks gorgeous by the way! I’m totally jealous.

    I wish you all the best in Florence!!
    Maaike Quinn @ Life with FlyLady´s last post…Have some fun with your family and friends

  2. My husband teaches World Cultures and one of our long term goals is to live abroad. Once our kids graduate high school and my husband reaches his 18th year teaching, we are heading over seas. It will make him a better teacher as he will have first hand experience of the cultures he teaches and I get to come along for the ride! It is a great perk he has teaching this subject in that the school expects him to take travel sabbaticals at some point in his career! We’re hoping to have at least 1-2 years to live overseas and it’s something we’ve been working toward for years. We are going to take small vacations abroad in the next couple years to help get acquainted with the areas we will one day eventually live. Can’t wait!!

  3. And by the way, I completely love your attitude according to this living abroad thing. I love to travel myself, and so many times people tell me they like to do that too, some day, bladiebla, and suddenly they are old. I don’t want that to happen to me, so I’m always looking for opportunities to do the things I love, and I must say that your trip is a huge inspiration :)
    Maaike Quinn @ Life with FlyLady´s last post…Have some fun with your family and friends

  4. Love, love, love!! Oh my goodness, this makes me long for the days when we were traveling and living all over the world! I hope you have a delighful 89 days and make the most of it and take lots of pictures and make lots of memories and then share them all here with us on your delightful blog! Blessings!!
    Carrie´s last post…Valentine Thoughts

  5. Ah, Florence. Such a wonderful city. Italy in general is not only beautiful but has some of the best food on the planet.

    We made our move to Germany nearly 10 years ago because of a good job offer…but it’s been an incredible opportunity that I never really thought I would have. I’ve learned so much and grown so much as an individual. And it’s of course brought my husband and I very close together as we went through the whole culture shock :)

    Looking forward to reading more about your adventures in Florence. A friend of ours just moved there from Capri so we’re probably going to be visiting her in the summer.
    Tiffany @ No Ordinary Homestead´s last post…The shutter project

  6. I hope you enjoy your adventure and living in Florence! I’ve been there several times, well that’s because I don’t really live far frome there :-) (Vienna, Austria). When spring is here I’d recommend to make a short trip to Montepulciano. One of my favourite Italian places and for you it would be something like a one and a half hour drive.
    Katharina´s last post…Valentinsherzen filzen

  7. Thanks for posting some of the steps that led to your adventure in Italy. I love how the details came together; what a wonderful experience you are having. I am also glad you don’t have to deal with the visa stuff; we live in Switzerland (we’re expats – my husband works for an international company – we apply for and receive residency permits each year) -so we understand Schengen :-)

    I was in Florence last March and we had two great church experiences – the first was the English church where we enjoyed Palm Sunday with olive branches! The 2nd was walking thru the old town eating Gelato that night, when we heard praise music – we followed our ears and walked in with our cups, joining in with the singing – and it was such a blessing.

    Keep the Italy posts coming! And the beautiful photos! Ciao

  8. Despite how romantic and exciting this all seems, God is in the details and this, too, is how He will gently move you and your family through the experiences of life that He has designed for you. It will be exciting to see how in the future He uses this time in Italy and the experiences your family will have for His glory! The tricky part is to keep your eyes open so that you can see it as it unfolds and experience the joy! And for us, your readers, we need to remember not to covet your path, but find joy and thankfulness in the one He has chosen for us. And someday, MAYBE, something just as exciting will be in the works for us. My husband and I experienced something very similar when after two previous attempts to move to California, God opened the door wide on the third time – and 20 years later, I realize how perfect it was for our family. I just have to keep telling myself that story over and over (and remember to be grateful) so I don’t forget in the hustle and bustle of life!
    Amy @ Homestead Revival´s last post…Wanna Barn Hop

  9. Wow! What an adventure!

    Sometimes I get so caught up in planning and I forget that the future happens one day at a time. I’m definitely going to have to bookmark this for ideas since we’ve been talking and talking about moving abroad. Thanks for the tips.
    Jennie´s last post…Getting Used to Simplicity

  10. I am loving this. So often we stand in the way of our own dreams! I love that instead of giving up to Real Life of a mortgage or job or daycare you figured out a way for your dream to be reality through reasonable decisions. And I love that you outline the hard choices you made here. I know you will have an amazing time!!

  11. This gives me so much hope! If my husband stays with the same company in 10 years or so (before we’re 40) he’ll get a paid sabbatical. I would love to be able to live in Ireland or Spain, and seeing you do this makes it seem so possible!
    Kait Palmer´s last post…Minor Thing Left Out

  12. What an incredible adventure! Are you writing a book about it? It would be a great way to share all your tips and photos and stories. Plus it would be a great read. Have a great sabbatical!
    I Live in an Antbed´s last post…C S Lewis on Love

  13. I love how you break tasks down and make them doable. . . small tasks (organizing your clothes closet) to large(moving to Florence!) I’m hoping to go to nursing school in a few years, and reading your beautiful blog has inspired me to start simplifying our household routines now, to make the transition to mama-in-school-full-time easier. Freedom in flexibility. . . you really said it all.
    carmina burana´s last post…Winter- refreshed

  14. This is very exciting to read about and I can’t wait to hear more. Would you mind terribly telling us what profession your husband is in? I’m just so curious.

    • He has done sales and project management, and a few more things. His last job was in commercial air conditioning, which kept him busy in Dallas with all the heat and extreme weather.

  15. When I first read you were taking a year off, I thought you were a bit crazy. Especially with kids. It did not help that I had just read the 4-hour workweek in which Tim says you need to move to another country to save money. I would like to stay home and save money!

    But this post has awesome lessons. Pay debt, live within your means, do research, and know when to take risks and enjoy life. My hat is off to you and the choices you made. I envy the experience the kids and your family will have while in Italy.
    Erika´s last post…Buying my Fabric Wholesale

    • Thanks, I knew it did sound crazy, didn’t it.

      • I love how honest Erika is.

        Me? I just thought, “WOW” and I was a bit jealous because my husband is very risk-averse.

        However, when you break it down as you did and make sure you have the money thing sorted, I think he would go for a 3-month stint somewhere :)

  16. While I don’t personally ever want to live overseas, I love the way the good decisions you have made all along allowed you do live your dream. It’s a lesson to anyone, regardless of what your particular dream is.

  17. Oh Rachel, I love reading about how all this is unfolding! I have another online friend who is RVing around the country with his wife and daughter. I love to see people live their dreams and hope to be among you guys some day soon!
    And I love ciao ya’ll! very funny!
    Living the Balanced Life´s last post…Is multitasking the key to productivity

  18. Kathleen D says:

    Loved this post! What a wonderful city you chose as your new home. My daughter studied abroad last summer in Florence and loved it. She took a cooking class in Florence that was just wonderful. We are still reaping the rewards from her summer in Florence! I visited her for too short of a time and would love to go back sometime soon. I have a girlfriend who wants to live in Italy (she visits it enough that she should just take the leap and move). Anyway, her favorite spot (and where she wants to live) is Montepulciano. So I would definitely add it to the list of places to go.

  19. It just sounds like such an amazing experience. I love reading your posts and finding out what your family is up to. I am envious of the simple life you live and how you became free of debt and “stuff”. I even tried my very own “No Spend Month”. I was slighlty successful, but I can do better. Have fun! Ciao!
    Paige´s last post…Love is in the air

  20. I am so glad you posted all the “hard work” side of it!!! Just adding a bit of reality to: “We jumped on a plane and headed for Italy for a couple of months…” It sounds so lovely and truly a great escape!!! Hope you are having a fabulous time!!! My hubs and I have walked that river path so many times – thanks for the memories!!! Lots of love…

  21. Karen (Scotland) says:

    This is so great to hear. Interesting to see all the hard work and preparation behind the immediate decision but also all the preparation and life decisions allowing you to reach a place where you COULD make such a big decision.
    Just enjoy yourself and learn as much as you can in your time over here in Europe!
    Karen (Scotland)

  22. So will Doug be going back to work after you return from Italy rather than taking the whole year off? What city will you settle in here in the States? I wish you and your family wonderful days of happiness during your trip! Taking a Sabbath is healthy!

    • His new job is one that he is really looking forward to, so he wanted to go back to work for this one. By that time he will have taken six months off, so he thought that would be enough. I’m not sure where we’ll settle when we get back, I think they’re still deciding where to place the company.

  23. Oh, friend. This makes me grin for you guys. Lovey love love love.
    Megan@SortaCrunchy´s last post…Our Give-LOVE Valentines

  24. First off, good for you for taking the plunge! I think it must take a lot of courage to actually up and move across the world. Your story makes me think of all the people who left Europe a hundred years ago to come to America, but without the benefit of Google!
    Thanks for sharing a bit of the how-tos. I’m bookmarking this post in case I ever get up the courage to move somewhere amazing!

    • Oh my gosh, you aren’t kidding about Google. I can’t believe I ever traveled without Google’s translator, email, and maps. I would be lost without it now.

      • I can’t even imagine planning a vacation without the internet now!
        I was looking at some OLD photos, probably 14 years old, of my kids hanging in the kitchen. There on the counter was a stack of 6 telephone books, white and yellow pages, for our local city and the large metro area. I am so glad we don’t need those anymore, lol!
        Living the Balanced Life´s last post…Reach out and take a hand

  25. Oh my gosh, this is amazing! Ever since I first read the post about your move to Florence (which coincidentally was the first time for me to read your blog) I have been inspired to do something similar. I really like how you broke down what it takes and it’s not just “a bird pooped on my head”. Unfortunately, we aren’t in the right time/position in our lives, but God willing, there will be a time when we can experience a different culture (or even just a different state for that matter!).

    Thanks again for all the details about what it takes. When people write about this stuff, it seems that they have “family money” (daddy’s trust fund) that allows them this kind of freedom. It seems like the two of you have made responsible, self-supporting choices and are now enjoying the rewards!

    All the best to your time abroad!!

  26. As I am standing here reading your post and all the comments, from my new home in the Netherlands (after a move from Japan), I see that many of us have a story to share. The Grace of God has allowed this midwest American family to have the adventure of a lifetime around the world, but as with you, many of our own decisions have put us in a position for it to be possible. The point is that it can be done, IF you want to do it. It is not overnight, and it takes planning and discipline. But it is possible, even for ordinary people like you and me. The real question is…what is it that you want to do badly enough to try to make it happen. Sometimes God closes doors, but we only know that if we try to go through them.

    All the best to you and your family. Florence is wonderful, but more than that, your memories will be priceless. Start a new blog as a journal for your adventures…when you go home you can have it turned into a coffee table book with very little effort.
    Tracey´s last post…FORGET IT FRIDAY

  27. Our family of five ‘upped and moved’ nearly 10 years ago to Kyiv, Ukraine. But as you so clearly wrote…not a quick decision and it involved a lot of work!

    I’m currently trying to simplify HERE — can’t even figure out how so much STUFF came to be in this flat — so that we can one day return to the States…where our children and their families are now living. We’ll know when the timing is right for the return.

    Enjoy your wonderful 89 days!
    ukrainiac´s last post…Happy Valentine’s Day!

  28. A little over a year ago, my family and I moved from the US to Switzerland. We will likely be here for 2-4 more years. Our situation is a little different in that we transferred for my wife’s job. But I had to quit my job, which I liked very much. Still, it is a great experience that we are all enjoying immensely. And I suspect that years from now my wife and I will look back on this as the best decision we ever made. Enjoy your ex-pat time.

  29. We are doing something similar, except my husband took an active-duty assignment for 1 year. I wrote you once and told you that I was in Italy, too. Currently, however, my children and I are living in England for 3 months – staying in a different cottage every 2 weeks. We had to come over on a tourist visa, since it is only for 1 year and he got the job kind of last minute, and I was impatient to begin my European adventure. The UK is about the only place in Europe that doesn’t doesn’t belong to the Schengen area. England is expensive, but it is kind of nice to be in a place that speaks my language while I am here alone (with my children). We’ll be back in Italy for another 3 months beginning in May. We’ll be coming back by train and stopping in Florence. Will you be there around May 11 or 12? Then it is back to Maine in time for my kids to start back to school (we are homeschooling this year since we are nomadic). If you would like to check out our adventures, I have a family blog at

  30. Your photos just take my breath away.
    Florence was Hubs’ and my favorite trip, and one we relive by looking at pictures often.
    It’s icing on the cake for me to hear that you are able to be there for this time without a debt load! Enjoy the city, soak in that Tuscan Sun…there’s a reason it’s spoken of that way… ♥

  31. What an amazing opportunity! You a wonderful example of a sweet & supportive wife to go on this adventure with appreciation for all your hubby does work-wise.

    How wonderful he has a job waiting for him when you return. Really seems like you’ve got ‘all your ducks in a row’ so you can sit back and ENJOY!! :)
    heidi @ wonder woman wannabe´s last post…Beloved-

  32. What a lovely place you have. Can you please me tell which, among the sites you mentioned, did you use to find your apartment (Craiglist, VRBO, Sabbatical Homes, etc.) Thank you Rachel.

    • I think we used the search filters on to find ours. It’s hard to remember because they all start looking the same after a while.

  33. I never saw the movie for “Under the Tuscan Sun”, but I’ve heard it was awful! The book is amazing though. If you get a chance to read it I think you’ll love it. It is about a retired couple who planned to move to Italy and buy a house to spend the rest of their lives in. It is funny and inspirational and the scenic views described are great. It is a true story also. Anyway, “in bocca al lupo” on your trip and have a safe journey back.

  34. We have talked about moving overseas- this encourages me that maybe it could be a reality!
    Katherine@YeOldCollegeTry´s last post…How To Curb Your Book Addiction

  35. Love it! My friend 32 year old friend Jeff at work is packing up and moving to LA to pursue his dream of acting before he and his wife have kids. She’s totally supportive and he’s going to be sleeping in a friends basement for a few months while he transitions. Carpe Diem!

  36. Lily (from Italy) says:

    Cosa farete a Firenze? ;)

  37. Ditto to what many have said: Job-sabbaticals and living overseas might not be for every family, but “freedom in flexibility” is a great reminder for us all!

    Looking forward to hearing about your Italian adventures!
    Lindsey´s last post…The Mother Load

  38. Marilyn Holeman says:

    I’m so excited that you’re able to do this! Our family spent 4 months in Switzerland when our kids were 6, 5, 3, and 2. (My husband’s job sent us.) We loved it and it was a marvelous experience.

    I have two comments. First, as far as timing is concerned, we home-schooled our kids, and so had a lot of flexibility. (That’s not the reason we home-schooled, but it was a nice by-product!) Our son, who was 2, doesn’t remember Europe; our six year old DOES.

    Second, as Christians, we are members of Samaritan’s Ministries. This is in lieu of health insurance. It is a program where Christians help other Christians with health needs. It is vastly less expensive than traditional insurance, which is but one of its advantages. You can “take it with you” oversees. It’s definitely worth looking into:

  39. I find your blog so inspiring. I’ve always been a lurker, but have to speak up today. At a time when most of my friends and siblings are buying homes and settling down, it’s really nice to find some encouragement toward living in a rental and aggressively paying down debt. Our daughter will be school-aged by the time we are debt-free, but I still think it will be so, so worth it!

  40. We have escaped to Italy also. Sold the house, quit our jobs, moved to Florence with our 4yo twins. Took a good 6+ months of planning, and we are here without income, but the choice still feels good. My husband is studying art here. What better city to do it in. Thanks for sharing. Maybe we’ll see you all at the playground on the Arno sometime :)

    • KarieAnn it was so fun meeting you and your kids this morning! What a fun coincidence to meet you and then come home and see this comment from you too!

  41. I appreciate you posting the “nuts and bolts” part of your move. Enjoy the apartment building is lovely, the tile room is amazing!

  42. Love the first installment of the adventure and the pics… Looking forward to more :) So good that you are enjoying it…
    angelvalerie´s last post…about the idea of blogging…

  43. I just wanted to thank you for posting this blog post. I have been coming back to this post again and again all week. We are in the process of relocating a few states away in the SillySimple family, and your goal of “freedom in flexibility” really resonates with me.

    There is something very very stress relieving to know you can afford to be flexible both on the financial front but also from an emotional stand point. Thanks for bringing it up again :-)

  44. I was just telling a good friend that my husband are thinking of taking 5 weeks off and living in Paris. Then I said to her, just take off to Paris, who does that??? And she sent me this link! What a treat! We went ahead and bought our tickets yesterday and are pretty close to renting an apartment. There are days I worry (what about my private practice? will my clients come back? etc) but ultimately I know this will be one of the great adventures of our lives and our marriage! Thanks for a being a trailblazer :) I look forward to reading about more of your adventures!

  45. VERY. COOL. What an amazing situation you guys ended up in. Perfect timing, perfect opportunity.

    And I literally LOL’d when I saw “Ciao, y’all!”

    Soak it up like a sponge…it’ll be over before you know it!

  46. I just stumbled upon your website when searching for meal planning spreadsheets, of all things. But when I added your blog to my RSS, this is the story that got me excited :) I love hearing about people who aren’t just sitting around letting life pass them by, but instead are taking an active role and living out their dreams. Spending a year in Italy is probably the dream of half the people in the US, yet hardly anyone does it (I can hear all of their excuses already!). So, congrats to you and your family on taking the leap and experiencing life to its fullest!

    FYI, check out this website: – a great resource for people taking “Career Breaks” like your family.

    Enjoy Italy!

  47. CapeCodRealtor says:

    Enjoying smallcultures with fond memories of Florence. I have lived in France with and without kids. I don’t understand commenters who say, “when the kids graduate…”. There is no better education in all of the humanities than experiencing cultures at every age. The 89 days is a drag, but if you relocate to another country for at least 90 days you can start again, and with high speed rail one could still commute to a job that way.
    I rented out my Cape Cod home for several weeks which paid for three months in France. I taught on exchange for 9 months. It’s all out there for the taking! Ciao!
    CapeCodRealtor´s last post…439-000 Home For Sale in Barnstable- MA 02601

  48. Wow, Freudian slip! Edit “smallcultures” to smallnotebook! As a home Stager I frequently retweet your tips on capecodrealtor1
    capecodrealtor´s last post…439-000 Home For Sale in Barnstable- MA 02601

  49. Wow, how fortunate, to be able to make the move to Florence. I’ve been spending the last year trying to figure out how to make that move myself. If I had a specialized skill, beyond an adminstrative assistant, I think it would be much easier. I am not even sure my Bachelor’s degree is specialized enough to help with finding employment once there.

    You are so very fortunate to be able to have the opportunity!