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    Home»Money»We Traveled to Italy With Family, Then Took a Week for Ourselves
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    We Traveled to Italy With Family, Then Took a Week for Ourselves

    Press RoomBy Press RoomAugust 19, 2026No Comments4 Mins Read
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    When my husband, brother-in-law, and I were invited to our mutual friend’s destination wedding in Tuscany, we promptly RSVP’d “yes!”

    My husband, brother-in-law, and I all live in the United States, but my husband’s parents live in Belgium, so we don’t see them often. We invited my mother and father-in-law to join us in Italy so they could spend time with our 1-year-old son. My mother-in-law suggested that my sister-in-law, her partner, and their 1-year-old daughter, who also live in Belgium, join the trip.

    Before I knew it, our trip turned into a multi-generational family vacation with a group of 10 ranging in age from 1 to 71.

    I was grateful that we were able to coordinate getting so many family members together at once, but I’m also glad my husband and I planned dedicated time for our family of three after the festivities.


    The author's son enjoys feeding some bunnies while in the Dolomites.

    After the author’s in-laws left the trip, her family of three enjoyed traveling on their own for a few days. 

    Courtesy of Renate Flanagan.



    Traveling with a large group was an exercise in logistics

    We looked for accommodations that were large enough to comfortably house all of us but also within our budget. We found an agriturismo, or traditional farm stay, in a small town called Santa Fiora. The town was cute, but it was about an hour away from our friend’s wedding location and most of the region’s attractions.

    We had to plan strategically about transportation. The few options we found for a vehicle that would seat 10 people were more expensive than renting two normal-sized cars that seat five people. Once I saw the narrow, winding cobblestone roads throughout Tuscany, I was glad we didn’t choose a large van, which would have been challenging to maneuver in medieval towns.

    My husband and I are “get out early to beat the crowds and heat” type of travelers. Our son regularly gets up at 6 in the morning and doesn’t care if we’re on vacation.

    On this trip, the rest of our family woke up hours after us and were lackadaisical about getting out the door. We often didn’t leave the house until around 11 in the morning. By the time we arrived at a town, it was time for lunch, and it was the heat of the day. This isn’t how our family of three usually operates.

    Then there was the food

    My father-in-law doesn’t eat pizza, pasta, or sauces — and we were in Italy. Another member of our group was lactose intolerant. On the other hand, my husband, son, and I are adventurous eaters and love experiencing a culture through its cuisine. We sometimes had to pass several restaurants before we found one with a menu diverse enough to satisfy everyone’s dietary preferences.


    The author's son eats pasta at a restaurant while sitting on her lap.

    The author said it was difficult to find restaurants that could accommodate the varied dining preferences within their party of 10. 

    Courtesy of Renate Flanagan.



    On one occasion at a pizzeria, I had already requested a table for 10. The wait staff was rearranging the tables to seat our group, while I awkwardly asked in broken Italian whether the pizzeria only served pizza. Answer: yes. We moved on to another restaurant that offered more options. It turned out to be the unexpected universal favorite meal of the trip for the entire family: donkey stew.

    Extending the trip without the extended family was the right move

    After a week, the rest of the family headed back to their respective homes. My husband, son, and I stayed for another week to explore the Dolomites in northern Italy, a bucket list destination of mine.


    The author and her son enjoy a view from a refugio in the Dolomites.

    The author and her son enjoy a view from a refugio in the Dolomites. 

    Courtesy of Renate Flanagan.



    During this time, we had the freedom to get up as early as we wanted to hit the hiking trails. Our active family hiked over 20 miles in 3 days without having to account for the rest of the family’s stamina levels.

    We loved stopping at a refugio, a mountain hut with a restaurant and sleeping accommodations along the hiking trails. In the middle of our hike, we could sip espressos, eat a warm meal, and use a bathroom with indoor plumbing. The Dolomites have been one of my favorite hiking trips to date.

    I’m glad we did a big family vacation while my in-laws are still healthy and active enough to travel. Because we live far from my husband’s family, I cherish the time my son gets to spend with them. I’m also glad we reserved part of the trip for our smaller family unit. It gave us a chance to choose activities we enjoyed without compromise.

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