This spring, I planned a two-week tour through Italy with my parents, who are both in their 60s. It was their first time visiting Europe, and I couldn’t wait to watch them discover one of my favorite countries.
Word quickly spread of our trip, and three additional family members asked to tag along. I soon found myself traveling around Italy with five relatives between the ages of 60 and 77.
Our trip was enjoyable, but there are three things I wish I’d planned differently — both for my sake and theirs.
We probably should’ve booked more organized day tours
Jenna DeLaurentis
I’d been to Italy six times prior to this trip.
Knowing the ins and outs of travel within the country, I avoided organized group tours. I figured my relatives wouldn’t want to spend the trip shuffling around in a bus from one city to another.
Instead, we prebooked only three excursions, including a guided visit to the Colosseum and a street-food tour in Naples. Otherwise, we were free to explore Italy’s sites on our own.
The lack of a rigid schedule was freeing but wasn’t always ideal.
In Rome, for instance, I naively assumed we could take a brisk, 2-mile walk to the Pantheon before it closed. My relatives’ walking pace, however, was slower than what I’m accustomed to when traveling with friends my age.
This put us behind schedule, and we had to skip a visit to the Trevi Fountain. In hindsight, a guided bus tour with scheduled stops would have been more convenient for our group.
My relatives also loved the three excursions we booked, so I wish I’d planned more guided visits to sites like Pompeii and The Vatican.
I should’ve briefed my relatives on useful travel apps before we left
Technology has revolutionized travel, from apps that instantly translate restaurant menus or provide step-by-step walking directions in foreign cities.
That said, traveling in 2024 is vastly different from when my relatives were younger, and not all of them were familiar with popular travel apps like Google Translate and Uber.
Had I given my family a list of apps to download before our trip and showed them how they work, they could’ve felt more comfortable navigating a foreign country.
I never quite knew where my aunts would end up while trying to follow directions on Google Maps.
After two mishaps, I wish I’d booked hotels over Airbnbs
Jenna DeLaurentis
When planning accommodation for our group of six, I turned to Airbnbs over hotel rooms — in part so we wouldn’t have to split up.
I prioritized rentals with scenic views and spacious outdoor balconies, but I wish I’d researched the nitty-gritty details of each listing more.
Our Airbnb in Sicily had gorgeous views of the mountains, but it also had a narrow, dark stairway that felt treacherous for my 77-year-old uncle.
If this had been a hotel, I probably could’ve called a staff member before booking to check in about accessibility.
As it was a rental, I relied on photos and self-written descriptions. Online, the person who listed the home seemed pretty nonchalant about the number of stairs required to reach the apartment.
Later, in Venice, we encountered issues with our Airbnb’s heating and WiFi. Although this wasn’t a huge deal and our host was communicative on the app, navigating these issues over chat made me wish I could’ve just spoken to a front-desk employee, like at a hotel.
Plus, with hotels, you can often easily move to another room if you have issues. With rentals, that’s often not an easy option.
Overall, I think hotels could’ve been more consistently reliable and easier to navigate for our group.
Despite a few mishaps, I’m grateful for the wonderful memories I made with my family
Jenna DeLaurentis
At the end of the day, a slightly subpar rental or missed visit to the Trevi Fountain didn’t ruin our trip.
After two weeks in Italy, we were exhausted and grateful for having made lifelong memories together.
Traveling with older family members was very different from vacationing with friends my age, but I’d do it all over again.
