• I planned a two-week tour of Italy with five relatives between the ages of 60 and 77.
• Not everything went to plan: We had some issues with our rentals and moved slower than I expected.
• Traveling with older family members was different from how I imagined, but I'd do it again

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

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

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

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.

• I went on a passenger train in Italy from Sicily to Naples that boarded a ferry to cross a strait.
• The train ride wasn't very expensive at about $30 and our journey took almost six hours.
• The views of the coast were amazing and the ferry ride was a special experience.

I enjoy riding around Europe via rail and have taken trains in Spain, France, Belgium, Bulgaria, Slovenia, and, recently, Italy.

Italy's rail system is immense and connects almost every corner of the country. I was recently even able to take a train to Naples from Sicily, which can be tough to access.

Sicily is separated from the mainland by the Strait of Messina, which is several miles wide and notoriously difficult to navigate.

Fortunately, state-owned railway company Trenitalia operates a train that goes through Sicily, crosses the Strait of Messina, then heads north to Rome.

Since there's no bridge connecting Sicily to the mainland, the train travels part of the way by ferry.

My journey began on land in Sicily.

I boarded my train at the platform of Messina Centrale in Sicily.

The train arrived in two segments, which passengers boarded separately.

Soon after leaving the station, the train rolled aboard a ferry.

My train had hardly left the station when it approached the waterfront and a special ferry.

It slowly crept down the pier and effortlessly rolled onto the ship, using tracks cut directly into the deck.

Once the train was secured, my journey continued.

After the train was secured on board, the ferry's engines rumbled and the vessel continued on its path across the notorious waterway.

The train doors opened and passengers were allowed to freely walk around the boat.

The ferry felt pretty standard.

Like other ferries in Europe and North America I've been on, this boat had plenty of indoor and outdoor seating, a small café serving snacks, and so-so bathrooms.

There were pleasant panoramic views during the ferry crossing.

Train passengers could stay in the car but I found the best part of the trip was taking in the views and fresh air from the outside deck.

The boat traveled through Messina Harbor then made a full turn, giving passengers impressive views of the towering seaside city.

The views continued for the rest of the trip.

It took us about 35 minutes to cross the waterway.

As we approached mainland Italy, an announcement asked passengers to reboard the trains. The ferry docked a few minutes later and the train cars slowly backed off the boat.

We stopped at San Giovanni station for about 20 minutes while the cars were reconnected. From there, we continued along the coast of Italy, passing long sandy beaches and the aquamarine Tyrrhenian Sea.

Eventually, after a few hours, I reached Naples — the end of my voyage.

It was cool to ride a train that goes on a ferry.

The train ticket from Sicily to Naples cost just under $30, which included carry-on luggage I could bring on board. In total, the trip took about six hours.

A flight from Sicily to Naples would've taken about an hour, though it'd likely cost more than double the price.

Plus, if I'd flown I would've missed this unique experience and views of so much of the gorgeous Italian coastline.