It has been my mom’s dream to visit Italy someday, so after her retirement (and more flexible schedule), we finally made it happen. It took quite a bit of planning and researching, but I think it went really well! Find out below what worked for us and what didn’t below.
Successes
It was a great trip overall, so there was a lot to share that worked. Here are the things that made the biggest impact.
1. Renting a car
When I planned our trip to Italy, I knew my grandmother would be traveling with us and it has been more and more difficult for her to walk long distances, so taking a train into a major city and spending days walking around was not going to work. I have driven in Europe before and after researching how driving in Italy would be, I decided to rent a car (big enough for all of us but small enough to fit into parking spaces and on narrow roads) and focus on driving through Tuscany and the northern region.
That turned out to be a great decision and we visited a ton of places that would have been difficult to reach with just public transportation. I also really enjoyed driving in Italy, with the winding roads, beautiful scenery, and all the roundabouts. We also had a ton of freedom to stop where we wanted to, leave when we wanted to, stock up on snacks in supermarkets, and be more relaxed (the kids napped most of the way) with just our family.
It took me a few hours to get used to driving in small towns where it seemed like the road was only wide enough for one car, but I quickly got the hang of it and those roads were usually empty anyway. I definitely recommend familiarizing yourself with the road signs (as with any other place), driving laws, and any other pertinent information (see mistake #2 below) before sitting behind the wheel.
Overall, it was very easy to drive in Italy and I am glad we chose that route.
2. Going in March
While there were some downsides to going in March (it was a bit chilly at times, nothing was growing in the vineyards yet, many trees were still bare, and some attractions were either closed for the season or were only open on weekends), they were fairly minor for us and the pros significantly outweighed the cons. Greener scenery would have been nice, but not at the expense of more crowds.
The quieter experience was by the far the biggest benefit of traveling during the shoulder season. In some hotels (which were mostly farm stays, or agriturismo as they call them), it seemed like we were the only ones there. The locals and hosts were always amazingly friendly, and combined with the fact that we were either the only ones or one of the two families there, it almost felt as if we were part of the family and had a more personal experience.
Some places were very popular and it might have been difficult to book them during the high season, especially on short notice (see success #4).
3. Planning in advance
This was a fine line to walk. I didn’t want to plan too much too far out, but I also noticed early in the trip that while my international coverage was free and I never had any problems in Europe before, internet was spotty and slow in Italy, even in cities. So after the first day, I made sure to have a route of all the places we wanted to go to the next day already planned out before we left the safety net of the hotel wi-fi. This was a baseline though – sometimes we ran out of time and removed things from our route. Ok, that happened often (see mistake #4).
It gave me peace of mind to start driving knowing where to go (even if plans changed later on). I only planned one day ahead and adjusted based on what everyone wanted to do or any other ideas we had, but it provided some structure to the day. Our only hard requirement was being back in the city we started from before our return flight 🙂
4. Booking hotels as we went
This might not have worked in the summer months, but since this was a road trip and we didn’t always know ahead of time where we would be at the end of every day, I didn’t book hotels for the whole trip before we left. Instead, I did it before going to bed (for the next night) or during breakfast, after figuring out our route for that day and having a rough idea of where we would end up in the evening.
I planned the route with about 3-4 hours of driving total (to leave enough time for sightseeing, activities, and to not feel like all we are doing is driving), looked for a place to stay in the vicinity of the last stop and in the general direction of the overall plan, and booked the one that best fit our needs – cost, room for everyone, ideally with provided breakfast, with bunk beds being a bonus.
We ended up staying in so many cool places – a villa with skylights and olive trees in the courtyard and a couple of blocks away from the beach; a castle in the hills overlooking sprawling vineyards with fairly lights and cozy chairs everywhere outside; a modern trailer on a vineyard farm with incredible views and my son’s favorite bunk bed of the trip; a desert oasis apartment with plants all around and the most welcoming host; a tranquil farm house in the Euganean Hills with the most beautiful scenery, delicious homemade food, and cows on the neighboring farm.
It has been magical, and I am not sure I would have found those places if I tried to look for something ahead of time.
5. Trying a variety of food places
I actually really liked the convenience of eating dinner at the hotel/farm stay – you can’t beat settling in your room, coming downstairs to eat, having some Italian wine, and going back to your room without any driving in between. And since those places are small, it’s not a bustling restaurant with a lot of loud people, but a more intimate atmosphere where you can really interact with the hosts and eat authentic, delicious food.
But we also ate at Turkish kebab diners, traditional pizzerias, cafes, family restaurants, and bakeries. I feel that we tried a lot of different foods, and by going to mostly small towns, we got to eat more like the locals do.
Mistakes
Even the most successful, best planned trips sometimes have pitfalls. Here are a few blunders that didn’t ruin the trip but gave me something to think about for next time (whether in Italy or not).
1. Not visiting major cities
I am not the biggest fan of large cities. The crowds, the usually overhyped landmarks, the overpriced food – did I mention all the people? I would much rather see the relaxed side of a place, how people truly live, have more space to myself instead of being shoulder to shoulder with other gawking tourists, and just generally be in a quieter area.
That being said, especially when it comes to Europe, the architecture can be downright gorgeous (I still have fond memories of Vienna, for example) and the history is usually unparalleled. I try to find a mix of both on trips.
I had a plan for this trip. Since we would be northern Italy, I planned on stopping by Florence and Venice. I had reservations about both – Florence was rather big and we would get there on our second day of the trip, when I was still getting used to driving in a new country and nervous about the narrow city streets, and I heard that Venice was extremely crowded and smelled horrible. But I was also looking forward to a part of them – Florence had a Galileo museum and Venice was famous for the canals.
In the end, my unease of driving in a busy city won and I latched on to the news about floods in Florence and decided it’s best to avoid the area. We still stopped by the neighboring Pisa, and as I suspected, it was underwhelming and touristy, but the streets weren’t terrible with Google guiding me. I was convinced that Florence would have been worse. Now I sort of wish of I sucked it up and went to Florence instead.
Later in the trip, we tried going to Venice. The plan was to park on the island (it was expensive, but safer than many other areas and more convenient and time efficient) and take a water taxi through the grand canal, look around, and head out. But we got there a bit later than planned and there was so much traffic trying to find a parking spot that we circled a few times, went the wrong way in a parking garage, nearly ended up having to pay for not even parking, and decided there wasn’t enough time to keep trying and then only having an hour or so in the city. Maybe we should have parked in Mestre and taken a bus or train to the island. I feel like that would have been a pain, but maybe it would have worked.
Then we had an opportunity to stop by Milan on the way, but mistake #2 threw a wrench in that plan too. So we didn’t go to any major cities, and just Pisa, Verona, and Melton (in France) for the medium-sized cities. I might come back and see Rome someday, but it would have been nice to see something on this trip too.
2. Almost running out of gas
This one was a combination of lack of knowledge, lack of preparedness, and time constraints.
The biggest issue (at least I keep telling myself) is that apparently all gas stations in Italy are closed on Sundays. The self-serve is open, but only if you pay with cash or a debit card. Credit cards can only be used inside with an attendant. For some reason, my debit card did not work anywhere in Italy (though I had no issues in other parts of Europe). I could not get cash (and until this point didn’t really need it) and could not use the self-serve pumps. No big deal, I can just pay inside, like I did the first time we filled up. Wrong!
One with hindsight 20/20 will say that I should have filled up the day before. And I probably should have. However, I had no idea that I wouldn’t have an option the next day (I even looked up a gas station close to our farm stay on the way out, which was going to be our first stop of that day), I had about a quarter left so it wasn’t urgent, and just like a lot of other hotels, this place required you to check in by a certain time so I was rushing to get there on time and figured I could get gas without that pressure. Without that “check in before” deadline, I would have filled up that night. If my debit card worked, I wouldn’t have had a problem at all. If only we didn’t spend most of our only cash (we brought some leftovers from other trips from home “just in case”) on that silly sightseeing wagon in Verona. It was just a perfect storm of problems that happened on the wrong day.
We stopped by a small town with a bank and an ATM, but my debit card would not go through. We went to a supermarket, and later at a small cafe, trying to see if the cashiers could charge my credit card and give me cash, communicating in broken Italian I learned on Duolingo and with Google Translate. Hours later, no luck besides exchanging a few Euro coins into a 10-Euro paper bill that the fuel pump would accept. Bought us a few more liters but nowhere near enough to reach our hotel, let alone stop by Milan. We started thinking of backup options. I found a farm stay on the way in case we couldn’t get far enough. In a pinch, we could sleep in the car. It would be massively uncomfortable, but better than being out in the cold. Speaking of the cold, we didn’t even turn on the heat during this time to try to stretch the gas as much as we could.
Another idea we had was finding a small, local farm/vineyard and asking them to help us get cash. That finally worked. The super nice lady had no problem charging my credit card and giving me cash after getting some from someone else who worked there. We bought some wine there too to help them out, gave one to the lady as a thank you and took the other for dinner. I will forever be thankful to that lady who saved us from certain doom (or close to it). And I will forever fill up my car in a foreign country when I get to half tank.
It was raining all day that fateful Sunday, and there wasn’t much to see on the way anyway, besides an adventure park in Milan that I was going to take the kids to (all of those parks were only open on the weekend because it was still early in the season, so that was our last opportunity), but since it was raining (and I think I heard later it actually snowed in Milan either that day or next), that probably wouldn’t have worked out anyway. So out of all the days to lose, this was probably the best one. We didn’t miss out on too much, just had a very stressful day.
3. Missing out on cooking classes
Speaking of missing out, I wish I did more research to find a cooking class while we were in Tuscany. The few I found didn’t work out because they were either only for adults (and my teenage son would have been the primary student), were only open during times that didn’t work out for us, or had a high minimum number of people. I wish I looked harder and I wish we spent more time in Tuscany. I think it would have been an amazing experience.
4. Trying to see too much
There is so much to see and do in Italy and we obviously didn’t even scratch or attempt to scratch the surface. My initial goal was to drive around Tuscany, but as I did my research, my list of cool places to see grew and I thought I could easily fit everything in. What I didn’t take into account though was that we had a good sized group (there were five of us), which makes it difficult to gain momentum, pivot, and remain organized. So while I could be more nimble on my own, trying to see all the things while herding the whole family proved a little stressful. All I did the whole trip was wake up, plan, eat, drive, see, drive, eat, see, drive, plan, sleep, and repeat.
Maybe I should have instead picked fewer places to go to and spent more time at them. Maybe I should have spent less time driving and more time at playgrounds, watching the kids play and enjoying the sun. But we did see so much, and I would hate to think that I would have missed some of it if we relaxed more. I think I just need to find a better balance somewhere in between.
5. Not slowing down
I have a fatal flaw of wanting to see a little of everything, so I tend to rush through and not really soaking in the experience. I feel that I have a limited amount of time for the trip, and I want to see as much as I can while I am there. Relaxing at a cafe sounds too luxurious for a trip to Europe where every day counts. The more I dawdle, the less I see, right? But maybe that’s not the point of travel. Especially with a whole group of people who are difficult to wrangle and get on the same page.
I should have slowed down, driven less per day, relaxed on the cozy chairs surrounded by fairy lights in a castle, not rushed through breakfast, and maybe even stayed somewhere for two nights instead of driving off to the next thing. But I am learning – I have only three different hotels booked for our next trip, and one of them is a single night at the airport before an early flight, so it will be in clusters, where we can drive around the area for the day and come back to our home base. And we won’t be rushed to get to the next destination. At least too much.
It’s all about learning our lessons, and this trip provided a lot of opportunities for those. Some things I did well and will keep in mind for the future. Some things I can definitely improve and do better next time.