I’m a Type A Trip Planner, And I Still Made These Mistakes For My Italy Trip. Here’s What To Avoid

Every year, my husband and I take a trip together, and planning it has become something of a hobby for me (although I refuse to admit it to my husband so he doesn’t take me for granted).

I genuinely enjoy looking up restaurant reviews on Google, comparing train routes, and optimising our itinerary to make the most of our precious annual leave days.

As a Type A planner, it goes without saying that I even have backup plans for my backup plans. Naturally, when we booked our trip to Italy, I thought I had followed my usual planning template and had everything down to a T.

Apparently, I did not.

Despite months of planning, I still made several mistakes that cost us time and most importantly, money. Don’t get me wrong, we still had an amazing time stuffing ourselves silly with pizza, while admiring the beautiful scenery along Tuscany.

If you're planning an Italian holiday anytime soon, read on to find out the mistakes I made so you don’t have to go through them.

I seriously underestimated the crowds at Lake Como

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The last time I went to Italy was 7 years ago. This was pre-Covid, and it was with my mum. While I had to manage her nagging, I do remember that Lake Como was picturesque and the crowds were manageable. Fast forward 7 years later, my husband wanted to go because their football team is doing well in the Italian league. So I thought, why not?

The first signs of trouble began at Milano Centrale - the main railway station in Milan.

We couldn’t get on the train we bought tickets for because the train was super packed. I was shocked. We had to wait for an hour and a half for the next train. Luckily we had seats near the front cabins.

When we arrived at Lake Como… wow. I wasn't prepared for how many people had the exact same idea as us.

Ngk, it's every bit as stunning as Instagram makes it look. The lake truly sparkles, and the villas look like they're straight out of a movie set.

One of the best ways to explore Lake Como is by ferry-hopping between towns. I assumed we could simply buy ferry tickets on the day, just like how it was years ago when I was there.

Big mistake.

The queue was incredibly long (and I was wrought with anxiety about whether we would even be able to get any tickets for the day!), and by the time we reached the ticket counter, we had to get into another lengthy queue to board the ferry. The ferry itself was so packed we had to squeeze around to find a place to stand.

When we were done at Bellagio and wanted to go back to Varenna to catch our train, we had to wait over two hours to get onto a ferry as there were just so many people waiting to board. And it was under the scorching heat.

It doesn’t end there as we had to stand in the train all the way back to Milan. It was back breaking after all that queuing we had already done in Como.

If you're visiting Lake Como, definitely book your ferry tickets online way in advance whenever possible. Don’t be like me and suffer.

I forgot the most important rental car question: Can our luggage fit?

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I spent weeks comparing rental car prices in Italy, as I wanted my la dolce vita moment driving through the rolling hills of the Tuscan countryside.

I compared fuel policies, insurance options, reviews, and whether it would be cheaper to drop off the car back in Florence station or if there was a way we could drive it to our next destination, Cinque Terre (we ended up sending the car back to Florence and taking the train).

What I didn’t check is whether the car can actually fit our luggage.

My husband has a gigantic luggage bag he usually brings on his Japan trips to buy his favourite stuff. He doesn’t have anything smaller, so he brought that with him to Italy too. He was nearly fined by Thai Airways for checking in a bag that’s too big, which was ultimately waived.

Fast forward to collection day.

The rental company staff took one look at our luggage and politely informed us that there was absolutely no chance everything would fit into the car I had booked.

Our only option was to upgrade to a larger vehicle on the spot. And if you've ever upgraded anything at the last minute while standing at a rental counter, you'll know it's rarely cheap.

Lesson learned: Don't just look at the car category. Check the luggage capacity specifications carefully. Better yet, search for the actual vehicle model online and watch a few YouTube reviews to see how much boot space it really has.

At least the expensive car was a comfortable ride throughout the Tuscany countryside.

I booked train tickets way too early

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One of the most common pieces of Italy travel advice you'll see online is to book train tickets early.

In an effort to secure the lowest prices possible, I booked several train journeys weeks in advance. Naturally, I chose the cheapest non-refundable fares because, in my mind, our itinerary was already set in stone.

What could possibly go wrong? As it turns out, strikes.

Train strikes are common in Italy, and we had to wait until a couple of days before to know if the strike will actually happen. We had to adjust parts of our schedule because of the transport disruptions. For one trip, we had to buy new tickets.

I'm not saying you should leave everything until the last minute (don’t ever do that). But I would think much harder about flexibility. Sometimes paying a little extra for a ticket that allows changes or refunds can be worth the peace of mind.

The cheapest train ticket isn't always the best value

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For several of our train journeys, I automatically searched for the cheapest available ticket option without fully considering what that actually meant.

What I later realised was that the cheapest option isn't always the most comfortable, especially when you're travelling with luggage. The cheaper ticket may also have more stops along the way, making it a long and uncomfortable ride if you have to keep an eye on your luggage stashed precariously somewhere.

On some routes, spending a little more on a regional or reserved-seat service can make a huge difference to your overall experience. We discovered (belatedly) that it could sometimes cost only an extra $10 or $15 to upgrade to a better ticket.

We took a Trenitalia Frecciabianca from Cinque Terre to Milan, and my poor husband couldn’t find a spot to store his giant luggage. He had to wait with his luggage until the next major stop (when a lot of passengers would disembark) so he could safely put it away.

Meanwhile, our experience on Italo, a private rail operator from Milan to Torino was nothing short of amazing. Great seats, snacks on board, and lots of space to store luggage (which we didn’t need to use since it was a day trip from Milan).

When you're travelling for several hours, comfort starts becoming part of the value equation. The next time you find yourself going straight for the cheapest option, consider if it’s actually worth the savings.

Even Type A planners can't predict everything

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Despite all these mistakes, Italy was still bellissimo.

We wandered through charming cobbled streets in dreamy Italian towns, ate more pizza and sipped on more aperol spritz than any responsible adult should, and created core memories we'll be talking about for a long time.

In many ways, these mishaps have become some of the funniest stories from the trip.

As a Type A planner, I'm still learning that the goal isn't to create a perfect trip. The goal is to create a trip that's flexible enough to survive imperfection.

Maybe next year's annual trip with my husband will finally be mistake-free. Maybe.

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