Travel to Italy – 3 Mistakes I Made (And How You Can Avoid Them)

montecatini in tuscany

It was this time last year when I was packing for my trip to Italy for the very first time.  Since this was our first visit (my husband and daughter with me), you can imagine how excited we were for the experience of tasting real pizza, authentic olive oil, and let’s not forget the luxurious wine. 

One of my first tasks in preparation for this trip was to create an itinerary so we could make the most of this rare chance to experience Italy.

Okay, here’s the rundown.

Our Jam-Packed Itinerary

Our first task when we stopped off the plane that would be our “home” for 9 hours was to pick up a vehicle in Milan and then make our way through the quaint towns of Tuscany to our destination.  Our charming Tuscan hotel was located in a picturesque little city called Montecatini. This was going to be our home base.

After two days of exploring our home base, we were going to purchase train tickets to Rome. We would spend the night there, and the next morning hit the pavement touring this ancient city.

At the end of the day,  it was back on the train to Tuscany. In the morning, we would drive to Chianti for a wine tour and lunch and then back to Montecatini. After a good night’s sleep, we would drive back to Milan, turn in our car rental and spend our last night in Italy. Whew!  

Oh! I almost forgot. We had to somehow squeeze in a tour of an olive farm where we would be able to enjoy fresh olive oil and see how it’s actually produced.

The Problem

Did we accomplish everything? Yes.  Did we enjoy everything?  Well, not exactly.  You see, we scrammed too much into our very ambitious schedule. Don’t get me wrong, we had a magical time but it definitely could have been a bit more relaxing if we had loosened our itinerary a bit so we could actually savor the moments.

Everywhere we visited we were asked about our plans. Maybe because we looked rush or maybe they were just curious.  When we rattled off our itinerary, the beautiful Italians looked at us with humorous grins and one even verbalized what the others were thinking, no doubt, “You Americans! Always on the go and always trying to do too much in such a short period of time.”

Well, they didn’t understand. We didn’t know when we would be able to return.  Maybe never.  So it was wise to do as much as possible, right?  Right??

One dapper older gentleman uttered with a playful smile, “You were in Montecatini yesterday, Rome today, and Chianti tomorrow?” Then he threw his head back in a roaring laugh and almost just as fast, his face took on a more somber tone, and he advised (in his broken but understandable English),

“Slow down….really enjoy yourselves. Don’t rush through this time like a train. Stop and have a glass of wine and admire the sunrise and sunset. Don’t spend your vacation driving all over the place because you’ll never enjoy anything.”

We smiled and politely dismissed ourselves and continued on our way.  On the train ride back to Montecatini, I had time to really think about what the old wise gentleman advised us.

Had we really pushed too much in our schedule?  I had to admit that we were very ambitious in our plans.

For instance, we had never been to Tuscany, let alone taking on the task of driving through the narrow and unfamiliar roads of a new country. And to make matters a bit more challenging, we couldn’t speak the language fluently enough to really understand the street signs (although we did take a crash course in how to read and navigate through the traffic of Italy).  Definitely stressful. 

And we were a wee bit cranky with one another due to the excitement of travel coupled with sleep deprivation.  So maybe that gentleman had a point after all. 

Three Mistakes And How You Can Avoid Them

So based on our reflection, if we could do it all over again, we would do the following:

1.  Your Itinerary Can Make or Break a Vacation  – Create an itinerary that is more leisurely and try to plan a trip where you can be more flexible. In other words, savor the experience.  Leave a day or two on your itinerary completely open. If you have a flexible schedule you won’t be rushed to complete everything on your travel wish list.  This will force you to take advantage of your new surroundings and slow down and relax.

2.  Experience the Culture – If possible, ditch the hotel for a rented cottage or apartment where you can live like a local and travel and explore on foot or bike.  Buy fresh produce or other goodies from the farmer’s market every day and enjoy cooking these foods.

If you don’t want to cook, buy items that require no cooking such as olive oil, bread (the focaccia was amazing), fresh fruit and cheese. Sip on your favorite beverage as you enjoy the view outside your window.

There is nothing like taking an entire day just to stroll through the city and getting lost down one of the social-media worthy streets and alleyways. In other words, really enjoy the experience instead of running around manically, as we did.     

3   Keep it Simple but Fun – It’s true that sometimes the best memories are those we share with awesome people – tasting gelato or truffles for the first time, good conversation with interesting strangers that soon become friends, or a nice glass of red wine by a roaring fireplace.

All in all, Italy was a trip that we will long remember, and we can’t wait to return.  It blew us away, but we wished we had taken the time to slow down and enjoy each and every experience along the way.

olives trees

What about you? Please share your travel to Italy tips (or any other destination) below.


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