Tips and Thoughts for Planning a Trip to Italy

Planning a trip to Italy can seem overwhelming with the sheer quantity of history and places to see. Just the name Italy is enough to conjure images of ancient ruins, rustic countryside villas, wine, pizza and pasta.

That was certainly the case for me while planning my visit. Now that I’ve returned from my 17-day trip, here are some of my general thoughts and top pieces of advice for planning a trip to Italy!

Disclaimer: This post may contain affiliate links. If you make a purchase through one of these links, I will earn a small commission. This occurs at no added cost to you.

My Initial Reactions

Holy freaking wow! Italy is an absolutely gorgeous country no matter where you go. From Venice’s captivating decay, Tuscany’s vibrant green and burnt orange towns, to the impressive cliffs of Capri. It’s all beautiful. Even amid Naples filth there are tucked away corners of mesmerizing urban cityscapes.

It’s not an exaggeration to say everywhere you look has the potential to leave you speechless if not for the fact that you know around the corner will be something equally, if not more so, impressive.

That’s not to say it gets boring or repetitive. After 17 days in Italy, I never once had the feeling like I had seen all this before. There are similarities between each region and town, but they all have their own unique landscapes, colors and personalities. This was good because it helped to keep each new destination fresh and new in my eyes.

Beyond the sheer beauty of Italy, it is filled to the brim with a lifetime’s worth of history, art and world-renowned food and wine.

My Related Content

Below are some of the articles I’ve written diving into these museums and churches.

• The Sights and Sounds of Florence’s Piazza del Duomo
• The Best Highlights of Florence’s Accademia Gallery
• Finding God and Gold in St Mark’s Basilica
• A Quick Visit to the Leaning Tower of Pisa
• My Top 8 Highlights of the Uffizi Gallery

Pizza and Pasta and Wine, Oh My!

Besides its history, probably the other thing Italy is most known for is its culinary scene. I’ll be honest, I kind of doubted whether it would live up to the hype. Not only did it life up to the hype; it surpassed it!

We only had two mediocre meals during our entire time in Italy, and even those two meals still weren’t bad.

Get pasta for lunch and dinner. Eat as much pizza as you want. Splurge at least once (my recommendation for an expensive meal is Florentine steak in Florence).

And then there’s the wine. I’m a snob when it comes to my alcoholic beverages. I hate most cabernet sauvignons and sauvignon blancs are alright but boring. I like my wine complex and interesting.

Again, Italy did not disappoint. Even the cheap house wines were better than most wines from my local wine shop. That said, make sure to try some Chianti Riservas and as many Brunello di Montalcinos as your wallet will allow.

Whether its wine or food, try to get what each region is known for as you’ll have the best ingredients and the most expertise at cooking those dishes. Some of my favorites were Rome’s carbonara and cacio e pepe, Florentine steak in Florence, and Tuscany’s Chiantis and Brunellos.

As far as cost is concerned, you can find great meals that are reasonably priced without too much difficulty. Ask your hotel or B&B for recommendations; they never failed us. If you want to find someplace on your own, go just one or two streets off the tourist path to find a cheaper meal. More often than not, these spots will likely have higher quality than the touristy places, too!

My Three Favorite Locations

Venice

Without question, Venice was my favorite place throughout our travels in Italy. The first things you notice in Venice are the many canals and waterways. Everyone knows these are what Venice is known for, but actually seeing them in person for the first time is an incredible experience.

Beyond the canals are the many narrow lanes and alleys to explore. Take time to get lost in Venice exploring these streets. See what you can find. I guarantee it’ll be the best time you spend here.

Related: A Walk to Discover Romantic Venice

Siena

Siena feels like a vibrant, lived-in city. Explore the various contrada (each a unique neighborhood with their own traditions) and see how many you can find. If you’re lucky, you’ll see a neighborhood parade showing off their pride.

After you’re done sightseeing for the day, relax in il Campo and watch it come to life with all the tourists and locals. It’s a magical scene watching everyone come out for the evening as the sky fades to black and the buildings begin to light up.

Cinque Terre

Picking a third is a little more difficult. I’ve seesawed between different places, but I think I have finally settled on the Cinque Terre. Each town is so visually pleasing with great food and a relaxing atmosphere.

Why I think it’s my third favorite location in Italy, though, are the hikes. I hiked one day from Riomaggiore to Manarola and the next from Vernazza to Monterosso. Both were physically challenging in their own ways and had amazing views overlooking the coastline.

If you can only do one, do the hike from Vernazza to Monterosso. It’s a little easier with a pleasant stroll along a trail that hugs the cliffside as you traverse peaceful forests with trickling streams overlooking vineyards and the vast Atlantic Ocean.

Book Main Attractions Ahead of Time

Italy has some of the world’s most well-known sights and locations in the world. With that comes tourists. Lots and lots (and lots and lots) of tourists. In fact, in 2019 there were nearly 100 million tourists that visited Italy.

Like I said, lots of tourists.

As a result, many of Italy’s top tourist attractions can have nightmarish lines for admission taking up much of your valuable time. Fortunately, there’s a very easy way to avoid many of these lines that a shocking number of people don’t seem to take advantage of.

Almost all of Italy’s top cathedrals and museums offer advance booking where you can select what time you’d like to visit. This allows you to avoid the hassle of waiting in line while giving you the convenience of visiting at a time convenient for your schedule. In fact, some attractions require advance tickets such as the dome climb for Florence’s and Siena’s duomos.

This saved us loads of time, particularly in Italy’s three top cities: Rome, Florence and Venice. It also lets you get guaranteed entry into some of these sights early in the day before they become swamped with other tourists. I honestly felt bad watching the people waiting in huge lines while we basically walked right into the Doge’s Palace in Venice.

Do your research, people!

Planning for Italy’s Weather

Italy is hot. You’ve probably heard that before, but it bears repeating. When we were there in early through late May, temperatures ranged from the mid-70s in Florence to upper 80s in Rome and Campania. Venice was undergoing an unusual cold and rainy streak of weather while we were there but is generally mid-60 to mid-70s during May.

The sun is also very hot (the sun is hot? Who knew!) and often unavoidable. Couple that with the large amount of walking you’ll be doing and it creates uncomfortable and exhausting conditions.

Fortunately, there are a couple ways to counteract the heat, keeping you happy and eager to explore the country.

Plan Frequent Rest Breaks

You’re in Rome or Florence and want to see everything! I understand the feeling, but fight that urge. One, there is way too much to see. It’s impossible to see everything. Two, if you don’t take some breaks, you are not even going to enjoy a lot of what you see because you’ll be so hot and tired. Besides that, your brain needs some time to sit and reflect on what you’ve seen every now and then to allow it to process everything fully.

At the very least, take a couple breaks in between stops for some water, snacks and a glass of the local vino. This gets you out of the sun and lets you slow down a bit.

Beyond that, I suggest trying to plan some time around mid-afternoon to head back to your hotel for a short nap. Yes, it takes away a lot of sightseeing time, but there’s so much to see it’s hard not to get both mentally exhausted from the sights and physically exhausted from the sun. If it weren’t for our afternoon naps, we wouldn’t have been able to enjoy much of Rome.

Take Advantage of Public Water Sources

One of my favorite small details of Italy were the many public water fountains scattered throughout each city. When you first see this, it’s okay to be a little dubious (we were), but I assure you the water from these fountains is safe and refreshing. We drank almost exclusively from these fountains during our trip and never had any adverse effects.

Filling your water bottle from these decorative fountains is just plain fun, too! It made me feel like I was in on something only locals knew about. It’s also a cheap way to get your water as restaurants and cafes all charge a nominal fee for water.

Fountains are everywhere. You have to keep an eye out, though, because sometimes they’re tucked away in corners or else blend in with buildings. Around the more decorative fountains, I noticed you could typically find a drinking fountain somewhere nearby.

Traveling Through Italy

Regional Trains

With the exception of Tuscany, we traveled from place to place via Italy’s excellent train infrastructure. We found traveling through Italy by regional train to be convenient, comfortable and efficient.

You can purchase tickets for regional trains ahead of time from ItaliaRail or purchase from the biglietteria (ticket office).

As with museums, I recommend purchasing them ahead of time to guarantee the time you want and avoid any undue stress once you arrive at the train station. You can just show up at your scheduled time, check the board for which binario (train platform) your train is arriving at, and then head there to wait to board.

Purchasing them ahead of time is also nice because the tickets will be on your phone. No paper waste that can easily get lost during your travels.

Intercity Trains

This is where things got a little sketchier. We used intercity trains for the Cinque Terre and the Campania region south of Rome.

Cinque Terre Express

The Cinque Terre Express trains were fine. They were within five minutes of their scheduled arrival time and pretty frequent. These trains were also comfortable, but the travel time between towns is so brief, you barely have time to relax before your arrival.

There are a few different types of tickets you can purchase. We bought the Cinque Terre Train Card which gave us unlimited use of the trains for the two days we were there and covered fees associated with hiking through the national park. It was very convenient for us, but your particular plans will dictate what ticket you need.

Circumvesuviana

The Circumvesuviana trains for the Campania region connecting Naples, Herculaneum, Pompeii and Sorrento are a different story.

If you’ve done any planning for this region, you’ve likely read some horror stories about Circumvesuviana trains being dirty, crowded and unreliable. I can confirm that two out of three of those are true. They can be crowded, and they are 100% unreliable. There is a lot of graffiti on the outside of the trains, but other than that I thought they were clean.

Like any city train serving major metropolitan areas, they were crowded in the morning. Late morning and early afternoon were fairly uncrowded times. I assume they get busy again later in the day as people are returning home.

My primary complaint is how unreliable these trains are. The schedule is just a suggestion. We took a total of six Circumvesuviana trains, none of which were running on time.

Another issue I had with these trains is it’s not always apparent where your train is going when traveling from north to south. There are different branches, and some trains will have a sign saying where it’s heading while some don’t (or if there is a sign, Michelle and I couldn’t find it).

My two biggest pieces of advice if you are taking the Circumvesuviana are to arrive early and ask someone to confirm where the train is heading.

Tickets for the Circumvesuviana are inexpensive, so there’s that at least. You need to purchase a ticket from the station’s biglietteria each time you ride.

There is another train you can use called the Campania Express that services the main stops. However, it runs much less frequently and is more expensive than Circumvesuviana trains.

Car Rental

We opted to rent a car to drive around Tuscany’s hill towns. It was expensive but much easier than trying to navigate this region by train or bus.

Many towns do not have convenient train stations making train travel difficult when you are trying to make the most of your time.

On the other hand, if you are only visiting Florence and/or Siena, you can easily do Tuscany by train. We used a train for Florence, but we had to do Siena by car because of how our itinerary was planned. Parking in Siena was expensive at around 24 euros per day. There is a free lot if you are lucky enough to arrive at a time when there are spaces available.

Tour Groups

I can’t write about visiting Italy without mentioning the tour groups. They are everywhere and they are frequently obnoxious, particularly in tight spaces.

To be fair, I understand the benefit of tour groups for some people. Someone else takes care of the planning and they give context to what you’re visiting. We went on a couple small tours in Sorrento and Tuscany, and we enjoyed both immensely.

Both of our tours were confined to six people and mostly out in the open. Tour groups like that are typically fine. They can be aggravating, but they didn’t affect my ability to enjoy where I was.

However, where they become overwhelming are when they’re in museums. These tour groups act like they own the space. It’s especially bad around famous and important pieces of art or history.

They gather around whatever the exhibit is taking up all the space and talk loudly, impacting non-tour group visitors’ ability to enjoy what they’re looking at.

There were times in the Vatican Museum where I was trying to look at something and no one in the tour group would move even slightly to accommodate me. To make it worse, they tend to stand there for much more time than is necessary. The tourists in the group act like they are privileged to stand there because they’re in a tour group and the guide rarely does anything to rectify this behavior.

(There were a handful of times where a guide asked people to step aside. Kudos to those awesome guides!)

By no means does this mean you should skip popular museums! Just be aware of the prevalence of these tour groups and try to plan around them by visiting early or late in the day to avoid them.

Planning a Trip to Italy?

Here are my itineraries for the cities we visited during our time in Italy. I’ll keep adding to this list as I publish new content.

• Cinque Terre
• Florence
• Pisa
• Siena
• Venice
• Volterra

If you’re already ready to book your trip, click the Expedia link here or in the sidebar to your right to start making those plans. Here are some tours we booked to help make your trip complete!

• Walking Food Tour in Sorrento
• Grottos, Faraglioni and Limoncello Tour Around Capri Island
• Full-Day Winery Tour in Montepulciano with Tasting and Lunch (includes other stops)

Resources to Book Your Trip to Italy

Whether you’re looking for tours, hotels or flights, here are some tools to help get you started planning your trip to Italy!

Look for activities and tours offered through GetYourGuide or Viator!

Still can’t find what you’re looking for? Check out my travel essentials pages for more of my recommendations.

Pin This Post!