How to Plan an Awesome Trip to Italy

September 17, 2022


Sitting down to plan our adventure in Italy, I realized that I'd forgotten how overwhelming planning a trip can be! Over the past couple of years, we've only traveled in order to visit family back in the US. So, I was out of practice when it came to planning a big international trip. If you're in the same boat that I was, I hope this article will help guide you as you plan your own exciting holiday in Italy.

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Pro Tip: If it's been a while since you've taken an international trip, be sure to check the expiration date on your passport, plus country entry requirements. Some countries require up to 6 months validity on your passport from the date of departure. If your passport expires before then, you may not be permitted to enter the country.

First Steps to Planning a Trip to Italy

If you've decided to visit Italy, you've already knocked out one big decision so, congratulations! Since Jeremy and I had only visited Italy once (Rome, during our college years), we were eager to explore the country about which everyone else raves. Spoiler: we were not disappointed, though we were extremely hot. 

When to Visit Italy

Speaking of the heat, the next question is - when should I visit Italy? If you have any flexibility in your schedule, the answer should be - NOT in July or August. I'd recommend visiting in either spring or fall, which I hear are lovely weather-wise, plus less crowded.

Vernazza waterfront and church

Vernazza, Cinque Terre

Due to Hong Kong still requiring hotel quarantine and Jeremy wanting to tack on a vacation after his work travel, we did not have flexibility with our travel dates. As a result, we ended up in Italy in July... during a heat wave. Although the wine was still good, sweating profusely while drinking it - not my favorite. 

Pro Tip on Summer in Italy: Many restaurants in Italy do not have air conditioning. And if they do, it's not usually the (freezing) air conditioning they have in the U.S. or in Asia during the summer. Sometimes the air inside is so hot and stagnant that it's better to sit outside where you might catch the occasional breeze, even if it is over 90°F / 32°C.

Planning Your Italy Itinerary

Deciding where to go in Italy is perhaps one of the most difficult parts of planning the trip. Obviously, Italy has too many beautiful places to see to cover them in one trip. We decided to focus on Northern and Central Italy for our adventure.

Since we were planning to visit in July, I'd hoped perhaps the northern regions would have cooler temperatures than in the south. Not sure if that's the case though.

View of Florence Cathedral from Tower

View from the tower of the Cathedral of Santa Maria del Fiore in Florence

First step of trip planning for me is some initial research using the Italy Lonely Planet book, various blogs, and watching vlogs on YouTube. Also, since almost everyone I know has already taken an epic Italy trip, I've been building a list of places that I want to visit for years. 

How Long to Visit Italy

Once I'd researched and mapped out places I wanted to go, I had a month-long itinerary in front of me. Jeremy told me we could go for 2 weeks. So I had to start cutting places. Eventually, we compromised on a 3-week itinerary in northern and central Italy. 

Pacing the Itinerary

The trick to planning a 3-week trip is to allow time for relaxation in some places so you don't get burned out. I'm not sure I completely accomplished this goal. But I wonder how much that had to do with the heat than it did with the pace of the trip.

Pisa pink and orange buildings

A square in Pisa

In general, we prefer to spend 2-3 nights in each place which allows for 1-2 full days in each location. This pace gives you plenty of time to explore. It also left time for relaxation without feeling like you're missing out.

Northern & Central Italy Itinerary

The northern and central regions in Italy have so many beautiful places to see - mountains, beaches, historic cities, and quaint villages. Since it was our first time to this region in Italy, we decided to stop in the main cities with a few smaller towns thrown in. 

Our 3-Week Italy Itinerary
  • Milan - 1.5 d / 2 nts
  • Cinque Terre - 2 d / 3 nts
  • Pisa - ~6 hours (stopped on way to Florence)
  • Florence - 2.5 d / 3 nts
  • Siena - 0.75 d / 1 nt
  •  Tuscany hill towns - Montalcino (stayed 2 nts), Montepulciano, Pienza
  •  Bologna - 2 d / 3 nts
  • Verona - 1.5 d / 2 nts
  • Venice - 3.5 d / 4 nts
Street in Montepulciano

Quiet street in Montepulciano

What We Missed

Although we would have liked to have visited places like Lake Como and the Dolomites, it was peak season, plus we were booking late. We didn't want to spend a fortune on accommodations since most were already full, just to be swarmed with crowds at the lakes and on trails.

Personally, I deal with crowds in cities better than on trails where I want peace to be able to appreciate the natural surroundings. So, I'm saving the mountain regions of Italy for a return trip in the off-peak season.

How Far Ahead Should I Book?

Since we planned our trip around Jeremy's work travel, we didn't end up planning it until May. To plan a trip to Italy in peak season only two months before traveling seems kind of crazy, but it worked out fine for us. Were there things we didn't see? Yes, but we did so much that we didn't miss them. 

If you're planning your trip well in advance of your trip, I recommend booking the following items in advance (especially if you're traveling during peak season).

Accommodations: 4-6 months 

If you know you're going to be traveling several months ahead, I'd recommend booking accommodations quite early. The earlier you book, the wider range of available (and affordable) accommodations you'll find. 

Rental Car: 2-3 months

As with accommodations, the earlier you can reserve your rental car, the more options you'll have available. If you're going to rent a car in Italy, keep in mind that you'll also want to make sure your hotel has parking or find a garage nearby.

Pro Tip: If you do not have an Italian or EU driver's license, you are required by law to have an International Driver's Permit (IDP) in addition to your driver's license to drive in Italy. If you live in the U.S., it's quick and easy to get an IDP at AAA. As opposed to in Hong Kong, where you have to go to the Licensing Office to get an IDP and it's a total pain.

Train Tickets: 1-2 months

For the most part, we chose trains as our mode of transportation to get around Northern Italy and I'd highly recommend them. The trains are comfortable, run frequently and to most destinations, and they're (mostly) on time. 

In order to make sure we got seats together and in the car we wanted, we booked them about 1.5 months in advance. Apparently tickets get more expensive closer to the date of travel so booking in advance will save you some money. Once we had our train tickets booked, I felt that helped to shape our itinerary. 

Museums & Cathedrals: 2 weeks or less (for most)

For most museums and cathedrals, you can buy your tickets online ahead of time. Normally, I don't like buying tickets to attractions in advance because it puts me on a schedule and I like having flexibility in my day.

But since we were traveling to Italy during peak season, I figured we should purchase in advance for the more popular places. Although I didn't love being tied to a specific time, I did enjoy skipping the lines for the ticket booths. 

Statue of David in Florence

Statue of David in Florence

Restaurant Reservations: 2 days to 2 months

Honestly, I'm the absolute worst at making reservations at restaurants. Again, it's mostly because I hate being tied to a time. Because we didn't make any reservations, we ate some pretty late dinners (9:30pm - 10pm).

Pesto gnocchi in Monterosso
Seafood Pasta in Venice

If you know where you'd like to eat before your trip or even a couple days in advance, it's worth making dinner reservations. If you don't, you might still be able to get into most places if you're flexible with your schedule like we were.

If you're trying to go to one of the more popular and sought-after Michelin-starred restaurants, you might have to reserve months in advance. 

Next Steps - Booking the Trip

Once you have a basic plan in place for your trip, it's time to start booking! Since I did not have much time, the planning and booking happened pretty much at the same time for me.

Booking Flights

If you're planning the same kind of itinerary that we did through northern and central Italy, you'll most likely find Milan is the best option for flights into northern Italy. Although Venice is another option, those flights seemed to be a bit pricier. I've also read that you can save money by flying into Rome and then taking a fast train up north from there.

Tip for booking flights: I start by searching on Skyscanner.com to see what flights are out there and which combination of airports and dates look the most affordable and work best with our timing.

Becky and Jeremy on water taxi in Venice

Private water taxi to the airport in Venice - expensive but worth it!

Our Italy Flights - In Case You're Curious

As you'll see from our itinerary, we flew into Milan (MXP) and left from Venice (VCE). Since we were booking one-way tickets anyway, it seemed the most convenient option. It might have been cheaper to return to Milan. But it would have taken a day away from our time in Venice, which we wanted to avoid.

While I was coming from Hong Kong, Jeremy was in Mumbai for work so he came from there. We both flew Qatar Airways and met up on a layover in Doha to fly to Italy together. 

Leaving from Venice, we saved some money on Finnair by choosing the option with the 11-hour layover in Helsinki. This flight worked out wonderfully as we were able to explore Helsinki - much cooler than Italy! Then, we continued on to Bangkok to spend a month in Thailand before returning to Hong Kong.

Finding & Booking Places to Stay in Italy

As tough as deciding where to go in Italy is, finding the perfect accommodations might be even harder. Even though I realized I wouldn't spend much time in the place, I still like to find places with a good location that have charm and a decent view.

Method for Finding Accommodations in Italy

For this trip in northern and central Italy, I spent hours scouring several hotel websites, but found that the choices and prices on Agoda.com and Booking.com were the best. For each place, I also looked at apartments on VRBO and Airbnb.

Since we were visiting during peak season and booking somewhat last-minute, choices were limited in certain places, like Cinque Terre. Especially since I was trying to stay under 150-200 USD per night. 

Bed and breakfast in Montalcino

B&B in Montalcino

Accommodations Booked in Italy

As a result of my extensive searching, we stayed in combination of hotels and apartments throughout our trip. Most of the places where we stayed met my criteria, but some were missing one thing or another. Overall, they were all decent places to stay in a central location and walking distance to most attractions.

I'll be writing a more in-depth review of our Italy accommodations in a separate post. In the meantime, here is a list of the places we stayed, the site where I booked it, as well as what each place cost.

Pro Tips: In VRBO and Airbnb, be sure to use the filter options to find places with the amenities you want. For example, you can filter to find places with a washing machine and air conditioning. Both were key considerations for us and not all VRBOs and Airbnbs have them.

Booking an Agriturismo in Tuscany

In Tuscany, we would have liked to stay at an agriturismo - accommodations that are on a working farm or vineyard. Agriturismi (plural of agriturismo) range from basic and rustic to luxurious with amenities, such as a swimming pool. Some of them include one or more meals in the package.

By the time we booked in May, the ones that I reached out to (with air conditioning) were fully booked already I've heard that agriturismi can book up as far as a year in advance during peak season. So, if you have your heart set on staying in one, you might need to plan your trip around that stay. 

Booking Transportation in Northern & Central Italy

When deciding what mode of transportation is right for your trip to Italy, here are some questions you may want to ask yourself. 

  • Are you traveling between cities or into the countryside?
  • Do you want the flexibility to stop in places without worrying about a train schedule?
  • How much luggage do you have?
  • Are you confident driving on narrow streets or in tiny parking garages?
  •  How comfortable are you driving in a country whose language you might not be familiar with?

Riding Trains in Northern & Central Italy

Ultimately, we decided to take trains as our main mode of transportation since we were primarily traveling between cities. Plus, when we looked at costs, renting a car seemed more expensive than taking the train. Also, we didn't want to worry about driving in traffic, parking, or increasing gas costs.

Train in Italy

Catching the train in Milan

Throughout the trip, we found that trains in northern and central Italy were an efficient and comfortable way to travel. The biggest downside was hauling our luggage to/from the train station and into the trains. 

Booking Train Tickets Online

We used Rail Europe to book our train tickets in Italy about a month and a half in advance of our trip. I found Rail Europe's site easy to navigate for looking at train schedules and selecting seats. They charge a small booking fee, so I purchased all of our trip's tickets at once to avoid paying multiple booking fees.

Becky and Jeremy on train with table

First class seats on the train.... cause sometimes we're fancy like that.

Once booked, you'll receive an email with a PDF of the tickets which you can print or pull up easily on your phone for the ticket collector. Though I recommend taking a screenshot of the QR code beforehand in case you lose service during the train ride.

Renting a Car in Italy

If you're planning to visit the Tuscan countryside or mountainous regions, such as the Dolomites, then renting a car is a good idea. Trains do not go to the small hill towns in Tuscany and taking a bus can be difficult. 

With this in mind, we rented a car from Florence for a few days in order to drive around Tuscany (with my parents). To start searching for rental cars, I used Rental Cars to compare prices. Once I found a deal, I booked online with Avis Rental Cars.

Rental car in Italy

Candid shot of my dad and Jeremy checking out the rental car at the Florence airport

Pro Tip: If you are trying to decide if you want to rent a car, remember that you'll also have to consider parking. Not all hotels in Italy offer parking. When they do, sometimes their parking garages are small with tight turns which can be tricky if you've rented a larger vehicle. 

Ordering Tickets for Museums, Cathedrals, Etc.

Despite my preference to keep my schedule flexible on trips, I booked a few of the more popular attractions in advance online. 

Here are the sites that I used to book the tickets in advance:

Basilica San Marco in Venice

Basilica San Marco, Venice

Once booked, you'll receive the tickets by email. Even though some of the instructions say you have to print them, they accepted the QR code on my phone for entrance.

What We Missed - Last Supper Painting in Milan: Most things we wanted to see still had tickets available two weeks before our trip. One thing we should have booked earlier was entrance to the Last Supper painting by Leonardo da Vinci in Milan. In order to preserve the painting, the number of visitors they let in each day is limited so tickets sell out. I recommend booking online as early as possible.

Other Things to Consider Before Your Trip to Italy

Now that you have your trip booked and you're getting closer to when you need to leave, here are some things you should consider to prepare for your trip. And for a more complete list, check out my Ultimate Guide to Preparing for International Travel.

Visa and Entry Requirements

Before any trip, it's important to check what the visa and entry requirements are for your nationality for the country or countries to which you're traveling.

As a U.S. citizen, no visa is required to enter Italy for tourism for stays under 90 days. 

Learn Key Phrases in Italian

Although English is widely spoken throughout Italy, it's nice to learn a few phrases before traveling to Italy. I used the free version of Duolingo to learn some basic Italian. Although I found it useful to improve pronunciation and comfort with the language, the app doesn't start with the most helpful phrases for travel.

Even if you don't pick up many phrases, I recommend learning how to correctly pronounce Italian words. That way, when you're ordering off a menu, you don't butcher words like 'tagliatelle' or 'pistachio' which we pronounce incorrectly in English. 

Tips for Packing for an Italy Summer Trip

Depending on the time of year that you visit Italy, the things you'll need to pack will change. Even after reading several packing lists for Italy, I wasn't sure what clothes I'd actually wear. So I did what I always do - overpacked... a lot.

My Favorite Outfit for a Trip to Italy

After spending three weeks in Italy this summer, I thought I'd share my thoughts on the best outfit to bring to Italy in the summer. Without a doubt, the outfit I preferred to wear in Italy was a light, summery dress (this one was my favorite for walking around during the day) with Keds white sneakers

Becky in black dress Milan
Becky in blue flower dress Milan

Even though I brought many shorts and t-shirts, a dress was more appropriate for visiting churches. To cover my shoulders, I just carried around a light scarf I bought in India years ago and threw it on before going into a church.

If you're thinking, it's not comfortable to walk around in dresses because of a certain thigh situation (ladies know what I mean). Then, I recommend wearing a pair of these Lululemon shorts underneath. Total game-changer for me.

Other Items to Bring to Italy

Other than clothes, I'd recommend a few other things you should consider bringing for an extended trip to Italy. 

  • Laundry detergent + clothes line: Even if you don't have a washing machine, you can handwash clothes in your hotel sink to avoid overpacking.
  • Adapter: A handy thing to have for any international trip. 
  • Portable charger: Especially important if you're using your phone as your camera.
  • Blister care: You'll be doing a lot of walking in Italy so having band-aids and blister care so you don't have to seek out a farmacia when you get a blister is a good idea.

Even if you forget something, you can find most everything you need in Italy. In fact, you should be sure to leave room in your suitcase in case you do a bit of shopping while you're there.

Final Thoughts

Preparing for a long trip to Italy can be overwhelming, but it's also exciting to put the pieces in place for an epic trip. It's key not to stress out overly while planning your trip. Because even if everything doesn't go exactly the way you planned it, you're sure to make unforgettable memories. 

Have you taken an extended trip to Italy or somewhere else? What steps did you find helpful when planning for your trip? 

Other Articles You May Enjoy

If you're thinking about planning a big trip, here are some other articles you may find useful:

Happy traveling!


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How to Plan an Awesome Trip to Italy
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  • What an incredibly comprehensive and well-researched post that doesn’t leave any questions unanswered, Becky. Having grown up near Munich, about 2.5h from Italy on the motorway, I usually visited Italy at least three times a year every year. I think you itinerary is briliant and yep, better leave the mountains for another visit off-season.

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