Italy is a beautiful country with a diversity of landscapes, food, architecture, and activities. It can be such a daunting task to figure out where to even begin planning your trip to Italy. When I planned my trip, I went down so many rabbit holes trying to determine where I should go, when I should go, how much I should budget, how to get around, and so many more questions. This is why I put together this guide on how to plan a trip to Italy to help you narrow all of this down so that you can plan a trip that works for you without having to spend the countless hours that I did trying to find these answers.
How to Plan a Trip to Italy
Step 1: Decide When You Should Go
When Is the Best Time to Visit Italy?
There are perks and drawbacks to visiting Italy in each season. The key is understanding YOUR priorities.
- Are crowds stressful or inconsequential?
- Is hot and sunny weather a must or are you open to mild or unpredictable seasons?
- Can you travel anytime or are there only certain times of year you have available for travel?
These are just a few of the prompts you should think through when you are trying to plan a trip to Italy.
The Almighty Shoulder Seasons (March – April, September – October)
I am a HUGE fan of traveling during the “less” popular times of year, if possible, anywhere I go. While crowds do not bother me too much, they are a major stressor for my husband. So. if he’s stressed, I’m stressed and that is not fun for either of us. To be clear, when you are traveling to touristy destinations you will never fully escape crowds, but reducing the number of people who are just there to breeze through and snap a few pictures is well worth it.
We traveled to Italy in October and found it to be absolutely perfect for finding this balance, especially in Venice.
Coming Soon: Best Time to Visit Italy: Why October Is Perfect (and What to Expect)
The shoulder seasons, whether it is in the spring or the fall, offer mild temperatures with a mild risk of rain. As long as you pack a rain jacket or plan to buy a cheap umbrella, you will be prepared for whatever the weather throws at you and still get to enjoy all the sights, while enjoying smaller crowds and lower prices.
The Underrated Low Season (November – February)
After having traveled to numerous destinations at a variety of times of year, I totally understand that sometimes you want to experience a place just as you see it on Pinterest. Maybe you want the summer sun shining down while you capture the most aesthetic picture sipping on a limoncello spritz beachside on the Amalfi Coast. There is nothing wrong with that! It’s your vacation!
That being said, I think there is so much to discover when you’re not clouded by thinking you have to do the same four things and taking the same four pictures as everyone else. This sort of uncharted territory is where so much excitement and discovery can occur, not to mention you can stretch your budget a lot further when prices are lower.
A couple of things to consider:
- In December, there are a few Christmas markets that may drive some traffic during this time, but from what I have read, they are most popular in Northern Italy and are not as big as they are in other parts of Europe..
- In February, Carnival is a big celebration that will drive crowds, but this is concentrated in Venice.
- My last piece of advice to consider for this season is that in some places, like the Amalfi Coast, businesses will close during the low season and the ferries do not run. It doesn’t mean that it is completely shut down, but the number of restaurants and hotels open will be reduced and exploration may not be ideal. Therefore, I’d save a destination like the Amalfi Coast for earlier in the shoulder season like we did or the high season.
The Iconic High Season (May – August)
This time of year is popular for a reason. The weather is beautiful and the cities are alive with activity and excitement. It is also the time of year that draws the most crowds since it lines up with summer vacations, not to mention the beautiful, sun-shiny weather.
I traveled to Rome in late May for a solo trip and I absolutely fell in love with the city. I had no problems going to restaurants, finding a place to stay, and getting tickets to my favorite attractions. That said, I would highly recommend planning as much as you can in advance – especially booking tickets at popular landmarks or museums and looking early for accommodations. The summer is a beautiful time to travel to Italy, it just requires a mental preparedness for dense crowds, which will require patience and planning ahead of time.
Step 2: Build Your Itinerary
How Many Days Do You Need in Italy?
Oh boy…this is a tough question. Honestly? I could spend months, years even, exploring Italy and I don’t know if it would ever be enough. However, like many of you, when I am planning a trip I have a limited amount of PTO and my goal is to use it strategically to see as much as I can within a short time. A lot of this depends on where you want to go, but bare minimum I would say you need 10 days to hit 2-3 cities. Even better would be a full two weeks, which is what we did. Determining the number of days you can travel is a crucial step when you plan a trip to Italy.
Check out my article A Realistic 2-Week Italy Itinerary for First Time Visitors for my full itinerary to ease the process as you plan a trip to Italy.
How to Choose Where to Go in Italy
Trying to pinpoint the places I wanted to travel to in Italy was the biggest decision I had to make. There are so many amazing places from Rome to the Amalfi Coast to Tuscany to Cinque Terre to the Dolomites, just to name a few. The key here is to focus on two to four places (depending on how many days you plan to travel) and really explore them. I will highlight a few places for you here that I would highly recommend for a first time trip. I will also add a few more regions that I know are absolutely on my list for a return trip to Italy.
The Musts
Rome
I have had the opportunity to travel to Rome twice. The first time was in 2019 for five days on a solo trip, and then again in 2024 for three days with my husband. If there is one place I would say you absolutely must include on your itinerary for your first trip to Italy, it is Rome. Rome is such an amazing city with history on every corner and the food, oh my goodness, the food is spectacular. The pizza and pasta here are to die for. Rome is the perfect city to explore and will leave you falling in love with Italy.
Coming Soon: A Guide to Eating in Rome: What to Know Before You Go to learn all my tips and tricks on eating your way through Rome and the best spots to eat.
Venice
The second stop I highly recommend including on your first trip to Italy is Venice. I read so many articles that said Venice is just a quick stop for a day or two. While you can absolutely have a wonderful experience in two days, if you have an extra day when you plan a trip to Italy I would add it here. The canals were so magical and the gondola rides are worth every penny.
Check out my article Venice is the Perfect Couples Destination : Here’s Why for my full guide to Venice.
The Runner-Ups
Amalfi Coast
The Amalfi Coast is stunning and truly is everything you see on Pinterest and Instagram. I put it in the runner up category, not because it isn’t amazing, but because if you only have a week then focus on Rome and Venice. However, if you have more time to spend in Italy, then going to the Amalfi Coast is a wonderful addition to your trip.
In my guide, A Realistic 2-Week Italy Itinerary for First-Time Visitors, I detail our full itinerary which included the Amalfi Coast, Florence & Tuscany, Venice, and Rome. Therefore, it is fully possible to do all of this in a 2-week trip. My recommendation is to prioritize Rome and Venice then layer in destinations like the Amalfi Coast depending on the length of your trip.
Florence & Tuscany
We LOVED Tuscany. Everything from the food to the wine to the landscapes was quintessential Italy and is a lovely addition to your trip. In my full itinerary, I detail how we maximized our experience here in just a few days. It is the perfect break from the hustle and bustle of Rome, but fair warning, a few days and Tuscany will leave you realizing that it is a must-return spot for your next trip to Italy.
The Return Trip
In the past, I often treated trips like I was never going to return to that country or place again so I would pack my itineraries so tightly that I couldn’t fully stop and smell the roses. However, I have learned that if you love a place, you will likely return. It may not be in the next year, or even five, but if you want to go back you WILL so there is no need to pressure yourself into trying to see everything in two weeks. Because, let’s face it, you can’t. The goal is to figure out the priorities for you and plan a trip to Italy around those priorities. I have shared my recommendations above for a first trip, so let’s explore a few places that are on my list for a return journey.
Tuscany
Remember how I said Tuscany will leave you wanting more? Well, Tuscany is at the top of the list for my husband and I for our next vacation. When we decide to plan a trip to Italy, we plan to spend a full week in this region relaxing in a small home in the Italian countryside sipping wine and eating all the pasta we can. We believe dedicating at least 4-5 days in this region is necessary to get the full experience. The great part is we had the opportunity to fully explore Florence during our first trip, so our return can be fully focused on the countryside.
Sicily
Sicily is a destination, not just a stop. I have done a great deal of research on this region, and while on a map it looks like a small island, it really is much larger than you may think. We fully intend to make a trip to Sicily in the near future with at least a week planned for our adventure. The food and history in this region is unique and requires a dedicated trip.
Puglia
This region is often neglected in travel guides, but I believe there is so much to offer in this region. Since it does not receive the same tourism attention as places like Rome or Florence, that can open up a lot of opportunities to explore off the beaten path. The food, architecture, and coastlines offer many perks from other regions without the same popularity as the well-travelled destinations.
Dolomites
This is another locale in Italy that has seen some attention in recent years, but still is off the typical tourist path. The dolomites are a huge mountain range that offers primarily nature-based activities, such as hiking and skiing. Transparently, I am more of a city gal but if being out in nature is up your alley, then the dolomites may be a great spot for you to explore.
Step 3: Arrange Transportation
How to Get Around Italy
The wonderful thing about Italy is most places are connected by trains, which makes it fairly easy to get around. However, it is not always as simple as just hopping on a train. When you have a structured itinerary and are a little jet lagged, it can be tricky to navigate a new transportation system in another language.
Coming Soon: For a thorough guide with all my lessons learned and key information for navigating the train system in Italy, check out my article How to Use Trains in Italy: A Practical Guide for First Timers.
The bottom line here is that the trains are your best bet to get around most of Italy, but it is helpful to have tips & tricks in your back pocket so that you can get around like a pro.
Step 4: Determine Your Budget
Budgeting for Your Italy Trip
My travel style is what I like to call elevated. We do not travel entirely in luxury, nor do we do hard-core, low-cost budget travel or backpacking. Our style falls more mid-range where we make mostly budget-conscious decisions while splurging on a few elements during our trip.
With that in mind, we all-in spent about $12,000 for two people for 15 days in Italy. This included all flights, transportation, accommodations, food, drinks, activities, and souvenirs (artwork is our favorite!). Therefore, this would approximately be about $6,000 per person. We did SO MUCH on our trip and had such a wonderful time that I can truly say that it was worth every dollar. There are likely ways to be even more budget-friendly, and absolutely more ways to splurge, but if your priorities are similar to ours budgeting a solid $5,000-$7,000 per person will enable you to eat wonderful food, visit fabulous places, and enjoy numerous activities.
When thinking about your budget, this is where evaluating the season that you travel during is so important, especially for accommodations. Prices on bigger line items like accommodations and flights are higher during the high season, whereas shoulder and low seasons may present more flexibility or deals.
Step 5: Book Activities
There are so many activities to choose from when travelling to Italy, which is exciting but also a little overwhelming. In my full itinerary, A Realistic 2-Week Italy Itinerary for First Time Visitors I included all the activities that we booked on our trip. However, I will link a few of our favorites below to get you started.
Amalfi Coast
Florence
Venice
Rome
Once again, I detailed and linked all the activities we did on our trip in my itinerary article. However, the ones above were some of the highlights throughout our trip and are a fantastic starting point as you plan a trip to Italy.
Step 6: Pack Your Bags!
Picking out what to pack on your trip to Italy is mostly dependent upon the time of year you travel and which cities you plan to visit. However, there are a few universal items to add to your packing list regardless of the season.
My Musts Include:
- Comfortable Walking Shoes
- Crossbody Bag
- Portable Charger
These are just to name a few of the essentials that sustained me through our Italy trip. However, I have more thorough recommendations for what you should absolutely pack and what you should leave at home.
Coming Soon: Packing for Italy: What You Need & What You Should Skip for all the details on what you should pack for your trip to Italy.
Common Italy Trip Planning Mistakes
1. Trying to Do Too Much
As we’ve explored in this article, there is so much to see in Italy. It is important to set the expectation up front that there is no way that you will experience the entirety of a country within ten days. Honestly, that is a great rule of thumb for nearly anywhere you travel, but is especially important for Italy. So, the key here is not to try and see everything, rather focus on 2-4 cities, depending on the length of your trip, that you are passionate about experiencing and then pace your trip accordingly.
2. Only Doing the Touristy Stuff
Many of the “touristy” places are popular for a reason. If you’re in Rome, of course you should go to the Colosseum. If you’re in Venice, you should absolutely take a gondola ride. My advice is not to avoid the classics, just to seek to walk a bit off the beaten path and open yourself to broader experiences that may come your way. Especially on a first time visit, it can be easy to pack in tour after tour, and trust me I have done that and loved it, but I have also learned the value of leaving space to stumble upon something you may not be able to plan for.
3. Not Learning a Bit About the Culture Before Your Trip
Part of my academic background is anthropology, which is the study of what makes us human. Therefore, I am inherently energized by learning about other cultures. What do people value most here? What are the customs around food and drinks? What is the historical significance of this landmark, city, artwork, etc? How do these differ by region? How are these influenced by their environment?
These are just a few of the questions that flow through my mind as I am planning a trip and often lead to uncovering nuances that enable me to immerse myself a step beyond a typical traveler. Even more important than reading about the culture before going, is leaving yourself open to learning while you are on your trip.
Coming Soon: Italy Travel Tips for First Timers, I explore some of these observations that I uncovered during my trip.
The Wrap-Up: How to Plan a Trip to Italy
While writing this article, I find myself inspired to travel back to Italy, so I hope that it has done the same for you. Whether you are a first-time visitor or an Italy savant, this step-by-step guide on how to plan a trip to Italy supplies you with all the foundational information you need to plan a wonderful trip.
