8 Tips for Planning Your First Trip to Italy

8 Tips for Planning your First Trip to Italy

8 Tips for Planning your First Trip to Italy

Italy travel planning.

9 parts exciting, 1 part overwhelming. Sound familiar?

It's super easy to lose the excitement and get overwhelmed when planning your first trip to Italy. In fact, it's normal. 

Everyone & their uncle have an opinion of where you should go, what you should see, and how much you should cram into your trip. 

This is where my advice to you comes in- take a deep breath, walk away from all the noise, and focus on what YOU want.

Think about what is at the root of your travel bug.

Ask yourself these questions: 

  1. Why do you want to go to Italy?
  2. What is it you are wanting to experience?
  3. (or Taste? Feel? Touch? See?)

Have you always wanted to walk down an ancient Roman road?

Do you dream of exploring medieval villages or hillsides covered with olive trees and vineyards?

Is meandering through churches exploring art + architecture on your bucket list?

Or maybe you want to eat your way through Italy? I knew we were bound to be BFF's.

Budget Tips for Italy Travel

8 Tips for Planning your First Trip to Italy

To help you get started making your own plans, I wanted to share some of my favorite tips with you.

These are the main things I love to share with friends, family + clients as they are planning their own adventures in Italy- the things that will help you enjoy, connect & make unforgettable memories during your trip! 

Ready? Here we go...

Slow down.

Less is more. Not only in your suitcase, but in your daily schedule and your overall itinerary.

Allow breathing time to really sink into a place and experience it. Don’t dash from one monument to another, or one destination to another.

You will never look back and say, "I wish we had gone through Italy faster."

Plan your trip around an event.

Sound crazy? 

The Italians know how to throw an epic party and there are so many religious, food and culturally rich festivals to experience all over the country and all throughout the year. 

It is a great way to meet the locals and will add a richness to your travel experience that is unbeaten! (Here's one of my favorites)

Book a Tour. (with a local guide)

I used to think tours were only for people who were afraid to explore on their own or wanted someone else to tell them what to see + do. 

This is not true. While there are tours that lean that way, if you do your homework you can find many wonderful tours for small groups that really give you a different perspective of the city or sight you are seeing.

They share the history, the stories, the architecture with you in a way that makes it all come alive. Worth its weight in gold I think!

Some that I recommend are:

The Roman Guy

Walks of Italy

Context Travel


My favorite tours? Food tours, of course.

Over the years, this has been the best money I have invested when I visit a place for the first time.

Food tour guides are kindred spirits. They know all the best tips, tell you places you shouldn’t miss as well as places to avoid.

They help you learn about the culture through its food and how history weaves through whatever you are eating and bonus, they are almost always friends with the shops and restaurants they take you to (because they've hand picked their favorite places) and you get to meet some new friends along the way.

These local guides also have the best tips for navigating public transportation, share which bar has the best aperitivo or coffee and all those little extras that make your trip fabulous.

I advise doing this type of tour the first 24 hours you are in a new location, so you can use these suggestions throughout your trip.

Excellent food tours to consider:



Stay Put.

Spend at least 4 nights per destination. (5+ is even better!) 

Even if you don’t consider yourself a “slow traveler” just trust me and try it.

The more you slow down and enjoy where you are, the deeper your experience, and the more chance you have at making some real connections with the place and the people.

Plus the longer you stay in one place, the higher your chances are to save a little money on lodging and decreased transit expenses.

 (* This 4-night rule gives you 3 full days to explore each place, which for me personally is the bare minimum.)

Support Small Businesses.

Running a small business anywhere is hard. But in Italy it seems even more difficult. 

I love to support small businesses by eating, shopping and staying local and avoiding big chain shops/hotels/restaurants when at all possible.

By booking directly with family owned lodging and locally run tours you are supporting the local economy, which leads to deep connections and rich experiences.

You can find some great local lodging ideas here.

p.s. You can support many Italian Small Businesses all at once by coming on one of our Umbrian Gourmet Tours. 🙂

Budget Tips for Italy Travel

Book Ahead.

I’m all for slow travel, but I’m also for being organized and cutting out unnecessary stress. Making certain reservations ahead of time will ease your mind, and often your wallet.

Things that can easily be reserved online ahead of time are: Hotels, high-speed train tickets + group tours. If you are going in high season or to any of the most popular places like the Uffizi Gallery in Florence, The Colosseum in Rome, or similar- you will be so glad to have bought your tickets ahead of time for the sheer ease of getting in and your wait time will be greatly decreased. 

At some places, reservations are mandatory (like the Borghese Gallery) and some sell-out months in advance (The Last Supper) so planning ahead is well worth it.

*By the way, Last Supper tickets go on sale 4 months in advance, so plan accordingly if you are headed to Milan.

Dinner Reservations.

Book your first night’s dinner reservations before arriving. I started doing this early on in my Europe travels and have never regretted it. (especially when traveling with my kids) 

I love the thrill of the hunt of a good place to eat, but get very grumpy if there is no plan and everyone is tired and hangry from a long day of travel.

Having a plan before we arrive takes the pressure off, and helps us enjoy easing into our new location. Bonus points if there is a great local place close to your lodging.

Plan on returning.

You literally cannot see and do it all.

I know how tempting it is to try and do too much. I challenge you to resist! Pick a focus for your trip or a small area to dive into and enjoy every minute. Seriously consider my #1 tip, "less is more" and see how much you enjoy your trip.

Bonus: by immediately planning your return trip on the plane, you’ll have something to keep you occupied and from crying into your Pellegrino the whole flight home.

p.s. Learning some Italian before you go is a great way to connect with Italy & make new friends while you are there.

Steal our exact Travel planning timeline!

(click the photo below)

Italy Travel Planning: Quick Resources

Find your perfect place to stay:

Explore tours & experiences:

Getting around:

Smitten Italy Travel Resources:

Like this guide? Pin it for later!

8 Tips for Planning your First Trip to Italy