How to Plan Your Perfect Trip to Italy - Part 1 Of Italy Planning 101

A beautiful, somewhat secluded spot along the Amalfi Coast…is this part of your ideal Italian Holiday?

A beautiful, somewhat secluded spot along the Amalfi Coast…is this part of your ideal Italian Holiday?

When you are planning your first trip to Italy, the most common question and concern is “How do I know where to go?”

 I get it.

It’s a big country and you want to do it all….

Visit the Eternal City…

Be seaside with a plate of fritto misto and an Aperol Spritz.

Shop for beautiful leather goods…

Visit the sculpture of David…

Sip wine and eat every carb imaginable….and cheese…and cured meat…

Drink your weight in coffee…

And, maybe even fall in love under the Tuscan sun.

 So much to do, so little time.

What first felt like the ultimate getaway, your own Eat, Pray, Love (and Eat Some More) adventure come to life, now has you in complete and total overwhelm.

It’s exactly how I felt when I planned my first two week trip to Italy in 2016.

Armed with my Rick Steves’ guide and a massive cup of coffee, I too set out to plan my Italian holiday, but wondered where to begin…and then began to freak out.

Sure, these guides tell you all about the cities you dream of, but how do you know which and how many are right for you?

Don’t worry, Bella…I got you!

Today I am going to give you step 1 for planning your ultimate Italy vacay, and in the  coming weeks, I’ll give you my other best tips so you’ll feel confident and equipped to have the time of your life (Italian love affair may or may not be included).

Step 1:

Ask yourself, “What kind of experience do I want to have?”

There’s not one way to do Italy.

And contrary to what others might tell you, you don’t need an unlimited budget to make this trip amazing.

What you do need, though, is a clear vision of the kind of trip you want to have this go-around.

I say “this go-around” because one thing you have to wrap your head around is that you WILL be back to Italy. Unless you have months on your hands, you can’t possibly see and experience all that Italy has to offer in one trip.  

Heck, I’ve been there 7 times and stayed 1-2 months there for most of those trips, and I still haven’t come close to doing or seeing it all!

So do yourself a massive favor now and let that sink in….this will already relieve so much of the fear and apprehension that can come from planning your trip. Nothing causes anxiety like thinking you have to do it all NOW or that you only have one chance!

Ok, now that we’ve got that out of the way, let’s get down to answering the question at hand.

You have to get clear about what you want the experience to be like.

There are several factors to consider….


Sense of luxury.

Sense of adventure.

How much you want to do on your own (i.e. zero to minimum tours/tour guides and you’ll figure it out with just a book/Google.)

Desired pace of the trip.

Solo or partner travel.

What kind of environment you long to experience the most (i.e. seaside, rolling Tuscan hills, lakes, mountains, city life, small towns.)

 Here are some questions to help you go deeper…

Do you want that adventurous, “just me and my backpack”, kinda trip?

Do you want to be able to pack all your favorite shoes, dresses, etc., roll up to the hotel, and feel pampered like a Queen?

How much time do you have?

How leisurely do you want to be able to go?

As an example, my first trip it was all about me and my backpack. That’s how I wanted it. I knew I was in for a bit of hustle and that it wasn’t going to a relaxing vacation. That wasn’t my intention…my intention was see as much as I could of the places that were of highest interest to me at the time (keeping in mind that I would be back) on a relatively moderate budget, and self-create the experience (read: no tour guides except the one I downloaded onto my phone from Rick Steves).

And so, I just took that backpack, I traveled during a time of year that wouldn’t require heavy clothes that would take up a ton of space (September), I narrowed my scoop to Rome, Amalfi Coast, Florence, and 3 cities in Tuscany (and even that was ambitious), and booked Airbnbs the entire way (just private rooms, not entire apartments) which saved me lots of money. I also gave myself some room at the end to see where the moment would take me, which is how I found Lucca, my now second home and the location of my yearly Pleasure Path Retreat (which could be perfect for you so check out all the details HERE).

That trip was sweaty, frugal so that I had more $ to eat what I wanted, fun as hell, and unforgettable.

But none of my other trips have been like that.

Because after that first trip, I got to know Italy a whole lot better.

For example, I realized I loved Tuscany the most and wanted to really explore that area.

I came back to it just 6 weeks after my first trip to Italy ended, and took an Italian language immersion class in Lucca, spending an entire month in Italy that go-around, and though I made it to Sicily, Rome, and Florence during that time, I was happiest for that trip just settling into life in Lucca.

During my subsequent trips to Italy, there were other realizations that came along the way.

For instance, I can safely tell you that I no longer want to visit Positano or Amalfi ever again (they are too touristy for my taste) but I love the Amalfi Coast and the other little jewels of town that run along it. So for sure, during one of my future trips, I’ll plant myself there and make my way to Capri to fulfill my goal of doing the Blue Grotto.

I also know I like small towns over big cities, I’m not that into museums, and which regions of Italy have the best seafood, cheese, cured meats, etc…so my follow up trips will center around visiting other smaller towns and enjoying as much of the local cuisine as my frame can handle. :)

My point?

You can have totally different types of trips and different vibes each time…you just have to decide what you want to experience this go-around.

So for today, I want you to close your eyes (after you’re done reading, of course…) and really feel into the kind of experience you want.

How slow, or fast, do you see yourself going?

Are your days spent wondering into museums, hopping off and on a tour bus, or walking around a little Tuscan town, sipping wine and savoring local cheeses and meats on top of crusty bread?

Are you sitting under one of those iconic orange and green umbrellas, dipping in the water, while a cutie pie waiter named Michele brings you a Spritz?

How hard do you want to work at your trip and how much do you want it laid out for you?

If you sat with it and thought you’d like a little more hand holding without the obnoxious overstuffed tour groups, have a moderate budget, want a bit of seaside, a lot of Tuscan countryside, and the a good amount to the most adorable Tuscan town you can imagine, then our Pleasure Path Retreat 2019 might be just the perfect fit for you. I’m happy to set up a time to talk with you about it so just go HERE and we can set up a time to chat.

Now, that you’ve got the vision, we can begin to move on to the next step of narrowing down the cities you’ll visit, but that’s for next time.

See you soon for more Italy Planning 101!

With love,