Plan Your Trip to Italy for First Timers 🇮🇹

Journey Wisdom
47 followers
3 Video Views·Mar 7, 2025
The sights and sounds of Italy are what dreams are made of, from the history, art, stunning
coastline, ancient cities, shopping, and of course, the food.
And yet it's no secret that it's also crowded, maybe a bit difficult to navigate or get around,
and some cities can be dirty, smelly, or even covered in graffiti, making it a bit tiring
to lug around all your things from place to place while managing a language barrier.
In this series recap, we'll cover our route, time of year we visited, how to get around,
money, tips for deciding which places you'd like to visit the most, and how to avoid travel
fatigue, some packing tips for the ladies, and the single ingredient for creating life
If you're new to KYD, we mostly travel in the United States, in our Airstream, and we
love cooking, cycling, national parks, and of course, our family.
But with our youngest going off to college, we wanted to mix things up and take a trip
with just the two of us.
And then, meet up with our friends for some big laughs.
I can't believe he said you were good looking.
I told you, I told you it was a long time ago, you never listened to me.
It was the name.
It's the name, Tony.
That's not even fair.
You call him Tony.
As soon as he said Tony, they're like, oh, Tony.
Tony.
Come on, look at this, look at this.
Bill.
I go.
We arrived on August 30th, and the weather was absolutely perfect.
September can be a busy time to visit Italy, but it's still considered the shoulder season.
Our route started in Rome, before we rented a car and traveled to Alberobello, the southern
region, and stayed in Etruglio, and then drove north, stopping in Assisi for one night, before
picking up our friends on our way to La Tavola Marche, an agriturismo that provided a once
in a lifetime experience.
We are the Gencios, my friend, la la la.
Then we were off to Florence, followed by the Cinque Terre, Parma, and Venice.
We also visited Lake Como, but the weather moved in and rain doesn't help much when making
a video.
We ended up switching our flight home from Rome to Milan to make it even easier.
Most people opt for public transportation, and rightfully so.
The trains and ferries in Italy are incredibly efficient, affordable, fast, and even fun.
The only real drawback we found is figuring them out.
Are you sure they're the right tickets?
No.
Are you sure this is the right platform?
No.
Are you sure this is the right train?
No.
Are you sure we're going to the right town?
No.
Because we're RVers at heart, we preferred to have our own car, so we could be on our
own schedule and experience more of the small towns between the destinations.
Back in our freedom machine.
This allowed us to go off the beaten path and change our plans, which allowed us to
stay in Alberobello and Assisi, two of our favorite places on the trip.
How fabulous was that?
It was fantastic.
Marco showed us everywhere, everything, so much information.
I'm glad you record in times like this.
I know.
Because there's things I forget and I don't want to forget them.
Yes.
So anyway, let's go poke around in the little stores.
I think I found something.
And then we're going to go pick up the walkers.
Okay.
But Assisi was beautiful.
It's the town that you want to see when you're in Italy.
Driving in Italy on our last trip, 22 years ago, wasn't as enjoyable.
Google Maps has changed the game for driving in another country.
The names of the roads may not sound familiar, but you'll know exactly how to get there.
In bigger cities where Uber Black was available, we used that.
Regular Uber wasn't available during our stay, but Uber Black was, and it was only
slightly more than a taxi, with reliable rates and rides that were far superior.
All the Ubers here are super nice.
And they're just as expensive as they have, so yeah, we're Ubering for now until we find something better.
Plus, there was no cash needed.
Speaking of cash, we only carry a debit card for the sole purpose of using ATM machines.
When using an ATM machine, you'll be asked if you want to exchange in the country's currency
or have your bank do it.
Always select your bank.
Right now, they will provide a much better rate.
There were ATMs just about everywhere, so we didn't have to carry too much cash.
We mostly used our credit cards, but be sure the cards you do use don't have a foreign exchange fee,
because those will add up fast.
We found that American Express wasn't accepted at most places,
so we upgraded our Southwest Airlines card to an international plan free of charges.
We also used Apple Pay for almost everything.
If you're unfamiliar, just add your cards to your iPhone and hold it in front of the machine.
It's super easy and lightning fast.
We used this at restaurants, grocery stores, and even tolls.
Tolls were the most convenient.
How much? 33 euro.
Really?
Yeah. I was wrong.
Surprisingly, food and lodging is usually cheaper in Italy than in the United States.
Most drinks were about 6 euro and a cup of coffee was under 2 euro.
We found incredible accommodations for 100 euro per night,
but we splurged for nicer vacation rentals when we were splitting the cost among our friends.
A hotel is more.
And a hotel would be more advanced.
And you're all together and we have coffee and breakfast.
So all we really need is the walkers to divide this puppy by three.
If you prepare and fly free on miles, like we did, there's a tremendous value in traveling to Italy.
For 12 dollars, for 12 euro, we're sitting here with a glass of Prosecco,
we're having a full meal, a warm meal, and you end with a cafe.
12 euro!
The time of year will dictate the biggest savings.
Using Google Flights to find incredible deals, even if you're using miles,
will help you zero in on the flights and times that use fewer miles.
When you arrive, lodging will be less, too, during off-season.
You might have to deal with a little weather, but far less people.
We prefer the shoulder season.
This way, the weather is cooling off, but there's a little less demand on the smaller cities,
helping you get around easily.
Now for some tips on where to go.
This is a big one.
Although the entire country of Italy fits into the size of California,
deciding where to go can be daunting.
Based on our research, which means a single Google search,
the average trip to Italy is about 10 to 14 days.
Two weeks is plenty of time to mix things up with a little city, country, and coast.
I have to relax.
Yes.
I just want to make sure I see it all.
Yes.
FOMO is a real thing.
Fear of missing out.
But be assured that your best experiences will come from what you create,
not just what you see.
So leave a little space to adjust your plans when you're there
and not have every second planned before you leave.
It's easy to get swept up in Instagram stories
about all the things to do and see in places like Rome, Milan, Naples, Florence, and Venice.
But we found the best parts of our trip were outside of these popular sites.
Certainly, the architecture of Rome, the art of Florence, are surreal.
And visiting places like the Colosseum or the Statue of David
are on the must-see list for a reason.
But that top 10 list can creep into every location.
And before you know it, you can feel saturated with tours and information.
We're a little tapped out on tours, so we didn't do the Parmesan tour.
Leaving little to no time to stumble across experiences
that will exceed your expectations.
We're going to go use hotel tonight.
We're going to find a hotel.
We're going to drive over to Bari.
We're going to stumble across things.
That, that is the way.
Taking this approach might also help avoid travel fatigue.
You might be thinking, I'm not worried about that.
I'll sleep when I get home.
But schlepping your bags from place to place
into trains, boats, and cabs can get tiring.
And every time we did it, we lost just a little bit of energy.
You can just set them down.
Oh, I don't have any cash though.
I'm all out of cash.
I want my car back.
By staying just one more night in each place,
we would have reduced the amount of times we had to pack and repack our luggage.
Digging a little deeper into fewer places might just be something to consider.
Now, what you got to do is you got to,
you got to tackle it corner by corner, okay?
In an effort not to ruin the zipper.
Corner one.
If on the other hand, you are dead set on seeing it all,
maybe just a backpack is the way to go.
Less is more with that kind of trip.
And it might be less about the spritz and souvenirs
and more about checking boxes.
But I'd put a spritz on my checklist.
It's a spritz.
That's all I need.
It's a little spritz.
I just need a spritz.
Tony, what's going on?
She's very angry.
Put them in here.
You ready, girls?
Okay, ladies.
I told you I had some packing tips,
but it's kind of long.
So if you're curious how I packed carry-on only
for three and a half weeks with 17 outfits,
and no, I did not use packing cubes,
just go to keepyourdaydream.com
slash packforitaly.
You'll find the video there
plus links to my favorite travel stuff.
For everyone else,
Mark shares tips for keeping things charged up
in another country.
Trish really did a great job
with this converter charger.
Not that you need this much stuff.
Not that an outlet can even handle
if you were to plug it in.
It just has options.
But what I really like is it has this extension cord.
This is one of the few places
where there's been a counter
underneath the outlet
other than like a kitchen
which it might just be in the way
to be charging camera gear.
Most of the time,
the outlets are on the ground.
And so if you don't have something like this,
then all your phone
and anything you're charging
is just sitting on the ground.
But with this,
we're able to use those floor outlets
and then bring it up to a table
and charge things where you want.
The other thing is
these things are wonderful
and you gotta have more than one anyway,
especially for us
because we're charging the GoPro
and the Canon
and phones
and stuff like a computer.
But the other thing about this,
it's great
but when you put a big Canon charger on this,
the weight tips back.
These little prongs
aren't strong enough
to hold that type of weight.
So it's been so much nicer
to do this.
And of course,
because it's big,
I can do this
while still charging
my GoPro batteries
or even maybe my laptop.
So big thumbs up on this.
We'll link the Amazon to that.
But like I said,
if you are bringing cameras
and computers and things,
you probably need more than one.
I mentioned in the beginning
that we'd share a single ingredient
for creating lifelong memories.
And that ingredient is spontaneity.
Spontaneity.
Last minute plans coming together.
Cheers.
When planning our trip,
we never imagined
hopping in a rental car
with no reservations
to a town we couldn't pronounce
or enjoying a polenta festival,
joining an ugly club,
or swimming in the sea
with our dresses.
But that's exactly what happened.
I'll eventually forget
half of the information
I heard on a tour
and my memory
of all the must-see places
will fade.
But I will never forget
these small experiences
that added up
to lifelong memories.
You'll never really know
what will happen on your trip.
One thing will lead to the next
and you'll get an idea.
Go with it.
Be spontaneous.
Leave time to go with the flow
and don't be afraid
to change your plans on the fly.
Your biggest memories
will come from
the smallest encounters.
To start from the beginning
of this series,
just use our playlists.
And if you're new here,
welcome!
Join us back in the States
as we travel across the country
and up the West Coast
for adventure and smiles.
So, I'm making hummus
and if you make one serving,
you might as well make two.
Right?
Wow.
We're just in the desert,
it seems.
And look at that
green mountain.
Wow.
Mesa Verde.
Hi!
How's it going in here?
Oh, you know.
