Sixteen days, a birthday dream, countless plates of pasta, plenty of wine, and one unforgettable trip through Italy.

Italy started with a puzzle.

For my 49th birthday, Dan handed me a wooden puzzle. Piece by piece, it revealed the words:

“We’re Going to Italy!”

And sitting behind it were travel books for Rome, Naples and the Amalfi Coast.

Apparently, we weren’t just talking about Italy anymore.

We were going.

The trip would be my big 50th-birthday adventure—although, if you know me, you know I don’t really believe in limiting a birthday celebration to one day.

I celebrate the birth month. 😂

So it feels especially fitting that, as another September begins, one of the first official stories of What’s Up w/ Wendi? is about the trip that started with a birthday puzzle and a place I had dreamed about visiting for years.

We Did Our Homework. And Then Some.

Before we left, Dan and I watched hours, and I mean hours, of videos.

Hotels. Cities. Restaurants. Things we had to see. Foods we had to try.

We researched and planned and watched other people experience Italy from our couch.

I am an overthinker.

This should surprise absolutely no one. 😂

So naturally, I wanted to know ALL THE THINGS before we went.

And then suddenly, there were no more videos to watch.

We landed in Rome.

I wish I could tell you there was this giant cinematic moment when I stepped off the plane, threw my arms into the air and announced, “I HAVE ARRIVED IN ITALY!”

There wasn’t.

Also, I was probably tired and wondering where my luggage was.

The realization happened more gradually.

We started walking. Exploring. Taking everything in. We hopped on a golf cart tour and started seeing Rome up close.

And every single thing seemed more incredible than the thing before it.

The architecture.

The history.

The realization that some of the things we were looking at had been standing there for longer than my brain could really comprehend.

And somewhere along the way, it hit me:

Holy crap. We’re in Italy.

Not watching a video about it.

Not planning it.

Not dreaming about it.

We were actually there.

And yes, Snoopy was there too.

Because apparently I am incapable of crossing an international border without a small black-and-white dog in my purse. 😂

But that is another story.

Planes, Trains & Automobiles — Italian Edition

Over the next 16 days, Italy became our own version of Planes, Trains and Automobiles.

We started in Rome, took the train to Sorrento, made our way to Positano, visited Capri, traveled to Puglia and eventually returned to Rome.

Our friends Joy and Todd traveled with us and joined us for our tours and plenty of adventures along the way.

But Dan and I had spent months dreaming about and researching this trip, and we also made sure there was time for just the two of us.

Time to wander.

Time to explore.

Time to occasionally abandon whatever plan we thought we had.

Which, for someone who just admitted to being an overthinker, may have been the most surprising part of the entire trip. 😂

And every stop gave us something completely different.

Positano looked like someone created a postcard and then somehow allowed us to walk around inside it.

Capri was gorgeous and just the right amount of bougie.

I was not mad about it. 😂

Rome had an energy all its own—ancient history sitting right alongside the hustle and bustle of a modern city.

And then there was Puglia.

Sometimes the Little Places Become the Big Memories

Dan’s family comes from the Puglia region, so there was something special about simply being there.

We weren’t tracing a family tree or knocking on doors asking if anyone recognized the family name. 😂

It was quieter than that.

It was knowing that this was the part of Italy his family came from and getting to experience a little piece of it ourselves.

We stayed in Monopoli, this adorable little coastal town on the Adriatic.

And yes, I now know it is on the Adriatic.

Geography may not be my strongest subject. 😂

Monopoli was filled with shops, restaurants and tiny stores selling meats and wines.

And then we found our pizza place.

You know how sometimes you find a restaurant while traveling and immediately decide there is absolutely no reason to continue exploring other options?

That happened.

We went back every day.

Pizza and a bottle of wine if the timing called for it.

Pizza and spritzes if that seemed more appropriate.

Although Italy has a very generous definition of when wine or a spritz is appropriate.

And I respect that.

Deeply. 😂

One night, Dan and I also found this little mom-and-pop restaurant for dinner.

Nothing flashy.

Nothing that felt designed for tourists or Instagram.

We could hear the kitchen crew talking and working in the background while we ate.

We ordered two appetizers, two incredible entrées and a bottle of wine.

When the check came?

About €62. With tip.

We looked at each other.

Looked at the bill.

Looked at each other again.

Are we reading this correctly?

The same dinner back home could easily have been $300.

And we probably wouldn’t have gotten the free entertainment of listening to an actual Italian kitchen crew working in the background.

It was simple.

It was delicious.

It felt real.

And it was one of those moments that doesn’t sound monumental when you describe it.

But those are exactly the moments I remember.

We Should Probably Discuss the Food

Being so close to the water meant seafood was everywhere—and incredibly fresh.

Somewhere along the way, spaghetti with clams became one of our favorites.

We ordered it once.

Loved it.

Found it somewhere else.

Ordered it again.

And again.

Apparently, this is how culinary traditions are born. 😂

Pizza became less of a meal and more of a travel strategy.

There was pasta.

There was seafood.

There were spritzes.

There was pizza.

And more pizza.

I would love to tell you I came home tired of Italian food.

I did not.

And, of course, there was wine.

So. Much. Wine.

About That Wine… 🍷

I haven’t always been a wine person.

Actually, before Dan, I was very much a sweet-wine girl.

Then I met Dan.

He introduced me to Sauvignon Blanc.

Apparently, Sauvignon Blanc was my gateway wine. 😂

Slowly, my tastes started changing.

And Italy took that to an entirely different level.

In Puglia, we drank Primitivo—one of Dan’s favorites—and throughout the trip I found myself trying wines I never would have ordered years ago.

Primitivo.

Amarone.

Reds that sweet-wine Wendi would have politely pushed aside while looking for something considerably sweeter.

My taste buds had changed.

And apparently this transformation required documentation.

Because Dan took all of our wine pictures and re-saved them into their own folder.

The folder is literally called:

“Wines We Drank.”

Not Italy Wine.

Not Favorite Wines.

Not even Wine.

Wines. We. Drank.

😂🍷

And, to be fair, there was actually a purpose behind this highly sophisticated archival system.

Once we were home, we wanted to be able to find those exact wines, or at least wines close to what we had tasted in Italy. Some of those bottles and grapes aren’t exactly sitting on every shelf back home.

So we photographed them.

Saved them.

Organized them.

Apparently our souvenirs needed a filing system.

And maybe that says something.

Because the wine wasn’t the only piece of Italy we tried to bring home with us.

There were bottles purchased from some of the wineries we visited. There were boxes of ceramics that slowly made their way across the ocean and have finally arrived. There’s now a bowl filled with ceramic lemons sitting on our kitchen table. 🍋

We’ve tried recreating some of our favorite dishes.

And we’ve embraced aperitivo time – which, frankly, did not require a lot of convincing. 😂

Little by little, we’re even creating our own Italian-villa-inspired backyard and pool oasis.

Apparently, we really weren’t ready to leave all of Italy in Italy.

But that might be another story…

So… What Was My Favorite?

Since we’ve been home, Dan has asked me what my favorite part of Italy was.

I don’t think that’s a fair question.

Positano was breathtakingly picturesque.

Capri had that bougie energy that I absolutely appreciated.

Puglia gave us a connection to Dan’s family, wonderful food and some of those tiny moments that somehow became some of my favorite memories.

And Rome?

I could go back tomorrow for a long weekend.

The food.

The architecture.

The hustle and bustle.

The history.

And the shopping.

Ohhhhhhhhh, the shopping. 🛍️😂

Let’s just say Rome and I have some unfinished business.

But if I have to choose one place?

Sorrento.

Sorrento 🍋

There was something about Sorrento that felt different to me.

It was calm.

Peaceful.

We could stroll everywhere without feeling like we needed to rush to whatever came next.

There was the water on one side and the mountains surrounding us.

The people were friendly and welcoming.

And there were lemons everywhere.

Seriously.

So. Many. Lemons. 🍋

Big lemons. Little lemons. Lemon decorations. Bright yellow tucked into seemingly every corner.

Sorrento was breathtaking without trying to be.

And relaxing in a way I don’t think I realized I needed.

Which brings me back to that whole overthinking thing.

Maybe That’s What I Miss Most

When I think about coming home from Italy, of course I miss the food.

I miss the wine.

I miss the views.

I miss the history.

I miss the little streets and the bright yellow lemons.

And I definitely miss the completely reasonable Italian philosophy that a spritz in the middle of the afternoon requires no explanation whatsoever.

But when I really think about it, I’m not sure any of those things are what I miss most.

I miss not necessarily having an agenda.

Which is probably a strange thing for an overthinker to admit.

At home, there’s always something.

Work.

Calendars.

Appointments.

Plans.

Places to be.

Things that need to get done.

In Italy, there was room to just… go.

Walk down a street because it looked interesting.

Stop because we were hungry.

Sit a little longer because the wine was good.

Order another spritz because… Italy.

Change the plan.

Make a new plan.

Or don’t have a plan at all.

And do all of it with my person.

For 16 days, I got to loosen my grip on the agenda and just go with the flow.

Maybe that’s why Sorrento stuck with me.

Maybe that’s why reading through these memories makes me want to get on a plane right now.

And maybe that’s why we’re already talking about going back.

The question in our house isn’t really:

“Will we go back?”

It’s:

“When?”

And for the record, Snoopy votes now.

❤️🍋