For the decade or so, my wife and I have wanted to visit Italy.  She went a handful of times as a child, and I had never been.  To celebrate our 15-year anniversary, we booked an 8-day trip.  To her credit, my wife did 95% of the planning and absolutely nailed it.  Here’s what we enjoyed the most along the way.  Hopefully, it’ll help you out for your future trip planning:

Eating. All of It. 

My number one goal for the trip: soak in the sensational food.  We made reservations at two restaurants along the way after doing some research.  However, we had the most fun (and success) walking the streets and picking out places that caught our eye. Let’s be honest: it’s all good. Most of the restaurants we came across were local and had been around for decades.

While I had my fair share of meat and pizza, I’d highly suggest pasta dishes.  You’ll find decent main courses and pizza pies in other countries, but it’s hard to replicate the pasta and sauces.

The two places we made reservations were La Giosta in Florence and Antica Pesa in Rome.  While we expected to break the bank at these spots, they proved to cost about as much as any other place we dined.  I’d recommend both!

Splurging on a Food Tour

By now, you likely understand I’m a big fan of food — which is why one of my favorite things to do was a walking food tour in Florence.  Our guide did a fantastic job letting us sample a wide variety of foods that were regional specialties.  There’s no way to try everything on your own, so small portions packed into a 3-hour walk certainly helps to diversify your eating options.

Our tour cost us about $75 per person — which is quite a bit more than the average price we paid for a meal.  However, it was well worth it.

We stayed at a spot just feet away from where the tour started.  More on that below.

Getting Lost in the History

On our first day in Rome, we visited a few of the top tourist spots — which were absolutely packed with people.  After working our way through the crowds while also trying to read signs and soak in the experience, we decided it might be more beneficial to visit the Coliseum and Roman ruins with a tour guide.  Again, it’s well worth the additional investment. The tour guide helps bring the buildings to life and paint a picture of how things have changed over the last 2,200 years.

We happened to stay at an Airbnb in Florence that had Netflix.  While it’s not the greatest series in the world, Roman Empire certainly helped showcase what life was like in ancient Rome.  It was enjoyable to watch right after seeing the sights.

BTW — the place in Florence was pretty sweet.  If you don’t mind some steep stairs, staying in a Medieval Tower in the middle of town is a memorable experience.  Feel free to check it out.

Visiting Smaller Towns

After navigating two tourist towns, some of the most fun we had was in the smaller towns of Verona and Trent.  Each town has beautiful architecture, centuries of history and spectacular food — minus the throngs of people.

In Verona, we came across an ancient arena that will be used during the closing ceremony for the 2026 Winter Olympics.  We stayed at Lady Capulet Apartments, a beautiful boutique hotel in the middle of a neighborhood that was just a 10-minute walk from anywhere you’d want to visit in town.

While visiting Trent, we took in the sights while doing our souvenir shopping.  It proved to be a much more enjoyable experience in Trent instead of Rome — and the views were fantastic!

Walking through Venice

We actually thought about skipping our daytrip to Venice, but the locals told us that would be a bad idea.  They were right!

This place looks like something out of a movie scene.  The waterways and buildings are absolutely beautiful.  While the food and shopping might cost you more than it would in other cities, it’s well worth your time — even if it’s just for a few hours.

At the suggestion of Rick Steves, we chose not to do a guided tour but just walk around and “get lost” on our own.

Hiking to the Sanctuary of Madonna della Corona

This was one of the last things we did on our trip.  This picturesque 17th century church is located between Trent and Milan.  It’s quite a hike to walk up (or walk down depending on where you park) but well worth the time.

After awhile, the churches in the major tourist towns all start to look the same.  This chapel truly stands out.

During the walk down, the stations of the cross are showcased as statues in scenes.  It makes the journey far more spiritual than you might expect — and was the most memorable part of the visit for me.

For a kid who grew up hearing about Italy and his Italian heritage, this trip was one I won’t soon forget.  The question isn’t if we’ll go back — but when? And where should we go when we return?

If you’re reading this, you’ve probably visited Italy before (or are about to).  I’d love to hear your suggestions to help us plan a future trip.  Email them over!