A More Than Two-Week Italy Itinerary

Everywhere we visited in just over two weeks in Italy

Ponte Vecchio

Before I share more of the details of what we did in each of the cities and villages we visited in Italy, I thought I would post a detail of our itinerary. As I write about each of the places, I will link from this article back to the post about the particular city or village (and will add links as additional posts are shared).

For the record, though, you should know that we did not establish this itinerary fully before we left. We left a lot of room to shift and make changes along the way. For example, we didn’t decide to book a train to Venice until the night before. And we didn’t book a place to stay in Perugia until we were two days out from driving there. The reason for this was that we thought we might want more time in Tuscany. And we did wish to explore Tuscany further, but we decided our desire to visit Perugia/Umbria was stronger.

You should also know a few other points, just in case you’re planning your own trip to Italy.

• This itinerary is not for everyone. Everyone should decide how busy or laid back of a trip they want before they start planning. The intention with this itinerary was to see as much of certain regions of Italy as we could in the time we had but at a reasonable pace, relatively speaking. We fit a lot in!

• We will never travel this exact itinerary again. But it was perfect for our goals of this trip.

• Mike and I walk a lot normally. (And I mean A LOT!) So we did not shy away from an itinerary that would require a good amount of walking. This factored in to the decisions we made on where to stay and other logistical decisions.

• We were gone just two days shy of three weeks. Many people have asked us: was three weeks too long? For us, it wasn’t. We had travel days on either side, plus we spent a day in London on the way back. In total, we spent 16 nights in Italy and 2 nights in London, England. We traveled a total of 20 days.

• This point will probably prompt you to ask me a lot of questions, and feel free to do that in the comments below, but… We each traveled with only a carryon and a personal item. We did not check a larger suitcase.

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Day 1 and 2: Bologna

We spent three nights in Bologna and enjoyed three mornings of cappuccinos and cornetti, but we only spent one full day exploring this incredible city of porticoes.

Be sure to read how much we enjoyed Bologna.

Italy: A Mini-Pilgrimage Through the Porticoes of Bologna

Day 3: Venice

After a quick breakfast at our new favorite bakery in Bologna, we walked to the train station and hopped on a high-speed train to Venice. There, we explored the canals, wandered the crowded streets, enjoyed fabulous seafood for lunch, and took a water bus to Murano to explore the glass factories.

Check out what we liked and didn’t like about Venice.

Unpopular Opinion: Venice Was Not My Favorite

Days 4 through 7: Florence

We checked out of our AirBNB in Bologna on day 4, and after another perfect cappuccino in Bologna, we headed back to the train station to catch another high-speed train. This time, we took a 35 minute train to Florence and made our way to another AirBNB where we spent four nights across the river (only a short walk) from the center of Florence.

Cathedral of Santa Maria del Fiore

Florence was filled with beautiful art, architecture, churches and cathedrals, and food and wine.

More links are coming, but read all about our favorite places to eat and drink.

Florence, Italy: What and Where We Ate

Day 8: Montalcino and Montepulciano

Montalcino

On day 8, we took a bus to the Florence airport and rented a car. At first, navigating the busy streets around the airport by car was challenging, but as we made our way south, the roads became less busy and the landscape quickly became filled with the cypress trees, grape vines, and olive trees Tuscany is well-known for. We navigated the hills, passed by a number of walled cities, and eventually made our way to Montalcino for lunch and a wine tasting. (Article coming soon about how much we enjoyed this city (and their wine) up on a hill, protected by a fortress.)

After lunch and a wine tasting, we drove to Montepulciano where we enjoyed a tour of the wine cellar in the middle of this medieval town. We stayed in Montepulciano for two nights, including my birthday.

Day 9: Montepulciano and Cortona

Let me count the ways I loved Montepulciano and Cortona. Spoiler: the article coming will tell you how I plan to return to this area of Italy as often as possible.

Days 10 through 12: Perugia (with a stop in Umbertide) and a side trip to Assisi

Perugia, Umbria

We left Montepulciano on day 10, drove through areas of Tuscany again, passed by Cortona with a longing to revisit, and continued into Umbria. After lunch in Umbertide, we continued to Perugia, where we spent nearly two days relaxing and getting to know this lovely city and part of a day visitng Assisi. (Spoiler: we almost destroyed our rental car navigating Perugia. Full story coming soon.)

Day 13: In transition

Ugh! We attempted to make our way to Sicily on day 13, which happened to be Halloween. We ended up in Rome, sort of, which was NOT on the original itinerary.

Days 14 through 16: Sicily

View from AirBNB looking toward Cefalù

Oh, Sicily. I can’t wait to tell you about this lovely island and the lovely spots of Cefalù, Termini Immerse, and Trabia. I’ll also explain why we skipped a visit to Palermo.

Day 17: In transition

Telling you about Italy would not be complete without explaining some of the frustrations of traveling to and from some of these lovely places.

But we also enjoyed some happy accidents, like the lunch we had in a small town near the Florence airport. We ate inside a family-owned and family-run restaurant where no one spoke English, and it turned into one of our favorite experiences and the best homemade pasta I think we had the entire trip. More to come when I post about this day.

Day 18 and 19: London and then home

London was a blast! With only a day and a half to spend in London, we made the best of it, and we have a camera roll of selfies to prove it.

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I will come back and fill this post with links as I finish additional articles about our travels through Italy. For now, I thought you might enjoy the full itinerary of what’s to come.

I hope you’ll comment below and let me know what you’re enjoying about our adventures in Italy. Feel free to drop questions in the comments if you want me to cover anything about our trip.

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