ITLY: Our 10 Day Italian Road Trip Itinerary

If you’re thinking of planning a trip to Italy, let me be the first person to tell you, “DO IT”!

Jake and I had an incredible time in Italy. We met amazing people, ate some of the best food I’ve ever had and saw beautiful sights.

I feel like I have so much I want to share with you, so I decided to make this ITLY series out of our experiences.

So, for the first installment of this series, I want to walk through our itinerary and why I chose the places we went to.

I do want to note because this was Jake’s first time ever out of the country we spent far less time in cities than some people would like. I didn’t want to overwhelm him with all a city can offer, so we gave ourselves just enough time to experience them.

We spent 10 fulls days exploring the Northern part of Italy (factor in 1-2 days for travel). Here’s a rough breakdown of our time, which I’ll go into more detail about further down:

Day 0: Travel

Day 1: Arrive in Venice

Day 2: Dolomites

Day 3: Dolomites

Day 4: Dolomites

Day 5: Florence

Day 6: Tuscany

Day 7: Tuscany

Day 8: Tuscany

Day 9: Tuscany

Day 10: San Marino

Day 11: Travel home

Day 0: Travel

Our flight left at 2:30 pm on a Friday afternoon, so I don’t really count this day in our itinerary because I still worked in the morning.

Day 1: Venice

We arrived in Venice around 9:15 am, so this was perfect to still get a full day in the city. *This is the point where you SHOULD NOT take a nap. Power through this day to get on a good sleeping schedule.* For us, 1 full day in Venice was the perfect amount of time. We saw all the sights we wanted to see and still had time to look around and find some really beautiful areas.

Plus, Venice is pretty magical at night! Staying in the city center for one night was most definitely worth it to wander around with a lot fewer people.

Day 2 - 4: Dolomites

After getting our rental car early on day 2, we were in for a 2.5-hour drive north into the mountains. We arrived early enough in the day that we still could go exploring (giving us 3 days rather than just 2).

The Dolomites had some of the most incredible views I’ve ever seen. This is truly a hiker’s paradise. But don’t worry, there are a million beautiful sights to be seen from the car as well. While you can access the Dolomites by public transport, in my opinion, renting a car is the way to go.

We stayed in the small town of Selva di Cadore which is just over the mountain (about 40 min via car) from where most people would make their home base, Cortina d’Ampezzo. We passed many hiking trails on our drive to Selva di Cadore, so you really can’t go wrong staying in the general area since even the drives offer spectacular views.

Day 5: Florence

Just an FYI, the drive from the mountains to Florence is a hefty one… over 4 hours to be more specific. An option could be to take a pit stop in Verona for one-day versus doing the whole drive at once… carry on.

There are a thousand things you can do in Florence and we didn’t get a chance to do most of them, but we did get a great taste of what the city is like. We stayed in the city center, which due to the short time we were in the city, I would definitely recommend.

Day 6 - 9: Tuscany

Soo we love wine. And Tuscany = wine country.

The great thing about having a car was we could choose the best area to stay for us. Personally, we love wine (give me a nice rose, and I’m good all day)., so we stayed in the heart of the Chianti hills knowing we would want to go to as many wineries as we could. But, we were still close enough to Florence, Siena, Pisa, or San Gimignano if we wanted to do a day trip to another city.

The possibilities in Tuscany are endless and it really is a perfect area for people who want to do many different things. Wineries, hiking, cities, it’s all within an hour’s drive!

Day 10: San Marino

Don't get San Marino mixed up with San Marzano tomatoes... totally different things.

I didn’t actually know until a couple of weeks before we got on the plane that San Marino is a small country within Italy. It’s not as crowded as other cities we went to, but the views from this small country are amazing and very doable to do in a day.

Day 11: Travel home

This is when we chose (or more likely didn’t have any vacation days left) to go home. If you have more time, I would recommend spending more time in the Dolomites or Tuscany, but you could also make a stop in Rome to add another major city to your itinerary!

I hope you have found this rough itinerary helpful! If given the choice to go back, we probably would have spent our last full day exploring more of Tuscany, but we still had a great time seeing the tiny country of San Marino!

Because we went at the beginning of October, this is a slower time for tourism in Italy. However, I still made sure to book things ahead of time just in case. While the fall is their rainy season, we had perfect weather every day we were there, so it’s really just a roll of the dice!

Feel free to use our itinerary as a jumping-off point for your own!

If you’ve been to Italy, what’s your go-to place?

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