Having only visited Italy for a short three days along the Amalfi Coast, I was extremely excited to come back for a more in-depth trip. My husband and I both agreed that we wanted a mixture of experiences during our 12 night Italy itinerary.
There’s so many questions about Italy so I wanted to take the time to write out our Italy Itinerary.  For our first time together, we decided to stay north and on the coast, skipping Rome, Amalfi, Milan for this trip. Italy is an incredibly easy country to travel through — renting and driving a car is rather relaxed for international driving, the trains are simple to use, and everywhere you go is picturesque.
Planning our itinerary, we chose to start our time in Tuscany where we had freedom to explore and have day trips. Afterwards, Florence made sense as we needed to drop the car off, so we headed into town for a few nights afterwards. Cinque Terre called our names after seeing the beautiful coastline, and we couldn’t get enough of sunbathing and the Mediterranean Sea. The final destination was tough to choose, but ultimately we went with Venice for a few reasons, the biggest being that the city is sinking. We came back from the trip feeling relaxed and loved every destination on our Italy itinerary.
(This post was first published on October 10, 2016 and has been updated on January 30th, 2019)

The First-Timer’s 12 Night Italy Itinerary

The First-Timer's 12 Night Italy Itinerary

Good To Know Before Traveling To Italy

  • Train travel in Italy is wonderful. I always recommend arriving a little early to the train station.
  • Renting a car gets you access to off-the-beaten path places, so I would encourage it for the first trip.
  • English is widely spoken, so do not worry about any language barrier!
  • Italian food is not a thing — each region has its own cuisine. For instance in Tuscany, the region is known for favorites like boar tagliatelle. Try new foods, and you’ll be wonderfully surprised!
  • Credit or cash? Both are important and many places accept credit. However, cash always wins, so be prepared to use it more frequently.
  • Taxis — before getting in, ask the price. In most places, the fares are set between airports and town centers.
Best time of year to visit Italy:Most travel guides would encourage the best of weather and the least amount of crowds. Somewhere in later September or early May is a great option. With that said, each season has its own magic.

12 Nights: Tuscany – Florence – Cinque Terre – Venice

Day 1: Land In Florence, Head To San Gimignano

Rent a car and make the short hour-and-a-half drive into Tuscany. San Gimignano is a great place to spend an afternoon, and couldn’t be a more beautiful place to begin your journey in Italy.
Read: What and Where Guide to San Gimignano.
Stay: The Villasanpaolo Spa Hotel Review or Book Here.
The First-Timer's 12 Night Italy Itinerary

Day 2: San Gimignano

If you felt like you didn’t spend enough time in San Gimignano, head into town early before the crowds and enjoy having the town all to yourself. From here, I would spend the day road tripping through Chianti. The iconic region is full of great towns and wineries to explore.
Read: One Day Road Trip Guide to Chianti. (A great day itinerary).
The First-Timer's 12 Night Italy Itinerary

Day 3: Siena

As you check out, pick out a few towns to stop along your way down south. Siena is a lovely place to stop off at to explore the square, and have a lunch. Arrive to your next hotel, where you can base yourself in the southern part of Tuscany.
Stay: Castello Di Casole
The First-Timer's 12 Night Italy Itinerary

Day 4: Siena, Exploring Val D’Orcia

We took a whole day to explore the Val d’Orcia region, through the hilltop towns of Montalcino, Pienza, and Montalpuciano.
Read: Mini Road Trip Guide to Siena. (The perfect day trip!)
The First-Timer's 12 Night Italy Itinerary
The First-Timer's 12 Night Italy Itinerary

Day 5: Head To Florence

As your final day comes to an end, the journey back to Florence is just as breathtaking. We arrived into town around 2, after checking into our hotel. The afternoon was amazing for our first Florence day to exploring the the iconic sights.
Read: A Weekend Guide to Florence.
Stay: The Hotel Bernini Palace.
The First-Timer's 12 Night Italy Itinerary
The First-Timer's 12 Night Italy Itinerary

Day 6: Exploring Florence

Wake up early to get the most of your day and to beat the crowds. I couldn’t recommend more doing an early-access tour of the Duomo and seeing David with a skip-the-line pass. A dinner in town, and sunset along the Ponte Vecchio is a must.
The First-Timer's 12 Night Italy Itinerary

Day 7: Head To Cinque Terre

The train ride into Cinque Terre is easy, with a normal stop in Pisa, you arrive in a short two and a half hours. Staying in Riomaggiore is a gem, and we loved having an afternoon to explore our base for the time in Cinque.
Read: The Nutshell Guide to Cinque Terre. / Where to Eat in Cinque Terre by Village
Stay: An Airbnb works beautiful in town, one with good reviews and you’re set. Use this link to sign up and get $40 off your first stay
The First-Timer's 12 Night Italy Itinerary
The First-Timer's 12 Night Italy Itinerary

Day 8: Cinque Terre

Waking up early to head to Vernazza and walking the trail to Monterosso was beautiful. It took around two hours to do, and the views were worth it. You can have lunch in Monterosso, and then take the train back to Riomaggiore. We went back into Corniglia to watch the sunset, and ended up having dinner in town.
The First-Timer's 12 Night Italy Itinerary

Day 9: Cinque Terre

One more day to soak in the sun and take a dip in the sea. This is a great coastline to pick a spot on a rock, and set up shop for an afternoon of swimming and sunbathing. In Riomaggiore, we found a great spot around the corner from the ferry, a few hundred yards south of the main harbor, where it was quieter. Our last night we had dinner in Manarola at Trattoria dal Billy, which was our best meal in the area.
The First-Timer's 12 Night Italy Itinerary

Day 10: Head To Venice

Wake up and take the train to Venice! The journey does take a bit, with transfers in Pisa and Florence, but in four hours time you’ll find yourself in one of the most magical places in the world. The afternoon was well spent getting oriented and exploring the seemingly endless canals. Our first Venice day felt like an absolute dream and was so happy we booked more than one day here.
Read: A Weekend Guide to Venice, Italy.
Stay: Hotel Metropole Venice.
The First-Timer's 12 Night Italy Itinerary

Day 11: Venice

You can easily spend a full day exploring Venice and still feel like you didn’t see it all. There’s much to do and see.
The First-Timer's 12 Night Italy Itinerary

Day 12: Venice

The final day, we ended up sleeping in, but originally had planned to go to Burano and Murano. These are amazing day trips and will be doing it next time we go!
The First-Timer's 12 Night Italy Itinerary

Day 13: Fly Home

Ciao Italia! Hope you enjoyed this Italy Itinerary and if you have any other questions, feel free to comment below!

Other Destinations To Add:

  • Lake Garda
  • Milan
  • Rome
  • Lake Como