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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

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The First-Timer's 12 Night Italy Itinerary


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I use Viator or Get Your Guide to find the best tours and experiences. They are my favorite tour search engines. I always check both as their inventory varies depending on the destination.

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  1. This was so fun to see! I love the picture and the food! The closest I have been to Italy is Las Vegas,…yeah so thanks for posting this. I mean yes I have read about it but…

  2. Great trip, it’s a shame travel is such an expensive pastime, I love driving in Europe.

  3. Thank you for the info. We are headed there this month on a cruise. Wondering if you would have any ideas on what to pack for the weather for Feb-Mar. Also, as far as money, you said credit cards and cash. Cash, as in, euros or American dollars?

    • Jessica Wright Reply

      You will definitely want to have some warmer layers, it’s quite cold in the winter. You’ll want to have local currency (euros), I would recommend pulling out of an ATM on arrival. Airport exchange is always the most expensive.

  4. I’ve been to Italy a few times and Lake Garda has been my favourite place to visit. I’d love to visit Venice and Florence too one day. This is a great itinerary and I agree that renting cars is great in Italy.

    Emily | Snippets of Emilys Life xx

  5. Seven years ago my daughter and I wanted to do a “girl’s trip” We considered many locations; Savannah, GA, Seattle, San Diego, etc. but then I heard about a 10 day “group tour” of northern Italy. While this was not something I would have ever considered, it occurred to me I would never get to share the trip with my daughter any other way. One consideration about this trip was the timing, February. Granted, there would be no tourist but it might be chilly. We bought down jackets and made our reservations.

    We flew into Milan. It had not snowed in 20 years and yet that day our flight was the last to land before the airport closed. This was not at all what we planned for but what an adventure. From Milan we toured Parma to see cheese being made, Modina to see how balsamic vinegar is aged, stopping at the Enzo Ferrari Museum which was fascinating, then to Bologna where I ate the best Bolognese sauce of my life, over to Lucca which is an ancient walled city with a tiny restaurant serving carbonara like I’d never tasted before, then up the coast to Cinque Terre which looked exactly like I had seen it in pictures and it did not disappoint, then to Turin to see the Shroud of Turin. Did I mention that every day from the moment we landed, it was like being inside a snow globe and everything was breathtakingly gorgeous covered in snow. I am sure it is all more beautiful in the spring and summer but this left me speechless.

    I say all of this to encourage anyone who might think they can’t travel alone or have never considered a “tour” to give it a try. My entire experience was wonderful. I have traveled many places; Madrid, Paris, Amsterdam, Belgium, even Monte Carlo but this trip was more than I could have ever dreamed. I would not take for the time shared with my daughter in a country that could not have surprised me or fascinated me more.

  6. John Gallup Reply

    Hi Jessica,

    Thank you for this wonderful blog! I have learned so much that has helped plan our trip to Italy and Switzerland this fall, from Sept 22- Oct. 17, followed up with a cruise from Venice to Athens.

    Thought you might be interested in our itinerary, all self-planned with your help. Arriving Venice, renting car for drive to Siusi, three nights with day trips to Alpe di Siusi and Ortisei (Seceda). Drive to Vale di Funes for photos, then to Lago di Braies for one night. Back to Venice and fly to Zurich, then train to Lauterbrunnen. Two nights at Hotel Staubbach then three nights in Murren. One night in Lucerne on the way to three nights in Varenna on Lake Como. Then off to Monterosso for three nights exploring the Cinque Terre. Stop in Pisa on the way to Greve in Chianti for five nights in an agriturismo/winery. Finally, a few days in Florence and then Venice.

    Again, thanks for all your great tips and photos. They have really helped me put this epic trip together.


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