Italy: Itinerary Ideas 10-14 Days

Italy is a big tourist hot spot in the global travel circuit, and I completely understand why! Fascinating architecture, a colorful history, and some of the world’s best food are just a few reasons why people are continually drawn to Italy!

After spending sixteen days in Italy with my family, and coming back to the country three more times after that, I feel like I can safely say this is a quality itinerary! This schedule has the perfect combination of iconic Italy, while also offering authentic experiences.



Take a look at my map below:



DAY 1- MILAN

You might not think it, but Milan has the most populated metro area in all Italy. It’s all about shopping and fashion, and not as much of the “historical” or “classical” Italy you might envision. My personal opinion on it wasn’t the best, but then again many people love Milan! If you want to skip a city though and add more time elsewhere- this is the one I’d axe.
With just one day, first check out the Duomo di Milano (and walk on its rooftop!) and the piazza in front. Nearby, check out the now “Instagram famous” Galleria Vittorio Emanuele II for some scenic shopping! It looks like a grand museum, but it’s actually just a super elegant mall. Nearby, you can also visit the Castello Sforzesco, and a handful of museums. If you’re an art lover, you can also see the famed “Last Supper” painting by Leonardo da Vinci at the Santa Maria delle Grazie Monastery.
Lodging: Hotel Teco Milano

DAY 2- VENICE

Early in the morning, take the train from Milan to Venice. This will take about 4.5 hours total, and you’ll arrive to the city on the water! 
Venice is magical, one of a kind, and its gondolas are a true icon of Italy. It’s also a place that many have a “love-hate” relationship with. Increased tourism (largely thanks to the mass amount of cruise ships) has made the city almost unbearably crowded in the summer, so have your patience and your wits about you! If you want to take good photos, getting up early is key!
On our first day, explore the beautiful canal filled streets. Stop of course at the  Rialto Bridge, and maybe the Chiesa di San Barnaba (the church from the Indiana Jones movie!). Afterwards, go up to the Campanile di San Marco for views of the famous city below! 
Next, hop over to St. Mark’s Basilica, and then spend time enjoying the beautiful chaos that is St. Mark’s Square. If you enjoy feeding pigeons, this place is for you! If you are up to it, you can beat the heat by visiting the Doge’s Palace. This was one of my favorite things in the city, and it’s well worth the entry fee. It also gives you the chance to walk through the famous “Bridge of Sighs”.
bridge of sighs, venice, doge's palace
The “Bridge of Sighs”
Lodging: Hotel Villa Igea

DAY 3- VENICE

On your second day, take a “Grand Canal” cruise of Murano, Burano, and Torcello. You can escape the crowds of the city, and see some truly beautiful places. Make sure to save money for some famous hand-blown glass from Murano! 
When you get back to the city, take a gondola ride through the canals. My suggestion is to do one in the evening, as you can save money and enjoy a more quiet and romantic experience.murano, venice, italy, colorful
Lodging: Corte del Paradiso Venezia

DAY 4- CINQUE TERRE 

Very early in the morning (I’m talking 5am), head back to the train station for a 5 hour ride from Venice to Levanto. To visit the famous 5 cities that constitute “Cinque Terre”, this is a good base to have, and it’s gorgeous too!
levanto, italy
Levanto, Italy
Once you’re settled, navigating the transit system to get to each of the five cities in one day is relatively easy. Take a short 20 minute train to Monterosso (or the ferry, weather permitting), and go from there! After Monterosso, you can either hike (about 2 hours) to Vernazza, or take a quick train or ferry. From there you can hike to Corniglia, then on to Manarola, and end in Riomaggiore. Once you’re ready, take the train back to Levanto for the night. If you have additional time- adding an extra here is a great idea. The Levanto bike trail is one of the most scenic in the world, and is highly recommended!!
Lodging: Link for hotels in Levanto

DAY 5- PISA + LUCCA + FLORENCE

Head back to your new favorite place, the train station! From here, you will head to the town of Pisa! You only need about an hour there to see the famous leaning tower, and then on to the small town of Lucca. In Lucca, check out the main plaza, and then rent a bike for the afternoon. When you’re ready, hop on the train again to Florence!pisa, italy, florence
Florence is chock full of things to do and see. In general though, on your first day you can:
duomo, firenze, cathedral, florence, italy
Il Duomo di Firenze (Florence Cathedral)
ponte vecchio, florence, firenze, italy
Ponte Vecchio (Old Bridge)
Florence, Duomo, Italy
Lodging: List of hotels in Florence

DAY 6- FLORENCE

Exploring on foot and happening upon unexpected sites is probably the best part about traveling through Italy, but once you’ve had a chance to eat some world-class meals, here is what you can do on your second day:
piazzale michelangelo
View from the Piazzale Michelangelo
Lodging: List of hotels in Florence

DAY 7- FLORENCE (Tuscany: San Gimignano, Monteriggioni, Siena)

There are of course countless companies running day trip tours to Tuscany leaving from Florence, so it can be hard to pick. Do your research, and you will find what you want! When I visited, my family had a driver take us to the small medieval towns of San Gimignano and Monteriggioni first.
In the afternoon, we headed to Siena. We had lunch, gelato, and got to admire the church and the main square. On the way back towards Florence, we stopped at  Fattoria La Tancia, a local vineyard. There we had a private wine tasting and olive oil tour. This was probably one of the most fun days we had (the wine possibly contributed to this!) and we bought a few things for them to ship home. Make sure you try some grappa too! In the evening, we headed back to Florence.
Lodging: List of hotels in Florence

DAY 8- ASSISI

The train ride to Assisi takes about 3.5 hours, and if you are a practicing Catholic, I especially recommend visiting this city! Assisi is of course the home of the famous animal-loving Saint Francis. Visiting the Basilica in his name is the main reason to visit, but the surrounding countryside views are incredible too!Assisi, St. Francis Cathedral, Italy
Assisi, Italy, Perugia
This city is a little less touristy-feeling than others in Italy, and you can get some really quality food here while learning about the 13th century saint’s life and legacy.
Lodging: Link to hotels in Assisi

DAY 9 – SORRENTO + AMALFI COAST

This is a long travel day! Start day by taking the 5.5 hour train from Assisi to Sorrento. Once you settle in, explore this quaint and scenic town! Walk around anywhere and you will see beautiful views (especially at sunset!)
Sorrento, Sunset, Italy
A Sorrento sunset
Sorrento, Vesuvius, Sunset
Mt. Vesuvius – as seen from the hotel window!
If you want to maximize your time, take a driving tour of the Amalfi coast! It is honestly one of the most absolutely scenic drives you can ever have in your life. If you can, stop over in the towns of Ravello and Amalfi! You can rent a car and do it on your own, or check out these affordable organized tours.
ravello, amalfi coast, italy
View from Ravello
Lodging: Imperial Hotel Tramontano

DAY 10 – SORRENTO (Capri)

From Sorrento, take a short public ferry out to the island of Capri. Famous for massive yachts and celebrity visits, it’s also where the ancient legend of the Sirens originated. It has so much beauty, but also a fascinating history.
capri
Capri Town

View of Faraglioni from Monte Solare

There is enough to do in Capri for a week, but with one day I’d recommend picking 1 or 2 of the following:
  • Visiting Anacapri, and riding the chairlift to Monte Solaro
  • Swimming in one of the private beach clubs
  • Taking a boat tour around the island, and seeing the Faraglioni rocks
  • Swimming in the eerie and one-of-a-kind Grotta Azzurra (blue grotto)
It’s very doable on your own, but if you prefer to have a guide there are some reasonable options for day tours here!
Lodging: Imperial Hotel Tramontano

 DAY 11 – SORRENTO (Positano)

Relax by the beach, or explore more of Sorrento’s small town. Known for its limoncello, it is all too easy to do!
Alternatively, you can do what I did! We rented a car and headed to the town of Positano for the day. Incredibly beautiful, you can roam around on foot for the whole day and be perfectly content!
Lodging: Imperial Hotel Tramontano

DAY 12- SORRENTO (POMPEII)

Today it’s finally time to learn about the dark side of that volcano you’ve been looking at all week! Visiting the archaeological site of ancient Pompeii is also one of the most memorable things you can do in central Italy. 
In 79AD, the still-active volcano of Mount Vesuvius erupted, burying the small city below in a thick blanket of ash. Since the poor townspeople didn’t quite understand what was happening, nearly 2,000 died. The city was abandoned, and lost to history. It was accidently “re discovered” in 1748 , and is now a fascinating place to visit. While a bit sad, and even creepy, it is remarkable to see the plaster “body casts” of the unfortunate victims and the poses they were in at the moment of their death.
It’s possible to arrange this on your own, but there are also many organized day trips. The site is large and has little signage, so I really recommend getting a guide at least while you’re there. Otherwise, you will miss out on so much information and context, and won’t really appreciate what you’re looking at.
All roads lead to Rome, so take the 2 hour train that evening, and off you go!
Lodging: Luxury Apartment Campo de Fiori

DAY 13- ROME + VATICAN CITY

I’ve had the privilege of visiting Rome on three separate occasions, and I’m still not tired of it. There is so much to do and see that it’s hard to chop it down to two days! However, in a nutshell, here’s what I’d suggest:
pantheon, rome
Outside the Pantheon
st peters basilica, vatican, rome
View of St. Peter’s Basilica
If you’re interested in spending more time in the Vatican, check out this list of organized tours here!
Lodging: Luxury Apartment Campo de Fiori

DAY 14- ROME

On your last day in Rome, make sure to knock out these bucket list items:colloseum, rome, italy
roman forum
Il Foro Romano (Roman Forum)
If you can’t decide, there is a huge lineup of guided day trips and sightseeing options on my Viator page. You could also rent a Vespa scooter if you’re feeling brave. When in Rome….
Lodging: Luxury Apartment Campo de Fiori

Save these images to help you plan!


Pin this for later!


As always, all reviews and opinions are my own. However, should you choose to book any of the hotels or activities linked above, please know I will receive a small commission. 

1 Comment

  • Reply Keeper Landwey August 8, 2019 at 3:17 am

    Wow, some really great places.

    I especially love the CINQUE TERRE and that Anacapri. Looks so beautiful.

  • Leave a Reply