Your Italian Itinerary

Planning a trip to Italy?  Then you need to read our Italian itinerary before booking a single thing. 

map of Italian itineraryA map of Italy showing a few of the destinations we cover on this page

The itinerary starts in Venice but you could easily adjust it and start in Rome. The 30 days is just a guideline and can be shortened or extended. Simply adjust the time in each place or leave something out. Click on the links for more information about each recommendation.

Our Tip

To really explore properly you need a car. If you don't have a car then leave out the smaller towns and focus on the big towns and cities, they can all be reached by train.

cars in Italy

Day 1 to Day 4

Venice Canal Scene

Our Italian itinerary starts in Venice. One tip before we start; postpone renting the car until after Venice - that will save you a bit of money as obviously a car won't be needed while in Venice.  Also, book your car before you leave home in order to get the best rates - this is the company we always use.

I'd suggest at least three nights in Venice as that will give you enough time to see the main sights and some of the less well known ones too. You'll love nights in Venice, once the sun set and the lights come on it really is a magical time:  far less crowded and the atmosphere is enchanting.

These are some of the restaurants to try in Venice and these are the hotels we like in Venice.

P.S. For personalized itinerary help click here.

Day 4 to Day 8

Italian Itinerary StopSirmione near Lake Garda

Venice is just the tip of the iceberg when it comes to the Veneto region, the region where Venice is located. Throughout the region you'll find quaint little villages, unforgettable scenery and much more - you could easily spend a month here.

Where to start? Well, our Veneto itinerary has all the best things to see in the Veneto and around Lake Garda so, pick the ones that appeal to you, and spend four nights/five days exploring - you'll find the itinerary here. 

Day 8 to 12

Milan CathedralMilan Cathedral

I highly recommend including a day trip to both Bergamo and Milan in your itinerary. These two cities offer a contrasting blend of medieval charm and cosmopolitan glamour, each with its own unique attractions.

Start your day in Bergamo, where the medieval old town perched on a hill will transport you back in time. Wander through its narrow cobblestone streets, marvel at the well-preserved architecture, and soak in the enchanting atmosphere. Don't miss the chance to explore the historic Piazza Vecchia, visit the magnificent Bergamo Cathedral, and take a leisurely stroll along the ancient city walls for panoramic views of the surrounding countryside. Bergamo's old town truly exudes a special and unforgettable charm.

In Milan, Italy's fashion and design capital, you'll find a vibrant blend of history, art, and modernity. Begin with a visit to the iconic Milan Cathedral, a masterpiece of Gothic architecture, and be sure to explore the exquisite interior. Nearby, the famous La Scala opera house beckons music enthusiasts to delve into its rich history and perhaps catch a world-class performance. Take a leisurely walk through the Galleria Vittorio Emanuele II, a stunning shopping arcade that epitomizes Milan's elegance and style. And no visit to Milan would be complete without experiencing Leonardo da Vinci's masterpiece, the Last Supper, housed in the Convent of Santa Maria delle Grazie.

In addition to its cultural and historical offerings, Milan boasts a reputation as a shopping mecca. From high-end fashion boutiques in the Quadrilatero della Moda to trendy concept stores in the Brera district, you'll find a plethora of options to satisfy your shopping desires - here is my Milan Shopping Guide to help you find those bargains.

With a day allocated to each city, you'll have ample time to soak up the distinct flavors of Bergamo and Milan. From the medieval charm of Bergamo's hilltop old town to the cosmopolitan allure of Milan's iconic landmarks, this dual-city experience promises a delightful blend of history, art, culture, and shopping that will leave you with unforgettable memories.


Next up is  Turin and the absolutely unmissable Piedmont

Turin was my old home town and it is absolutely amazing - one of Europe's greatest cities. Take a leisurely stroll along the elegant boulevards lined with beautiful architecture, and marvel at the grandeur of landmarks like the Mole Antonelliana, which houses the National Cinema Museum. Don't miss the chance to visit the iconic Turin Cathedral, home to the mysterious Shroud of Turin, and explore the regal Palazzo Reale with its opulent rooms and extensive art collection.

Spend sometime in the beautiful Langhe region of Piedmont where you'll find villages like Neive and some great countryside hotels too. Piedmont, is renowned for its exquisite culinary offerings and world-class wines. Indulge in the region's gastronomic delights, from the rich truffle-infused dishes to the velvety Barolo wines. Explore the picturesque countryside dotted with vineyards and castles, and perhaps embark on a wine tasting tour to savor the flavors of this renowned wine-producing region.

To see all that Piedmont offers have a look my 10 days in Piedmont Guide.


P.S. For personalized itinerary help click here

Langhe PiedmontA misty morning in the Langhe

Day 12 to Day 15

Base you yourself for three nights in Levanto, which is on the doorstep of the Cinque Terre and is the ideal base to explore. My Cinque Terre Guide explains why you should stay here rather than in one of the Cinque Terre villages. While here take a day trip to Portofino.

Day 15 to Day 17


Escape the bustling crowds of the Cinque Terre and venture towards the hidden gem of Tellaro, nestled along the picturesque Gulf of Poets. This charming town, often hailed as one of Italy's loveliest, exudes an irresistible allure yet remains delightfully undiscovered by international tourists. Here, you can immerse yourself in the authentic Italian coastal experience, with its quaint streets, colorful houses, and breathtaking sea views.

Tellaro's unspoiled beauty and tranquil atmosphere offer a respite from the more popular tourist destinations, allowing you to savor the genuine local charm. Stroll along the narrow lanes lined with vibrant flowers, soak up the sun on the beaches, or indulge in delicious seafood delicacies at the waterfront trattorias. As you explore the town, you'll feel a sense of tranquility and serenity, as if time stands still in this idyllic coastal haven.

What sets Tellaro apart is its authenticity and its ability to transport you back in time. You'll discover a slower pace of life here, where locals gather in the piazzas to chat, children play in the streets, and the salty breeze carries whispers of ancient maritime tales. It's a place where you can truly connect with the essence of Italian coastal living.

While the Cinque Terre may lure in the crowds, Tellaro's untouched beauty allows you to experience a more intimate and authentic side of Italy. Here's my essential guide to Tellaro to help you plan your visit.

Day 17 to Day 21

Florence at night

After that head off to Tuscany.

Include a night in Lucca or Siena (here's our city guide to Siena) or, better yet, extend your time and spend a few days in both of them, then a day in Pisa, followed by 3 nights in Florence. While in Florence, a day tour of the Tuscan winelands is a great idea. You can either do this yourself or take a tour. 

Personally, I'd add a few more days (at the very least) to explore the Tuscan countryside - explore by bike or on foot to really appreciate Tuscany. Not sure where to begin? Well, here's one of the walks I love.

Here are a few other towns you may wish to visit if you add an extra few day (better still a week) to your Tuscan vacation:

San Gimignano: Known as the "Town of Fine Towers," San Gimignano (click for more) is a medieval hilltop town that is famous for its 14 surviving towers, which were once used to signal wealth and status. The town is also known for its fine Vernaccia wine, and its well-preserved historic center, which is a UNESCO World Heritage Site.

Montepulciano: Situated in the Val di Chiana, Montepulciano is a charming hilltop town that is known for its Renaissance architecture, winding streets, and panoramic views of the surrounding countryside. 

Pienza: Located in the Val d'Orcia, Pienza is a small town that was completely redesigned in the 15th century by Pope Pius II to be the perfect Renaissance city. There are some wonderful walks in Tuscany following pilgrim trails, this is one of the best.

Cortona: Perched on a hill overlooking the Val di Chiana, Cortona is a charming medieval town offering stunning views, ancient Etruscan walls, and a quaint historic center. 

The Forgotten Hill Towns of Tuscany: You can read about these wonderful hill towns here.

If you've got the time, a fabulous add-on would be Le Marche - it's one of Italy's best kept secrets. Here are some of the places you might want to visit.

Umbria too, with towns like Spello, Assisi, Orvieto and Montefalco is delightful.

P.S. For personalized itinerary help click here

Day 21 to Day 24

Next it is Rome. Spend at least three nights here, although longer is always better when it comes to Rome. These are the top attraction you will not want to miss.

When in Rome I always stay in Trastevere at the Santa Maria. Their breakfasts, under the orange trees, are unforgettable.

For dinner try the Tramjazz - a great view of the city and the food is good too.  If you would like a restaurant with an amazing view then it's hard to beat the Aroma near the Colosseum. Otherwise try La Nduja. 

Besides the obvious tourist attractions spend a morning at the Campo dei Fiori and a day of eating and shopping as suggested in our guide.  

| Tip

Rome has a lot to offer: visit the Pantheon, the Trevi Fountain, Piazza Navona, the Spanish Steps and more on a walking tour with a break for gelato or coffee

Day 24 to Day 30

Positano, Amalfi Coast

You've now seven days to visit the Amalfi Coast and the Island of Capri. Here's more on the towns and islands you don't want to miss. 

Perhaps save a couple of days to make a trip down to the Cilento area too - it is an undiscovered paradise filled with picturesque villages, beautiful beaches, ancient cities and a little village where the only inhabitant would love for you to keep him company. Read more about the Cilento here.

After that return to Rome or Venice (whichever you are leaving from).

More Southern Italy

If you're looking to add a touch of Southern Italy to your Italian itinerary, consider reallocating your time or prioritizing certain destinations. While it may require adjusting your plans elsewhere, the enchanting offerings of Southern Italy are well worth it. Here are some enticing ideas to consider for your journey.

Also, have a look at our guide to the south - it covers everywhere from Calabria, to Sicily to Sardinia and everything in-between. You should find somewhere to capture your heart.

The south is truly like that. It captures your heart in an instance, and I have to admit that I have fallen victim to its charms. We are seriously thinking of retiring somewhere in the South of Italy one day.

Why do I love the south of Italy so much? Here's the answer!

P.S. For personalized itinerary help click here

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