Two Week Classic Italy Itinerary

Updated February 2024, Two Week Classic Italy Itinerary was originally published in February 2021

Italy is a country that seems to bring travelers back again and again. And I think this two week Italy itinerary is a great introduction for first-timers, mixing in historical gems, famous sites, and beautiful landscapes and countrysides. 

I’ve been to Italy several times over the years, I even lived there for a brief few months, in fact, we plan to move back in the next few years.

So with this time spent in Italy over the years I’ve created an Italy itinerary to help most first-time visitors tick off the main sites on their list. 

Two weeks in Italy is the perfect amount of time to begin exploring the classic northern cities to get a feel for the country. But more time is always better right?

You could spend two weeks in any one of these places alone, but I know many of you are trying to make the most of your 14 vacation days. 

Want to combo the north and the south? Check out my South Italy road trip itinerary and start planning

Need Travel Insurance and Evacuation Services for Italy?

Start shopping for travel insurance plans over at IATI Insurance. Readers of the Adventures of Nicole get a 5% discount off your plan.

The Adventures of Nicole partners with Global Rescue to offer the world’s leading medical evacuation and security advisory services. To travel with peace of mind, shop evacuation coverage at Global Rescue.

One Day In Rome, Rome One Day, One Day Rome, Rome, Italy

Days 1 & 2: Rome 

Rome is the perfect city to begin your two week Italy itinerary from, well connected by flight from major cities in Europe, North America, and the Middle East, and by train from other European destinations. 

Of course, two days in Rome will feel like a bit of a race trying to visit all the famed sites of the city, so if you do have more time I recommend you add some days to Rome. If you have to shorten your time in Rome, it’s still possible to see most of the highlights on a quick one day in Rome itinerary.

Check out various Rome day tours on Get Your Guide

Things To Do In Rome

  • Colosseum
  • Vatican City
  • Pantheon
  • Trevi Fountain
  • Spanish Steps
  • Piazze Navona

Where to stay in Rome

Bagnoregio, Italy

Day 3: Bagnoregio

Your next stop on this two week Italy itinerary in a citadel founded by Etruscans over 2,500 years ago, Bagnoregio seems to rise impossibly from the Valley of Calanchi. While the actual Civita di Bagnoregio is gorgeous to witness, it is quite small, making it a great stop off to break the journey between Rome and Tuscany up.

Due to continuous erosion, Bagnoregio has been nicknamed ‘the town that is dying’, with wind and rain eating away at the tiny ancient town.

Civita di Bagnoregio is reachable by a 300 meter suspension bridge that connects Bagnoregio to the village of Civita.

Shop various tours to Bagnoregio on Get Your Guide

Things to do in Bagnoregio

  • Porta San Maria
  • San Donato Church
  • Museum Antica Civitas
Florence Cathedral, Santa Maria Cathedral, Florence, Tuscany, Italy
Santa Maria Cathedral, Florence

Days 4-6: Florence, Siena & Pisa

Welcome to Tuscany, a region synonymous to the outside world with Italian culture, wine, art, and cuisine. 

Of course, Florence is the beating heart of Tuscany, home to countless Renaissance pieces and architecture.

Siena is a perfect stop to immerse in Tuscan history and art, and no trip to Tuscany would be complete without a visit to Pisa to see the famous Leaning Tower either. 

I’d recommend spending nights 3, 4, and 5 in Florence and making a day trip to Pisa and Siena on your two week Italy itinerary.

Get the most out of your time with a day tour of Florence

Things To Do In Florence

  • Santa Maria Duomo
  • Piazza della Signoria 
  • Ponte Vecchio
  • Giotto’s Campanile
  • Piazzale Michelangelo
  • Palazzo Vecchio
  • Piazza della Repubblica

Things To Do In Siena

  • Duomo di Siena
  • Il Campo & Torre del Mangia
  • Centro Storico

Visit both Pisa & Siena, as well as the Tuscan countryside as a day trip

Leaning Tower of Pisa, Pisa, Italy
The Leaning Tower of Pisa

Things to do in Pisa

  • Leaning Tower
  • Piazza del Duomo
  • Corso Italia
  • Santa Maria della Spina
  • Piazza dei Cavalieri

Where to stay in Florence

  • Budget: Hostel Archi Rossi is situated in Florence’s historic center, close to the Santa Maria Novella Train Station, making it a convenient and inexpensive option. Book a bed on and
  • Midrange: Hotel Centro is a great option for midrange budget travelers. Centrally located and close to both sites and the train station. Compare rates on and
  • Splurge: San Firenze Suites & Spa is highly recommended for those on bigger budgets. The rooftop pool offers epic views of the historic center of Florence. Check rates on and

Looking for more ideas? Check out these 20 off the beaten path destinations in Italy to add to your bucketlist

Cinque Terre, Italy
Cinque Terre

Days 7 & 8: Cinque Terre

Truth be told, despite having drooled over photos of Cinque Terre for years, I still haven’t visited myself. My last time when I was living in Italy for a stint of time I had planned to make a three-or-so day trip to visit Cinque Terre, but my plans were thwarted by heavy rains and storms that ravaged much of Italy in 2018.

So seeing as I don’t have first-hand experience, but still wanted to include the beautiful ‘Five Lands’ of Cinque Terre on the itinerary, I’ll turn you over to Dan Flying Solo to help you plan your trip to Cinque Terre.

Things to do in Cinque Terre

  • Walk between the villages
  • Explore Portovenere
  • Take a boat cruise for a different perspective

Where to stay in Cinque Terre

You’ll have some decisions to make regarding where to stay in Cinque Terre as it is comprised of five different villages. 

If you’re looking for easy beach access Monterosso al Mare is going to be your best bet. If a picturesque is of utmost importance, then Manarola and Vernazza are going to be the best options. If sea views are what you’re looking for then Riomaggiore and Corniglia are going to be the best for you.

One thing to consider with many of the accommodations in the five villages of Cinque Terre is that most will require a steep walk to reach them. This is something to consider when selecting where you’ll stay.

Parma Cathedral, Cattedrale di Parma, Parma, Italy
Cathedral di Parma

Days 9-11: Parma & Bologna

Continuing from Tuscany and the Ligurian wonder of Cinque Terre, make the journey into the region of Emilia-Romagna to visit the culinary gems of Parma and Bologna on your two weeks in Italy. 

Parma is a buzzing city, home to none other than the famous Parmigiano Reggiano- better known as parmesan. Bologna, on the other hand, is the largest city and capital of Emilia-Romagna, home to Europe’s oldest university, and is a quintessential foodie hub. 

I would recommend staying in Bologna and making a dar trip to explore Parma so you don’t have to shuffle belongings around so much.

Shop a variety of tours of Parma and make the most of your visit

Things to do in Parma

  • Visit a Parmigiano Reggiano factory 
  • Cattedrale di Parma
  • Palazzo della Pilotta
  • Parma Baptistery
  • Teatro Farnese 
  • Piazza Garibaldi 
Bologna, Italy

Things to do in Bologna

  • Go on a Bologna food tour
  • Take a cooking course
  • Santuario di Madonna di San Luca
  • Bologna Canals
  • Piazza Maggiore
  • Asinelli Tower
  • Piazza Santo Stefano + the 7 Churches
  • Neptune Fountain
  • Archiginnasio

Check out these tours of Bologna to check out the arts, cuisine, and more the city has to offer

Where to stay in Bologna

Verona, Italy

Day 12: Verona

On to Verona, the capital of the Vento region, and famed home of Romeo & Juliet. But Verona is more than the home of Shakespearean characters. The city is loaded with Roman history, beautiful architecture, idyllic bridges, and ornate churches. 

If you have a bit more time, Verona makes for a great jumping-off point for those who want to include Lake Garda and even beyond into the Dolomites on their Italy itinerary.

Explore Verona without the headache of planning it yourself with these Verona day tours

Things to do in Verona

  • Centro Storico
  • Verona Arena
  • Piazza Bra
  • Ponte Pietra
  • Juliet’s House
  • Piazza della Erbe
  • Piazzale Castel San Pietro
  • Arco dei Gavi
  • Basilica of St. Anastasia

Where to stay in Verona

Venice, Italy
Venice at sunrise

Days 13 & 14: Venice 

Wrap up your two week Italy itinerary in none other than Venice. While the obvious main attraction to Venice is its countless canals, there’s a lot more to Venice than initially meets the eye.

If you can manage, I’d recommend spending a night wandering the narrow alleys and crossing the famed bridges over the Venice Canals at night. On my second visit to Venice, my friend Sally and I never could locate the hostel a girl on the train had recommended and we spent the entire night roaming around Venice, having the place entirely to ourselves.

Our train had arrived around midnight at Santa Lucia Station. We followed the directions we had scribbled down but when we arrived at what we thought was the location there was no hostel to be found (99% sure we were not in the right place, knowing us). It was there we met a police officer named Guiseppe who tried to help us and then ended up roaming around Venice all night with us, giving us the grand local tour. 

Things to do in Venice

  • Catch the sunrise from Ponte Rialto
  • Wander the narrow alleys
  • Go on a gondola ride
  • St Mark’s Basilica
  • Piazza San Marco

Enjoy your visit without all the planning and book a tour of Venice

Where to stay in Venice

Venice, Italy

Have Any Questions About This Two Week Italy Itinerary?

Ask in the comments section below.

Leave a Comment

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.

Scroll to Top