Are you excited about your upcoming two-week Italy vacation but a bit overwhelmed with the Italy trip planning?
Trying to answer those burning questions:
What are the best places to visit in Italy? And, what are some of the bucket list items I need to include in the Italy itinerary?
No worries! This two-week Italy itinerary includes some of the most popular things to do in Italy, and which cities to include in your Italy itinerary.
From the fashion-forward streets of Milan to wine tastings in Tuscany and the ancient Roman ruins of Rome, this Italian vacation is a fully immersive experience you will never forget!
This 14-day itinerary breaks down some of the top things to see in each city, with a brief description of each!
I have also included the recommendation for how long to stay in each city. This is purely personal, and more of a suggestion than a recommendation.
Consider this 14-day Itay itinerary a guide to help you plan your ultimate Italian vacation. Adjust the number of days per city as desired!
This guide is designed to help reduce some of the stress and let you plan that once-in-a-lifetime Italian vacation!
How to Get Around Italy
Getting around by Train
The public transportation in Italy is phenomenal!
We have been stationed OCONUS in Germany, and we have found that the train system in Italy is incredible.
Italy has high-speed trains that can quickly take you from one city to the next. The more local trains (regional trains) are also great options and tend to be cheaper.
We booked an overnight train from Venice to Milan for the experience. However, I strongly suggest taking the faster train to adhere to your Italy trip planning itinerary.
Tip: Look for the luggage lockers at the train station. They are an excellent option for storing your suitcases until your check-in accommodations are available.
Note: Some links may be affiliate links. That means I may make a commission if you use my links to purchase at no extra cost to you! Full Disclaimer here.
Renting a Car
My husband has rented cars in many places. There are some pros, such as having the freedom to travel on your own schedule. There are some things to consider when renting a car in Italy.
Gas
Gas prices are more expensive in Europe, and are charged by the liter
Parking
If you’re renting a car, you will constantly be navigating parking, and in many cities, it can be a headache.
Ultimately, you will have to weigh the pros and cons and determine which transportation method is best for your Italy road trip!
For Train tickets and reservations: check out OMNIO.
The Ultimate 2-Week Itinerary to Italy
Days 1-2: Milan
Milan is a beautiful introduction for your Italy vacation!
Hopefully, you’ll arrive at Milan’s international airport first thing in the morning, to start your trip! Consider storing your bags until check-in, and start exploring!
You can see most of Milan in two days with this itinerary!
What to do in Milan, Italy
See the Milan Duomo
Visiting the Milan Cathedral is the perfect stop for your first day in Italy!
Grab a coffee and a pastry at one of the local cafes on Duomo Square and enjoy the beautiful cathedral!
Once you’re fueled up, head to the Milan Duomo to climb the rooftop!
If you’re not afraid of heights, this is a must-see attraction while visiting Italy!
Window Shop at Galleria Vittorio Emanuele II
If you love fashion, you must prioritize the Galleria Vittorio Emanuele II on your Italy trip planning!
It is Italy’s oldest shopping mall, and one of the most beautiful attractions in Milan!
Tip: It’s walking distance from the Duomo, so you can easily walk through after exploring the Milan Cathedral
Check out the Sforza Castle
Whether you want to see some of the famous works of Leonardo Da Vinci, or explore the beautiful castle grounds, Sforza Castle is worth the stop!
Tip: It was about a 15-minute walk from the Milan Duomo to Sforza Castle. For those who prefer not to walk, you can easily take the metro.
Relax at Parco Sempione
Parco Sempione is probably one of my favorite parks in Italy. It is beautiful! Also, if you’re traveling to Milan with kids, it’s the perfect thing to do! There are rides and fun attractions for the little ones to enjoy!
Tip: The Parco Sempione is just past the Sforza Castle.
Take a Food Tour
Oh my goodness, how I love food tours! They truly are one of the best ways to learn about a city’s cuisine and culture.
Italy Trip Planning Tip: I recommend booking a food tour for every city.
Unfortunately, the food tour we took isn’t listed. But here are some great food and wine tour options!
Be sure to read this Milan Italy Itinerary Guide: How to Spend Two Amazing Days in Milan.
Days 3-4: Verona
Next up on your 2 weeks in Italy itinerary is the beautiful city of Verona.
Verona is one of the quintessential Italian towns. Its beautiful rustic buildings and Roman ruins make it a bucket list location!
In fact, Verona is called “Little Rome” because of the Roman ruins scattered throughout the city. The city even has its own Verona Arena!
Getting to Verona from Milan
Verona is only two hours away by train.
Several trains run throughout the day, so you can easily start your day early!
For detailed train information and tickets, check out OMNIO.
Noteworthy things to do in Verona, Italy
Visit the Verona Arena
Although smaller than the Rome Colosseum, the Arena di Verona is older and more intact.
In fact, the Verona Arena hosts live shows and performances, but they are only from June to September.
Tip: Purchase your skip-the-line tickets ahead of time! The lines to enter can be very long.
Guided Tours of the Verona Arena
Walk around the Piazza Bra
The Piazza Bra is an enormous square in the city, and it is beautiful!
The Piazza Bra feels like the heart of the city!
Enjoy a coffee and breakfast at one of the restaurants, and enjoy the view of the Arena. It’s the perfect place to start your day!
Tip: If you’re interested in a hop-on, hop-off tour bus or other vehicle-guided tour, this is a large hub for these types of tours.
It’s also a great place to rent an e-bike or scooter.
Explore the Gothic-Style Scaliger Tombs
The Scaliger Tombs belong to the Della Scala Family, a prominent family in the city.
The tombs are beautiful, and quite unique to anything I’ve seen.
The Scaliger courtyard is only open from June to October, but if you’re traveling to Italy outside this window, you can easily see some of them through the iron fence.
Visit the Basilica di Santa Anastasia
This Basilica is Verona’s largest church, and one of the must-see spots in Verona.
The cathedral is beautiful! Don’t let the simpler exterior fool you, the inside is filled with beautiful frescos.
Climb up the Piazzale Castel San Pietro
Across the Adige River from the Verona City is the Piazzale Castel San Pietro.
This Medieval fortress sits on a large hill, giving you the most beautiful views!
I have to admit- the climb is a little intense, but totally worth it.
Tip: A bar and cafe on the hill make it a perfect place to enjoy the best views.
Explore the Piazza delle Erbe
The Piazza della Erbe is Verona’s oldest piazza, and is so charming and beautiful. It dates back to the Roman times, when it was the center of political and social life.
Today the square is filled with ancient and modern structures, giving it a unique feel.
There are restaurants and coffee shops throughout the Piazza, and even has the city’s central market.
Check out Juliet’s Courtyard
If you are a Shakespeare fan, or love the story of Romeo and Juliet, then stop by to see the courtyard and rub Juliet’s breast for your own love story!
Tip: You can purchase tickets ahead of time through the official site. Another great option is to purchase this audio guided tour of Juliet’s Home.
There is so much to explore during your two days in Verona!
Read this more detailed Two-Day Itinerary of Verona, before your big trip!
Days 5-6 Venice
Venice should be a bucket list location for all those wanting to travel Italy!
Venice is known as the “floating city” and made up of over 100 tiny islands!
So imagine all of the beautiful bridges and squares that you will discover in this city! One of the best things to do in Venice is to wander around and explore the streets and canals!
There is so much to explore in this city; if you have extra time, consider adding these top things to do in Venice!
If you want to rearrange this Italy itinerary, learn how to have the perfect day in Venice.
Italy Travel Tips: If you’re traveling to Venice with kids, include some of these fun activities!
Getting from Verona to Venice
The easiest way to arrive in Venice from Verona is by train. On average, the train travel time is 1 hour and 15 minutes.
Italy travel Tip: The main train station is right in the middle of the city. As soon as you walk out, you will see the water. It’s a gorgeous site!
Incredible things to do in Venice during your 2-week Italy Itinerary
Take a Gondola Ride
Taking a Gondola Ride is one of Italy’s most iconic and best things to do!
Gondola rides last about 30 minutes and are a bit of a splurge on your vacation to Italy.
But it’s one of those activities one must check off the European bucket list!
Tips: The Gondolas are scattered throughout the city. Waiting to enjoy a Gondola ride at sunset would be a beautiful experience and give you some of the best photo opportunities!
Enjoy a Boat Ride on a Vaporetto
The Vaparetto, the city’s water bus, offers a different perspective and a beautiful view of the city!
Taking the Vaporetto is very versatile for your experience in Italy. It’s a fantastic way to get from one location to the next, by cutting out significant walking time.
You can even enjoy a boat tour of Venice Island and take day trips to the popular neighboring islands of Burano and Murano.
Venice Tip: Take the Vaparetto down the Grand Canal! This is one of the best ways to take beautiful photos of the Rialto Bridge.
Walk through Piazza San Marco
The Piazza San Marco is one of the main tourist attractions in Venice. This beautiful and large plaza is home to St Mark’s Basilica and St Mark’s Bell Tower.
Tip: If visiting Italy during peak season, prioritize visiting the Piazza San Marco first. It gets very crowded!
Visit St Mark’s Basilica
St Mark’s Basilica and bell tower are right on Piazza San Marco, making them the best next stop on your Venice itinerary.
The St Mark’s Basilica and Bell tower is one of the most sought-out things to do in Venice.
St. Mark’s Basilica Tour with Bell Tower Tickets.
Admire Doge’s Palace
Doge’s Palace is an architectural wonder. The magnificent gothic palace sits right on the water and is gorgeous!
Tip: Walk around and admire the building from afar! Its ornate details make it one of the most popular and favorite things to see in Venice.
The palace, once home to the Doge of Venice, is now a major attraction.
There are several different Palace tours and exhibit options. For additional information, check out the official site.
Tip: Be sure to book your tickets in advance.
Days 7- 8: Rome
The next destination on your two-week Italy itinerary is Rome.
For your first visit to Rome, the city may feel somewhat intimidating. Honestly, there is so much to see and do, and the Rome city itself is impressive!
Rome is filled with ancient history, and seeing the Roman ruins throughout the city is so special —it feels like stepping back in time!
Italy Trip Planning Tips: Because Rome is so large and has so much to see, adding a third day to your itinerary would be a fantastic idea!
In this two-week itinerary in Italy, I suggested two days in Rome and one day in Vatican City, just to separate the two.
The Vatican City is in Rome; you won’t need to travel.
Read this guide for the perfect three-day itinerary of Rome, which includes the Vatican City.
If you want to dedicate a single day to Rome, this One-day itinerary Guide prioritizes the main attractions and provides excellent tips to help you make the most of your day.
These are some essential things to know if traveling to Rome with kids.
Getting to Rome from Venice
If you have chosen to take a road trip through Italy with a rental car, the trip will take roughly 5 hours and 40 minutes. This long drive will need to be incorporated into your itinerary.
Ideally, the best option is to take the high-speed train from Venice to Rome, which takes 3 hours and 20 minutes to 3 hours and 50 minutes.
We booked a night train. Leaving Venice around 11:00 pm, and arriving in Rome at 6:00 am.
I wouldn’t recommend it if you’re traveling with little kids. We wanted to check it off our bucket list, but it made for an exhausting next day.
Tip: If you choose to take this route, consider storing your luggage once you arrive in Rome. There are a couple of luggage storage centers in the city.
Best Things to Do in Rome, the Eternal City
Visit the Colosseum
Visiting the Colosseum in Rome is probably one of the most important things to do during your 14-day stay in Italy.
The Colosseum is magnificent! This first trip to Rome and the Colosseum will undoubtedly be a once-in-a-lifetime experience. Soak it in!
The lines for the Colosseum can be so long. You must purchase your tickets ahead of time.
Skip-the-line guided tour visit of the Colosseum and Roman Forum
Roman Forum and Palatine Hill
Just a short walk from the Colosseum is the Roman Forum and Palatine Hill.
The Roman Forum is really neat to see! I could start visualizing the ancient Roman city center.
The Roman Forum may not be as grandiose as the Colosseum, but it’s worth seeing!
Walking up the Palatine Hill gives you a great view of the Roman Forum.
Ensure a return visit by experiencing the Trevi Fountain
Legend has it, if you stand with your back facing the fountain and throw a coin into the water, it will guarantee a second visit to Rome.
The Trevi Fountain gets very busy! If you find yourself there midday, enjoy the views from afar!
Walk around Piazza Navona
Piazza Navona is one of Rome’s most famous squares. Walking through it felt like the heart of the city!
There are many restaurants and cafes in the square. When it is not crowded, this is an excellent place to let the kids run around if you’re visiting Rome with kids.
Visit the Pantheon
The Pantheon is one of the city’s oldest and most intact ancient Roman buildings.
Purchase tickets for the audio-guided tours ahead of time to avoid the long lines!
Admire the Spanish Steps
The Spanish Steps is one of the widest staircases in Europe! Walking up this beautiful staircase will give you some stunning city views.
If you have little time left, or are not up for the climb, the view from the base of the Spanish Steps is also beautiful, and can be a great place to relax!
Day 9: Vatican City
There is quite a bit to do in the Vatican City. If you can, try to dedicate a day to the Vatican City.
Italy trip planning Tips: If you don’t have enough time to dedicate a full day to the Vatican City, prepare for a full morning or afternoon here. And start first thing in the morning!
Top things to do in the Vatican City
Vatican Museums, Sistine Chapel & the Vatican Gardens
The Vatican Museums are probably the most elaborate and memorable museums I have visited!
You can easily spend three or more hours in the museums.
Tip: The Sistine Chapel is included with the Vatican Museum tours, and is towards the end of the exhibits.
Enjoy the Vatican Gardens! There is a little restaurant along the beautiful green lawns. It’s a nice break after the exhibits!
Vatican Museum and Sistine Chapel Skip-the-Line and Audio Guided Tours.
St Peter’s Basilica
St Peter’s Basilica is one of the largest churches in the world.
I would set aside at least 2 hours for the Basilica.
You’ll want to climb the Dome of the Basilica if you’re not afraid of heights.
I’ve been told that the panoramic views from the Dome are some of the best in the city!
Walk around St Peter’s Square
St Peter’s Square is very impressive, and absolutely worth a visit.
If you decide to forgo the Vatican Museums and Basilica during this two-week trip to Italy, I recommend that you at least visit the Square.
Italy Travel Tips: For Vatican City, purchase skip-the-line tickets. You can also purchase general admission tickets through the official website.
For a guided visit and additional tour options:
Vatican Museums and Sistine Chapel
Days 10-12: Florence and Tuscany
This stretch of the itinerary should be a little bit more relaxing than your days in Rome.
Florence is a city rich in the arts. In fact, it was the birthplace of the Renaissance.
There truly is so much to do in Florence, that I wanted to include two days of this 2 week itinerary to this fabulous city, and an additional day for a day trip to Tuscany.
How to get to Florence from Rome
The drive from ancient Rome to Florence is estimated at 3 hrs.
Traveling by train can cut travel time by half, with the high-speed trains making the trip in 1 hour and 30 minutes.
Top things to do in Florence
Walk around the Piazza del Duomo
The Piazza del Duomo is a really popular spot to visit, and one of the city’s main attractions.
The Piazza is surrounded by stunning buildings, including the incredible Cathedral of Santa Maria del Fiore and its bell tower.
It’s the perfect starting point for your day in Florence. Grab a coffee and croissant at one of the local bakeries, and fuel up for the day.
It’s the perfect place for a beautiful photo op!
Explore The Santa Maria Del Fiore Cathedral
The beautiful facade of this Neo-Gothic masterpiece is one of the prettiest I have ever seen!
The extensive details of the colored marble and embellished details, set this cathedral apart from other Italian cathedrals.
Relax at the Bobli Gardens
The Bobli Gardens are quite large, and have served as an inspiration for other gardens in Europe.
If you enjoy parks and gardens, I would defitienly recommend that you incorproate them into your 14 day itinerary of Italy.
Tip: The Bobli Gardens are located in the Oltrarno district, just across the Arno river.
Enjoy a snack and view for the Bardini Gardens
The Bardini Gardens are just walking distance from the Bobli Gardens, making them a fantastic option next.
The Boboli Gardens are quite large, with beautiful statues and fountains throughout.
The Babini Gardens felt more intimate.
There is even a cafe at the top of the hill, making it a perfect place for a little picnic. Also, the view of Florence is fantastic!
Walk across the Ponte Vecchio Bridge
The Ponte Vecchio Bridge is one of the most unique bridges in Italy.
It’s a medieval stone bridge, with original shops built in.
Originally these shops were fishermen’s markets, but they were later changed to jewelry shops.
Florence Tip: Once you’ve explored the bridge, be sure to enjoy the view from Ponte Santa Trinita Bridge.
See the Statue of David at the Galleria dell’Accademia
The Accademia Gallery is one of the top-visited museums in Florence.
It includes many of Michaelangelo’s greatest works, such as the Statue of David, as well as an extensive collection of other famous works, including antique instruments owned by the Medici Family.
Tip: If you are a lover of art, then you should also include the Uffizi Gallery.
Guided Tour: David, Duomo & Uffizi Gallery
Hang out at the Piazza Della Repubblica
This Piazza is impressive! The Piazza Della Repubblica was rebuilt in the 1860s, and is now a very busy city centre for Florence.
Florence Tip: There are so many restaurants! Many of the horse-carriage tours, and other walking tours, meet here
If you’re traveling to Florence with kids, you should prioritize this square. It has a beautiful carousel in the center—my son loved it!
Take a Day Trip to Tuscany
There are so many guided tours to choose from. We loved our guided tour to the Chianti regions.
The tour included transportation, which was a huge plus.
Getting out of Florence opens up to a beautiful country—and truly, what two-week trip to Italy wouldn’t be complete without a day in wine country?
Guided tours of Tuscany: Chianti Region
Day 13: Pisa
Make a quick stop to see the Leaning Tower of Pisa.
How to get to Pisa from Florence
According to the information on Google maps, the drive from Pisa to Florence is about 5 minutes faster than taking a regional train.
The regional trains take about 1 hour and 20 minutes; however, some high-speed trains take less than an hour.
Seeing the Leaning Tower of Pisa
The leaning tower of Pisa is about a 25 minute walk from the train station, so plan accordingly.
The city of Pisa didn’t look appealing at first. But once you arrive at the leaning tower, the grounds are beautiful!
This 2 weeks in Italy itinerary only allotted time to see the leaning tower, take some photos, and head back to the train station.
Days 13-14 Genoa
I wanted to include the city of Genoa over other coastal cities in Northern Italy.
Cinque Terre is one of the most popular destinations; however, Genoa often gets overlooked.
Because of this, the city can feel less crowded, which is especially nice during the Summer months.
How to Get to Genoa from Florence
If you include a stop at the Leaning Tower of Pisa, the train ride to Genoa will take around 2 hours.
If you decided to bypass Pisa, the journey by train from Florence to Genoa is 2 hours and 40 minutes.
There are so many incredible things to do in Genoa.
If you only have one day in Genoa, this is a perfect itinerary!
Top things to do in Genoa
Walk around the Centro Storico
Genoa is filled with medieval narrow alleys called Caruggi. Interestingly, they were constructed like labyrinths, which was a defensive mechanism for the city.
This old town has such a gritty yet authentic feel, that you can’t help but appreciate.
Visit the Genoa Aquarium
I have to admit, this is one of the most impressive aquariums I have seen, and it’s the perfect activity if traveling to Genoa with kids!
This is also a really nice rainy-day activity!
Enjoy the Promenade
If it’s a sunny day, be sure to spend some time on the promenade. It is lined with restaurants and playgrounds, making it a perfect stop for a break.
Visit the Maritime Museum
If you love naval history, the Maritime Museum should be one of the top things to do in Genoa.
There is even a full-sized replica Genoese submarine you can explore.
Enjoy the Boccadasse
The Bocadense is a neighboring fishing village, with beautiful buildings right on the coast.
It’s an enjoyable walk on the promenade from the Genoa city center.
The beaches can be the perfect late afternoon activity if you’re visiting Italy in summer!
My final thoughts on this ultimate two-week itinerary of Italy
Consider this 2 weeks of Italy a guide for your upcoming Italian vacation!
I have highlighted some of the most-popular attractions for each city; however, there is so much to see in each spot.
When you’re in the Italy trip planning process, look at all of the cities in this 14-day itinerary and decide if the lengths of stays for each seem right for you.
This is your trip!
And don’t be afraid to switch out a city or two for a different destination. Maybe you’ll want to take a day trip to Lake Como?!
I would love to hear about your trip! Let me know in the comments!
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