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Italy is an absolute must-visit for any world traveler. From the Colosseum in Rome and the sprawling Duomo di Milano in Milan to the ruins of Pompeii, there are endless sights and activities to take in. Whether you choose to spend your days exploring cities or basking on beach fronts, visiting iconic destinations such as the Uffizi in Florence, or scoping out Milan’s fashion scene, here is the perfect 2 week Italy itinerary with Amalfi Coast to see it all!
2 week Italy Itinerary with Amalfi Coast
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Italy has a little bit of everything—from its rich history and art to off-the-beaten-path markets, festivals, and small towns.
You can explore pristine landscapes in Northern Italy like the Dolomites or Lake Garda, admire masterpieces by Michelangelo or Leonardo da Vinci, and revel in vibrant street performances in Florence.
Here is a snapshot of 2 weeks in Italy itinerary,
- Day 1 in Rome: Explore Rome’s iconic landmarks (Colosseum, Roman Forum, wander through the neighborhood of Monti in the afternoon/evening)
- Day 2 in Rome and Vatican City: Head to the Vatican City. In the afternoon visit Sant Angelo, Trevi Fountain, Spanish Steps
- Day 3 in Rome: Visit the Pantheon, Piazza Navona (or Villa Borghese). Start for Venice in the evening
- Day 4 in Venice: Wander the San Marco plaza and visit its main attractions, go on a gondola ride
- Day 5 in Venice: Head to the Venetian Islands – Burano, Murano, and Torcello. Start for Milan in the evening
- Day 6 in Milan: Explore the finest in Milan – Cathedral, Galleria Vittorio Emanuele II, The Last Supper, etc.
- Day 7 in Florence: Start for Florence, visit Accademia, Ponte Vecchio & Arno river banks
- Day 8 in Florence: Another day in Florence. Visit Florence Cathedral, Uffizzi Gallery, Piazza Della Signoria, and later the Piazza Michelangelo for sunset
- Day 9 in Pisa: Day trip to Pisa from Florence
- Day 10 in Chianti: Day trip to Chianti from Florence
- Day 11 in Siena: Explore Siena for a day
- Day 12 in Pompeii & Sorrento: Start for Amalfi. You can keep Naples or Sorrento as a base (this will allow you to visit Pompeii on a half-day tour)
- Day 13 in Amalfi & Positano: Explore Amalfi Town and Positano
- Day 14 in Capri Island: Hang out on Capri Island, enjoy the Blue Grotto tour
| Day | Place | Overnight |
| Day 1-2 | Rome | Rome |
| Day 3 | Rome | Venice |
| Day 4 | Venice | Venice |
| Day 5 | Venice | Milan |
| Day 6 | Milan | Milan |
| Day 7-8 | Florence | Florence |
| Day 9 | Pisa | Florence |
| Day 10 | Chianti | Florence |
| Day 11 | Siena | Florence |
| Day 12 | Pompeii | Sorrento |
| Day 13 | Positano Amalfi town |
Sorrento |
| Day 14 | Capri Island | Sorrento |
Planning a trip to Italy for first-time visitors
Visiting Italy for the first time can be a daunting task. It is easy to become overwhelmed with all of the things to see and do. Let us help with these essential planning tips,
Getting to Italy
It’s important to understand the geography of Italy – it is located on the continent of Europe in the southern part, with Rome as its capital city and Milan being its largest city.
If traveling from overseas, particularly from North America or Asia, it might be wise to start in either Rome or Milan because each has an international airport with multiple flight companies that offer direct connections.
Visitors with US and Canadian passports do not require a visa to enter the country and stay for 90 days; however from 2023, an online authorization – ETIAS – is required prior to travel.
Those who need entry visas may already have them, as the same visa used for visiting European or Schengen countries will typically get you into Italy as well.
That said, there are numerous ways to explore this gorgeous land once you are here.
We recommend train travel, whilst enjoying the convenience of its high-speed service when traveling across large distances or opting for cheaper regional trains when hopping between cities at a slower pace.
You can also choose day tours that show off some of the very best of Italy’s many destinations in a short period of time.
Starting this 2 week itinerary with Rome
Rome is the perfect city to kickstart this 2-week itinerary. Rome is served by the Roma Fiumicino Airport (which is the largest in the country), and the Ciampino Airport.
From either airport, you can take a train to get to the city center – Roma Termini (the largest train station) and then take trains to other Italian cities.
Getting to Rome city centre from the airport,
Commuting in Italy
We used a mix of day tours and trains (high-speed and regional) for our sightseeing plans in Italy, and it worked out very well.
- Eurail Pass for Italy is great for train travel in the country
- We also used a city pass wherever we stayed for 2 days or more like the Vatican and Rome pass which offers free admission to certain sites, and free unlimited public transportation along with a hop-on and hop-off tour. This pass is valid for 3 days.
Where to stay in Rome
Staying at a centrally located hotel in Rome is the perfect way to make the most of your visit.
From Termini Station to Piazza Navona and Pantheon, there’s an amazing selection of places to explore on foot – no matter how short or long your trip may be.
We stayed at Prassede Palace Hotel and walked to the Colosseum early morning for pictures.
The hotel also had cafes and restaurants nearby which made breakfast easy! The rooms were spacious for two, and the staff was very helpful! Book your stay here
Other hotel recommendations: Leonardo Boutique Hotel Rome Termini | Condotti Boutique Hotel
Now, let’s go over the day-by-day Italy itinerary,
Day 1 of the 2 week Italy Itinerary: Explore Rome
For the first 3 days of your Italy itinerary, you will explore the prime landmarks of ancient Rome.
In the afternoon and evening, wander the lanes of the Monti neighborhood, and check out numerous piazzas, trattorias, and cute shops!
Because we stayed at the Prassede Palace Hotel in Rome we walked to the Colosseum and arrived there in 15 minutes at sunrise. We had enough time to take photos and enjoy the grounds before the crowds started.
It is free to visit the Colosseum complex, but there is an entry fee to visit the interiors. There are different ticket access levels where you can visit various floors, the arena, and the underground.
A ticket to the Colosseum also includes entrance fees for the Roman Forum and the Palatine Hill, with or without a guide. Here is a detailed guide to visiting the Colosseum
Colosseum Complex: Roman Forum & Palatine Hill
The Colosseum is an incredible work of ancient architecture, symbolizing the advanced engineering and historical greatness of the Roman Empire.
With its impressive four-story structure, it could accommodate up to 50,000 spectators at a time – which is quite something considering when it was constructed (and completed in only a decade)!
The Colosseum was built by Emperor Vespasian in 70 AD and opened in 80 AD by his successor Titus.
Today, this impressive monument remains an iconic sight for tourists visiting Italy. It’s an enduring reminder of Rome’s glorious past and its achievements in art, architecture, and engineering.
This guided tour offered us an amazing fast-track entry inside bypassing lines and crowds. However, what really made it special was that we had a knowledgeable guide on hand to explain each site’s history with background stories, trivia, and interesting anecdotes.
This made our exploration even more interesting as it enriched our understanding of the sites; we highly recommend this tour!
We explored the ruins site, along with the Roman Forum and Palatine Hill. The Roman Forum is undoubtedly one of the iconic photo spots in Rome!
While this site was once a bustling public square during the ancient Roman Empire, it was left to decay as the empire fell.
Now, what remains is a beautiful ruin site, with some of its most impressive monuments standing tall despite their age.
The columns of the Temple of Julius which stand testifying to its former grandeur, and the Arch of Constantine which make it an awe-inspiring sight even in its deteriorated state, are some fine examples.
A walk around the Forum will transport you back in time and leave you mesmerized at how history has survived time’s test! It is truly a must-visit spot for anyone visiting Rome!
Once you have had your fill of the Colosseum and the Forum, head over to the Palatine Hill located on one of the Seven Hills of Rome.
This hill is not only the most popular but also it is steeped in Roman history and legend. Some notable facts include that it was the area where several Roman emperors as well as nobility resided.
You can explore what is left of this district during guided tours.
Highlights of Monti neighborhood
Monti is a wonderful neighborhood in Rome that deserves to be explored for at least 3-4 hours in the afternoon.
From sights to sounds and smells, there are so many attractions to discover along these narrow lanes.
In particular, Monti is home to several local boutiques filled with fashionable clothes and accessories, making it the perfect place for a shopping spree of one’s own.
Not to mention, you will also find unique places tucked away behind piazzas that serve up some delectable Italian cuisine.
So pick a trattoria or a cafe and sit down for lunch.
Then cool off with a gelato at the Piazza dell Madonna dei Monti, one of the popular squares in the city.
Next, make your way to Trajan’s Market.
With nearly two thousand years of history, it’s no surprise that the prominent site has attracted tourists since ancient times. Halfway down Trajan’s Market lies the renowned Church of Santa Maria di Loreto.
Commissioned by Pope Pius IV in the 16th century, this Baroque structure features a wonderful facade and numerous frescoes, which are only a few of the spectacular features here.
The Colosseum stands at one end, while at the other end you can experience a whole different kind of grandeur; just head to Piazza Venezia and marvel at the sights from this great pedestal!
Finish sightseeing at the Quirinal Palace. Being one of the three current official residences of the Italian President, the palace has years of history attached to it.
Located high upon the Quirinal Hill – the highest of Rome’s seven hills – this is a perfect spot for catching magnificent sunsets from the large piazza surrounding it.
Day 2 of the 2 week Italy Itinerary: Explore Rome & Vatican City
On day 2 of the Italy itinerary, visit Vatican City and its prime attractions such as St. Peter’s Basilica, Sistine Chapel, and the Vatican museums with a guide.
After exploring the Vatican, stop by the Castel Sant’Angelo for an hour, before making your way to the heart of Rome.
Created in 1929 after the Lateran Treaty, the Vatican City as it is known today, is a worldly example of a European microstate situated within the boundaries of Rome.
Famous for being the centre of Catholic church control and its Holy See, the small country has much to offer, and you can easily spend one day in Vatican City.
For the purposes of this Italy itinerary, we will spend half-day only.
Now, you can get to the Vatican quite easily.
Depending on where you are staying you can even walk to Ponte Umberto (bridge), over the River Tiber, and then arrive at Saint Peter’s Square.
We took the sightseeing bus tour and were dropped off right in front of the Castel Sant’Angelo, and then we walked to the Vatican.
We had a hop-on and hop-off tour included with our Rome Pass.
Vatican City Highlights
Once at the Vatican, take the time to wander St Peter’s Square and take in the ambiance of this unique microstate.
At the square, you will find the 3 main attractions of Vatican City that we will cover in this itinerary.
Start at the St Peter’s Basilica, which is recognized as one of the premier structures in all of Europe. It is open to the public and free of charge.
Drawing world-renowned architects like Donato Bramante, Michelangelo Buonarroti, Carlo Maderno, and Gian Lorenzo Bernini during its period of construction in the late 15th century, it is often celebrated as a masterpiece of Renaissance architecture.
For centuries St. Peter’s Basilica has been seen as one of the holiest places in all Catholicism due to it being home to the burial place of Saint Peter.
In addition to that, some of Christianity’s most beautiful art pieces can be found within this Basilica such as Michelangelo’s Pietà, his frescoes on the ceiling, and Raphael’s tapestries.
Next are the Vatican Museums. With 26 distinct museums, beautiful ancient Roman and Egyptian artifacts, religious objects, brilliant artwork, and more – this complex is one of the largest public museums in the world!
Of course, the standout highlight is the Sistine Chapel, hosting masterpieces by some of the biggest names in the Renaissance era; Michelangelo, Sandro Botticelli, Pietro Perugino, Pinturicchio, and Domenico Ghirlandaio.
Due to its immense popularity with locals and tourists alike, we suggest booking a guided tour in advance – tickets can otherwise be hard to come by! Here is a 2 hour tour that you can book
After sightseeing, you can grab a bite to eat in one of the restaurants in the Vatican before making your way to Rome!
Castel Sant’Angelo
The first stop after the Vatican is Castel Sant’Angelo.
Castel Sant’Angelo was originally constructed by Emperor Hadrian to serve as his mausoleum. It served this purpose until the 5th century, and later on, it was adapted into a fortress and a castle by the Pope.
Today, you can visit Castel Sant’Angelo to explore its ancient history as well as discover some interesting pieces of art housed in its museum. Here is an entry ticket to the castle (visit for 1 hour).
As you wander through its halls, you’ll find a permanent photographic exhibition featuring several works of Italian photographers over the 18th and 19th centuries.
Be sure to admire the River Tiber and various bridges from the museum.
Up next is the Trevi Fountain. Built in the 18th century and located in the center of Rome, Trevi Fountain is an iconic monument renowned for its beauty.
This stunning Baroque masterpiece is the largest fountain of its kind in the city, featuring sculptures of gods and deities alongside a stunning waterfall effect, it’s no wonder that Trevi Fountain continues to be one of the most popular attractions in Rome.
Although it will be crowded in the afternoon, you can still capture a crowd-free photo here from the sides of the fountain!
End the day’s itinerary at the Square of Spain or Piazza di Spagna. Climb the steps to get to the Trinità dei Monti church, atop one of the city’s hills.
Take ample photos and then enjoy the lovely square.
The Steps are a crowd puller, but here is another reason why you should visit the Piazza Di Spagna – and it is for its shops and restaurants, and the vibe that the square oozes – it is always bustling with activities!
Here you will find high-end designer stores such as Prada and Gucci which line up this area’s beautiful pavements.
And if you’re hungry, there are plenty of cafes, bars, and restaurants to enjoy an exquisite Italian meal whilst cradled by Piazza Di Spagna’s romantic atmosphere.
Day 3 of the 2 week Italy Itinerary: Explore more of Rome. Start for Venice
On day 3 of this 14-day Italy itinerary, visit the Pantheon, followed by the Piazza Navona (you can swap this for Villa Borghese and museums).
In the evening, start for Venice.
Pantheon
Start your day bright and early at the Pantheon.
Originally built in 27 BC and then rebuilt by Hadrian in 126 AD, the iconic architecture of the Pantheon has withstood two millennia of history and still stands as a stunning example of classical design.
Once a temple dedicated to many Roman gods, it is now a Catholic Church and it is completely free to explore.
Set aside 30 minutes to an hour to visit the interiors and then sit down for coffee and croissant at one of the cafes located at the square.
Being free, and a touristy site, visitors line up at the entrance 30-40 minutes prior to the gates opening – so we highly recommend heading there before 08:00 am to beat the rush.
Piazza Navona
After the Pantheon, it is time to visit another popular spot in Rome – Piazza Navona. This piazza is another free attraction, and it is home to many beautiful Baroque architectures such as Bernini sculptures, and fountains.
Wander the square, enjoy some souvenir shopping or take photos! If you like, you can chill out at the square with gelato!
Alternate attraction: Instead of Piazza Navona, you can visit the Borghese Gardens (for free), along with the Villa Borghese (art museum) before bidding adieu to Rome!
Read: Our detailed 3 day itinerary for Rome
In the evening, start for Venice. We recommend opting for a high-speed train. It takes about 3 hours to get there. Regular trains take 3 hours 45 minutes.
- Trains depart from Rome Termini Station and arrive at the Venezia Santa Lucia.
- Driving takes 6+ hours, one way.
Where to stay in Venice?
For a short trip to Venice, we recommend staying by the Grand Canal or the Saint Lucia Station. If you are looking for budget options, the neighborhood of Mestre is a good option.
On our very first trip, we stayed at the Campanile Venice Mestre and loved it. The room was spacious and the Grand Canal was a short bus ride away. It was a mid-budget property, which was very well-maintained and clean.
Lots of nice places to eat around, but nothing fancy though.
Here are some hotel options in the heart of Venice: Palazzo Veneziano – Venice Collection | Hotel Campiello
Day 4 of the 2 week Italy Itinerary: Sightseeing in Venice
Enjoy your first day in Venice with a nice breakfast by a canalside cafe. We were up bright and early, and enjoyed the quiet canal lanes in the morning.
After breakfast, we head to the landmark San Marco Piazza to check out the St Mark’s Basilica, Campanile tower, and the Doge Palace.
We highly recommend joining a 3-hour guided tour like this one – Piazza San Marco, and the Doge Palace tour to cover all the important sights.
Piazza San Marco and highlights
San Marco Piazza inspiringly combines stunning architecture, incredible views, and a one-of-a-kind atmosphere, making it an absolute must for any traveler to Venice.
The centerpiece of the square is none other than St. Mark’s Basilica – an iconic structure of incomparably beautiful Byzantine design and gold mosaics; climbing up the Campanile bell tower that stands right beside it, will reward you with spectacular views of the city.
St. Mark’s Basilica is one of the most beautiful churches in the world. Although it is not the oldest or the largest church in Venice, its Byzantine architecture and stunning interiors pull any traveler to it.
With its intricate designs and beautiful setting on the waterfront, St. Mark’s Basilica is a must-see for anyone visiting Venice.
Doge Palace is another iconic building in Venice. The palace was originally built as a residence for the Doge or the administrator, and over the years the palace complex has been extended and modified.
With a guided tour, you can visit the museum and its art galleries, as well as check out the opulent rooms.
We recommend booking a 3 hour tour of the complex which includes a combined guided tour of the Doge’s Palace & St. Mark’s Basilica.
The tour also walks you to the Bridge of Sighs. The Bridge of Sighs is one of the popular Venice Instagram spots.
As part of this tour, you can also climb to the San Marco bell tower and take in the views of Venice and the waterfront area. With a ticket, you can go up and down the bell tower exclusively via lift (no steps).
Note that in some months, due to extreme weather conditions, access to the tower may be suspended.
Next, wander the waterfront of San Marco Square.
But don’t leave without stopping by one of the two popular cafes at St Mark’s Square – Caffè Lavena or Caffè Florian – the latter being particularly worthwhile since it dates back all the way to the 18th century.
After a quick stop at the cafe, walk along the Riva degli Schiavoni, which is the waterfront area of Venice. This location is perfect to capture everything that Venice is known for – waters, gondolas, and beautiful architecture!
You will see the San Giorgio Maggiore Church from across the canal, which is breathtaking.
Read: How to spend one day in Venice
Lunch and Rialto Bridge
Plan to get to the Rialto Bridge next. The Rialto Bridge is one of the most famous and beautiful bridges in Italy.
It spans the Grand Canal and connects the San Marco and San Polo districts in Venice.
The bridge dates back to 1524 when it was built to replace an older wooden bridge that collapsed. The current version of the Rialto Bridge was completed in 1990 after being destroyed by fire during World War II.
We recommend sitting by the Rialto Bridge for lunch, choosing a restaurant or cafe – opposite Riva del Ferro, or by the promenade.
It is touristy, and maybe a little pricey but it was so amazing to sit by the canal, and enjoy a pizza and wine whilst taking in the bustle and hustle of the surroundings!
Go on a gondola ride
Late afternoon (after lunch) instead of walking, go on a gondola ride in Venice! This still remains to be one of our favorite memories from our first Italy trip.
You can choose a private ride (35-45 minutes), or a shared gondola ride (shared by 5 other guests with or without a commentary).
We opted for a private gondola ride with a photoshoot, and it was a beautiful experience.
With a gondola ride, you can see all landmarks and quiet alleyways from the comfort of your seat. This will really allow you to appreciate the beauty of Venice – a city built on canals!
A gondola experience can be expensive when booking a private tour, but you can save money by booking a group ride. GetYourGuide runs specials on rides, so do check it out.
T Fondaco Rooftop Terrace
After the ride, head over to the rooftop of T Fondaco – a shopping complex where you can enjoy an amazing view of the city from above. This is perfect during sunset!
T Fondaco is located near the Rialto bridge, and it is completely free to visit the terrace (but it does require you to reserve a time slot online).
Alternate sightseeing: San Polo District and Castello district
If you are not keen on the gondola ride, feel free to swap that for a walking tour of the San Polo district.
This district is located on the west end of San Marco and across the Grand Canal (via the famous Rialto Bridge).
You can visit the Basilica of Santa Maria Gloriosa Dei Frari and the Church of San Giacomo di Rialto. There are lots of places to hang out and eat dinner in the district.
From San Polo, you can also explore the Castello district. The neighborhood of Castello is the largest of all the districts, and it borders St. Mark’s Square and is home to luxury hotels, as well as some casual bars.
Here you will find the Instagrammable Libreria Acqua Alta (bookstore). The shop means, “Book Store of High Water” and it is one of the popular places in Venice for its unique ambiance.
Day 5 of the 2 week Italy Itinerary: Visit the Venetian Islands, then start for Milan
On day 5, go on a half-day tour to the Venetian Islands. We took a guided tour, but you can plan this yourself. In order to get to the islands, water buses or Vaporetto is the main mode of transport.
Here is the 5.5 to 6 hour day tour that we booked, and we left on a motorboat from the St Mark’s area.
We recommend starting early (right after breakfast) to make the most of your day.
Just off the coast of Venice, are the three islands of Burano, Murano, and Torcello.
Burano is renowned for its brightly painted houses, often in pink and rainbow hues, while Murano is famous for its glassworks.
On a visit to Torcello, you can observe many ancient sites such as a 7th-century cathedral and bell tower which were built using local limestone.
Each island is located a 15 to 20-minute ferry ride away from one other. You will find sightseeing attractions as well as restaurants where you can grab a bite to eat.
We particularly loved Burano’s colorful quarters, and also visited the glass-making factory in Murano and picked up a few souvenirs.
Each island offers its own unique attractions, and you can spend a couple of hours in each, before returning to Venice by evening (to get to Milan by train).
Start for Milan in the evening: Milan is served by the Milan Malpensa Airport, which is one of the busiest airports in the country.
But because you are in Venice you can take the high-speed train and get to Milan in about 2.50 hours.
- Trains depart from Saint Lucia Station in Venice and arrive at the Milan Centrale
- Driving takes 3 hours, one way
Where to stay in Milan?
For a short trip, we recommend staying at the center (Zone 1 of Milan or near the Duomo), or Milan Centrale Station.
We stayed near the Central Station at the c-Hotel Atlantic Milano and it was perfect. Rooms were spacious for two, and there were lots of affordable restaurants nearby.
Other hotel recommendations: Starhotels Anderson | Park Hyatt Milan
Day 6 of the 2 week Italy Itinerary: Explore Milan
We enjoyed exploring Milan, and we think it is a perfect base to explore the Lombardy region and other places in the northern part of Italy including Lake Como and Cinque Terre villages, or travel all the way to the Principality of Monaco.
For this 14-day Italy itinerary, you only have one full day to explore, and we will cover the primary city landmarks!
Milan Cathedral
The most important attraction in Milan is its Duomo. We highly recommend starting at the cathedral in the morning, and if you want the best photos then be there at sunrise or at least before 08:00 am.
It is a 7-minute ride from c-Hotel Atlantic Milano, where we stayed.
Duomo di Milano is the largest church in Italy, the second largest in Europe, and the third largest in the world!
Along with being the most iconic landmark of the city, it has quite a remarkable history; it took almost six centuries to build but now stands as one of the prettiest cathedrals in Europe!
Visiting the Duomo is not free, you can book the tickets here.
Although from the outside you can only witness part of its grandeur, visiting the rooftop offers expansive views and gorgeous terraces to wander, and we highly recommend adding this to your one day in Milan itinerary.
Set aside 1-3 hours here including exploration time at the archaeological site located underneath the Duomo.
We booked our cathedral tickets with rooftop access by lift and the archeological and museum site. You can book the tickets here
Up next is the Galleria Vittorio Emanuele, one of the oldest shopping arcades in the world. And it is located just in the Piazza Duomo, and there are cafes and restaurants nearby where you can stop for brunch or lunch!
Spend time inside the Galleria and admire all the beautiful ceilings and if interested pop by designer shops – you will find all the major designer brands here including Prada Milano!
The Last Supper, hop on and hop off tour, shopping
After lunch, make your way to see Leonardo da Vinci’s The Last Supper. It is located in Santa Maria Delle Grazie and is a popular attraction in the city.
Do book tickets to the Last Supper early to avoid disappointment.
We recommend using the Hop-on and Hop-off tour to get to Santa Maria Delle Grazie, and along the way see the Sforzesco Castle and in the evening get down at the Sempione Park.
If you wish to go shopping, then you can skip the park and instead head to Via Montenapoleone and the famous Quadrilatero Della Moda.
Read: How to explore Rome Florence Venice in one week in Italy itinerary
Day 7 of the 2 week Italy itinerary: Arrive and explore Florence
On the morning of day 7 of your Italy itinerary start for Florence in Tuscany.
There are 20 direct trains from Milan to Florence each day, and when you stay by the Milan Centrale catching an early morning train will be a breeze (plus there are lots of coffee shops inside to warm up).
Getting to Florence,
- Milan to Florence by high-speed train is less than 2 hours
- Driving time is 3.50 hours+
Where to stay in Florence?
We recommend staying at the center of Florence for this itinerary. Firenze Santa Maria Novella or Stazione di Santa Maria Novella (train station) is located within walking distance of the centre.
We stayed at the La Terrazza sul Duomo B&B and which had amazing views of the Florence Cathedral from its terrace.
You can access the rooftop at any time of day for sunset views, coffee, or pizza time! The boutique B&B was clean with a private bathroom and their breakfast was very generous too.
Other hotel options: Grand Hotel Cavour Florence | Hotel Vasari
Florence is one of Italy’s hidden gems, a beauty that cannot be matched. An amazing range of art and culture awaits visitors in this ancient city, making it unlike any other.
It is the birthplace of the Renaissance period and its streets are filled with inspiring markets from that time; iconic sights such as Piazza Della Signoria boast awe-inspiring creations like Michelangelo’s David, while other world-renowned museums hold unforgettable masterpieces by Da Vinci, Botticelli, and Raphael.
Galleria dell’Accademia
With half day for sightseeing in Florence (on day 7), check off one of the museums – Galleria dell’Accademia. This is where you will find the statue of David and other art exhibits.
You must book a timed entrance ticket ahead of time to avoid disappointment. Set aside 1.50 hours to visit and see everything inside the Galleria dell’Accademia.
In the evening, wander down cobblestone streets lined with large open-air markets and vibrant cafes and then take a leisurely stroll along the Arno riverbank taking in its many famous bridges.
Ponte Vecchio, a medieval arch bridge, built over the Arno River is an important city landmark, so don’t miss it.
For dinner, head back to the Duomo area. There are small trattorias where you can grab a drink, pizza, and tiramisu.
If you like to shop, you will find a lot of high-end designer brands as well as affordable labels in the city centre.
Day 8 of Italy Itinerary 2 weeks: Explore more of Florence
Spend the next day in Florence exploring another Renaissance museum and this one is quite popular as well.
The Uffizi Gallery in Florence is every art lover’s paradise! This amazing Renaissance-era gallery houses some of the most beautiful and esteemed pieces of artwork in the world, from centuries past to ones still being produced today.
From Giotto and Raphael to Boticelli and Michelangelo, many historically significant Italian painters are represented here.
You can view ancient sculptures, cultural masterpieces, precious religious artifacts, and stunning medieval frescoes in the gallery.
You will need at least 3+ hours at the Uffizi Gallery. We highly recommend booking tickets ahead of time as it gets sold out for weeks. Here is where you can book your tickets.
From the Uffizi, make your way to the Piazza Della Signoria, which is a large public square. This piazza is surrounded by iconic Florentian landmarks such as the Palazzo Vecchio (which is a town hall today), a copy of Michelangelo’s David statue, fountains, and other stunning statues.
You can sit down at a trattoria by the square – there are sit-down cafes to casual bars where you can grab a bite to eat.
In the afternoon, you can visit Museo Galileo – perfect for science lovers. This museum is housed in an 11th-century building known as Palazzo Castellani.
The collection dates back to the Medici and Lorraine Grand Dukes’ era and includes some originals belonging to the great astronomer himself. Book your entry ticket here
Another option is to go shopping or wander in and around the pretty Piazza Della Repubblica. This is the Roman heart of Florence and the main square in the city, and it is surrounded by shops and cafes (you can also stop here for lunch if you like).
The Column of Abundance is located here and it marks the area where the Roman Forum once stood. This column dates back to 1431.
Piazza Michelangelo
From the heart of the city, make your way to Piazza Michelangelo. It is a short walk or a hike to get there, but it is all worth it for the views!
You can also get to the entrance of the viewpoint by bus or taxi, and there are small cafes and a parking area.
Piazza Michelangelo is a free attraction and we highly recommend visiting for sunset. The entire city of Florence with its iconic landmarks will greet you from this viewing platform!
Read: 2 days in Florence itinerary | 3 day Florence itinerary
Day 9 of Italy Itinerary 2 weeks: Day trip to Pisa from Florence
Keeping Florence as a base, embark on a few day trips to explore more of the beautiful Tuscany region (we will share tips to customize this 2 week Italy itinerary below if you do not wish to spend a lot of time in Tuscany).
Now, Pisa is located approximately 90 kilometers (56 miles) from Florence, and the best way to get to Pisa is by train.
It is home to centuries of history, culture, and heritage and is a must-add to your 2 week Italy itinerary.
Getting to Pisa from Florence
Once you’re in the city, getting around is easy; everything is within walking distance of the Leaning Tower. Pisa is quite a compact city so the best way to explore it is on foot.
Things to Do in Pisa
From the iconic Leaning Tower of Pisa to a variety of museums and historical sites, there is no shortage of things to do in Pisa.
The Leaning Tower of Pisa:
Of course, no trip to Pisa is complete without seeing the famous Leaning Tower. This bell tower was built between 1173 and 1372 and is one of the most recognizable landmarks in all of Italy.
You can climb the 294 stairs to get a spectacular view from the top or simply admire it from the ground.
Being a popular attraction, lines start forming as early as 9:00 am and don’t get any shorter all through the day.
We highly recommend buying skip-the-line tickets, especially since you are going to be in Pisa for just a day.
Here are the tickets – Combined ticket to Leaning tower of Pisa and Cathedral
You can also book a guided tour of the Tower (tickets extra), the Cathedral, and the Baptistery
Piazza dei Miracoli:
The cobblestone streets surrounding this large plaza are home to several iconic monuments and structures including the Leaning Tower, Pisa Cathedral, and Baptistery.
This square has been declared a UNESCO World Heritage Site due to its unique architectural beauty.
Pisa Cathedral:
This Romanesque-style church dates back to 1092 and features beautiful marble sculptures throughout its interior.
It also houses many important works of art such as mosaics, frescoes, and stained glass windows that are worth checking out during your visit.
Cemetery Campo Santo:
This cemetery is one of the seven UNESCO World Heritage Sites in Tuscany. The interiors of Camposanto are an example of early Renaissance art which adorn the walls of the impressive buildings of the Camposanto.
There is an entry fee to get inside, and here you can also see the ancient Roman sarcophaguses and frescoes of the Master of the Triumph of Death.
Santa Maria della Spina:
The Santa Maria della Spina is a small Gothic church located on Lungarno Gambacorti on the banks of the river Arno.
Here is a detailed one day in Pisa itinerary to help you plan your trip! With so much natural beauty combined with rich cultural heritage, it’s no wonder why people love visiting Pisa every year.
Day 10 of Italy Itinerary 2 weeks: Day trip to Chianti from Florence
Day 10 of the Italy 2-week itinerary is all about taking it slow and enjoying rolling hills, picturesque vineyards, and delicious wines in Tuscany, the birthplace of Chianti.
Tuscany has long been known for producing some of the world’s best wines, and Chianti is no exception. This full-bodied red is made with a blend of Sangiovese grapes grown in the villages surrounding Siena and Florence.
You can book a guided wine tour that includes pick up and drop off from your Florence hotel.
Depending on the chosen tour, you’ll explore several different types of Chianti, from traditional Tuscan blends to super-Tuscan versions made with other grape varieties like Cabernet Sauvignon or Merlot.
Some tours such as this one also include a light lunch.
Other than sampling you can also visit vineyards and talk to experts – learn about the history and culture behind them.
You’ll get an inside look at how local winemakers craft their wines using traditional techniques passed down over generations.
We enjoyed our wine-tasting tour, and it was a fun way to explore Tuscany, take it slow and also taste some great Chianti wines.
Day 11 of Italy Itinerary 2 weeks: Explore Siena for a day
The Tuscan city of Siena is an old-world city teeming with rich culture and history. This beautiful Italian city is full of winding streets, stunning architecture, and delicious food.
It’s the perfect place to explore for a day or make your home base while traveling through Tuscany.
Siena can be easily visited from Florence,
- Florence to Siena is 1.25 hours by train
- You can also get to Siena by bus. Buses leave right outside the Santa Maria Novella station in Florence and cost around the same as a train ride
- Day tours combine multiple stops in Tuscany from Pisa, Siena, Chianti, and San Gimignano
Here’s all that you can discover in one day in Siena,
The Piazza del Campo:
This world-famous square in the heart of the city is the main attraction in Siena.
It dates back to medieval times and hosts many festivals throughout the year, like the Palio di Siena horse race which has been running since 1659 (when it was formally organized).
The race is held twice a year in the summer months of July and August.
In addition to its tourist attractions at the piazza, it also offers plenty of cafes and restaurants where you can enjoy a traditional Italian meal or just watch the locals go about their daily lives.
Visit Siena Duomo (Cathedral):
The Duomo dates back to 1196 and features intricate marble floors and frescoes as well as breathtaking stained glass windows.
To enter the cathedral, you can book a Cathedral guided tour that covers the Cathedral, Piccolomini Library, Museum, Panorama and “Duomo Nuovo”, Crypt, Baptistry, Beneath the Cathedral, and Gate of Heaven (which is at the very top of the cathedral).
Explore museums:
Siena has a number of fascinating museums which are perfect for art lovers or those looking to learn more about Italian culture and history.
Head to the Museo Civico, located on the first floor of the city hall – Palazzo Pubblico to learn about Siena.
Then there is the Museo della Tortura aka Torture Museum, just a few steps from Piazza del Campo – all showcasing the unique history and culture of Siena!
Right across the Duomo is Santa Maria Della Scala, a museum. It was a medieval hospital before and is considered to be one of the oldest in Europe.
You can discover fresco-laden hallways, archives of archaeological finds, and exhibits in the hall of relics.
Here is a detailed guide to spending one day in Siena
Traveling to Rome and then the Amalfi Coast:
In the evening of day 11, start for Rome and stay there overnight. This will allow you to connect to Amalfi/Sorrento for the last leg of your 14 day Italy itinerary.
We are traveling from Florence to southern Italy via Rome to break the journey and make use of time for sightseeing on day 12.
You can also travel by train overnight to get to Sorrento (a 7 to 8-hour ride).
Another option is to stay back in Tuscany and explore more of the region (and even travel to San Marino – we will discuss this in an alternate trip sample below).
Read: Rome and Amalfi Coast itinerary 7 days
Day 12 of Italy Itinerary 2 weeks: Start for Amalfi from Rome. You can keep Naples or Sorrento as a base (this will allow you to visit Pompeii on a half-day tour)
After arriving in Rome make your way to the south. We recommend keeping Sorrento as a base and then exploring the Amalfi Coast.
If interested, this is the perfect opportunity to stop by Pompeii and Naples before checking into your Sorrento hotel.
- Rome to Sorrento: Trains from Rome to Sorrento via Napoli Centrale and Napoli P. Garibaldi take around 3.50 hours. Flixbus offers routes that take around 4.50+ hours, one way.
- Rome to Pompeii is 240 km (149 miles) away. The easiest way is to take a train from Roma Termini station directly to Pompeii Scavi-Villa dei Misteri station, which is located right outside the archaeological site. The journey takes about 2 hours via high-speed trains, and tickets can be purchased at the train station
- Pompeii to Sorrento train station is 30 km (18 miles) away. It will take about 30 minutes to arrive in Sorrento
Once you arrive in Pompeii, set aside 3 hours to explore the archealogical site and grab lunch/food before starting for Sorrento.
Although the city of Pompeii was destroyed by a volcanic eruption in 79 AD, it has been remarkably well-preserved due to the thick layers of volcanic ash that blanketed the city.
Today, Pompeii is one of the most popular tourist destinations in Italy, and it’s easy to see why. A visit to Pompeii is like stepping back in time – there are numerous homes, temples, public baths, and more to explore, all well-maintained and full of treasures.
Be sure to visit the Roman Forum, which was the main square in Pompeii where people would gather to socialize and do business.
When you are short on time, a guided tour will be super handy!
Plan to arrive in Sorrento by evening, and check in to your centrally located hotel like the Elys Suites.
After that, head outside for a walk in the city centre and enjoy your dinner in Sorrento.
Tip: You can also skip Pompeii, directly arrive in Sorrento and explore the city, and make arrangements for sightseeing on the Amalfi Coast.
Tours: You can visit Pompeii from Sorrento and back as well, on a day tour
Where to stay on the Amalfi Coast?
There are countless hotels and Airbnbs on the Amalfi Coast. However, we recommend keeping Sorrento as a base.
We will share our favorites below,
- Elys Suites (Sorrento): Elys Suite is centrally located and each room has its own balcony and is spacious inside. The hotel is located in the central part of the city, and from here you can easily get to sightseeing in Sorrento and beyond. Book your stay here
- Other places to stay in Sorrento: Hotel Regina Sorrento (with a view) | Sorrento Pool&Suites (affordable)
- Terrazza Duomo (Amalfi town): Amalfi Town is a good spot to call home and this one, in particular, is located by the Cathedral, and you can also book rooms with views of the piazza and the Duomo. Click to check availability here
- Rosa e Valentino (Ravello): Another village where you can stay overnight is Ravello. Rosa e Valentino is a simple accommodation for a comfy stay. They offer a buffet breakfast, and you can even rent bicycles from the property. Check prices and book your stay here
Day 13 of Italy Itinerary 2 weeks: Explore Amalfi Town and Positano
Soak in the beautiful cliffside views of the Amalfi on days 13 and 14 of your Italy itinerary. Start for Amalfi town and Positano from Sorrento.
You can use public transportation (bus, ferry) or you can book a day tour that covers both towns from Sorrento.
Getting to Amalfi and Positano:
- From Sorrento to Positano, ferries depart approximately every two hours and take about 40 minutes to get there
- After exploring Positano, you can take the bus to get to Amalfi town (one-hour bus ride) Or a taxi will take you there in 30 minutes
- Day tours: There are lots of day tours available from Sorrento to Amalfi and Positano, such as this one
- You can also add a third village such as Ravello on a day tour
Day tours are great if you want a guide to take you around, without having to figure out all the parking and public transportation routes. However, if your plan is to relax at the beach, then this will not work for you – as tours are slightly fast-paced.
Things to do in Positano and Amalfi town
Rent a sunbed and enjoy the sun at the Spiaggia Grande or Laurito Beach in Positano.
Spiaggia Grande is the main beach of Positano (also known as Positano Beach or Marina Grande), and it is located super close to the city center.
You can rent sunbeds and umbrellas for around 20 euros. You will also find a restaurant here along with shower stalls and washrooms.
You can also opt to eat at any of the cafes with water views such as Il Tridente or La Terra to enjoy a nice Italian meal!
Beyond the beaches, there are landmarks such as the Santa Maria Assunta which you can visit.
You must set aside the second half of the day for Amalfi town. Positano to Amalfi town is 40 to 55 minutes by road.
If Positano was super crowded, you can also rent an umbrella or sunbed at the Spiaggia Grande Amalfi beach here. This beach is located by the SITA bus stop, and it also has a small free area.
You can also walk the waterfront area and later go sightseeing.
Amalfi Duomo is one of the primary cultural highlights on the coast. This cathedral dates back to the 9th century and boasts a stunning exterior with large arched windows and intricate mosaics adorning the facade.
The entry fee is 3 euros, and it is worth spending time to see the inside.
There are tons of cute trattorias and decades-old baked shops where you can savor local delicacies such as the Pasticceria Pansa.
Read: One day in Amalfi itinerary
Day 14 of Italy Itinerary 2 weeks: Hang out on Capri Island, enjoy the Blue Grotto tour
On your very last day in Italy, enjoy a small group tour of Capri Island, and the Blue Grotto from Sorrento.
Gorgeous Capri Island is known for its glamor and glitz on the coast with its blue waters dotted with yachts.
People from all over the world including celebrities flock to the area to unwind on the beaches and the villas.
With this day tour, you will get to explore this unique place and also enjoy an excursion to the Blue Grotto.
The tour includes a ferry ride to Capri where you will explore the island along with the Natural Arch and the Faraglioni Rocks, and then visit the Blue Grotto on a boat.
Being a full-day tour, you will also have time for a swim and go snorkeling. Snacks are also provided onboard.
This excursion includes pick up and drop off from your Sorrento hotel and when back, you can return to Rome to fly out.
Read: 4 day Amalfi Coast itinerary
2 weeks Italy Itinerary Sightseeing Map
14 day Italy Itinerary with Cinque Terre and main cities
The above Italy itinerary for 2 weeks covered the best of cities, and beaches with the wine region. There are some days when overnight or evening travel will be needed to make the most of your visit.
If you wish to take it slow, we recommend keeping 3-4 cities as a base and then taking day trips to explore more of the region.
In the itinerary below, you will be able to keep Milan as a base city to visit the Lombardy region and also take a day trip to Monaco.
It also gives you 3 full days in Cinque Terre so you can hike and explore all 5 villages with ease.
It, however, doesn’t include any time in Tuscany or the Amalfi Italian coast.
| Day | Place | Overnight |
| Day 1-2 | Rome | Rome |
| Day 3 | Rome | Venice |
| Day 4 | Venice | Venice |
| Day 5 | Venice | Milan |
| Day 6-7 | Milan | Milan |
| Day 8 | Monaco | Milan |
| Day 9 | Lake Como & Bellagio |
Milan |
| Day 10 | Verona | Milan |
| Day 11 – 13 | Cinque Terre | Cinque Terre |
| Day 14 | Milan | Rome (fly out) |
Visiting Cinque Terre: Quick tips
The beautiful coastline of Cinque Terre is known for its picturesque views, colorful cliffside houses, Mediterranean climate, and delicious food.
It is a region located on the Italian Riviera in Liguria.
The name translates to “five lands,” which refers to the five villages that make up the area— Monterosso al Mare, Vernazza, Corniglia, Manarola, and Riomaggiore.
The villages are connected by a network of trails that offer breathtaking views of the Mediterranean Sea and nearby vineyards.
How to get to Cinque Terre:
The best way to get to Cinque Terre is by train from cities such as Milan or Florence. The villages are on the Genoa – La Spezia line, with Monterosso being the only one served by long-distance Intercity trains.
- Milan to Cinque Terre is 3+ hours by train
- Driving takes about 2.50 hours
There is no shortage of things to do in Cinque Terre! From hiking on one of the many trails that connect the villages together to sunbathing on one of its many beaches, you can make your trip as active or as relaxed one as you like.
Cinque Terre is also compact as compared to the Amalfi Coast, and here you can also explore some of the local wineries or take part in some water sports like kayaking or snorkeling around Manarola’s harbor.
14-day Italy Itinerary with Tuscany and main cities
This 14-day Italy itinerary excludes any beach time and focuses on city sightseeing and cultural experiences.
It is not super fast-paced as you can keep Florence as a base to visit Tuscan villages in one week of your 2-week trip.
| Day | Place | Overnight |
| Day 1-2 | Rome | Rome |
| Day 3 | Rome | Venice |
| Day 4 | Venice | Venice |
| Day 5 | Venice | Milan |
| Day 6-7 | Milan | Milan |
| Day 8-9 | Florence | Florence |
| Day 10 | Pisa | Florence |
| Day 11 | San Gimignano & Chianti |
Florence |
| Day 12 | Siena | Florence |
| Day 13 | Volterra | Florence |
| Day 14 | Lucca or San Marino |
Florence |
About San Marino:
San Marino is a European microstate and you can explore it from Florence (via Rimini) using trains. Here is a detailed guide to transportation from Florence to San Marino.
Alternatively, if you would like to swap any of the day trips from Florence above, you can visit Cinque Terre on a day tour. More details here
Read: Most beautiful cities to add to your Italy bucket list
Italy Travel Guide
Planning a trip to this amazing country should be an exciting experience, but it can also be overwhelming if you don’t know where to start.
Fortunately, we’ve got some tips to make planning your Italian holiday a breeze. Let’s take a look at what you need to do before booking that flight!
Step 1: Pick your Destination(s) and Accommodations
The first step when planning any trip is deciding where you want to go and where you want to stay. Are you looking for a romantic getaway in Venice? Or would you rather explore ancient ruins like those in Pompeii?
Based on your personal style you can customize any of the 3 itinerary samples above.
Once you’ve selected a destination, we recommend making hotel or Airbnb reservations early to avoid disappointment.
Step 2: Consider Your Transportation Options
Once you know where you want to go, it’s time to think about how you plan on getting there.
Rome and Milan are perfect entry points to the country.
But…Italy also has several major airports and high-speed trains that make traveling between cities relatively easy.
You could also rent a car and navigate around the country on your own schedule if that appeals more than relying on public transportation. But keep in mind in most cities and even on the Amalfi driving, and parking are a hassle.
Instead consider small group tours to make the most of your visit.
Whatever method of transportation works best for your needs, be sure to book it as soon as possible so that everything is set for when you arrive.
Step 3: Make Plans for Sightseeing and Activities
Italy is full of historical sites, beautiful scenery, delicious food, and other attractions worth exploring while visiting the country. Research which places are must-sees during your stay—and then make sure they are part of your itinerary!
Book tickets ahead of time if necessary (or make reservations) so that nothing gets missed during your travels.
And don’t forget about booking tours with local guides who can provide insider knowledge into the areas being visited.
Step 4: Budget
You can make your trip to Italy as affordable as you want, or splurge!
Italy is not one of the most expensive countries in Europe, and by visiting in the off-season and choosing smaller towns to explore you can keep your travel expenses low.
- Plan ahead: By planning ahead for your trip to Italy, you can save hundreds (if not thousands) of dollars. Booking flights and accommodations in advance is one way to save money, as is researching restaurants and attractions before you leave home.
- City transport passes: You can also take advantage of discounts offered by certain hotels and attractions if you book far enough in advance. Additionally, many cities throughout Italy offer discounted passes for multiple attractions—be sure to look into these before booking individual tickets for each attraction separately.
- Be flexible: We do recommend staying at a centrally located hotel, but this will require a moderate budget. If you want to keep expenses lower, you can look at hostels or Airbnbs outside major tourist centers. Note that cities charge a tourist tax, which is levied per person, per day in hotels. It is to be paid in cash when you check out. Tax amount varies by the city administration.
- Eat Like a Local: Eating is one of the best ways to immerse yourself in the culture when traveling abroad—and it doesn’t have to break the bank either! One way to save money on food without sacrificing quality is by eating like a local whenever possible. Instead of dining at touristy restaurants with inflated prices, hit up local cafes (trattorias) for cheap yet delicious meals that will give you an authentic taste of Italian cuisine (and maybe even some insider tips from locals). A coperto (charge of 1-3 euros) is real, and it is usually added to any sit-down restaurant or where servings of bread and, oil is made available at the beginning of the meal.
Step 5: Packing for your trip to Italy
Here is the Italy packing list to ensure your trip is stress-free and enjoyable.
- Clothing: Since each region of Italy has its own climate, it’s important to pack accordingly. For summer trips, light layers are best, such as cotton shorts and t-shirts during the day, and a lightweight jacket for cooler evenings.
- For winter visits, pack warmer options like jeans, sweaters, and a coat or jacket with a hood that can protect from rain. You may also want to bring an umbrella if visiting during the rainy season (November –February).
- When it comes to shoes, comfortable sneakers are essential for sightseeing all day long – but don’t forget dressy shoes if you plan on going out at night!
- And sun protection essentials – hats, sunglasses, and sunscreen are must-haves!
Other travel essentials
In addition to clothing necessities, here are some travel essentials that will come in handy while traveling around Italy:
- a good camera
- reusable water bottle
- Universal adaptor
- phone charger
- passport/visa documentation (if required)
- credit cards/cash; medications/first aid supplies
Italy is a beautiful country teeming with vibrant culture, exquisite cuisine, and spectacular sights.
From the bustling streets of Rome to the peaceful canals of Venice, there’s so much to explore!
And don’t forget to sample as much of the local cuisine as possible—olive oil-based kinds of pasta and fresh seafood are must-tries!
No matter what type of traveler you are, an Italian vacation will provide an unforgettable exploration into one of Europe’s most treasured countries.
Pin: 2 weeks in Italy itinerary with Amalfi Coast: Italy Travel Guide
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