The Perfect Three-Week Itinerary for Your First Visit to Italy!

Like this article? Share it with your friends!

Looking for the perfect three-week itinerary for your first visit to Italy? You’ve come to the right place!

From cities brimming with history to colorful little coastal towns, and from art and architecture gems to beautiful beaches and charming country roads, Italy has much to offer every type of traveler.

And who can ignore the pasta, pizza, Prosecco and gelato?

But there is just so much to see and do that planning your first visit to Italy can be both overwhelming and time-consuming. It was for me!

So I thought I’d share our itinerary, to help you if you are looking for the perfect 3-week itinerary for your first visit to Italy!

Our primary goal for our first visit to Italy was to check off our bucket-list art and architecture items. So the Big Three cities of Venice, Florence and Rome anchored our three-week itinerary.

In addition, we wanted to experience a little bit of coast and some time in the Tuscan countryside, so we added in the Ligurian Coast (the Cinque Terre!), the Amalfi Coast, and the Val d’Orcia. We started our trip in Venice and flew back home from Naples.

If you are planning a shorter visit to Italy, be sure to check out our suggestions for 10-day Italy itineraries!

And now, here is our perfect three-week itinerary for your first visit to Italy:

DAYS 1-3 OF YOUR 3-WEEK ITALY ITINERARY: VENICE

Plan on arriving in Venice no later than mid-morning on Day 1, to maximize your time here. You’ll be dealing with jet lag if you’ve flown in from another time zone. You will have two days in Venice: two half-days and one full day, to enjoy this aging but still gorgeous city.

Here are some Venice experiences you must not miss:

Touring the Basilica di San Marco and the Doge’s Palace

The two most iconic attractions in Venice are the spectacular multi-domed St. Mark’s Basilica and the majestic Doge’s Palace, both located on the famous St. Mark’s Square.

This small-group tour is an efficient way to see both sights! It includes access to the terraces of St. Mark’s for gorgeous views, and you can opt for early access to the Doge’s Palace. With a knowledgable guide, you won’t miss things of import.

Check pricing and availability on this skip-the-line tour of St. Mark’s and the Doge’s Palace now!

Or opt for this highly-rated small-group tour, which also includes a gondola ride, another bucket list Venice experience.

Sunrise at the Piazza San Marco

Even if you hate waking up early, give up some early morning zzzs to catch sunrise at the Piazza San Marco. It’s worth the sacrifice!

You’ll be able to enjoy the famous square with just the pigeons and a few other early risers for company. You’ll be able to actually see all the beautiful architecture without being rocked by the sea of people that collect here later in the day.

And seeing the sun’s rays light up the buildings along the Grand Canal on your way to the Piazza is a memory you will cherish forever.

Getting Lost in Venice

No visit to Venice would be complete without getting lost in the quiet outlying districts of Venice.

Dorsoduro and Canareggio (which contains the Jewish Ghetto) are districts to consider for your aimless wandering.

Take the time to stroll the little streets. Cross little bridges over side canals and linger a while in the little piazzas, to watch children play on the cobblestones and residents going about their day.

This is your glimpse into the real Venice!

Part-Day Trip To Murano and Burano

Murano is a group of islands famous for its blown glass.

All the glass-blowers from Venice were reportedly banished to Murano, to prevent an accidental fire from destroying Venice.

Among the things to do in Murano, you can wander the pretty streets, browse the glass shops, watch an artisan blow glass, and pose for a photo by the striking Comet Star glass sculpture.

Burano is famous for its brightly colored houses, and for its traditional lace. Your photos of Burano will light up your Instagram feed!

Murano and Burano, sometimes in combination with Torcello, make for one of the most popular day trips from Venice. You can visit on your own, or on a guided tour.

Visiting San Giorgio Maggiore

San Giorgio Maggiore is the little island you can see across from the Piazza San Marco, with a tower that looks exactly like the Campanile of Venice.

Head to this little island by vaporetto and go up to the top of the tower for beautiful views of the Venetian skyline and the Piazza San Marco.

You’ll also get stunning views of Giudecca, another of the outlying islands in the Venetian archipelago.

READ MORE: HOW TO SPEND TWO PERFECT DAYS IN VENICE

On Day 3, take an afternoon train to La Spezia on the Ligurian Coast of Italy. We use Omio to book train travel in Europe!

From La Spezia, a local bus will bring you to the little coastal town of Lerici, your home for the next two days.

DAYS 4-5 OF YOUR 3-WEEK ITALY ITINERARY: THE LIGURIAN COAST

Home to the renowned Cinque Terre towns, the Ligurian Coast also serves up delectable regional cuisine…it’s the area where Genovese pesto was born!

In this part of Italy, the towns are the attractions, so just wander around and enjoy the beauty all around you!

Exploring the Cinque Terre

If you’re into food, wine, great views, hiking or photography, the five Cinque Terre towns of Riomaggiore, Manarola, Corniglia, Vernazza and Monterosso al Mare will make you swoon with delight.

We explored the towns over two days, the first day by local train and the second day by boat.

The towns are picture postcard perfect, with colorful houses tumbling down cliffs and terraced fields cut into hillsides.

The area is famous for its wine, honey and basil. Fresh fish is plentiful. People either farm or fish, but tourism has taken over the region, making the towns extremely crowded in season.

But definitely a must-visit on your first trip to Italy!

READ MORE: TWO DAYS IN THE MAGICAL CINQUE TERRE

Exploring Portovenere

This (somewhat) lesser known little town on the Bay of Poets stole our hearts.

If you take the ferry from Lerici to the Cinque Terre, Portovenere is your first stop. Its waterside homes are tall and jammed together. In earlier times, the design acted as a defense for its residents.

The Chiesa di San Pietro, built on a high rock overlooking the water, offers fabulous photo ops.

The arches in the compound frame the beautiful blue Ligurian Sea, and the unassuming black-and-white church facade looks stunning against a blue sky.

Discovering Lerici and San Terenzo

The adjoining coastal towns of Lerici and San Terenzo offer the colorful houses on hillsides characteristic of the Ligurian Coast, as well as gorgeous views over the Bay of Poets.

Each little town has a castle, and the castle-to-castle walk on the promenade next to the water is a great way to get some exercise away from the busy Cinque Terre.

The area offers less crowded hiking trails, beaches, and a more laid-back experience of the Ligurian Coast, for some chill time in between hectic days.

READ MORE: LERICI AND PORTOVENERE

On Day 5, take an evening train to Pisa, for a brief stop to see the Leaning Tower before heading to Florence.

We deposited our bags at the Pisa Centrale train station and walked to the Field of Miracles, pausing to take photos at a bridge over the peaceful Arno River.

The Field of Miracles is home to Pisa’s Duomo complex…the cathedral, the Leaning Tower, the Baptistery, and the cemetery. We were lucky to have a spectacular sunset the evening we visited!

After you look around and take photos, you can take a taxicab back to the station. It cost us about eight euros. Next, on to Florence, the cradle of the Renaissance!

DAYS 6-9 OF YOUR 3-WEEK ITALY ITINERARY: FLORENCE

As John Ruskin said in his Mornings in Florence, when you visit Florence, “you will begin to wonder that human daring ever achieved anything so magnificent.”

There is just so much to gawk at and experience in Florence that four months wouldn’t be enough, let alone four days. But here are some top sights and experiences you will love:

Climbing a Tower to Enjoy Views of the City

Florence has not one, but several structures you can climb, for those magnificent views of the red rooftops: from the Duomo di Firenze and Giotto’s Campanile (the Bell Tower right next to the cathedral), to the Torre di Arnolfo at the Palazzo Vecchio, and the Torre di San Niccolò,

We chose the Arnolfo Tower at the Palazzo Vecchio for those classic photos of the Dome and the Bell Tower next to each other.

But if you are up for the Duomo climb, go for it, and be sure to book your time slot in advance! This highly rated tour, which includes the dome climb, is a great option if you also want to learn about this fascinating cathedral.

Doing a Gelato Crawl

If you love gelato, you will never want to leave Florence. Opt for gelato artigianale, generally made fresh at the store with natural ingredients. Florence boasts a number of acclaimed gelateria, some of which have been in business for decades.

From the impeccably-made classics at Vivoli to the innovative flavor combos at Gelateria dei Neri, you will not want for choices in Florence!

READ MORE: MY TOP TEN GELATO PLACES IN ITALY 

Getting Your Art Fix at the Uffizi Gallery

The masterpieces in the Galleria di Uffizi are too numerous to be able to enjoy in just one visit.

So do your research before your visit and pick some favorites that you definitely do not want to miss. It can become overwhelming as you progress through the gallery, so give yourself enough time to take some short breaks in between rooms.

Tip: This gallery contains Doni Tondo, the only completed panel painting by Michelangelo that you can see today, so make sure you don’t miss it!

We highly recommend a guided tour, to get the most out of your visit to the world-famous gallery.

Exploring a Church…or Two!

Museums are not the only places where great art and architecture can be seen in Florence.

Apart from the Duomo di Firenze with its famous frescoes by Vasari, the Basilica di Santa Croce is well worth exploring.

The Santa Croce church holds the tombs of greats such as Michelangelo and Galileo, as well as marvelous frescoes by a number of artists.

Enjoying a Green Break in a Garden

Take a break from intense doses of art to wander in one of the green spaces in the city. We wandered around in the Boboli Gardens, across the River Arno.

The Giardino Bardini and the Rose Garden below the Piazzale Michelangelo, also both in the Oltarno District across the river, are other options.

Both gardens have spectacular bloom displays in season, as well as spectacular views of the city. The wisteria bloom in the Bardino Gardens is a coveted time to visit!

Watching the Sun Set Over Firenze

Take the bus to the Piazzale Michelangelo or to the Basilica di San Miniato al Monte one evening to watch the sun set over the city and the lights come on. It’s an experience you will never forget!

If you get up to the church a little earlier in the evening, you can also explore the interior…it’s gorgeous!

READ MORE: 10 BEST THINGS TO DO ON YOUR FIRST VISIT TO FLORENCE

DAY 10 OF YOUR 3-WEEK ITALY ITINERARY: SIENA

On Day 10, take an early morning bus to Siena. One day in Siena will allow you to enjoy its major sights, but you want to give yourself enough time to experience its medieval charm.

Here are the must-not-miss experiences in Siena:

Taking a Stroll in the Piazza del Campo

Siena’s town square is one of the most magnificent in Europe. It’s large enough that Siena holds a horse race (the Palio) twice each year on a track set up around the perimeter of the plaza! 

Here you’ll see the Torre del Mangia, which was the tallest tower in Italy when it was built. You can climb to the top for panoramic views!

Right next to it is the Palazzo Pubblico, Siena’s Town Hall.

The Piazza is a great place to stroll first thing in the morning, when it’s relatively empty, or after dinner, when it is bustling and you can enjoy a post-dinner gelato while people watching.

Exploring the Duomo Complex

The Duomo di Siena complex includes not just the beautiful cathedral, but also a museum, a crypt, a wall you can climb for fabulous views, and the Baptistery.

All of these sights are stunning and will take up pretty much the rest of your day.

Tip: Do not miss the Piccolomini Library when inside the Duomo! It is accessed through an entrance about mid-way on the wall to your left as you walk into the cathedral.

READ MORE: ONE DAY IN SIENA

DAY 11 OF YOUR 3-WEEK ITALY ITINERARY: THE VAL D’ORCIA

Siena makes a great base from which to explore some of the surrounding Tuscan countryside as a day trip. 

We hired a car and driver for the day as a splurge because my husband and I both wanted to relax and enjoy the views from the road.

But you can also rent a car for the day and drive yourself if that’s your preference, the plus being that you can pull over when and where you choose!

We chose to tour the Val d’ Orcia, one of Tuscany’s six UNESCO World Heritage Sites. Here are some of the highlights from this drive:

Historic Abbeys and Chapels

Abbazia Sant’Antimo is a beautiful abbey set in the midst of olive groves and vineyards.

It’s an active monastery, and you can listen to the monks doing Gregorian chanting if you visit at an appropriate time of day.

I loved the interior of the abbey: it is rustic and simple yet with beautiful lines. A change of pace from the ornate intricate interiors of the Duomos in the larger towns and cities!

You will be entranced when you see the little Chapel of the Madonna di Vitaleta. This is the iconic chapel that features in so many images of the Tuscan countryside!

Charming Hill Towns

We stopped to tour three towns: Montalcino, Pienza, and Montepulciano.

All of them offer commanding views of the countryside below, along with little streets lined with shops selling, among other things, local wines and cheeses.

Pienza is famous for its Pecorino cheese, Montalcino for its Brunello wine, and Montepulciano for its Vino Nobile.

Each town offers architectural sights, but just wandering around to absorb the charm of these little hillside retreats is a wonderful way to spend your time.

Just being there is enough to experience la dolce vita!

The Tuscan Countryside

After months of drooling over photos of the Tuscan countryside with the rows of cypress trees snaking across the landscape, it was sheer heaven to be able to actually see it in person.

We visited in the fall, when the hillsides were bare.

The gray clays, with lines of trees curving through it, made for some dramatic scenes.

Spring is another lovely time to visit, when the hillsides are fresh green, and wildflowers provide color.

Both Siena and the Val d’ Orcia are popular day trips from Florence, if you’d like to limit the number of times you move.

READ MORE: A DRIVE THROUGH THE VAL D’ORCIA

DAY 12 OF YOUR 3-WEEK ITALY ITINERARY: ORVIETO

On Day 12, catch an early morning train to Orvieto for a taste of the neighboring region of Umbria. Orvieto is a hill town built on a volcanic rock. It is a beautiful little town and can be easily explored in one day.

If you’d rather not move for just one night, head straight to Rome and visit Orvieto for the day. Orvieto is one of the most popular day trips from Rome.

Here are some must-not-miss experiences in Orvieto:

Exploring the Duomo di Orvieto

With a beautiful glitzy facade and a stunning interior, the Duomo definitely deserves top billing on the list of sights you do not want to miss in Orvieto.

Luca Signorelli’s fresco cycle in the San Brizio Chapel is the pièce de résistance, but there are numerous other details to admire.

Shop for Ceramics

After you explore the Duomo, spend some time browsing the ceramic shops in the plaza. Orvieto is known for the quality of its ceramics.

You can also look out for shops as you wander the side streets.

Pozzo di San Patrizio

The well of St. Patrick is an engineering marvel built in the early 1500s.

At the time, the pope was in hiding in Orvieto and wanted to augment the town’s water supply in the event of a siege by the Holy Roman Emperor.

The central part of the well is surrounded by two ramps in a double helix design, with the two never meeting, so that mules carrying bags of water could go up or down without facing oncoming traffic. Genius!

You can go down the ramp to the bottom of the well and climb back up the other ramp, just like the mules did in times past.

READ MORE: ONE DAY IN ORVIETO

DAYS 13-16 OF YOUR 3-WEEK ITALY ITINERARY: ROME

On Day 13, take an early morning train to Rome, the Eternal City.

“Methinks I will not die quite happy without having seen something of that Rome of which I have read so much,” said Sir Walter Scott, and I think we would all agree!

It is thrilling to walk the streets in the historic center of Rome and see your history lessons from school come to life.

Just like Florence, Rome has so much art, history and architecture to offer that a few days will just allow you to see some highlights.

Here are some must-not-miss experiences for your Rome itinerary:

Visiting the Galleria Borghese

We visited only one museum in our time in Rome and that was the Borghese Gallery.

It houses many of Bernini’s famous works, including the Rape of Proserpine, Apollo and Daphne, and David.

It also contains many of Caravaggio’s masterpieces, including Sick Bacchus and Boy with a Basket of Fruit.

Just these few works make the price of admission worthwhile if you are an art buff.

You have to reserve your slot for the Borghese Gallery well in advance, and show up on time, because they admit a limited number of visitors in each time slot. There’s plenty of time to admire the art and take photos, and I loved our visit here.

Climbing up the Dome of St. Peter’s Basilica

Even with an elevator that saves 300+ steps, I found the trudge to the top of St. Peter’s Dome leg-busting. There are 551 steps in all, if you are thinking about doing all of them! But, oh, the views from the top!

All of Rome is spread out below you, and you can walk around the viewing area and take in the panoramas on all sides.

Gawk at the Interior of Saint Peter’s Basilica

The interior of the Basilica is, of course, not to be missed either!

It houses, among other great works of art, Michelangelo’s Pietà. The folds of the Virgin’s robes look so real that it is difficult to tell that it’s made of marble.

There’s also Bernini’s baldachhino to admire: it’s a huge sculpted bronze canopy over the high altar.

The stunning square in front of the church was designed by Bernini, and Michelangelo designed the dome.

Touring the Vatican Museums

It’s worthwhile taking a guided tour of the Vatican Museums, so you don’t miss any of the highlights, and also get some context and explanations for the bewildering amount of art you view.

If you choose a tour with the option, you can get in early to see the Sistine Chapel, before it’s officially open.

We did the Walks of Italy tour and enjoyed it very much. The crowds can get suffocating during the day, so be warned.

Visiting the Ancient Rome Sights

Allow for a full morning or afternoon to visit the Colosseum, the Roman Forum and Palatine Hill, and the Pantheon. If you want to see the inside of the Colosseum, buy your tickets in advance to conserve time, or opt for a guided tour.

I loved wandering around the ruins of the Roman Forum. We also climbed to the top of Palatine Hill for views of the ruins and the city.

The Pantheon, the only one of the three that’s still preserved in its entirety, is an amazing structure. Two thousand years after it was built, it still stands solid and functions today as a church.

Enjoying a Night Tour of the Sights of Rome

The monuments of Rome look amazing at night, when they are lit up. After dinner one evening, take the time to walk around the historic center, enjoying the sights in a whole different light!

READ MORE: THE BEST THINGS TO DO IN ROME!

DAYS 17-20 of Your 3 weeks in Italy: SORRENTO

On Day 17, take an early train to Naples. Pre-book a private transfer from the Naples train station to Sorrento, your base for the last leg of your three week Italy itinerary, or from spring to fall, take the Campania Express or the Circumvesuviana.

You can do day trips from Sorrento to various places in this part of Italy.

Here are the highlights you’ll want to include:

Exploring Sorrento

Spend the remainder of day 17 exploring the town of Sorrento, with its bustling piazzas and streets lined with shops selling everything limone.

From the Piazza Vittoria, where you can enjoy the view from its scenic overlook, you can walk down to the Marina Grande, Sorrento’s harbor.

Driving the Amalfi Coast

On Day 18, you will visit the spectacular Amalfi Coast.

We hired a car and driver for this day trip, so that both my husband and I could sit back and enjoy the stunning views without needing to worry about driving the notoriously difficult cliff-hugging road.

With wonderful water views all along the drive and several pretty towns to explore, this is definitely a must-do drive. Stop to explore pretty Positano, amazing Amalfi town, and romantic Ravello. You won’t be able to stop taking photos!

READ MORE: DRIVING THE SPECTACULAR AMALFI COAST OF ITALY

Spending a Day on the Isle of Capri

On your itinerary for Day 19 is a day trip to the beautiful Isle of Capri, just a short ferry ride from Sorrento.

Capri is sometimes labeled a tourist trap, but if you move away from the main piazza in Capri Town and explore the rest of the island, you will be pleasantly surprised by its quiet charm and extravagant beauty.

The island has two towns, Capri and Anacapri. Both offer beautiful walks, gorgeous gardens, and breathtaking views of the famous Faraglioni rocks and the deep blue waters around the island.

You can also do a boat tour, to include or not include the much-touted Blue Grotto.

READ MORE: ONE DAY IN CAPRI

Visiting the Ruins of Pompeii and Herculaneum

Our original plan, when developing our perfect three-week itinerary for Italy, was to visit Pompeii and Herculaneum on our last day.

But unseasonably warm weather and a spot of ill-health caused us to change our plans that morning, and we ended up doing a second trip to Capri, which we thoroughly enjoyed.

But Pompeii and Herculaneum are both on our list for our next visit, as is a visit to Vesuvius, the volcano that destroyed the two ancient towns.

If you do plan to visit, and you have the time on the day of your arrival in Naples or departure from Naples, you might want to pop into the archaeological museum in Naples, which houses many artifacts from the two sites.

And that brings us to the end of the perfect three-week itinerary for your first visit to Italy!

Day 21: Depart for home or your next destination!

On your final day, take your pre-arranged transfer to the Naples airport for a flight back home.

THREE WEEK ITINERARY FOR YOUR FIRST VISIT TO ITALY: OVERVIEW

Days 1-3: Venice
Days 4-5: The Ligurian Coast (Cinque Terre, Lerici and Portovenere)
Days 6-9: Florence
Days 10-11: Siena, with a day trip to the Val d’ Orcia
Day 12: Orvieto
Days 13-16: Rome
Days 17-20: Sorrento, with day trips to the Amalfi Coast, Capri and Pompeii
Day 21: Depart from Naples

With less time in Italy…

Don’t have three weeks in Italy? If you have two weeks, I suggest still covering Venice, Florence and Rome, and adding in one of the three extensions: the Ligurian Coast from Venice, or Tuscany from Florence, or Sorrento and the Amalfi Coast from Rome.

If you have ten days, pick two of the three big cities, and any one extension. We have a round-up of more than a dozen 10-day Italy itineraries from which to choose!

With more time in Italy

If you have even more time, consider the Emilia Romagna region, where you’ll find lots of things to do in Bologna, many of which involve gastronomy! Or spend some time in the gorgeous Dolomites or at one of Italy’s beautiful lakes.

Or go further south for a few days in beautiful Puglia, or a trip down south to Sicily. Another option in the south is beautiful Sardinia.

“You may have the universe if I may have Italy,” Giuseppe Verdi is reported to have said.

And after your first visit to Italy with this perfect three-week itinerary, you will feel the same way!

When to go to Italy

It’s hot in the summer in most parts of Italy.

May-June and September-October offer great weather, but these months are part of peak season and you will feel like all the world is there with you on your trip.

I suggest mid-April to early May or mid-September to early October. You should still expect other visitors, but fewer than in peak season.

Other things to consider when Planning your Italy trip

If you are especially interested in a monument or sight, check the web site to make sure it isn’t under restoration during your planned travel time.

During our first visit, many sights were covered with scaffolding, including one half of the Rialto Bridge in Venice and the facade of the Orvieto Cathedral.

Open jaw flights might be a little more expensive but will save you from having to retrace your steps back to your starting point. Trust me, you’ll want to use every day to the fullest when in beautiful Italy.

You should make reservations for especially popular experiences prior to your arrival in Italy: for example

— the climb to the cupola of the Duomo di Firenze, Michelangelo’s David in the Accademia Gallery in Florence, the Uffizi Galleries in Florence,

— The Colosseum, the Vatican, and the Borghese Gallery in Rome,

— and the Doge’s Palace and St. Mark’s Basilica in Venice.

If you plan to visit many fee-based sights, consider passes such as the Firenze Card or the Roma Pass.

Keep your valuables safe

Rick Steves considers money-belts and tamper-proof day bags smart choices when traveling to crowded places.

Many places in Italy are very crowded, even in shoulder seasons. We took both on our trip, and it was comforting knowing our valuables were safe when we were caught up oohing and aahing at the sights or taking that perfect shot for Instagram!

Train Travel in Italy

Within Italy, trains are very convenient. High speed trains are perfect for long distances, and regional or local trains for short legs.

Freccia and Intercity trains require reservations. We booked Venice to La Spezia and Rome to Naples ahead of time.

For a lot of very useful information on train travel in Italy, click here. Trenitalia is the government-owned primary train company in Italy. Italo is the other popular train operator.

We buy Europe train tickets on Omio: the website is in English and very easy to navigate, and you will find both Trenitalia and Italo trains!

Book your Italy train travel today!

Did you find this article informative? Pin it for later reference!

Like this article? Share it with your friends!