14 days (two weeks) in Italy Itinerary

Frequently topping polls of the most beautiful countries in the world, Italy is a diverse destination that deserves — and invites — repeat visits. That said, it’s perfectly possible to pack plenty of unforgettable experiences into a well-planned 2-week vacation. The question is, how to choose where to go? Read on to discover an excellent Italy itinerary for 14 days that’ll see you discovering Milan, Venice, Bologna, Florence and the fabulously scenic Cinque Terre in immersive style.

Is two weeks in Italy enough?

As touched on above — and revealed below — having two weeks in Italy will able you to cover a lot of ground and a rich range of experiences, no matter where your interests lie.

From enjoying fine food and world-class art, to impossibly pretty walks on the wild side, the 14-day Italy itinerary detailed below is nothing but diverse as it offers an authentic taste of the country — not to mention a taste of la dolce vita! — in Milan, Venice, Bologna, Florence and the charming towns of the Cinque Terre.

Can’t quite stretch to a two-week vacation? Our 10 days in Italy itinerary has you covered.

Or, if you have even less time — and are perhaps planning to visit Italy as part of a bigger trip around Europe — our 5 days in Italy itinerary could come in handy as you plan your trip.

Keen to visit Rome? You might want to check out our fine-tuned 7-days in Italy itinerary, which kicks off in the Eternal City. 

Alternatively, if you fancy doing a deeper into certain regions of the country, browse our North Italy itinerary, and take inspiration from our Amalfi Coast itinerary.

Undecided about your vacation duration? Browse all our Italy itineraries, or talk to our local Italy experts to have them curate your perfect trip.

Day 1: Arrive in Milan and see top attractions

After arriving in Milan and checking into your hotel, waste no time in heading out to explore some of the city’s central areas for easy access to attractions. 

You could, for example, begin with visiting the iconic Duomo di Milano — one of the largest Gothic cathedrals in the world, no less. One of the best things to do in Milan this sets the tone for the duration of your 14 days Italy Itinerary.

Have a head for heights? Take the elevator or climb to the Duomo rooftop for stunning city views.

Afterwards, stroll the elegant Galleria Vittorio Emanuele II — a 19th-century shopping arcade that boasts a bounty of designer boutiques — ahead of enjoying dinner in a traditional Italian restaurant within the Galleria.

Where to stay

When it comes to choosing where to stay in Milan, first-timers might want to focus on accommodation around the Piazza del Duomo.

Located in the center of the city, it’s close to stacks of top attractions, not least the cathedral.

Talking of which, chic Room Mate Giulia is located a few steps away from the cathedral, and several rooms also come with a private outdoor terrace.

Looking for lively nightlife and a big choice of bars and restaurants? Browse accommodation in Navigli.

Day 2: Explore Milan’s magnificent art

Day 2 of this 14 days Italy Itinerary is largely devoted to discovering Milan’s incredible art, beginning with seeing Leonardo da Vinci’s The Last Supper in the refectory of the Dominican convent of Santa Maria delle Grazie, a UNESCO’s World Heritage Site. 

Note that booking tickets is compulsory, and you'd be wise to bag yours well in advance.

Next, head to the Sforza Castle (Castello Sforzesco) — an historic fortress that houses some rather special art, including Michelangelo’s unfinished Pietà Rondanini.

In the afternoon, take time to explore the bohemian Brera district, stopping off in the Pinacoteca di Brera art gallery to see masterpieces by notable Italian artists, before visiting La Scala Opera House (Teatro alla Scala) — one of the world’s most prestigious opera houses. 

Come the evening, stroll to the canalside Navigli district to enjoy a tasty traditional Milanese aperitivo before dinner. 

Day 3: Transfer from Milan to Venice

Day 3 will see you rise early to transfer from Milan to magical Venice.

How to get from Milan to Venice

Take the high-speed train from Milano Centrale to Venezia Santa Lucia. Taking around 2.5 hours, the journey serves scenic views of the Italian countryside. 

Once in Venice, transfer to your accommodation via vaporetto (water bus) or a private water taxi.

After checking in, start your exploration of this enchanting city with a leisurely stroll to see the picturesque Rialto Bridge ahead of enjoying dinner at a canal-side restaurant.

Editor’s tip: read more on getting around Italy.

Where to stay

Wondering where to stay in Venice? If you’re not on a budget and want to be close to stacks of top attractions, check out places to stay around Piazza San Marco. 

St. Mark's Square, St. Mark's Basilica, and the grand Doge's Palace will be right on your doorstep, as will lots of high-end places to shop and eat.

Another good option — especially for art lovers — is to browse accommodation in Dorsoduro — you’ll be close to the Accademia Gallery and Peggy Guggenheim Collection.

Day 4: Visit Venice’s top attractions

Day 4 of this 14-day Italy itinerary will see you experiencing some of the best things to do in Venice, starting with the beautiful Basilica di San Marco on Piazza San Marco.

A bedazzlement of golden mosaics and Byzantine architecture, the Basilica also serves incredible views from its lofty terrace.

In the afternoon, take a tour of the Doge’s Palace — a Gothic masterpiece that showcases Venice’s political history — and don’t pass up the chance to walk across the iconic the Bridge of Sighs, which was formerly used to lead prisoners to their cells.

Round off your day with another iconic Venetian experience — taking a glorious gondola ride through the city’s canals ahead of dinner.

Day 5: Explore Venice’s islands and art

On day 5, we suggest exploring beyond the city itself by taking a vaporetto to Murano — an island that’s famed for its glass-making traditions.

After seeing artisans at work — and shopping for unique souvenirs — continue to Burano island. 

With its colorful houses and longstanding lace-making traditions, it’s another scenic place to pick up pretty presents for the folks back home, and to enjoy lunch.

Come the afternoon, return to Venice to visit the Peggy Guggenheim Collection in the Dorsoduro district. Set in a former palace, this remarkable modern art museum boasts works by Picasso, Pollock and Dalí.

Finally, head to Accademia Bridge at dusk to see a sublime sunset ahead of enjoying your last dinner in Venice.

Day 6: Transfer from Venice to Bologna

Day six will see you depart Venice for bella Bologna, where a (literal) feast of fabulous experiences await in Italy’s foodie capital.

How to get from Venice to Bologna

Simply take a high-speed train from Venezia Santa Lucia to Bologna Centrale. Taking around 1.5 hours, it’s a slick and scenic route, which means you’ll have time to start exploring Bologna’s historic center that same afternoon.

For example, get your bearings at Piazza Maggiore. Home to the iconic Gothic Basilica di San Petronio, this is the city’s main square.

Come the evening, take a leisurely walk through the Quadrilatero Market — an historic area filled with food shops serving local delicacies — before tucking into tagliatelle al ragù (a traditional Bolognese pasta) in a nearby trattoria.

Where to stay

First up, a word of warning — Bologna’s accommodation mostly caters for business travelers and prices can more than double during the city's peak trade-fair periods (March to early May and September-December).

Most visitors understandably opt to stay in the splendid Centro Storico, where you find everything from five-star luxury to well-heeled business hotels — all priced accordingly.

For a quieter, more affordable stay, check out the Santo Stefano neighbourhood.

Day 7: Uncover culture and cuisine in Bologna

There’s no better way to appreciate exactly why Bologna is the food capital of Italy than taking a food-themed tour or cookery class for a taste of its culinary treasures, among them mortadella, Parmigiano Reggiano and balsamic vinegar.

Many tours include stops at local markets and food producers, while cooking classes typically include lessons on how to make tortellini or lasagne.

Come the afternoon, it’s time to uncover the city’s history and culture, starting out with visiting the Archiginnasio of Bologna, the first seat of the University of Bologna.

A highlight here is the fascinating Teatro Anatomico — an 18th-century anatomical theatre.

Into art? Don’t miss the Pinacoteca Nazionale di Bologna, a renowned museum that showcases Italian masterpieces.

Day 8: Transfer from Bologna to Florence

Florence awaits on day 8 of this 14-day Italy itinerary. Think Renaissance majesty, world-class art, and out-of-this-world food.

How to get from Bologna to Florence

Take a high-speed train from Bologna Centrale to Firenze Santa Maria Novella station. 

The journey takes just 35 minutes, which means you’ll have plenty of time to explore Florence’s historic center after checking into your accommodation.

Start out at Piazza del Duomo, which is home to the magnificent red-domed Florence Cathedral (Santa Maria del Fiore) before strolling Piazza della Signoria and the Palazzo Vecchio, Florence's town hall.

Next, head to the nearby Ponte Vecchio — a charming medieval bridge lined with shops — before ending your first day in Florence with dinner at a local trattoria to sample authentic Tuscan cuisine.

Love fine food? Find out about must-try foods in Florence.

Where to stay

Good news — Florence has accommodation options to suit all tastes, as revealed in our full guide to the best area to stay in Florence. 

If you’re a first-timer — and short on time — the pretty places to stay in the Duomo area come most recommended, as you'll be right in Florence’s historic heart.  

Meanwhile, accommodation in the Uffizi area is especially great for art and culture lovers.

Day 9: Uncover art in Florence 

Day 9 is devoted to visiting some of Florence’s best museums and galleries, starting out at one of the world’s greatest art museums — the Uffizi Gallery.

Be sure to book tickets in advance — this place is always packed with folks wanting to see masterpieces by Botticelli, Leonardo da Vinci and Michelangelo.

Next, head to the Accademia Gallery to soak up remarkable Renaissance art. While Michelangelo’s David sculpture is an essential highlight, the collection of historic instruments is another fascinating must-see.

Art devotees will also want to visit the Basilica of Santa Croce. Famed for being the burial place of Michelangelo, Galileo, its Giotto frescoes and Brunelleschi’s Pazzi Chapel are also well worth seeing.

Editor’s tip: you’ll find more inspiration in our itinerary for the perfect weekend in Florence.

Day 10: Savor fresh air and flavors in Florence

Spend the morning of day 10 in the Oltrarno district — a pretty place that’s packed with artisan workshops, with the Pitti Palace former royal residence on hand to satisfy culture vultures through its museums.

We also rate taking a stroll through the fragrant Boboli Gardens, perhaps working up an appetite before heading to Mercato Centrale to spend the afternoon taking in the sights, sounds and fragrances of a bustling market that brims Tuscan specialties. 

After lunching in the market and shopping for local souvenirs — including olive oil and artisan-crafted leather goods — take a final through Florence’s ravishing Renaissance streets ahead of dinner.

Fancy exploring a little further afield? Find out about the best day trips from Florence.

Day 11: Transfer to the charming Cinque Terre

Day 11 will see you leave Florence for the captivating UNESCO-designated charms of the Cinque Terre — a clutch of five enchanting towns on the Italian Riviera.

How to get from Florence to the Cinque Terre

Spoiler alert: taking the train is the most convenient way to get from Florence to the Cinque Terre, but read on for a run-down of all the options.

By car

Day 12: Hikes and culture in the Cinque Terre

Day 12 of this Italy itinerary is devoted to soaking up the magic of the Cinque Terre through a scenic morning hike, with the Sentiero Azzurro (Blue Trail) handily connecting the villages along the coast.

A popular segment is the 2-hour (or so) trail that runs between Monterosso and Vernazza.

That said, the Vernazza to Corniglia trail is every bit as beautiful.

Later, depending on which village you arrive in at the end of your hike, spend the afternoon at a slower pace to appreciate the scenery and architecture around these parts.

Picture yourself, for example, enjoying a long lunch in the tiny village of Corniglia before strolling its charming streets and visiting the Gothic-Ligurian San Pietro Church.

Alternatively, you could take a cooking class in Riomaggiore or Manarola to learn how to make local dishes like pesto or focaccia.

Come the evening, head to Manarola’s picturesque harbour to dine and enjoy local Sciacchetrà wine while watching the village light up at dusk.

Day 13: Cinque Terre's captivating coast

Day 13 will see you enjoy that shimmering sea we’ve been raving about, with most boat tours departing from Monterosso, and including stops at all five villages. 

There’s no better way to soak up the charm of the colorful cliffside villages and dramatic coast at one fell swoop.

If you fancy taking a dip, head to Monterosso’s sandy beach or Riomaggiore’s rocky coves.

Come dusk, don’t miss the chance to round off your time in the Cinque Terre — and Italy — by heading to a viewpoint to enjoy a magical sunset. For example, the romantic Via dell’Amore coastal path between Riomaggiore and Manarola is a beautiful spot to do just that.

Not sure when to take your vacation? Read upon the best time to visit Italy.

Day 14: Return to Florence ready to depart

Day 14 marks the end of this 14 days in Italy itinerary.

If you have time, enjoy a last stroll around your base village before returning to Florence for your flight home, or to connect to your departure city. 

Final thoughts: ahead of taking the plunge, read up on how to plan a trip to Italy, and take inspiration from our Italy itineraries.

Not keen on planning? No problem! Contact our local experts to have them take care of every last detail.