14 Days In Italy - 5 Unique Itineraries

Frequently topping polls of the most beautiful countries in the world, Italy is a diverse destination that deserves repeat visits. That said, it’s perfectly possible to pack plenty of unforgettable experiences into a 2-week journey. The question is, how to choose where to go? Read on to discover our unique, fully customizable 14 days Italy itineraries.

See our 10 days in Italy itineraries below, or get inspired by duration: 5 days - 7-days - 10 days - North Italy - South Italy

Itinerary #1: From Venice to Florence: A Grand Tour of Northern Italy

From the canals of Venice and the coastline of Cinque Terre to the designer boutiques of Milan and the streets of Florence, Northern Italy has plenty to offer. Experience it all with this comprehensive 14-day trip.

On the first day, you will be transferred to your hotel. On the second day, you will be met by a private guide and taken on a beautiful Venice city tour. On the third day, you will embark on a trip to the enchanting islands of Burano and Murano.

The fourth day is reserved for exploration and leisure in Venice. On the fifth day, you will enjoy a journey by train, arriving in Milan. The remainder of the day is yours to explore Milan. Your guide will accompany you on a walking tour of Milan on the sixth day.

Embark on a train journey to Como on the seventh day. Take advantage of the day to soak up the atmosphere of this beautiful region. On the eighth day, you will enjoy a short ride to Lugano, Switzerland. On day nine, treat yourself to a boat trip on Lake Como. Then enjoy a leisurely tenth day.

Your driver will transfer you to the railway station on the eleventh day for your onward journey to Cinque Terre. Embark on an exciting adventure to explore the picturesque villages of Cinque Terre on day twelve.

The thirteenth day is yours to spend at your leisure. On day fourteen, you will be transferred to the airport for your departure flight. Read more.

Gondolas in Venice © Shutterstock

Itinerary overview

Check this overview of the 14 days Italy itinerary.

Day one

Arrival in Venice
Overnight in Venice

Day two

Sightseeing tour in Venice
Overnight in Venice

Day three

Murano and Burano boat tour
Overnight in Venice

Day four

Free day in Venice
Overnight in Venice

Day five

Train to Milan, and free time in the city
Overnight in Milan

Day six

Sightseeing tour in Milan
Overnight in Milan

Day seven

Train to Lake Como
Overnight in Como

Day eight

Lugano and Lakeside villages
Overnight in Como

Day nine

Lake Como boat tour
Overnight in Como

Day ten

Free day in Como
Overnight in Como

Day eleven

Train to Cinque Terre
Overnight in La Spezia

Day twelve

Exploring Cinque Terre and around by train
Overnight in La Spezia

Day thirteen

Free day in Cinque Terre
Overnight in La Spezia

Day fourteen

Transfer and departure from Florence

Interested? Don't miss the opportunity to book this trip now.

Cinque Terre National Park UNESCO World Heritage Site, Liguria, Italy

Itinerary #2: classic Italy - Rome, Florence & Venice

This 14-day Itinerary is for everyone - learn how to cook pasta in Rome, sample the best gelato in Florence, hike Cinque Terre and explore Venice on your own. This trip is packed with highlights for the whole family.

Rough Guides tip: buy this trip as a Guidebook in our shop.

On day one you'll be transferred to your hotel, and the rest of the day is yours to enjoy at leisure. The second day is dedicated to the Colosseum and Forum Romanum.

Join a small group cooking tour on the third day. On day four you will travel to Florence via high-speed train. Explore Florence leisurely on an e-bike on the fifth day.

Join a cooking class in central Florence on the sixth day of the journey. On day seven you will experience the beauty of Chianti's rolling hills and indulge in its flavours.

Take a regional train from Florence to La Spezia and enjoy the eighth day at leisure. Enjoy a guided hike from Monterosso to Corniglia, experiencing the stunning coastal Blue Trail on day nine.

Day ten is for leisure, exploring and relaxing.

Travel to Venice by train on day eleven and experience a private walking tour of the city. Take advantage of day twelve, and spend it at leisure in Venice. Enjoy day thirteen at leisure, bidding farewell to Italy.

Your final day concludes with a private transfer from your hotel to the airport for your departure flight. Read more.

Colosseum, Rome © Farbregas Hareluya/Shutterstock

Colosseum, Rome © Fabregas Hareluya/Shutterstock

Itinerary overview

Check this overview of the 14 days Italy itinerary.

Day one

Arrival in Rome
Overnight in Rome

Day two

Colosseum half-day tour
Overnight in Rome

Day three

Traditional cooking class & market visit
Overnight in Venice

Day four

Transfer to Florence
Overnight in Florence

Day five

E-bike tour of Florence
Overnight in Florence

Day six

Traditional Pizza & Gelato making
Overnight in Florence

Day seven

Chianti wines and olive oil tour
Overnight in Florence

Day eight

from Florence to Lerici - La Spezia region
Overnight in Lerici

Day nine

Sentiero Azzurro hiking tour
Overnight in Lerici

Day ten

Day at leisure at Lerici
Overnight in Lerici

Day eleven

Train to Venice
Overnight in Venice

Day twelve

Venice walking tour and gondola ride
Overnight in Venice

Day thirteen

Day at leisure
Overnight in Venice

Day fourteen

Transfer to the airport

Feeling curious? Take a step forward and book this trip now.

Uffizi art gallery in Florence, Tuscany, Italy

Itinerary #3: highlights of Italy - Rome, Amalfi Coast, Cinque Terre and more

This 2 week Italy itinerary is nothing short of highlights: spend the first few nights in the capital city of Rome before moving down south to Naples. From here, you will discover the Amalfi Coast before heading to Florence.

On the first day, you will be collected at the airport and transferred to your hotel. Explore the Colosseum and Forum Romanum in a small group tour on the second day.

On the third day, you will discover the Vatican on a half-day tour. Travel to Naples by train and experience the birthplace of Pizza on day four.

On day five you will join a local guide to explore the heart of Naples. Visit Pompeii and Mount Vesuvius on day six.

A journey along the picturesque Amalfi Coast awaits you on day seven. Board a high-speed train to Florence on the eighth day. On day nine embark on a guided tour of Florence.

Travel to La Spezia, and enjoy your tenth day in leisure time. On day eleven, you will join a full-day tour of Cinque Terre with a private guide and a Cinque Terre card.

Days twelve and thirteen a dedicated to Milan. Take a train to Milan and spend the day at leisure. Then explore Milan on a group tour.

Depart from Milan on the last day of your Italian trip with a private transfer to the airport or train station, bidding farewell to Italy. Read more.

Positano, Italy. Amalfi Coast © iacomino FRiMAGES/Shutterstock

Itinerary overview

Check this overview of the 14 days Italy itinerary.

Day one

Arrival in Rome
Overnight in Rome

Day two

Colosseum half-day tour
Overnight in Rome

Day three

Vatican half-day tour
Overnight in Venice

Day four

Transfer to Naples
Overnight in Naples

Day five

panoramic tour in Naples
Overnight in Naples

Day six

Pompeii & Vesuvius with wine tasting or pizza lunch
Overnight in Florence

Day seven

Sorrento, Positano & Amalfi day trip
Overnight in Naples

Day eight

Transfer to Florence
Overnight in Florence

Day nine

Transfer to La Spezia
Overnight in Lerici

Day ten

Day at leisure at Cinque Terre
Overnight in Lerici

Day eleven

Exploring Cinque Terre and around
Overnight in Lerici

Day twelve

Transfer to Milan
Overnight in Milan

Day thirteen

Best of Milan walking tour
Overnight in Milan

Day fourteen

Transfer to the airport in Milan

Looking for an unforgettable experience? Don't waste time, book this trip now.

bridge-naviglio-canal-milan-italy-shutterstock_215803660

Bridge Naviglio, Milan, Italy @ Shutterstock

Itinerary #4: A delightful family journey through Italy

Embark on a remarkable 14-day family adventure through Italy, immersing yourselves in a world of culinary delights, historical wonders, and breathtaking landscapes.

Arrive in Rome on day one, where you will be transferred to your hotel. On the second day, join a small group tour of the Colosseum and Forum Romanum. Day three promises an exciting culinary experience as you join a small group cooking tour in Rome.

Travel to Florence via train on the fourth day. On day five, embark on an e-bike tour of Florence in a small group. Day six offers a hands-on experience as you join a 3-hour cooking class in central Florence.

Indulge in the beauty of Chianti's rolling hills on day seven with a half-day tour. Take a regional train from Florence to La Spezia, and enjoy the eighth day at your leisure.

On day nine, go on a privately guided hike from Monterosso to Corniglia, traversing the stunning coastal Blue Trail. Day ten invites you to explore and relax at your own pace.

Travel to Venice by train on day eleven and embark on a private walking tour. Make the most of day twelve, spending it at leisure in Venice.

On day thirteen, enjoy a day of leisure, bidding farewell to Italy on your own terms. Conclude your Italian adventure on the final day with a private transfer from your hotel to the airport.

St Peter Cathedral, Vatican, Rome, Italy @ Shutterstock

Itinerary overview

Check this overview of the 14 days Italy itinerary.

Day one

Arrival in Rome
Overnight in Rome

Day two

Colosseum and Forum Romanum tour
Overnight in Rome

Day three

Traditional cooking tour in Rome
Overnight in Rome

Day four

Transfer to Florence
Overnight in Florence

Day five

E-bike tour of Florence
Overnight in Florence

Day six

Traditional Pizza & Gelato cooking class in Florence
Overnight in Florence

Day seven

Chianti wines and olive oil tour
Overnight in Florence

Day eight

Transfer to Cinque Terre
Overnight in Cinque Terre

Day nine

guided hike from Monterosso to Corniglia
Overnight in Cinque Terre

Day ten

Day at leisure at Cinque Terre
Overnight in Cinque Terre

Day eleven

Train to Venice
Overnight in Venice

Day twelve

Day at leisure
Overnight in Venice

Day thirteen

Venice islands
Overnight in Venice

Day fourteen

Transfer to the airport

Cathedral of Saint Mary of the Flower in Florence © Shutterstock

Itinerary #5: Experience the splendours of Northern Italy

Experience a mesmerizing 14-day Italy itinerary through the enchanting region of Northern Italy. Explore its captivating history, breathtaking landscapes, and cultural gems.

On the first day, you will arrive at Venice's Marco Polo Airport, where you will be transferred to your hotel. On the second day, indulge in a delicious breakfast before a private guided tour of Venice.

On the third day, venture out to the captivating islands of Burano and Murano. Take the fourth day to explore Venice at your own pace.

On the fifth day, bid farewell to Venice and go on a comfortable train journey to Milan. Your sixth day begins with a captivating walking tour of Milan.

Journey to the picturesque region of Como on the seventh day. On the eighth day, continue your exploration with a short ride to Lugano, Switzerland, a town nestled on the shores of Lake Lugano.

Day nine presents an opportunity to indulge in a guided boat trip on Lake Como. On the tenth day, enjoy a leisurely pace in one of the world's most beautiful destinations.

Your driver will transfer you to the railway station on the eleventh day, where you will start a scenic train journey to Cinque Terre. Spend the twelfth day exploring the picturesque villages, hiking along the rugged coastline.

On the thirteenth day, enjoy a day of leisure, allowing you to relax, explore more of Cinque Terre. Finish your trip on day fourteen as you are collected and transferred to the airport.