How To Spend 14 Days In Italy - Five Unique Itineraries
Book your individual trip, stress-free with local travel experts
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 14-day trip. The question is, how to choose where to go? Read on to discover five unique itineraries for how to spend 14 days in Italy. Alternatively, if you’re planning to visit Italy for a week, dive into our suggested 5 day, 7 day or 10-day itineraries.
Tailor-made travel itineraries for Italy, created by local experts
Itinerary #1: From Venice to Florence: A Grand Tour of Northern Italy
From the atmospheric canals of Venice and the picturesque coastline of Cinque Terre to the trendy designer boutiques of Milan and the Renaissance-infused streets of Florence, Northern Italy has plenty to offer. Experience it all with this comprehensive 14-day trip.
On the first day upon arrival at Venice's Marco Polo Airport, you will be transferred to your hotel. After a delicious breakfast on the second day, you will be met by your own private guide and taken on a wonderful Venice city tour.
On the third day, you will embark on a memorable trip to the enchanting islands of Burano and Murano, nestled within the Venetian lagoon.
The fourth day is reserved for independent exploration and leisure in Venice. Take the opportunity to immerse yourself in the city's unique charm.
On the fifth day, you will enjoy a comfortable journey by train, arriving in Milan. The remainder of the day is yours to explore Milan at your own pace. Your guide will accompany you on a captivating walking tour of Milan on the sixth day. Discover the city's rich history and cultural treasures as you visit one of the oldest churches in the world.
Embark on a scenic train journey to Como on the seventh day. Take advantage of the day to soak up the atmosphere and charm of this beautiful region. On the eighth day, you will enjoy a short ride to Lugano, Switzerland, a picturesque town nestled on the shores of Lake Lugano.
On day nine, treat yourself to a fantastic guided boat trip on Lake Como. Then enjoy a leisurely tenth day at your own pace in one of the most beautiful destinations in the world.
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. Take the opportunity to relax, explore more of Cinque Terre. On day fourteen, you will be collected and 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.
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 with skip-the-line access in a small group tour.
Join a small group cooking tour to learn how to make traditional Roman and Italian dishes on the third day. On day four you will travel to Florence via high-speed train with included transfers.
Explore Florence leisurely on an e-bike in a small group tour on the fifth day.
Join a 3-hour cooking class in central Florence to learn the art of making traditional Italian pizza and gelato 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 on a half-day tour.
Take a regional train from Florence to La Spezia, the gateway to Cinque Terre, and enjoy the eighth day at leisure.
Enjoy a privately guided hike from Monterosso to Corniglia, experiencing the stunning coastal Blue Trail with sweeping views over the crystal clear waters on day nine.
Day ten is for leisure, exploring and relaxing at your own pace.
Travel to Venice by train on day eleven and experience a private walking tour of the city, starting from the Saint Mark's area and delving into the history of Venice's powerful maritime empire.
Take advantage of day twelve, and spend it at leisure in Venice to soak up the enchanting atmosphere.
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, marking the end of your incredible Italian adventure. Read more.
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. Tuscany and Cinque Terre await and finally - the fashion capital Milan.
On the first day, you will be collected at the airport and transferred to your hotel. The rest of the day is free to spend at your leisure. 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, including the Sistine Chapel and Vatican Museums. Travel to Naples by train and experience the birthplace of Pizza on day four. Private transfers to and from the train stations are included.
On day five you will join a local guide to explore the heart of Naples, uncovering its artistic influences and rich history. Visit Pompeii and Mount Vesuvius, two iconic sites of the Campania region on day six.
A journey along the picturesque Amalfi Coast, stopping in Sorrento, Positano, and Amalfi 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, discovering the secrets and history of the influential Medici Dynasty.
Travel to La Spezia, the gateway to Cinque Terre, and enjoy your tenth day in leisure time. Private transfers to and from the train stations are included.
On day eleven, you will join a full-day tour of Cinque Terre with a private guide and Cinque Terre card, exploring the charming coastal villages.
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, visiting landmarks like the Duomo and La Scala opera house.
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, 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. The remainder of the day is yours to enjoy at leisure. On the second day, join a small group tour of the Colosseum and Forum Romanum, enjoying skip-the-line access.
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, and settle into the heart of the Renaissance city. On day five, embark on an e-bike tour of Florence in a small group, led by a knowledgeable guide.
Day six offers a hands-on experience as you join a 3-hour cooking class in central Florence, mastering the art of making authentic Italian pizza and gelato.
Indulge in the beauty of Chianti's rolling hills on day seven with a half-day tour, immersing yourselves in the flavours of the region. Take a regional train from Florence to La Spezia, the gateway to Cinque Terre, and enjoy the eighth day at your leisure, exploring the charming towns.
On day nine, go on a privately guided hike from Monterosso to Corniglia, traversing the stunning coastal Blue Trail with sweeping views over the crystal-clear waters. 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 of the city. Make the most of day twelve, spending it at leisure in Venice to soak up the enchanting atmosphere.
On day thirteen, enjoy a day of leisure, bidding farewell to Italy on your own terms, whether it's with a final stroll through the picturesque streets or a visit to one of Venice's famed islands. 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, nestled within the Venetian lagoon. Take the fourth day to explore Venice at your own pace, wandering through its narrow alleys, browsing local shops, and savouring the delectable Venetian cuisine.
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, accompanied by a knowledgeable guide. Discover the city's rich history as you visit awe-inspiring sites such as the historic churches and immerse yourself in its artistic heritage.
Journey to the picturesque region of Como on the seventh day, relishing the serene beauty and charm of this lakeside haven. On the eighth day, continue your exploration with a short ride to Lugano, Switzerland, a town nestled on the shores of Lake Lugano, offering breathtaking vistas.
Day nine presents an opportunity to indulge in a guided boat trip on Lake Como, surrounded by stunning landscapes. On the tenth day, enjoy a leisurely pace in one of the world's most beautiful destinations.
Your driver transfers 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, and immersing yourself in the vibrant colours of Cinque Terre.
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.
St Mark's Square from the Grand Canal. Venice, Italy © volkova natalia/Shutterstock
Itinerary overview
Check this overview of the 14 days Italy itinerary.
Day one
- Arrival in Venice
- Overnight in Venice
Day two
- Guided city tour in Venice
- Overnight in Venice
Day three
- boat trip to Burano and Murano
- Overnight in Venice
Day four
- Free day in Venice
- Overnight in Venice
Day five
- Transfer to Milan
- Overnight in Milan
Day six
- Guided city tour in Milan
- Overnight in Milan
Day seven
- Transfer to the Como region
- Overnight in Como
Day eight
- Lake Lugano
- Overnight in Como
Day nine
- boat trip on Lake Como
- Overnight in Como
Day ten
- Day at leisure at Lake Como
- Overnight in Como
Day eleven
- Train to Cinque Terre
- Overnight in Cinque Terre
Day twelve
- Exploring the Cinque Terre
- Overnight in Cinque Terre
Day thirteen
- Free day in Cinque Terre
- Overnight in Cinque Terre
Day fourteen
- Transfer to the airport and departure
Cinque Terre, Italy
You might also want to browse our customisable Italy itineraries or talk to our local Italy experts.
The Rough Guide to Italy and related travel guides
In-depth, easy-to-use travel guides filled with expert advice.
Travel advice for Italy
- Eating and drinking in Italy
- How to get to Italy
- Getting around Italy: Transportation Tips
- Shopping tips for Italy
- Sports and Outdoor activities in Italy
- Travel Tips Italy for planning and on the go
- Best time to visit Italy
- How To Spend 7 Days In Italy - Eight Unique Itineraries
- How To Spend 10 Days In Italy - Eight Unique Itineraries
- How To Spend 14 Days In Italy - Five Unique Itineraries
Find even more inspiration for Italy here
- Unforgettable things to do in Tuscany
- Where to stay in Venice area by area
- Where to stay in Rome: an area by area guide
- 25 fun facts about Italy you didn't know
- Plan a weekend in Florence day-by-day
- 20 best beaches in Italy
- The best things to do in Italy
- Must-try foods in Florence Italy and where to find them
- The 30 best places to go with kids
- Most beautiful places in Italy
