Italy itineraries: 14 day long trips

St. Mark's square in Venice. Photo: Shutterstock
St. Mark's square in Venice. Photo: Shutterstock

Italy is a country that effortlessly combines rich history, stunning landscapes, delectable cuisine, and vibrant culture. With so much to see and do, planning the perfect itinerary can be a delightful challenge.  Read on to discover five hand-crafted itineraries for your 14 days in Italy.

See more of our Italy itineraries: 5 days - 7 days -10 days - North ItalySouth Italy

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

From the serene canals of Venice to the rugged coastline of Cinque Terre, from the high-end boutiques of Milan to the charming streets of Florence, Northern Italy is a treasure trove waiting to be explored. This 14-day adventure encompasses it all.

Itinerary summary

Here’s an overview of this 14-day Italy itinerary:

  • Days 1-4: Venice

  • Day 5: Train to Milan, free time.

  • Days 6-7: Milan

  • Days 8-10: Como

  • Days 11-13: Cinque Terre

  • Day 14: Depart from Florence.

St. Mark's Square in Venice. Photo: Shutterstock

Day 1: Arrival in Venice 

Arrive in Venice, where you'll be greeted and transferred to your hotel, setting the stage for your Italian adventure.

Day 2: Venice City Tour

 A private guide leads you on a mesmerizing Venice city tour, revealing the city's rich history, intricate architecture, and hidden gems.

Day 3: Discovering Burano and Murano

 Immerse yourself in the artistry of Burano and Murano, two captivating Venetian islands renowned for their glassblowing and colorful houses.

Day 4: Free Day in Venice

 Enjoy a day at your own pace, strolling Venice's labyrinthine streets, sampling local cuisine, or exploring its charming neighborhoods.

Day 5: Train to Milan

 Board a train bound for Milan, Italy's fashion and design capital, where you'll have the afternoon and evening to explore as you wish.

Day 6: Milan Walking Tour 

With a local guide, embark on a Milan walking tour to admire iconic landmarks, historic architecture, and the city's vibrant culture.

Day 7: Journey to Como 

Take a scenic train ride to Como, a region surrounded by the serene beauty of Lake Como. Use the day to absorb the atmosphere.

Day 8: Lugano, Switzerland 

Venture into Switzerland with a short ride to Lugano, a charming lakeside city, offering a delightful change of pace.

Day 9: Lake Como Boat Excursion 

Set sail on Lake Como, reveling in a boat trip that unveils breathtaking vistas and visits charming lakeside towns.

Day 10: Free Day in Como 

Enjoy a leisurely day in Como, exploring its picturesque streets, savoring local cuisine, or simply relaxing by the lake.

Day 11: Train to Cinque Terre 

Hop on a train to Cinque Terre, a coastal gem known for its colorful villages and dramatic scenery.

Day 12: Exploring Cinque Terre 

Dive into Cinque Terre's enchantment as you explore its villages, linked by scenic train rides and offering hiking adventures.

Day 13: Leisure Day 

Day thirteen grants you the freedom to unwind and explore Cinque Terre at your own pace, capturing the essence of this coastal haven.

Day 14: Departure from Florence 

Your journey comes full circle as you're transferred to Florence's airport for your departure flight. Don't miss the chance to embark on this grand Italian escapade. Book your trip now.

Ready to explore without the organizing hassle? Secure your trip through us.

Menaggio on Como Lake in Italy. Photo: Shutterstock

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

Embark on a 14-day journey through the heart of Italy, where pasta-making in Rome, gelato-tasting in Florence, hiking in Cinque Terre, and exploring Venice await. This adventure is tailor-made for families, promising a wealth of unforgettable experiences.

Itinerary summary

Here’s an overview of this 14-day Italy itinerary:

  • Days 1-2: Rome

  • Day 3: Cooking class in Rome, then transfer to Venice.

  • Days 4-7: Florence

  • Days 8-10: Lerici (La Spezia region)

  • Days 11-13: Venice

  • Day 14: Departure from Venice.

Colosseum. Photo: Shutterstock

Day 1: Arrival in Rome 

Your adventure begins with a smooth transfer to your hotel in Rome. As the sun sets over the Eternal City, you'll have the evening to explore at your leisure, perhaps savoring your first taste of authentic Roman cuisine.

Day 2: Colosseum and Forum Romanum 

Dive into history on day two as you embark on a half-day tour of the Colosseum, where gladiators once battled, and the Forum Romanum, where the stories of ancient Rome come to life through its mesmerizing ruins.

Day 3: Roman Culinary Delights 

Today, you'll become a culinary expert as you join a small group cooking tour. Learn the secrets behind crafting perfect pasta and savor the flavors of Rome in the heart of the city.

Day 4: Journey to Florence 

Bid farewell to Rome and board a high-speed train to Florence, the cradle of the Renaissance. Arriving in Florence, you'll have the rest of the day to explore the city's artistic treasures or stroll along the picturesque Arno River.

Day 5: Florence on Two Wheels

 Discover the charm of Florence effortlessly on an e-bike tour. Glide through its historic streets, passing iconic landmarks, and absorbing the Renaissance ambiance that permeates this city.

Day 6: Pizza and Gelato Magic 

Delve into the art of Italian cuisine on day six with a cooking class in central Florence. You'll learn to craft authentic pizza and delightful gelato, ensuring you can savor these flavors long after your trip ends.

Day 7: Chianti's Delights 

Escape the city for a day and venture into the enchanting Chianti region. Here, rolling vineyards, olive groves, and charming villages await. Sample the region's renowned wines and indulge in its culinary delights.

Day 8: From Florence to Lerici - La Spezia Region 

Travel by regional train from Florence to Lerici, nestled in the scenic La Spezia region. Lerici's coastal beauty and tranquil atmosphere offer a delightful change of pace.

Day 9: Hiking Cinque Terre's Blue Trail 

Lace up your hiking boots and embark on a guided hike along Cinque Terre's iconic Blue Trail. This coastal path promises breathtaking views and a deeper connection with the region's natural beauty.

Day 10: Leisure in Lerici 

Day ten is your opportunity to unwind, explore Lerici's charming streets, or simply relax by the sea, embracing the serene atmosphere of this coastal gem.

Day 11: Venice Beckons 

Bid farewell to Lerici and travel by train to the captivating city of Venice. Venice's unique charm and captivating canals make it a highlight of any Italian adventure.

Day 12: Venice's Secrets Revealed 

Discover the hidden treasures of Venice on day twelve with a private walking tour that takes you off the beaten path. In the evening, savor a romantic gondola ride through Venice's enchanting waterways.

Day 13: Farewell to Italy 

On your penultimate day, savor your final moments in Italy. Whether you choose to explore further or simply soak in the Venetian atmosphere, make the most of your time.

Day 14: Departure 

Your journey concludes with a private transfer from your Venice hotel to the airport, laden with cherished memories of classic Italy. Don't miss this opportunity - book your trip now and step into the allure of Italy's classics, where each day is a chapter of wonder and discovery.

Ready to hit the road without the planning stress? Let us book this trip for you.

Florence duomo. Photo: Shutterstock

Skip the hassle of planning and booking

Our local experts can plan wonderful trips for you in Italy. Simply get in touch when you would like to travel. We will then create a personalized itinerary, which you can amend until you are totally happy with every detail of the booking. All of our planned itineraries can be tailored to meet your specific needs.

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

Embark on an unforgettable 14-day odyssey through Italy, brimming with iconic destinations. From the eternal charm of Rome to the enchanting Amalfi Coast, the picturesque Cinque Terre, and the cosmopolitan allure of Milan, this journey promises to be a symphony of Italian highlights.

Itinerary summary

Here’s an overview of this 14-day Italy itinerary:

  • Days 1-2: Rome

  • Day 3: Vatican, then transfer to Venice.

  • Days 4-7: Naples

  • Day 8: Transfer to Florence.

  • Days 9-11: Lerici (Cinque Terre)

  • Days 12-13: Milan

  • Day 14: Departure from Milan.

St. Peter's Square in the Vatican. Photo: Shutterstock

Day 1: Arrival in Rome 

Your adventure commences with a warm welcome at the airport, followed by a transfer to your Rome hotel. Take your time to settle in and get a taste of the Eternal City.

Day 2: Roman Marvels - Colosseum and Forum Romanum 

Dive headfirst into history with a small-group tour of the Colosseum and Forum Romanum on day two. Wander through the echoes of ancient gladiatorial battles and the remnants of Rome's political heart.

Day 3: Vatican Splendors

 Uncover the Vatican's treasures on a half-day tour, exploring its artistic and religious wonders. The Vatican Museums, Sistine Chapel, and St. Peter's Basilica await your discovery.

Day 4: Naples - The Birthplace of Pizza 

Depart for Naples by train on day four, where the world-famous pizza was born. Immerse yourself in the culinary delights and vibrant streets of this historic city.

Day 5: Naples Unveiled 

Join a local guide on the streets of Naples to delve into the heart of this city, uncovering its rich culture and vibrant atmosphere.

Day 6: Pompeii and the Mighty Vesuvius 

Experience history's haunting echo as you visit Pompeii, a city frozen in time by the eruption of Mount Vesuvius. Cap off the day with a wine-tasting or authentic pizza lunch.

Day 7: Amalfi Coast Delights 

Day seven unfolds a journey along the breathtaking Amalfi Coast, where cliffside villages, azure waters, and dramatic landscapes create a picture-perfect scene.

Day 8: Florence Awaits 

Board a high-speed train to Florence on the eighth day, transitioning from the coastal charm to the artistic elegance of Florence.

Day 9: Art and History in Florence 

Immerse yourself in the artistic legacy of Florence with a guided tour. Florence's renowned museums, galleries, and architectural wonders await your exploration.

Day 10: Tranquil Time in La Spezia 

Travel to La Spezia on day ten, where you'll have the day at leisure. Unwind in this tranquil coastal town, savoring its serene ambiance.

Day 11: Cinque Terre - A Gem by the Sea 

On day eleven, set out on a full-day tour of Cinque Terre with a private guide and a Cinque Terre card. Discover the charm of these five seaside villages.

Days 12 and 13: Milan - Cosmopolitan Charms 

Traverse to Milan by train, where you'll spend day twelve at your leisure, exploring its designer boutiques, cultural treasures, and vibrant streets. On day thirteen, delve deeper into Milan's secrets with a walking tour.

Day 14: Departure from Milan 

Conclude your Italian sojourn with a private transfer to Milan's airport or train station. Bid farewell to Italy, carrying the memories of its captivating highlights with you.

Craving a hassle-free journey? Reserve your spot now.

Amalfi coast. Photo: Shutterstock

Itinerary #4: A delightful family journey through Italy

Prepare for a 14-day family escapade in Italy, where each day promises a new adventure, delectable flavors, historical marvels, and awe-inspiring landscapes.

Itinerary summary

Here’s an overview of this 14-day Italy itinerary:

  • Days 1-3: Rome

  • Days 4-7: Florence

  • Days 8-10: Cinque Terre

  • Days 11-13: Venice

  • Day 14: Departure from Venice.

Grand Canal gondola trip in Venice. Photo: Shutterstock

Day 1: Arrival in Rome 

Your Italian odyssey begins in Rome on day one. A warm welcome awaits as you're transferred to your hotel, setting the stage for your exciting journey.

Day 2: Roman Marvels - Colosseum and Forum 

Romanum Dive into history with a small-group tour of the Colosseum and Forum Romanum on day two. Explore the ancient gladiatorial arena and the heart of ancient Rome's civic life, brought to life by an expert guide.

Day 3: Culinary Exploration in Rome 

Day three takes your family on a culinary adventure with a small-group cooking tour in Rome. Learn to craft Italian dishes, indulging in the art of pizza and pasta-making.

Day 4: Florence Beckons 

Travel to the enchanting city of Florence by train on the fourth day. Florence, renowned for its art and culture, awaits your exploration.

Day 5: Florence Unveiled - E-Bike Tour 

On day five, embark on an e-bike tour of Florence with your family. Traverse the city's enchanting streets, discovering its hidden treasures in a small group.

Day 6: Pizza & Gelato Cooking Class 

Day six offers hands-on fun for the whole family with a 3-hour cooking class in central Florence. Learn the secrets behind crafting perfect pizzas and delightful gelato.

Day 7: Chianti's Rolling Hills 

Indulge in the natural beauty of Chianti's rolling hills on day seven with a half-day tour. Savor the flavors of local wines and olive oils in the heart of Tuscany.

Day 8: Tranquil Time in Cinque Terre 

Travel by regional train from Florence to La Spezia, and enjoy a leisurely day on the eighth day, immersing yourselves in the tranquil ambiance of Cinque Terre.

Day 9: Coastal Hike and Blue Trail 

Day nine is an active adventure as you embark on a privately guided hike from Monterosso to Corniglia, traversing the stunning coastal Blue Trail.

Day 10: Family Relaxation

 Enjoy a day of leisure and relaxation on day ten, exploring Cinque Terre's enchanting villages or simply unwinding at your own pace.

Day 11: Venice Beckons 

Travel to the magical city of Venice by train on day eleven, where a private walking tour introduces your family to its unique charm and history.

Day 12: Venice's Secrets 

Day twelve is yours to savor Venice at your own pace, allowing your family to explore its maze-like streets, canals, and hidden gems.

Day 13: Venice Islands

 Enjoy a leisurely day exploring the islands around Venice on day thirteen, each offering its unique character and allure.

Day 14: Farewell to Italy 

Your Italian family adventure concludes on day fourteen, as you bid farewell to Italy. A private transfer from your hotel ensures a smooth departure, leaving you with cherished memories of an unforgettable journey.

Seeking a stress-free adventure? Let us take care of the arrangements.

Manarola in Cinque Terre. Photo: Shutterstock

Itinerary #5: Experience the splendors of Northern Italy

Embark on a captivating 14-day Italian odyssey, from the enchanting canals of Venice to the rugged beauty of Cinque Terre, experiencing the rich cultural tapestry and natural wonders of Northern Italy along the way.

Itinerary summary

Here’s an overview of this 14-day Italy itinerary:

  • Days 1-4: Venice

  • Days 5-6: Milan

  • Days 7-10: Como region

  • Days 11-13: Cinque Terre

  • Day 14: Departure from Cinque Terre.

Milan from the rooftop of Duomo. Photo: Shutterstock

Day 1: Arrival in Venice 

Your Italian adventure commences as you touch down at Venice's Marco Polo Airport. A seamless transfer awaits to whisk you away to your hotel, where your Northern Italy odyssey begins.

Day 2: Venice Unveiled - Guided City Tour 

Day two greets you with a delightful breakfast before embarking on a private guided tour of Venice. Wander its iconic canals and immerse yourself in its unique charm.

Day 3: Island Escapade - Burano and Murano

Day three beckons with an excursion to the captivating islands of Burano and Murano. Witness the artistry of local craftsmen and soak in the colorful scenery.

Day 4: Venice at Your Pace

Enjoy the freedom to explore Venice at your leisure on day four. Stroll through its winding streets, discover hidden gems, or simply savor a leisurely day in this enchanting city.

Day 5: From Venice to Milan

Bid Venice farewell on day five as you board a comfortable train to Milan, Italy's fashion and design capital.

Day 6: Milan's Cultural Treasures

Day six begins with a captivating walking tour of Milan. Uncover the city's cultural and historical gems, including its magnificent cathedral, the Duomo.

Day 7: Como's Picturesque Charms

 Venture to the picturesque Como region on day seven, where the stunning Lake Como and charming towns await your exploration.

Day 8: Tranquil Lake Lugano 

On the eighth day, enjoy a short journey to Lugano, Switzerland, nestled on the shores of Lake Lugano. Discover the harmonious blend of Swiss and Italian cultures.

Day 9: Lake Como's Serenity by Boat 

Indulge in a guided boat trip on the pristine waters of Lake Como on day nine. Savor the tranquility and breathtaking scenery.

Day 10: Leisurely Day at Lake Como

Day ten is yours to enjoy leisurely moments at Lake Como, appreciating its beauty at your own pace.

Day 11: Cinque Terre Bound

 On the eleventh day, your driver escorts you to the railway station to embark on a scenic train journey to the rugged beauty of Cinque Terre.

Day 12: Exploring Cinque Terre's Villages 

Day twelve invites you to explore the charming villages of Cinque Terre, hiking along its breathtaking coastline. Discover the unique character of each village.

Day 13: Leisure Day in Cinque Terre

Enjoy a relaxed day of leisure on day thirteen, offering you the opportunity to delve deeper into the magic of Cinque Terre.

Day 14: Farewell to Italy Your

 Northern Italy expedition concludes on day fourteen as you are collected and transferred to the airport, bidding a fond farewell to the wonders of this remarkable journey.

Ready to explore without the planning burden? Book your trip today.

Lugano in Switzerland. Photo: Shutterstock

Further reading…

For detailed Italy trip itineraries that bring your dream vacation to life, explore our Insight Guides' expertly crafted plans. Download one now for unforgettable 7-day and 14-day journeys, carefully curated by our Italy guidebook authors.