A 2-week Italy trip would enable you to link the north and south of the country and give you a richer experience. Here we have provided seven of the best itinerary ideas that showcase some of the highlights that Italy has to offer.
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1. Classic Italian Cities in 14 Days
This classic itinerary would take you to explore the most representative Italian cities with diverse experiences, including ancient architecture, food and wine tasting, stunning fishing villages, and canal boating.
- Days 1–2: Venice
- Days 3–5: Milan
- Days 6–7: Cinque Terre
- Days 8–10: Florence
- Days 11–14: Rome
You would start your trip from Venice. Explore the heart of the city on a walking tour and take a gondola ride across the canal. We would also arrange a special food tour for you if you are a foodie or would like that. Explore five different bars for the delicious Venetian aperitifs (wines and local snacks).
with a city walk in Milan to see the landmarks and an original work of da Vinci — The Last Supper. Catch a 1-hour train to Como and enjoy a food and wine tour around Lake Como with a boat ride.
Next, you would go to Milan. Embark on a city walk to see the landmarks and an original work of da Vinci — The Last Supper. Catch a 1-hour train to Como and enjoy a food and wine tour around Lake Como with a boat ride.
Next, transfer to Cinque Terre to explore the colorful fishing villages. Explore the enchanting Cinque Terre National Park and embark on a scenic tour from Manarola and Riomaggiore (two of the five towns) and admire the views of the Mediterranean Sea along the way.
Travel from Venice down to Florence. In Florence, begin your tour with a walking exploration of its central area, including the famous Florence Cathedral, Piazza della Signoria, etc. For culture lovers, the Uffizi Gallery and the Accademia Gallery cannot be missed. Allow half a day for the galleries and half a day for a food tour.
Finally, you would go to Rome. Take a private trip to the Colosseum with your local guide. They would take you to the top floor to enjoy an exclusive bird's-eye view. Go to the Vatican and marvel at the delicate frescoes and statues. Then, embark on a walking tour to visit Rome's beautiful squares and the Trevi Fountain.
2. 2-Week Family Highlights from Rome to Milan
This itinerary with a relaxed and comfortable pace of travel was created for families. Following the itinerary, you and your kids would experience outdoor activities together, immerse yourselves in Italy's rich history and culture, and explore its breathtaking natural landscapes.
- Days 1–3: Rome
- Days 4–7: Florence
- Days 8–10: Venice
- Days 11–14: Milan
In this itinerary, you would begin in Rome with an exploration of the famous Colosseum and the Vatican. For a more interesting experience for kids, we would recommend a biking city tour to discover the heart of Rome, including some beautiful plazas and the Trevi Fountain.
Then, head to Florence. There, we recommend a city walking tour to get an overall impression and insights into the city, and then visit the galleries to get to know the Renaissance better.
In Florence, have a light hiking tour of its surrounding green hills. During the hiking trip, you would have the chance to enjoy one of the best panoramic views of Florence, visit a quaint rural area, and see the place where Galileo Galilei lived and died.
In Venice, explore the city with a walking tour and a gondola ride. Take a family island-hopping adventure to Murano to see the majestic Cathedral of St. Donato and the captivating work of expert glassblowers and hop to Burano. There your family could take your time to wander through some colorful houses and streets.
During the last stop, Milan, embark on a city tour to learn about the highlights of the city, including the famous shopping arcade, the Duomo of Milan, and Sforza Castle. Then, catch a 1-hour train to Como and enjoy a food and wine tour around Lake Como with a boat ride.
3. 2-Week Italy Adventure from North to South
This itinerary would lead you down the length of Italy — from northern Venice to central Florence and Rome and on down to the southern island of Sardinia, enabling you to experience the charm and character of different parts of Italy.
- Days 1–3: Venice
- Days 4–7: Florence
- Days 8–10: Rome
- Days 11–14: Sardinia
At the first stop, Venice, you could go on a 2-hour walking tour to see the city highlights and embark on a 1-hour gondola ride to experience the charm of its canals. Then, hop to the Murano Island for more sightseeing.
When in Florence, start with a city-sightseeing walking tour, then take a cultural trip to the galleries to appreciate its Renaissance masterpieces. We also recommend a 3-hour gelato and pizza cooking class to find out the secrets of Italian cuisine from a professional chef.
Then, you would go to Rome. During a visit to the Colosseum with your private guide, you could learn how big animals, such as elephants, used to be taken in for the entertainments (if you would prefer to hear about another aspect of Roman history, our guides are very knowledgeable and flexible). Pay a visit to the Vatican and stroll through the city to see some stunning squares.
At the climax of the tour, head south to Sardinia and see its beautiful sea views, where you could enjoy a stroll along the beach, dive into the crystalline waters for a refreshing swim, and savor fresh seafood dishes paired with locally produced wines.
4. 2-Week Italy History and Culture Tour with Sicily Exploration
The biggest feature of this itinerary is that you would have the opportunity to explore Italy's largest island — Sicily, where you could enjoy a relaxing vacation.
- Days 1–3: Rome
- Days 4–6: Florence
- Days 7–8: Venice
- Days 9–14: Sicily
In this itinerary, you would spend 1 week exploring Rome and Florence's historical sites, museums, and squares, as well as having a food tasting experience.
Then, fly to the stunning island of Sicily and stay for a week. You would explore two of the island's most popular towns — Palermo and Taormina. Palermo is renowned for its rich history and stunning architecture. Enjoy a walking tour to explore its historical sites, including the Norman Palace, the Palatine Chapel, and the Royal Gardens.
Take a half-day trip to explore Monreale's UNESCO-listed Duomo. Through the cathedral and its artwork, you could learn about the Norman conquest of Sicily and the cultural exchanges between different civilizations.
You could also savor traditional Sicilian cuisine at local markets and street food stalls, trying specialties like arancini (rice balls), panelle (chickpea fritters), and cannoli (ricotta-filled pastries).
Then, you would transfer to Taormina. Join a 7-hour off-road excursion to explore the majestic Mount Etna volcano. Finally, you would have some free time to relax or explore the town at your own pace.
5. 2-Week Food Tour from Milan to the Amalfi Coast
If you enjoy Italy's food and natural landscapes, seek a romantic and relaxing getaway, and also wish to experience the diverse culture of Italy, this itinerary comes highly recommended. It is especially suited for couples.
- Days 1–3: Milan
- Days 4–5: Venice
- Days 6–7: Bologna
- Days 8–10: Florence
- Days 11–14: The Amalfi Coast
Your romantic journey would begin in Milan, Italy's fashion capital. Begin your city exploration with a guided tour to uncover the gems of the city, such as the renowned shopping arcade, the Duomo of Milan, and Sforza Castle.
After the city walking tour, embark on a food and wine tour around Lake Como. During the food tour, you could enjoy a boat ride and a visit to a charming village.
Next, transfer to Venice to explore the charming water city. Embark on a gondola tour and admire the views along the Grand Canal. We also recommend a guided tour of Venetian aperitivo and savor the local delicacies.
The third stop is Bologna. This place might not be included in a typical itinerary, but if you're a food lover and want to learn more about Italian culinary culture, we highly recommend it. Take a trip to an ancient vinegar factory for a balsamic vinegar-tasting tour, witness the process of Parmigiano Reggiano, the iconic Italian cheese, and enjoy an authentic two-course lunch.
Then, go to Florence. Start a guided city walking tour and explore some of the famous galleries. Enjoy Florence's cuisine on a food tour. Head to nearby Chianti and visit a family-run winery while enjoying a taste of their award-winning vintages.
You would end your trip in the romantic Amalfi Coast region. Along the coastline, you would visit the charming towns. Wander through the medieval streets, explore old cathedrals, pass by the vibrant terraces, and bathe in the gentle sea breeze.
6. 2 Weeks in Italy and Switzerland
Two weeks for a trip to Italy and Switzerland is a very feasible prospect. This time would allow you to explore the essence of these two countries. This itinerary highlights the culture and history of Italy alongside the scenic beauty of Switzerland's mountains and alpine towns.
Week 1: Italy
- Days 1–2: Rome
- Days 3–4: Florence
- Days 5–6: Milan
Week 2: Switzerland
- Days 7–8: Zermatt
- Days 9–11: Interlaken
- Day 12: Lucerne
- Days 13–14: Zurich
In the first week in Italy, you would visit Rome, Florence, and Milan. Spend 2 days in each city to visit their top attractions, including the Colosseum, the Vatican, the Trevi Fountain, the Uffizi Gallery, and the Duomo of Milan as well as having a food tour in Florence.
Then, catch a train from Milan to Zermatt. There, visit Matterhorn Glacier Paradise, where you could marvel at panoramic views of the Alps. Next, go to Interlaken. There, you could explore Mürren, a car-free haven, accessible only by cable car, which enhances its peaceful atmosphere and allows you to fully immerse yourself in the pristine mountain surroundings.
A trip to the famous Jungfraujoch — "the Top of Europe" — is included in the itinerary. Take a train to the Jungfraujoch and you would arrive at the highest train station in Europe. From the observation decks on the mountain, you would see magnificent glaciers and mountains as well as beautiful views of Italy, France, and other surrounding countries.
Next, you would pay a visit to Lucerne. Take scenic boat trips across Lake Lucerne and board the steepest cogwheel railway in the world to ascend to the summit of Mount Pilatus.
Finally, you would head to Zurich. There, you could relax and explore the city at your own pace.
7. Italy and Greece in 14 Days
Greece, renowned for its abundant ancient-Greek-mythology sites and picturesque islands, is a popular destination that's often paired with a trip to Italy. Two weeks are suitable for a classic Italy and Greece trip.
Week 1: Italy
- Days 1–3: Rome
- Days 4–5: Florence
- Days 6–7: Venice
Week 2: Greece
- Days 8–9: Athens
- Days 10–11: Santorini
- Days 12–14: Mykonos
If you're considering a winding-down travel pace from historical exploration to laid-back island escapes, we recommend starting with Italy before heading to Greece.
Spend a week in Italy to explore the classic trio of Rome, Florence, and Venice. Marvel at the grandeur of the Colosseum, delve into Vatican City's treasures, immerse yourself in the rich history and art of the Renaissance in Florence, savor its culinary delights, and cap off your Italy adventure with a serene gondola ride and a city walking tour in Venice.
Afterward, catch a flight to Athens. Begin your Athens adventure with a day trip exploring the city center's landmarks and the majestic Acropolis, where its grandeur stands out against the backdrop of the blue sky and fluffy white clouds.
When you leave Athens, you would embark on an island vacation. Head to Santorini and Mykonos to enjoy a sunset cruise, beach time, and island exploration.
If you are traveling with kids, we suggest a more relaxed pace. In Italy, visit Rome and Florence. In Greece, visit Athens and just one island. You could check out this suggestion by seeing our 14-Day Italy and Greece Family Highlights Tour.
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