Italy in 2 Weeks: Tips, Routes and Must-See Destinations for 14 Days
Discover Italy in 2 weeks: iconic cities, scenic coastlines, hidden gems. Follow this 14-day itinerary packed with tips for an unforgettable trip.
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Planning a trip and wondering how much you can see in Italy in 2 weeks? With 14 days, you can visit the country’s most famous cities while also exploring charming towns and beautiful coastal spots like Cinque Terre.
This itinerary is perfect for first-time visitors who want to see the classics, but also for anyone looking for a mix of history, culture, food, and amazing views.
Ready to start your Italian adventure? In this guide, you’ll find tips, routes, and the best places to visit during your 14-day Italy trip.
Day-by-Day Italy 2-Week Itinerary
This itinerary takes you through famous cities, charming towns, and beautiful coastlines for a trip full of culture, history, and amazing food. In two weeks, you’ll start in Rome, explore Florence and Tuscany, enjoy the sea in Cinque Terre, feel the energy of Milan, and finish among the canals of Venice.
Each section includes practical tips on what to see, where to eat, and where to stay. Whether you travel by train or rent a car, this route keeps travel times short and gives you time for spontaneous stops.
Now let’s break down your Italy adventure, one stop at a time.
Days 1-3: Rome - The Eternal City
Start your trip at the Colosseum, one of the most iconic landmarks in the world. Walking through the ancient arena and imagining gladiator battles is an unforgettable experience.
Just a short walk away, the Roman Forum takes you back to the heart of political and social life in ancient Rome. After a morning of history, head to the Trevi Fountain. Don't forget to throw a coin into the fountain: according to legend, it means you’ll come back to Rome one day.
During the second day, cross the Tiber River to visit the Vatican Museums, home of Michelangelo’s breathtaking Sistine Chapel ceiling. Don’t miss St. Peter’s Basilica and, if you can, climb to the top of the dome for one of the best views of Rome. Spend the afternoon in Piazza Navona, sipping a cappuccino while street performers bring the square to life.
For your last day, slow down and explore Trastevere. With its cobblestone streets, colorful buildings, and lively piazzas, it’s the perfect place for a relaxed lunch or an aperitivo at sunset.
Queues in Rome can be very long, so booking skip-the-line tickets will save you hours. The two most important ones? The Colosseum tour and the Vatican Museums visit. Both often sell out very fast, so be sure to reserve them as soon as possible.
Where to Eat in Rome?
When in Rome, food is a big part of the experience. Try a plate of cacio e pepe or carbonara at a traditional trattoria like Osteria da Fortunata. For something quick, grab a panino at Roscioli or treat yourself with a creamy gelato from Giolitti.
Where to Stay in Rome?
Picking the right hotel in Rome can make your trip even better. Here are three good options for every budget:
- Hotel Sonya: Comfortable and close to Termini Station.
- The Social Hub Rome: Stylish, modern, and with a pool.
- citizenM Rome Isola Tiberina: Trendy design plus amazing views.
Days 4-5: Florence and Tuscany Charm
After the busy days in Rome, Florence feels like stepping into a Renaissance painting. Begin with a visit og the Duomo, the city’s most famous landmark. Climb Brunelleschi’s dome for an amazing 360° view of terracotta rooftops and Tuscan hills. Next door, you’ll find the Baptistery of San Giovanni and Giotto’s Bell Tower, both worth a quick look for their beautiful details.
Walk to Ponte Vecchio, the oldest bridge in Florence, lined with jewelry shops shining in the sun. Love art? Don’t miss the Uffizi Gallery, home of Botticelli’s Birth of Venus and works by Leonardo da Vinci.
On the second day, leave the city for the Tuscan countryside. Siena is a great choice, with its medieval streets and Piazza del Campo, famous for the Palio horse race. Want something smaller? Go to San Gimignano, a fairytale hill town known for its towers and world-class gelato.
Finally, end your day with sunset views from Piazzale Michelangelo: it’s unforgettable.
Where to Eat in Florence?
Florence is heaven for foodies. Try a bistecca alla fiorentina (Florentine steak) at Trattoria Napoleone. Osteria All’Antico Vinaio is famous for sandwiches and traditional flavors. And don’t miss gelato at Gelateria La Carraia, locals love it!
Where to Stay in Florence?
Florence offers a wide range of places to stay, from simple guesthouses to elegant hotels in historic buildings. To make things easier, here are three options that cover different price ranges:
- The Social Hub Florence Lavagnini: Modern vibe, social spaces, and even a pool. Perfect for young travelers.
- Globus Urban Hotel: Central location near the Duomo, elegant design, and great value for money.
- FH55 Hotel Calzaiuoli: Stylish 4-star hotel in the historic center, between the Duomo and Piazza della Signoria.
Day 6: Pisa and Lucca Stopover
Leave Florence and head to Pisa to see one of the most famous landmarks in the world: the Leaning Tower of Pisa. It’s in Piazza dei Miracoli, a UNESCO World Heritage Site that also includes the beautiful Cathedral and Baptistery. Yes, it’s touristy, but it’s worth it. Take the classic photo “holding up” the tower and, if you have time, climb to the top for a wonderful panorama.
After Pisa, drive about 30 minutes and reach Lucca. This lovely Tuscan town is known for its Renaissance walls, which you can walk or cycle on for amazing views. Inside, you’ll find narrow streets, pretty squares, and the unique Piazza dell’Anfiteatro, built on an old Roman amphitheater.
Where to Eat in Pisa and Lucca?
In Pisa, avoid the tourist traps right next to the Leaning Tower and head a few streets away for something authentic. Osteria dei Cavalieri is a great option if you want traditional Tuscan dishes in a cozy setting. For a quick snack, try Il Crudo for fresh seafood or grab a coffee at Filter Coffee Lab, one of the city’s trendiest cafés.
In Lucca, slow down and enjoy the local flavors. Trattoria da Leo is a must for tordelli lucchesi, a hearty stuffed pasta. If you have a sweet tooth, stop by Pasticceria Taddeucci for their famous buccellato, a sweet bread with raisins that locals love. For dinner, Osteria Baralla offers a warm atmosphere and authentic Tuscan recipes inside the historic walls.
Where to Stay in Lucca?
Lucca is small and charming, so staying inside the historic walls is the best way to enjoy its unique atmosphere. Most hotels here have a boutique feel, with elegant rooms and a cozy vibe that makes you feel like a local.
Whether you’re looking for something budget-friendly, a stylish mid-range option, or a romantic luxury stay, here are some great picks:
- Bella Addormentata e il Principe Calaf: A cute B&B with a fairytale name, great breakfast, and lovely balconies.
- Albergo San Martino: Classic Italian charm, right in the historic center.
- San Luca Palace Hotel: Elegant rooms, top-rated service, and breakfast included.
Days 7-8: Cinque Terre - Coastal Beauty
Get ready for two days of pure seaside magic in Cinque Terre, one of the most beautiful places in Italy. These five colorful villages sit on the cliffs of the Ligurian coast and are connected by hiking trails plus train routes.
Begin your visit in Monterosso al Mare, the biggest village and the only one with a sandy beach. It’s the best spot for a swim or a lazy day in the sun. Next, visit Vernazza, often called the most charming village, with its pastel houses and a small harbor. Don’t miss Manarola, especially at sunset when the whole town glows with the warm light.
On your second day, if you love walking, try part of the Sentiero Azzurro (Blue Trail). The views are amazing, and every turn looks like a postcard. Not into hiking? No problem: the local train connects all the villages quickly and at a cheap ticket price.
For something extra special, book a boat tour along the coast. Seeing the villages from the water, especially at sunset, is an unforgettable experience.
Where to Stay in Cinque Terre?
Cinque Terre is one of Italy’s most popular destinations, so accommodation sells out very quickly, especially in summer. If you want to stay in the heart of the villages, book as early as possible. For a little more space and better prices, consider nearby towns like La Spezia, just 10 minutes away by train.
Here are three great options for every budget:
- Pensione Sorriso (Vernazza): Simple and cozy, great location with breakfast included.
- Hotel Souvenir (Monterosso): Comfortable rooms, close to the beach, and perfect for exploring.
- Grand Hotel Portovenere (Portovenere): Stunning views, luxury comfort, and an unforgettable experience on the Italian Riviera.
Days 9-10: Milan - Fashion & Culture
After the coastal beauty of Cinque Terre, head north to Milan, Italy’s fashion and design capital. Even with just one day, you can see the city’s main highlights.
The first stop should be in Piazza del Duomo, the heart of Milan. The Gothic cathedral is stunning: don’t just admire it from the outside, climb up to the rooftop for incredible city views. Next, walk to the Galleria Vittorio Emanuele II, a beautiful 19th-century arcade filled with luxury shops and historic cafés.
In the afternoon, visit Castello Sforzesco, a grand castle that now hosts museums plus art collections. If you have time, finish your day in the Brera District, known for its artistic vibe, charming streets, and great spots for an aperitivo.
Queues in Milan can be long, especially for major attractions, so book in advance! These tours are worth it:
👉 Book your Duomo Rooftop Fast-Track Access for Incredible city views without waiting in line.
👉 Book The Last Supper Guided Tour! Tickets sell out quickly, so don't forget to book in advance!
👉 Book The Best of Milan E-Bike Tour. See all the hidden gems on a bike. Tour available in English and Dutch!
Where to Eat in Milan?
Milan is full of great food spots, from traditional trattorias to trendy bars. For a classic Risotto alla Milanese, book a table at Trattoria Masuelli San Marco or Antica Trattoria della Pesa, two historic places loved by locals. If you want the famous cotoletta, try Ratanà, a stylish spot serving authentic Milanese dishes with a modern twist.
For something quick, don’t miss Luini, near the Duomo, for their legendary panzerotti, a must-try Italian street food. Craving pizza? Head to Pizzeria Spontini for a thick, cheesy slice. In the evening, join the Milanese tradition of aperitivo at the Navigli canals. Mag Café and Spritz Navigli are popular for great cocktails and snacks with a view.
Where to Stay in Milan?
Milan has something for every traveler, from stylish design hotels to modern apartments in the city center. Whether you want to stay close to the Duomo, near the train station, or in a trendy district, here are three excellent choices for every budget:
- aparto Milan Ripamonti: Affordable, social atmosphere with great facilities.
- iQ Hotel Milano: Modern, comfortable, and close to Central Station.
- Sonder by Marriott Bonvoy Torre Velasca: Elegant apartments in the heart of Milan, ideal for longer stays.
Days 11-14: Venice - Romance on the Canals
Your Italian adventure ends in one of the most magical cities in the world: Venice. Famous for its canals and bridges, this is a place to explore slowly. Stop at Piazza San Marco, the main square. Here you’ll find St. Mark’s Basilica with its golden mosaics and the Doge’s Palace, a beautiful example of Gothic architecture. For amazing views of the city and lagoon, climb to the top of the Campanile.
After that, wander through Venice’s narrow alleys until you reach the Rialto Bridge, the most famous bridge in the city. It’s a great spot for photos and a quick visit to the local market.
No trip to Venice is complete without a gondola ride! It may feel touristy, but gliding through the canals at sunset is a magical experience. For a quieter side of the city, take an early morning walk or visit Cannaregio, a peaceful neighborhood with local charm.
On your last day, take a boat tour to Murano and Burano. Murano is famous for glassmaking, while Burano will charm you with its colorful houses plus lace shops: perfect for photos and a relaxing stroll.
👉 Book your Murano and Burano Boat Tour!
Where to Eat in Venice?
Taste local specialties like sarde in saor (sweet-and-sour sardines) or bigoli in salsa (thick pasta with anchovy sauce). For a quick snack, stop at a bacaro for Venetian tapas called cicchetti paired with a glass of wine.
Try Cantina Do Spade or Osteria al Squero for an authentic experience.
Where to Stay in Venice?
The city is full of charming boutique hotels and elegant historic buildings, but rooms fill up fast, especially in high season. Here are three options for every budget:
- Hampton By Hilton Venice Isola Nuova: Great value, breakfast included, and modern comfort.
- Alle Guglie Boutique Hotel: Beautiful boutique stay in Cannaregio, close to local life and easy access to main attractions.
- Palazzo San Luca: Elegant suites in a prime location between Rialto and San Marco, perfect for a luxury Venetian experience.
How to Get Around Italy in 14 Days?
With so many iconic cities and scenic routes, choosing the best way to move around can make a big difference in your trip. Here’s what you need to know about trains, cars, and flights.
Train Travel vs. Car Rental
For most travelers, trains are the easiest and most practical option. Italy has one of Europe’s best high-speed rail networks, connecting cities like Rome, Florence, Milan, and Venice in just a few hours. For example, you can travel from Rome to Florence in just 90 minutes without worrying about traffic or parking.
When should you rent a car instead? If you want to explore the Tuscan countryside or stop at small towns like Siena or San Gimignano, renting a car gives you the freedom to travel at your own pace.
Domestic Flights for Long Distances
For most of this itinerary, flights aren’t necessary. Trains are faster and easier for city-to-city travel. But if you want to add Sicily or Sardinia to your trip, a short domestic flight can save you time. Just remember:
- Airports are far from city centers, so pay attention to the transfers.
- Security checks and boarding add extra time (unlike trains, where you just reach the station and hop on).
If you’re only visiting the mainland, skip the flight and stick with railway routes.
How to Stay Connected While Travelling in Italy for 2 Weeks?
Staying online in Italy is essential for checking train times, navigating with Google Maps, or sharing your photos. Public Wi-Fi can be slow and unreliable, so the easiest solution is an eSIM.
With a virtual SIM, you don’t need a physical SIM card or change your number. Just download an app, choose a plan, and you’re connected in minutes.
👉 Get your eSIM from Saily!
This is my personal favorite due to its very easy-to-use app. Perfect for frequent travelers! Use the code milanized5 for a 5% discount!
👉 Get your Airalo eSIM with an additional 15% discount!
Affordable for Italy or Europe-wide plans, great for short trips.
Setting them up takes less than 5 minutes: download the app, scan the QR code, and you’re ready to go! No roaming fees, no stress! \o/
You need to make sure your phone supports eSIM before you buy! It's very important! 😉
Best Time to Visit Italy for a 2-Week Trip
Italy is stunning all year round, but the experience changes significantly with the seasons.
Spring (March to May)
This is one of the best times to visit. The weather is mild, flowers are blooming, and cities aren’t overcrowded. You can comfortably explore Rome, Florence, or Venice without dealing with the summer heat. Just pack a light jacket for the evenings.
Summer (June to August)
Summer means long sunny days and vibrant energy, but it’s also the busiest season. Expect high prices, packed attractions, and temperatures reaching 35°C (95°F) in some cities. If you love beaches and boat trips, this is the perfect time for a visit to the Amalfi Coast, Cinque Terre, or Sardinia.
Autumn (September to November)
Autumn brings cooler weather, fewer crowds, and beautiful colors in the countryside. September still feels like summer, while October and November are ideal for food lovers thanks to wine and truffle festivals.
Winter (December to February)
Winter is the quiet season (except during Christmas and New Year). Prices drop, cities are less crowded, and festive decorations make everything magical. Northern Italy also offers top ski resorts in the Alps and Dolomites.
| Season | Weather | Crowds | Best For |
|---|---|---|---|
| Spring | 15-22°C | Low-Medium | Gardens, wine tours, city sightseeing |
| Summer | 25-35°C | High | Beaches, islands, boat tours |
| Autumn | 15-25°C | Medium | Food festivals, scenic countryside |
| Winter | 0-12°C | Low | Christmas vibes, ski trips, museums |
Conclusion
Two weeks in Italy will fly by! Plan your trip, but leave some room for surprises. These little moments, like sipping an espresso in a quiet piazza or wandering through a colorful street in Cinque Terre, are what make your journey unforgettable.
Most importantly, enjoy the Italian way of life. Slow down, taste the food, and take your time. Italy isn’t just about the sights; it’s about all the experiences.
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