Catherine - Savvy Family TravelOne moment you’re wandering through ancient ruins that shaped Western civilization. A few days later, you’re gazing upon turquoise water beneath dramatic coastal cliffs.
We spent several months traveling through Italy, and this 14 day Italy itinerary pulls together some of our absolute favorite places. Our route combines iconic cities, unforgettable food, and some of the most beautiful coastlines in Europe.
You’ll check off bucket-list sights while also discovering quiet corners that make Italy so addictive. Here’s exactly how to spend two weeks in Italy.
14 Day Italy Itinerary
Italy has an incredible train network, which makes traveling between cities relatively easy. Where possible, we avoid unnecessary backtracking.
| Day | Destination | Travel Distance (by Train) |
| 1–4 | Rome | |
| 5–7 | Amalfi Coast | Rome to Almalfi: 2 hour 50 min |
| 8–9 | Florence | Amalfi to Florence: 3 hour 45 min |
| 10 | Pisa | Florence to Pisa: 1 hour |
| 10–12 | Cinque Terre | Pisa to Riomaggiore: 1 hour 15 min |
| 13–14 | Genoa | Monterosso to Genoa: 1 hour Genoa back to Rome: 4 hr 45 min |
Planning Tips for Your 14 Day Italy Itinerary
Before diving into the day-by-day itinerary, here are a few things that will make your trip run smoothly
Book Popular Attractions Early
Italy’s biggest attractions do sell out. Make advanced ticket reservations via the official ticketing sites for:
- Colosseum tours
- Vatican Museums
- Duomo Dome climb
- Accademia Gallery (David)
- Uffizi Gallery
- Borguese Gallery
We booked tickets weeks in advance.
For the Vatican, we found they were sold out. We ended up buying resale tickets on GetYourGuide, which at least came with skip the line access.
Pack Light
Italy’s cobblestone streets and stairs make heavy luggage a nightmare. Rolling suitcases through historic districts is not fun. Packing light will make switching accomodations easier throughout your 14 day Italy itinerary.
Bring:
- Comfortable walking shoes
- A reusable water bottle
- Brimmed hat
- A credit card without foreign transation fees
- A small daypack (worn on your front in any busy areas to avoid pickpocketing)
Travel by Train
High-speed trains connect most of the cities in this itinerary.
The easiest route:
- Rome to Naples to Amalfi Coast
- Naples to Florence
- Florence to Pisa to Cinque Terre
- Cinque Terre to Genoa (then either fly home from Genoa or return to Rome for your retun flight)
Train travel in Italy is surprisingly smooth and more relaxing than driving. If you do not want to book a private tour for Amalfi, this would be the part of the 14 day Italy Itinerary where you’d want a rental car.
Days 1–4: Rome
Rome is the perfect place to begin your 14 day Italy itinerary. Firstly, because so many flights fly directly here, but also because its one of the most rewarding experiences in Italy and it feels great to start with a bang.
Ancient history blends into everyday life. Roman numerals, arches, road systems, and aqueducts still influence modern society today.
Day 1: Arrive and Settle In
If you’re flying from North America, you’ll likely arrive in the morning.
Fresh air and a hearty meal is our favorite way to combat jet lag. So explore at your own pace today, hitting a few of Rome’s most iconic historical sites.
Start at the Pantheon, which is remarkably well preserved considering it’s nearly 2,000 years old.
Then head to the Trevi Fountain and make sure to check out our Trevi Hack on Instagram before you go!
Later, stroll through Trastevere, a neighborhood of narrow cobblestone streets, ivy-covered buildings, and some of Rome’s best restaurants.
Day 2: Vatican City
You’ll visit another country today. Vatican City is the smallest country in the world, but it holds some of the most famous art on the planet.
The Vatican Museums are enormous so you’ll want an enitre day in the Vatican City so you don’t have to rush through its treasures.
Next, visit St. Peter’s Basilica.
The scale of this church is hard to grasp until you’re standing inside it. It’s the largest church in the world and an architectural masterpiece.
Some notes on timing your Vatican visit:
- The Pope makes public addresses on Sundays at noon and Wednesdays between 9 and 9:30.
- The Vatican Museums are closed on Sundays.
Day 3: Ancient Rome
The Roman Forum was once the center of Roman political life. Walking through it feels like stepping into a history book. Of course, the highlight is the Colosseum.
We recommend taking a guided tour — it makes the experience much more engaging, especially if you’re traveling with kids. Standing inside this massive amphitheater and imagining gladiator battles happening nearly 2,000 years ago is pretty surreal.
Nearby you’ll also see Trajan’s Column, which tells the story of a Roman military campaign through detailed carvings spiraling up the stone.
End the day wandering through:
- Piazza Navona
- Campo de’ Fiori
Both are lively squares filled with restaurants and street performers.
Day 4: Rome’s Hidden Gems
Use your final Rome day to explore a few lesser-known spots or you could add-in the Borguese Gallery (book ahead).
We loved visiting:
- Basilica of San Clemente
- Santa Maria in Trastevere
- Largo di Torre Argentina
That last one is famous for its Roman ruins and the colony of cats that now live among them.
Don’t miss our full guide to Family Friendly Rome ideas.
Days 5–7: Amalfi Coast
Now, we’ll trade ancient ruins for coastal views.
Take a train from Rome to Naples, then transfer toward the Amalfi Coast. You can transfer by train, pickup a rental, or hire a multiday guide for this segment of the 14 day Italy itinerary.
Day 5: Positano, Sorrento, & Amalfi
Positano is probably the most famous village along the coast. Colorful buildings cascade down the cliffs toward the sea.
Spend the day:
- relaxing at the beach
- wandering narrow staircases
- browsing small boutiques
Later, visit the town of Amalfi and its beautiful cathedral and explore Sorrento.
Day 6: Ravello
If Positano feels glamorous, Ravello feels peaceful.
Perched high above the coastline, Ravello offers some of the most breathtaking views in Italy.
Two must-see spots:
- Villa Cimbrone Terrace of Infinity
- Villa Rufolo Gardens
Both offer panoramic views that stretch endlessly over the Mediterranean.
Day 7: Pompeii
Today you’ll step back nearly 2,000 years.
The ancient city of Pompeii was buried by the eruption of Mount Vesuvius in 79 AD. Walking through the ruins is eerie but fascinating. You’ll explore preserved streets, homes with frescoes, and ancient bakeries.
It’s one of the most remarkable archaeological sites in the world.
Catch an evening train to Florence.
Days 8–9: Florence
Next stop: the birthplace of the Renaissance.
Florence inspired artists, scientists, and thinkers who shaped the modern world. According to UNESCO, one-third of the world’s most valuable art pieces are in Florence.
Day 8: Florence Highlights
Start with the Duomo Complex and climb Brunelleschi’s Dome for one of the best views in the city. (Book in advance)
The complex also includes: Florence Cathedral, Giotto’s Bell Tower, Baptistry (a must see), and the Duomo Museum.
In the afternoon, explore piazzas, dine al fresco, and shop.
End the day at Piazzale Michelangelo.
We brought a bottle of wine and watched the sunset while street musicians played nearby. It was one of our favorite evenings in Italy.
Day 9: Art & Florence’s Hidden Corners
Start at the Uffizi Gallery, home to masterpieces like Botticelli’s Birth of Venus. If you want to skip Uffizi or weren’t able to secure tickets, check out alternative ideas in our Florence Guide.
Then cross the Ponte Vecchio, the famous medieval bridge lined with shops.
Next explore Oltrarno, Florence’s artsy neighborhood filled with workshops, cafés, and trattorias.
Day 10: Pisa
We are heading to Cinque Terre next, but we’ll see another famous landmark on the way.
Take a morning train to Pisa. The Leaning Tower of Pisa is one of the most recognizable landmarks in the world. And somehow, seeing it in person is still surprising.
The entire Piazza dei Miracoli is beautiful, make sure to explore the Cathedral and the Baptistery in addition to admiring the famous leaning tower.
You only need 2–3 hours here, making it a perfect stop between Florence and Cinque Terre.
Days 10–12: Cinque Terre
Cinque Terre might be the most picturesque place in Italy. Five colorful villages cling to cliffs along the Ligurian coastline, connected by hiking trails and trains.
We based ourselves in Vernazza, which felt central to everything. If you aren’t sure which town you want to stay in, this article will help you design the best Cinque Terre town for your style.
During the day the towns fill with visitors, but in the evenings they become wonderfully quiet.
Day 10: Riomaggiore & Manarola
You’ll arrive in the early afternoon after your visit to Pisa.
Start in Riomaggiore, the southernmost village. Colorful houses stack above a tiny harbor.
Then head to Manarola, the viewpoint above town offers one of the best sunset spots on the coast.
Day 11: Vernazza & Corniglia
The hike between Vernazza and Corniglia is one of the most beautiful in Cinque Terre.
Corniglia sits high above the sea and feels quieter than the other villages.
Day 12: Monterosso
Monterosso is the largest village and the only one with a sandy beach. Spend the day relaxing by the water or taking a ferry along the coast.
After days of hiking and exploring, it’s the perfect way to slow down.
Days 13–14: Genoa
Genoa ended up being one of our biggest surprises in Italy.
It’s gritty, historic, and far less touristy than many cities on this itinerary. And its old town is one of the largest medieval centers in Europe.
Day 13: Explore Genoa
Start in Via XX Settembre, Genoa’s grand shopping street. The covered porticos feature incredible frescoes and mosaics.
Next explore the old town through Porta Soprana, the medieval gates that once protected the city. Nearby you’ll find Christopher Columbus’s childhood home.
And of course, indulge in amazing food. Genoa is the birthplace of pesto, and the focaccia here is unforgettable.
For more attractions to consider on your 14 day Italy Itinerary, check out our Genoa itinerary with 36 fun ideas.
Day 14: Day Trip from Genoa
One of the best things about Genoa is its convenient location along the Ligurian coast.
We have an article full of Genoa day trip inspiration for your final day, including:
- Camogli
- Portofino
- Santa Margherita Ligure
- Nervi
These seaside villages feel quieter and more relaxed than the Amalfi Coast which is perfect for relaxing those tired feet at the end of two weeks in Italy.
Is 14 Days Enough Time in Italy?
I’ll be honest, it’s far better to spend a week in each city. However, we aren’t all blessed with that kind of budget or PTO.
Two weeks is enough to see an incredible variety of Italy, from ancient history to coastal villages. And it still leaves room to slow down and enjoy the food, culture, and atmosphere that make Italy unforgettable.
Pin this article for future trip planning:
Catherine – Savvy Family Travel
My favorite pastime is finding fun, interesting experiences to share with family and friends.
I’m a mom of two energetic and curious boys. My tireless husband provides comic relief, is our favorite photographer, and an expert navigator.
I’m a firm believer that travel with kids doesn’t have to be intimidating or expensive. It can be affordable, epic, and, dare I say, even relaxing!
Are you a travel loving parent too? I’d love to meet you, please reach out via Messenger and say “hi!”
Based in: Milwaukee, Wisconsin USA
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