The Ultimate 2-Week Italy Itinerary

Are you picturing images of Roman ruins, vast stretches of vineyards, and scenes of gondoliers singing “O sole mio” through the winding canals of the floating city? Then you’re conjuring up images of Italy!

If you have fourteen days at your disposal, you can discover the true essence of the boot-shaped country by following our 2-week Italy itinerary.

From traversing the winding streets of the eternal city of Rome to meandering down the romantic canals of Venice, the next two-weeks promises an adventure filled with rich history, breathtaking landscapes, and unparalleled cultural experiences.

We want you to leave Italy feeling like you’ve truly understood the country, so we’ve carefully crafted this two week Italy itinerary to not only take you to some of Italy’s most iconic destinations, but also to some hidden gems we discovered on our own trip.

At A Glance: A Summary of This 14 Day Italy Itinerary

For those who don’t have much time, below is a quick summary of this 14 day itinerary. Later in this guide, we’ll share more detailed information about what to do, where to stay, and where to eat at each place.

• Day 1-3: Rome (3 nights)
• Day 3-5: Tuscany (2 nights)
• Day 6:8: Florence (2 nights)
• Day 8-11: Cinque Terre (3 nights)
• Day 11-12: Verona (2 nights)
• Day 12-14: Venice (2 nights)

We followed this two-week itinerary in the summer of 2023 with our two daughters (aged 15 and 11). We all fell in love with the culture and lifestyle of Italy and were enamored with its ancient history and modern flavors.

We had 12 nights; but I’ve added an extra night to Tuscany and Cinque Terre to take it to 14 days, which in hindsight, is what we wish we did.

We had four nights in Paris before arriving in Italy, and if we were to do it again, we’d drop France and just spend the extra time in Italy.

We loved Paris, but much preferred Italy and it would have saved us money and exhausting travel time.

The Ultimate 2 Week Italy Itinerary

Below is how we recommend you spend 14 days in Italy, covering Rome, Florence, Tuscany, Verona, Cinque Terre and Venice!

Later in the guide, we’ll discuss how to get around Italy and how to navigate this itinerary.

Stop 1: Rome, The Eternal City (3 Nights)

Begin your Italian adventure in Rome, where ancient ruins, Renaissance art, and delicious cuisine converge.

Rome is the capital city of Italy and the former capital of the Roman Empire. It’s a city that receives over 10 million international tourists a year, making it one of the top 20 cities in the world.

And there’s a reason for this! The city is packed with historical attractions and world-famous landmarks, including the Seventh Wonder of the World, the Colosseum. Don’t miss out on a chance to walk the ancient Roman Forum and marvel at awe-inspiring Roman engineering at the Pantheon and immerse yourself in the city’s millennia-old history.

Rome is a walkable city, with chances to discover hidden gems in the backstreets. You can indulge in authentic pasta dishes at local trattorias, and don’t forget to toss a coin into the Trevi Fountain for good luck.

Rome’s enchanting atmosphere will set the stage for the wonders that lie ahead.

What to Do in Rome

Here were the highlights for us on our three day stay in Rome. Click on the links to learn more about each experience.

• Roman Street Food Tour. An absolutely must for foodie fans who want to learn more about Rome’s cuisine. It’s not all pizzas and gellato, I promise you!
• Roman Forum and Palatine Hill and the Colosseum. No trip to Rome is complete without seeing the Colosseum and ancient ruins of the Roman Forum. We recommend you do to a guided tour of this so you can skip the lines and learn about the history and engineering from a knowledgeable guide.
• Vatican City Tour, the world’s smallest country and home to the Catholic Church. The Vatican can be explored in a day, but it’s also best to do a guided tour so you can skip the lines – especially for the Vatican Museum and Sistine Chapel that sees waiting times of up to 3 hours.
• The Pantheon, a former Roman temple and Catholic Church, and the final resting place of famous Roman artist Raphael, as well as Italy’s first king, Victor Emmanuel.
• Trevi Fountain, an iconic landmark known for its intricate baroque design with statues and turquoise pool. Throw a coin over your left shoulder for good luck.
• Spanish Steps, a picturesque old staircase connecting Piazza di Spagna to Piazza Trinità dei Monti.
• Explore Trastevere (and other cool Rome neighborhoods)
• Wander the Streets of Rome
• Rome Catacombs, which are located just outside the city, and are a network of underground passages housing tombs of Rome’s Christians and Jews in the 5th century.

Where to Eat in Rome

As our apartment rental host told us, “choose a restaurant, any restaurant, they’ll all be good. It’s Trastevere. Forget waiting in line.”

So that’s my advice to you – it possibly works for all of Rome.

Stay away from the touristy piazzas and head to the side streets and surrounding neighborhoods for fantastic food in Rome. Here are some a couple of suggestion:

• Mama Eats in Trastevere. Our favorite restaurant on the trip – 100% gluten free and I’m talking pastas, pizza and tiramisu. At an affordable price. They can make dishes non-gluten free as well.
• Gelateria del Teatro is also one of the most appreciated and loved ice cream parlors in Rome in the artisan field since 2006.
• Fiore has great street food – perfect for lunch and quick snacks.

Where to Stay in Rome

We loved staying in the Trastevere neighborhood. We could walk to all top Rome attractions from there while having the experience of staying in a more local area with fantastic food options and bustling nightlife.

Plus, the streets are so pretty!

We booked this lovely home rental (it was spacious and lovely with a fantastic host) and also considered this apartment rental in the same neighborhood.

Stop 2: Tuscany, Rolling Hills, Charming Villages and Grapevines (2 Nights)

Next, venture into the picturesque landscapes of Tuscany, known as Italy’s wine growing region.

Experience the romance of the region as you explore vineyards, olive groves, and charming hilltop towns.

Sip on world-renowned wines in Chianti, wander through the medieval streets of Siena, and marvel at the iconic Leaning Tower of Pisa.

Tuscany’s beauty is not just in its scenery but also in its warm hospitality and delectable cuisine.

We loved our Tuscan farm stay and could have easily stayed longer, which is why I recommend three nights, instead of our rushed two!

What to Do in Tuscany

Tuscany is a huge region filled with many small villages, attractions, wineries, and more.

Plan your trip well and focus on the villages and area near to your farm stay – which is one of the best things to do in Italy! Click on the links for more information.

• Stay at a Tuscany Farm Stay, this is the best way to feel the laid-back, authentic lifestyle of Tuscany. Ours was incredible! Some of the best wine I’ve ever had.
• Take a Tuscany Cooking Class. We did ours at our farm stay, but you can find them across the region. Tuscan food is different from most Italian cuisine, specializing in cheese and, of course, Florentine Steak.
• Wine Tasting, a must-do when visiting Tuscany. We did one at our farm stay, but there are plenty of places that offer wine tasting in the small Tuscan towns.
• Civita di Bagnoregio, a unique and picturesque 7th century town on hill with incredible architecture. It’s famous for its pedestrian bridge which connects to Bagnoregio village.
• Bagni San Filippo, a small hot spring with mineral rich pools and beautiful waterfalls.
• Fosso Bianco hot springs, which are better for a swim and offers a chance to relax with mud masks
• Visit Sienna for a day, a medieval city in Tuscany known for its historic buildings. Our favorite duomo of Italy, Siena Cathedral, is located here.
• I also heard great things about San Gimignano, which is another medieval town known for its well-maintained watch towers.

Where to Eat in Tuscany

We mostly ate at our farm stay, but we have a full post on some great restaurants in Tuscany.

Here are some of the places we liked the most:

• La Vecchia Latteria in Siena was one of the best gelatos we had in Italy.
• Caffè Fiorella in Siena has great coffee.

Where to Stay in Tuscany

I’ve mentioned it enough now to let you know we loved our Tuscan Farm Stay at Tenuta di Mensanello. I thnk an agritourismo stay is the best way to enjoy Tuscany.

You can read our full post with all the details on our agritouismo at Mensanello.

It had everything: rustic working farm experiences, gorgeous views, and their own wine, beer, olive oil, pasture-raised pork, and farm to table experience.

Stop 3: Florence, Renaissance Splendor (2 Nights)

A short journey from Tuscany brings you to Florence, the birthplace of the Renaissance.

The city is known for its art culture, and is where you can admire masterpieces by Michelangelo, Leonardo da Vinci, and Botticelli at the Uffizi Gallery, as well as see the original Statue of David by Michaelangelo.

Don’t miss a chance to climb to the top of the Duomo for panoramic views of the city, and stroll across the Ponte Vecchio over the Arno River.

Florence’s artistic legacy and architectural wonders will leave an indelible mark on your Italian sojourn.

What to Do in Florence

Florence is packed with attractions, museums, art galleries and tours. Just wandering around is an adventure.

We were able to see and do a lot in our two days stay because we joined some walking tours for a highlight overview.

It saved us from getting overwhelmed as well! Click the links for more in-depth information and stories.

• Boboli Gardens, is a historic park created for the Medici family, but was opened to the public in 1766. It’s a fine example of Renaissance landscaping.
• Villa Bardini Gardens, another peaceful park with colorful flowers and Renaissance architecture. Don’t miss the views from the terraced bar!
• Wander Oltrarno Neighborhood, a vibrant and quirky neighborhood full of boutiques, cafes and bars.
• Tuscan Food and Wine Tour in Oltrarno. This is a great chance to find the best Florentine Steak in the city and learn about the regional cuisine of Florence.
• Catch the sunset from Piazzale Michelangelo or Ponte Vecchio. The Piazzale Michelangelo has sweeping views across the whole city, whereas the Ponte Vecchio, a medieval stone closed arch bridge, is lit up in hues of soft yellow and orange during golden hour.
• Florence Guided Walking Tour, this is the best way to see the highlights and also allows you to skip the line to see The Statue of David and climb to the top of the Duomo.
• Statue of David at Accademia Gallery, is a must-see for anyone visiting Florence, whether you’re an art lover or not. It’s one of the world’s most famous statues and is much more impressive in real-life than in pictures. You can see the outlines of muscles and veins, the attention to detail is extraordinary.
• Uffizi Gallery is a must for art lovers and is where you can find original pieces from the Renaissance period’s greatest artists, including Raphael, Botticelli, Michelangelo, Leonardo da Vinci, Caravaggio and more.
• Piazza della Signoria is a bustling square outside Palazzo Vecchio and is a great spot to grab an espresso and do some people-watching.
• Pitti Palace is a Renaissance palace that now contains an art museum.

Where to Eat in Florence

You’re always one corner around a great place to eat in Florence. Plus, it’s the home of gelato, so enjoy. As they say, When in Florence…. eat gelato every day.

And Florence is also the place to eat Florentine steak and visit a wine window.

• Mercato Centrale for food market
• La Carraia was the best gelato I had in Italy
• La Terrazza Rooftop Bar (small and busy so get here early)
• Caffè Gilli oldest cafe in city famous for espressos
• Babae Wine Window
• Ditta Artigianale Riva d’Arno has great coffee
• Trattoria BBQ in Oltrarno has great Florentine steak
• Ostaria dei Centopoveri – you’ll thank us for this local favorite – cheap with great food.

Where to Stay in Florence

We really enjoyed our stay at Hotel Palazzo dal Borgo in Florence which we booked using points. It had a great location, a separate room for the girls, and included breakfast. See rates and availability.

These places also come recommended:

1. Repubblica Firenze Luxury Apartments | UNA Esperienze (Bucket list luxury Florence accommodation + with stunning views)
2. Bellavista Impruneta Hotel Ristorante (A taste of the countryside close to the city)
3. Hotel David (Family owned in a great location)

Stop 4: Cinque Terre, Coastal Paradise (3 nights)

From Florence, head to the ruggedly beautiful Cinque Terre region, which is a string of five seaside villages perched along the Italian Riviera.

Hike scenic trails with breathtaking views of the Mediterranean, relax on tranquil pebble beaches, and savor freshly caught seafood.

The charm of Cinque Terre lies in its simplicity, where each village tells a unique story against a backdrop of cliffs and azure waters.

What to Do in Cinque Terre

Cinque Terre is an ideal region to stay for three nights as it offers you a little more relaxation after a busy week in Italy.

So, take plenty of time to wander slowly. It was our girl’s favorite place we visited in Italy.

• Hike the coastal Blue Trail between the 5 towns. Monterosso to Vernazza is said to be the most beautiful section.
• Catch a sunset in Manarola
• Take a boat tour of the Five Lands – the best thing we did and a great way to see the towns from a different perspective.
• Relax on the beach in Monterosso, our favorite beach in Cinque Terre.
• Kayak at Monterosso and admire the architecture from the water
• Head to Riomaggiore for a vibrant and unique nightlife experience.
• Try the local wine! 

Where to Stay in Cinque Terre

We stayed in an apartment in La Spezia and caught the train in to the Five Towns.

I would have much preferred to stay in Monterosso al Mare for two nights and using this as a base to get around.

From here, it’s easy to visit the other four towns either by hiking, by boat, or by train.

Riomaggiore is also a good place to stay with more accommodation options.

Where to Eat in Cinque Terre

Below are some places we dined at during our visit to Cinque Terre and highly recommend.

• Bar Gianni Franzi in Vernazza – exellent lunch by the water
• Nessun Dorma in Manarola has drinks, charcuterie boards, and views.
• Buy the fried seafood cones – cheap and easy to go food!
• Sorbetteria Gelateria 5 Terre in Manarola is 100% gluten free crepes and ice cream.

Stop 5: Verona, A Taste of Romance (2 Nights)

As you approach the end of your 14 day Italy journey, visit Verona, the city that was said to inspire the story of Romeo and Juliet.

Wander through well-preserved medieval streets, explore the Roman Arena, and visit Juliet’s balcony.

Verona’s romantic ambiance and cultural richness make it a perfect prelude to Venice.

Verona is one of my favorite places in Italy (I’ve been twice) and I prefer it to Venice, but you don’t need a lot of time here.

However, I think Verona is a great base as you can easily catch the train into Venice for the day, which is cheaper than staying in Venice itself.

What to Do in Verona

• Julite’s Courtyard and Balcony, the number one attraction in Veronia. You need tickets for the balcony, but it’s worth it. I loved it!
• Verona Arena, a huge, well-preserved Roman Amphitheatre built in 30 AD.
• Torre di Lamberti, an 84-meter-high tower built in 1172. This is a great place to see views of the city.
• Castelvecchio Museum, set in a medieval castle known as a military base. It’s surprisingly good!
• Roman Theater, not to be confused with Verona Arena, is a great place to catch a performance in the evenings.
• Go for a bike ride around the city. This is a great way to admire the architecture and feel the beat of the city. Our bike rentals came with our apartment stay, but you can find bike-sharing rentals in Piazza Cittadella.
• Giusti Gardens is a beautiful, manicured garden behind a palace. It was my favorite garden that we visited on our trip and is known for its hedge maze.
• Piazza Bra, the largest piazza in Verona and is famous for its cafes, restaurants and bustling atmosphere.
• Piazza delle Erbe, formerly the town’s forum in Roman Times, and now a peaceful square.

Where to Eat in Verona

Below are some of the places we ate at in Verona and loved!

•  Bim Bum Bam Cafe/ Bar in Veronetta neighborhood for cheap Apertivo
• La Costa in Bra had delicious and affordable pizza with views of the Verona Arena
• Cafe Filippini on Piazza Erba – great gluten free carbonara and tiramisu

Where to Stay in Verona

We were meant to stay at The Hotel Milan and Spa, but it does not have a 4-person room so we were placed in their sister apartment rental property The Verona House, which was excellent, and we could still use the amenities at the Hotel Milan & Spa.

We chose it because of the extraordinary views of the Verona Arena from their exclusive Terrace Sky Lounge and Bar.

Obviously, with views like this, you know the hotel is centrally located to all the action. See rates and availability here for Hotel Milan & Spa and click here for rates and availability here for Verona House.

Stop 6: Venice, The Grand Finale (2 Nights)

Finally, arrive in the enchanting city of Venice, where winding canals and historic architecture create a magical atmosphere.

It’s known as the sinking city, since the whole city is built on stilts over the water and is slowly sinking each year.

Venice is a walkable city and is best seen on foot, but you can also cruise along the Grand Canal in a gondola, which is an iconic thing to do in Venice.

Be sure to explore St. Mark’s Square and get lost in the narrow alleys of this water-bound city.

Venice, with its timeless beauty, concludes your two-week odyssey through the splendors of Italy.

What to Do in Venice

• Visit the Doge’s Palace, a Venetian Gothic palace that was once the residence of the Doge of Venice and a government office. It was one of my favorite attractions in Venice, but make sure you get the first tour of the day.
• Bridge of Sighs, also part of the Doge’s Palace tour, is a beautiful bridge that connects the palace to the prisons.
• Rialto Bridge, the oldest bridge on the Grand Canal and the most beautiful, as well as the Rialto Bridge Market for souvenir shopping.
• St. Mark’s Basilica, the cathedral church of the Patriarchate of Venice and the most beautiful. Be sure to admire the plethora of golden mosaics that adorn its walls.
• Acqua Alta bookstore, a hidden gem in Venice that’s not so hidden anymore. Each room is stuffed with books, and it has a garden with a book staircase that you can climb (great for Insta pictures!)
• Walking Tour, St. Mark’s Basilica & Gondola Ride, this is a great way to spend a day in Venice learning about its history and seeing the main sides.
• Admire the view from Accademia Bridge, one of the four bridges on the Grand Canal. From here, you get a wonderful view overlooking the Rialto Bridge and the canal.
• Explore Dorsoduro district. Venice’s student district, for indie shops, urban eateries, and vintage fashion boutiques.
• Take a day trip to Murano and Burano to see how Venetian glass is made.

Where to Eat in Venice

Below are some places we dined at in Venice and would highly recommend.

• Choclate tasting at Vizio Virtue Cioccolateria
• Suso gelato – our last gelato in Italy was a good one!
• Al Vapiretto Trattoria, that served delicious pasta and pizza at a reasonable price.
• Da Fede on the Campo Margherita in Dorsoduro. Delicious last Italina meal!
• Bacaro Risorto Castello for great cicchetti – a must to eat in Venice.
• Harry’s Bar which created the Bellini

Where to Stay in Venice

As mentioned, we stayed in Verona and traveld to Venice for the day. If staying in Venice, here are a few Venice hotels to consider:

How to Get Around with this 14 Day Italy Itinerary

Getting around Italy is simple. You can either hire a car or get around by train.

You won’t need a car for most of the destinations on our itinerary – really only Tuscany.

After adding up the cost of train travel (for four of us) versus car (plus taking into account convenience and saving time) we decided to rent a car in Rome and dropped it off upon arrival in Verona.

Then we used it to travel between destinations.

The big issue was getting from Cinque Terre to Verona – it would have taken up an entire day by train, as you had to backtrack to Milan first to get a connecting train to Verona.

We had free parking in Cinque Terre, so only had to pay extra for parking in Florence.

Trains are pretty good in Italy, so this may be a preferable option, especially if you have more time.

We did encounter traffic between Florence and Cinque Terre, but it did not delay us too much. We caught at rain from Verona to Venice which was effortless and cheap.

Find your car rental at DiscoverCars.com (our preferred booking site) and purchase your train tickets via Omio.

If you did not want to travel to this region of Italy independently, check out thse tours from our friends at the Globus Travel or Cosmos Tours. Use our discount code below.

In Summary: Italy Two Week Tour

That was our magical two-week tour of Italy, and as you can see, there’s a lot of great places to visit in this itinerary.

I wish we had longer, there is so much in this area to see and do.

If you have more time, you could consider adding Lake Garda and Lake Como which are also in this region and could be an excellent addition to your Italy itinerary if you have more time.

You could also explore the South of Italy, and add Naples or Sorrento to visit Pompeii, but I would skip the Amalfi Coast since it’s way too touristy now – Positano is also very expensive, and we personally think Cinque Terre has more charm. But that’s just us!

So now you’re ready for an unforgettable journey through the landscapes of Northern Italy, where you can taste the flavors and absorb the history of Italy from Rome to Venice.

This itinerary has the perfect blend of ancient wonders, artistic masterpieces, and the natural beauty that defines this captivating country. Buon viaggio!