La Dolce Vita: The classic two-week Italy Itinerary

When I started planning the Italy itinerary for 14 days with my family, I realised that this small country packs quite a lot. We wanted to immerse in the history and culture and that meant limiting travels to a few places. It was not easy to choose between Cinque Terre and Amalfi coast or drop them entirely for more time to enjoy the Tuscan landscape. Should a day to Milan – Italy’s fashion capital – be squeezed in? And we didn’t even venture to southern parts of Italy or Sicily.

It will take a few more trips to cover all that this beautiful country has to offer, but I believe this is a good 2-week Italy Itinerary for a first-time trip. We did the classic Rome-Florence-Venice Itinerary and added Amalfi coast for some R & R.

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Head to Piazza Michelangelo in the evening for stunning views of Florence.

Italy Itinerary Overview

Florence (3 nights) – Venice (3 nights) – Amalfi (4 nights) – Rome (4 nights)

Train travel to cover the classic Rome – Florence – Venice-Amalfi Itinerary

My daughter enjoys train travel a lot, and car travels not so much. So we took trains connections to all the cities and that worked out well. Even coming from India, I was told that I would find driving and parking to be a nightmare in the cities of Rome, Florence and Venice. Also, that the Amalfi coast would be packed with summer traffic, so we didn’t rent a car at all. Sigh, there went my husband’s dream of driving a Ferrari in Italy!

It was easy enough to check schedule and train fares at Trenitalia website and book online. Fares are quite reasonable if you book 2-3 months in advance. The only thing you need to make a note of is the train station names in Italian – Roma Termini for Rome, Venezia Santa Lucia for Venice, Firenze S. M. Novella for Florence, Napoli for Naples and so on. For a couple of journeys, I found the schedules offered by the competing high-speed Italo more convenient and chose that over Trenitalia. The best thing is to look up both options from point A to point B and then choose.

Look up seat61 website for detailed information on train travel in Italy.

Italy has been high up on my Europe Bucket List and I am so glad to have explored this lovely country with my family.

Day 1: Rome to Florence

We took a flight from Delhi to Rome via Paris and landed at Roma Fiumicino Aeroporto (or Leonardo da Vinci International Airport). Trenitalia runs a train directly from Fiumicino airport to Florence, and that’s what we had booked in advance.

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Train travel is fun and easy in Italy.

A short taxi drive got us to our cozy 2-bedroom apartment around the corner from Ponte Vecchio (see the Airbnb listing here). It was already late evening by the time we settled in the apartment, we strolled around the area to get our bearings.

Note: In case you are starting your trip at Rome, Leonardo Express is the train that connects Roma Fiumicino airport to Roma Termini station in just 1/2 hour. This train runs every 15 minutes, check the Trenitalia site for more information on Leonardo Express.

Day 2-3: Florence

With a 4-year old child in tow, it was not possible to see either the Uffizi or the Academia. But I wasn’t completely in despair. This city is an open-air museum.

Like Rick Steves says, where else can you stroll the same pedestrian streets walked by Michelangelo, Leonardo, and Botticelli while savoring the world’s best gelato?

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The spectacular Duomo in Florence.

We spent 2 days strolling the streets and feasting our eyes on the beauty that is Florence. Don’t miss the city’s spectacular Duomo, and if climbing up is your thing to do, climb the 414 steps of the bell tower adjacent to it for panoramic views. But for the best views of the city, head to Piazza Michelangelo. The sunset time is the best to see Ponte Vecchio bridge over the river Arno, and Florence lay before you.

We had left the last day in Florence for a day-trip to see some of the Tuscan landscape. To be honest, one can easily spend a week in this gorgeous area – relaxing, flitting from one lovely town to another, feasting on good wine and food. Alas, we had all of one day and it was memorable.

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The medieval town of San Gimignano.

We had booked this day tour with Chianti Drivers. The trip started with a quick stop at Monteriggioni, a walled town in Tuscany. The views offered of the surrounding Chianti region from here are delightful. Then we spent the afternoon in the beautiful town of Sienna. We also got a chance to stop at a local vineyard and taste some of their produce. We couldn’t have asked for a better stop in the evening than the charming medieval town of San Gimignano.

Also, read – 8 Amazing day trips from Amsterdam

Day 4 – 6: Venice

There is quite nothing like Venice. Charming in parts. Touristy and overpriced in parts.

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One can watch the Grand Canal for hours!

When we reached Venezia S. Lucia train station in the evening from Florence, the first sight of the canals was fascinating despite the traffic. We chose to take a private water taxi to reach our hotel – The Westin Europa & Regina – which occupies a marvellous location on the Grand Canal.

And no, Venice is not just for couples. My daughter loved Venice, she couldn’t get enough of walking over bridges and looking out at all the gondolas swaying in the canals.

Apart from seeing the top attractions in Venice, you must keep some time in wandering aimlessly. Venice is built for aimless walking and getting lost. A great way to explore Venice is to visit its markets. If you cant take the smell of the fish market, there is the food and veggies market that we visited just to get a local flavour. We went wandering around the city starting with Piazza San Marco and ending at the Rialto market. St. Mark’s Basilica – the most famous of the city’s churches – is not to be missed.

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Piazza San Marzano is lined with cafes and boutiques.

Next day was spent in visiting nearby islands of Murano and Burano. The first visit was to Murano with its famous glass blowing factories. It was mostly empty before lunchtime when we reached. I highly recommend a glass blowing factory tour. The creativity, flair, detail to perfection is mind-boggling. The glass artefacts are expensive for sure, but you can see why they are world famous. Then there is the island of Burano – known for handmade lace, and more colourful and full of tourists.

Day 7-10: Amalfi coast

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The stunning Amalfi coastline.

We took a direct train from Venice to Napoli train station and then a 1.5-hour taxi ride to reach Amalfi. Think coastal mountains plunging into the blue sea in a vertical scene of precipitous crags, sun-kissed villages and forests.

The historic and luxurious Hotel Santa Caterina was to be our base to explore Amalfi coast for the next 3 days. You might prefer Sorrento town as a base that is better connected via ferries to all Amalfi towns or the charming, cliff-hugging town of Positano. But we found Amalfi town perfect, more because of the elegant Santa Caterina.

The trip to Amalfi was to be a break in our sightseeing packed Florence-Venice-Rome Itinerary. The plan was to practice La Dolce Far Niente or ‘the sweetness of doing nothing’.

We spent a lazy afternoon at the photogenic town of Positano. Walk its narrow, steep streets to find little boutiques and cafes. The public bus that we took back to Amalfi was itself an experience. It seemed at a few points that the driver was keen to plunge the bus headlong into the sea, but veered away last minute!

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The cliff-hugging town of Positano.

We had kept a full day aside for Capri – a popular day trip destination. I loved Capri – wish we had time to stay overnight here.

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Capri is beautiful.

One of the top attractions in Capri is the Blue Grotto, but unless you are coming in the off-season, be prepared for 2/3 hours wait at the entrance to see the cave where light reflection causes a gorgeous blue all around. We had limited time on our hands and ended up doing a boat ride around the island. Loved it! A bus ride got us to Anacapri – the more subdued sibling of Capri on the island. We strolled around the town, bought some linen clothes, ate gelato and chilled.

The next morning was a quick visit to Ravello, a bohemian town that sits high in the hills above Amalfi. Do visit the Villa Cimbrone here – this 12th-century villa has delightful gardens with stunning views of the ocean. The evening strolling around the town of Amalfi capped the easy time spent on this delightful coast.

Also, read – Hvar, Croatia: One of the 10 most beautiful islands in the world

Day 11 – 14: Rome and the Vatican

Rome was the end destination of our 2-week Italy Itinerary. You could choose to keep it in the beginning if jet lag is a big issue. The journey comprised a car ride to Napoli station and further a direct train connection to Roma Termini. An elegant apartment listed on Airbnb in the heart of the city (just 100 m away from Pantheon) suited us well.

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One of the 7 New Wonders of the World.

The next 2 days were spent taking in the top sights in the city. One full day is needed to see the Colosseum, Forum and Palatine Hill properly. Don’t skimp on time here. We enjoyed this trio and the Capitoline Museums.

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The vast Forum, a marketplace gives you the sense of what Roman empire was like.

It was difficult to get my 4-year-old interested in all the art and architecture in Florence, or in the exhibits at the Capitoline Museums in Rome. But ancient Roman sites are a different story! She really enjoyed the open ruins of Colosseum and Forum.

You cant go to Rome and not visit the Vatican, keep a day aside for this city-state. Even with high expectations and despite the crowds, the opulence, history and the breathtaking art and architecture would leave you speechless.

We spent a day walking around the prominent piazzas of the city, visiting the Pantheon – a 2000-year-old temple – and further to Spanish Steps – a fun place to go to in the evening for people watching.

Do read – 4 days in Rome: Journey into the vivid cultural past 

Do check out these family-friendly Itineraries to other European countries –

Two-week Itinerary for the best places in Croatia

Greece with kids: A 10-day itinerary for a family trip

Places to visit in Turkey: The classic ‘Cultural Triangle’ Itinerary


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Author: Shweta Singhal

Hi! I am Shweta, the zest behind this blog . I play several roles – parent to a 6-year old, adventure enthusiast, travel blogger, generally open to trying out new things in life. Besides travel, I love books and theatre and art. I would love to hear from you; do drop a comment. Join me on Instagram / Twitter @zestinatote.

24 thoughts

  1. Italy is such a country where you want to return again and again. It is a treasure house of classic sights and experiences. We have visited Rome, Florence, Pisa, and Venice on separate occasions but want to explore more of the interiors of the Amalfi coast next time we are in those parts.

  2. This is a great workable itinerary for any one wishing to go to Italy. Your photos are quite beautiful. What I like about the many of the European cities are that the old town is self contained with lots of open plazas and eating places and all the historical places are nearby.

  3. I did a similar trip for 17 days in a car. Yes train journey is more exciting. Car for family of 4 worked out cheaper. Missed Murano and Burano but did west of Italy. Your post was like revisiting. Great pictures.

  4. This itinerary is perfect! Covers about all the Italy must dos. A lazy afternoon at Positano is such a dream! As an artist, I would love to spend a month painting there, but let’s be realistic, taking a month off is not possible. This is a good balance especially with kids.

    1. You would find many charming spots in amalfi coast to sit and paint. We need to do some R & R at a beach / ocean destination with every trip to keep everyone happy.

  5. That’s a neat 2 weeks plan. You may plan one for covering south of Italy. I have covered few of them in my AtoZChallenge, but I am sure you will love Ostuni and Alberobello…

  6. Gosh how lovely to spend two weeks travelling round Italy. Like your daughter, I prefer trains to cars – and I’ve also travelled a bit on the Italian system. It is remarkably easy, even if like me, you don’t speak Italian! I’m now off to plan a visit to some of those bits of Italy I have missed!

    1. It was quite easy to move around in trains without knowing a word of Italian. I would love to go back to explore the more off-beat places in Italy.

  7. What a perfect itinerary! A family member just asked us to put one of these together for them for next summer – I’m just going to point them to you! Thank you!! 😉 Gorgeous photos, too!

  8. Well done with this itinerary. I did only a week here and felt it was too rushed. I definitely need to go back to Italy, especially Florence and the Amalfi coast. Definitely taking some tips from here. And definitely adding 2 weeks to the next visit despite having done Rome and other places earlier. I know i will love visiting these again.

  9. I know exactly what you mean by having a really hard time choosing between all the amazing places to visit in Italy. We went for one week only and struggled with the same decisions – Amalfi or Cinque Terre, Sicily or not, Italian Dolomites, etc, how to choose between all these and which ones to drop altogether. We chose one one week itinerary exactly like how you’ve covered the first week, which meant, unfortunately, that we had to drop all of Cinque Terre, Amalfi Coast (we did visit Capri which was gorgeous as well), Sicily, Milan and Dolomites. One week was too less, and it seems so as 2 weeks for you guys. Calls for another trip!

  10. We love Italy and always try and get there ate least once a year. We love the north with its lakes and mountains. It’s not the stereotypical image of Italy but we love it. We are flying to back to Italy in a few weeks but this time we are staying in Sorrento.

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