How I Spent 3 Weeks in Italy in Winter

Manarola Cinque Terre Girl View Sunny

The land of pizza and pasta, vino and gelto… Oh, and insane architecture, history and art, of course! Visiting Italy has always felt like a mere dream of mine, and is a place my late father had always talked about travelling to. I guess you could say he was my main inspiration for spending so much time exploring and immersing myself in the Italian culture and beauty. Before moving to London at the end of December, I knew I had to tick off this bucket list destination with my favourite travel buddy (my mum!), but I needed to do it slowly. The thought of just seeing a city or two here wasn’t going to be enough for me; I had to see it all!

Italy in its high season can be extremely crowded with tourists, plus the heat is something I wouldn’t want to deal with either. In Winter, you’ll find hotel prices drop, cities are significantly quieter and the weather, while chilly, is pleasant in my opinion. Ah, I’m having some serious Italian withdrawals (and food withdrawals) writing this post!  

Planning a trip to Italy?! Here is my exact itinerary, accommodation, highlights & lowlights:

Bellagio Lake Como Girl

Lake Como: 2 Nights

No wonder the rich and famous own property along Lake Como, it is a seriously picturesque part of Italy set at the foothills of the alps. While it is known as an upscale resort region, you can definitely see it on a budget if you base yourself in Como, and Winter is a great time to go! Not only is the town square covered in Christmas lights by night, but the Christmas Markets just by the lake in Como are filled with delicious food and mulled wine! Spend an afternoon riding the Funicular up to Bruante for awesome views of the lake and town. I highly suggest getting on a bus and heading to Tremezzo, then catch a ferry across to Bellagio (my favourite) to wander the cute streets and have lunch, too.

How to get there: I flew into Milano Bergamo airport and then took a bus to the Milano Centrale Train Station (1hr). From there you can take a direct train to Como S. Giovanni Station (1hr). 

Where I stayed: In Riva Al Lago – a super affordable and well-located accommodation option. We were just opposite the lake down a small street and close to restaurants, the bus station and train station! They even have hostel options if you’re on a budget.

Burano Colourful Town Venice
Suso Best Gelato Venice Canals

Venice: 3 Nights

Venice was a city that completely surprised me in so many ways. It was a lot less crowded and dirty than everyone lets on, but I think that’s what you get when you travel in the off-season! You definitely need 2 full days to explore the canals, and attractions, along with a day trip to Burano. It’s the most colourful little town I’ve ever seen, plus I think I found the best pizza of my trip here. Another foodie tip: prepare your tastebuds for the best gelato of your life at Suso (the Opera flavour is next level!)

How to get there: From Como S. Giovanni Station, take a train back to Milano Centrale (1hr), then change here and go on direct to Venezia Santa Lucia Station (2hr, 25min). Make sure your train is heading to this station, not Venezia Mestre or you’ll still be on the main land and have to get yet another train to the island!

Where I stayed: Hotel San Maurizio – I was really happy with this affordable find, especially in a city like Venice where travel expenses can be quite high! This cute little hotel is located just a few minutes from a Vaporetto stop, a 5 minute walk to St Mark’s Square and many other attractions.

Cinque Terre Riomaggiore Vernazza Best Views

Cinque Terre: 3 Nights

You’ve most likely seen the photos on Instagram and Pinterest, but let me assure you, Cinque Terre is even more stunning in real life! The area is made up of five towns (hence ‘Cinque Terre), which means you’ll definitely need 2 full days to really appreciate all it has to offer. While the hikes may be quite tough, you won’t even care about your shaky legs and loss of breath when you see the views along the coastline and on through to each town. If that’s not for you, then you can easily jump on a train to get around! I have some pretty great food memories here too; pizza in Monterosso, and prawn gnocchi and gelato in Vernazza. To top it all off, in December, you’ll find that the tourist numbers are low, which made my time there all the more special.

How to get there: This was probably one of the longer travel days I had (hence why I decided to spend 3 nights here!) From Venezia Santa Lucia, take a direct train to Firenze Santa Maria Novella (2hr, 5min). Switch trains here and head to La Spezia Centrale (2hr, 30min), which is the closest main city to Cinque Terre. From here you can then take a local train to your chosen town!

Where I stayed: Affitacamere Elisabetta – After visiting all 5 towns, I feel Vernazza was definitely the right place to stay! It was one of the only towns that actually had a supermarket and restaurants open during the winter time and I loved the open waterfront area. This BnB accommodation is a steep walk up a few sets of stairs on the way to the Corniglia hike, but I mean, when you’re getting incredible views over the ocean and the whole of Vernazza from above, it’s worth the hike. I’d highly recommend Elisabetta’s place as an affordable accommodation option.

Florence Duomo Museum Michaelango's David

Florence: 3 Nights

Ah Firenze, the capital of Italy’s Tuscan region, filled with stunning architecture and art dating back to the Renaissance. Take in the popular sights like the Duomo, and Michelangelo’s David, along with countless churches and museums. I highly recommend taking a stroll over the Ponte Vecchio, through the Boboli Gardens and then on to Piazza Michelangelo for sweeping views of over the city and its terracotta rooftops.Plus, if you find yourself in Florence in December like myself, you’re in for a treat as the Christmas markets and decorations are in full swing!

How to get there: Head back to La Spezia Centrale and from here you can jump on a train direct to Firenze Santa Maria Novella! (2hr, 30min)

Where I stayed: Characteristic Artist’s Apartment (Airbnb) – This super cool loft style apartment was a nice change after staying in so many hotels. Not only is it located in one of the only areas in Florence that isn’t overcrowded with tourists, but it’s just a quick walk away from the Duomo and many restaurants and other attractions. Plus, having a kitchen and washing machine finally is always a bonus.

Sign up to Airbnb here and get $50AUD in travel credit!

Sorrento Pizza Pompeii Day Trip

Sorrento: 2 Nights

The southwestern coastal town of Sorrento completely surprised me, and is one of the places I actually miss the most. Sitting up high on a cliff, looking out along the coast to the Bay of Naples, the town square was bustling with locals and cute cafes. You could spend hours wandering through the little alleyways, sipping on Limoncello and shopping; that’s exactly what I did! Plus, Sorrento is the perfect place to stay if you want to head to Pompeii for the day. The city that was once destroyed by the eruption of the still active Mount Vesuvius in 79 A.D., is now a well-preserved archaeological site and is a place in Italy you cannot miss if you’re a history buff like myself.

How to get there: Firstly, head back to Firenze Santa Maria Novella and take a direct train to Napoli Centrale (3hr). From here, take a regional train to the end of the line to Sorrento (1hr). 

Where I stayed: Marina Piccola 73 – This hotel was a bit out of our price range, but seeing how it was right on the water and included an amazing buffet breakfast, we couldn’t resist! It really made our stay in Sorrento all the more special and unique.

Positano View Amalfi Coast
Positano Girl on Beach Amalfi Coast Winter

Positano: 2 Nights

You cannot deny that Positano (and the Amalfi Coast in general) is probably one of the most romantic and picturesque places in Italy! In the Summer, the beach above littered with sun lounges and umbrellas, but in the Winter it is quite different. You’ll find that hotel prices drop dramatically, you probably won’t want to take a dip in the freezing water and many businesses sadly close for a few months. Don’t let this scare you away, though, as I still managed to fall in love with the Amalfi coast in just a day and a half. Jump on a bus and head down the coastline toward Amalfi for some pizza by the sea and wander around the streets with the locals.

How to get there: From the Sorrento Train Station, you’ll find the buses out the front that will take you straight to Positano and along the Amalfi Coast. There are two stops in Positano, so make sure you figure out which one is closest to your hotel, or you’ll end up getting off in the wrong town like I did and having to find our way back!

Where I stayed: Positano Art Hotel Pasitea – The Amalfi Coast isn’t too cheap, but visiting in Winter will ensure you get hotel prices at a fraction of the price compared to the high season! We scored this hotel with a great balcony covered in bougainvillea, looking out over the ocean and down on Positano (a.k.a. a dream come true!) I wouldn’t even want to know how much it costs in Summer, but all I can say is it was worth the price, plus the location was great as the town bus stops right outside, making it a lot easier to get around this steep town!

Rome Trevi Foundation Vatican View

Rome: 4 Nights

Where do I even start with Rome!? Well, it firstly, it ended up being a city I really really enjoyed for many reasons. You obviously need to hit up all of the hotspots, like the Colosseum, Trevi Foundation, Spanish Steps and Pantheon. Plus, while you’re here, you can head over to a whole other country – the Vatican City! Here you’ll find some of the most breathtaking artwork and architecture in the world, from the Sistine Chapel to St Peter’s Basilica (head to the top of the dome for the view above!) If these are attractions that tickle your fancy, you’ll definitely need 3 full days in Rome to fit in other sites like Castel Sant’Angelo, Giardino Degli Aranci at sunset, the Roman Forum and obviously stuff your face with Italian food, of course!

How to get there: It’s a bit of a trek to get from Positano to Rome, but well worth it! Firstly, take a bus back to Sorrento Train Station where you’ll just be left in awe with the views out your window again (1hr). From here you’ll take the Regional Train again back to Napoli Centrale (1hr). Lastly, take a direct train to Roma Termini (2hr, 25min). To get to your accommodation, you’ll most likely have to then take the Metro or a Tram as well.

Where I stayed: Zia Pia al Pigneto (Airbnb) – I wasn’t too sure about this tiny little Airbnb at first, but it really grew on me in the end. While it isn’t located very centrally or close to many attractions, you do get a feel for local life in the Pigneto neigbourhood as there are pretty much no tourists in the area! It ended up being a lot cheaper to stay here and get a tram and metro into the city each day, plus we could cook in the kitchen and save a lot of money!

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Venice Girl on Bridge Italy Winter


  • Venice completely surprised me and ended up being one of my favourite cities I’ve visited in a long time. I thought it would be overcrowded and dirty, but in the off-peak season, it was quite the opposite. Plus, it’s nice walking around and not having to worry about traffic!
  • Cinque Terre’s hikes quite literally took my breath away because they were freakin’ tough, but the insane views along the Italian coastline made up for the struggle, that’s for sure. You hear and see so much on social media about how quaint and picturesque the towns of Cinque Terre are, but why do people fail to mention the hiking!? That was the best part.
  • Sorrento was a place I knew would be beautiful, but it ended up surpassing my expectations. From our hotel right on the water to the Christmassy, buzzing atmosphere in the town, I really fell in love with this city. I think the fact that shops and restaurants were actually open here, compared to the Amalfi Coast, really added to the experience!


  • Florence was a city I definitely enjoyed, but it was definitely my least favourite city we visited in the whole three weeks. I guess the constant rain didn’t help, but I also feel that we (personally) should’ve only stayed 2 nights instead of 3!
  • Rome ended up being a total surprise to me; I loved it a lot more than I thought I would! The only thing that really deterred from our experience were the people trying to sell you selfie sticks and souvenirs at every single tourist attraction. Usually it doesn’t bother me too much, but when they harass you and shove things in your face and hands constantly, it kind of puts a dampener on the experience. But, there isn’t much you can do in those situations but walk away and not speak to them!
  • Positano, while freakin’ beautiful, was a ghost town in December. We could barely find anywhere to eat, plus you don’t really need much time at the beach when it’s that cold! You could easily just do a day trip to Positano and Amalfi from Sorrento in Winter instead. Don’t get me wrong, I still managed to fall in love with the Amalfi Coast!
  • The food was something I was super excited for, but was sadly left super let down. Maybe I had high expectations, but even the places locals recommended to us were not great and overpriced. I can easily say I had some of the worst food of my life here, but also some of the best! The pizzas and Prosecco didn’t disappoint though, that’s for sure *salivates*.

Rome Secret Keyhole View Garden


  • I travelled with a backpack instead of a suitcase, and it was definitely a smart idea. Seeing some people struggle to get on and off trains, up and down stairs and along the cobblestone streets with their suitcases was enough to make me realise taking a backpack was the right decision (even if my shoulders felt as though they were going to break!)
  • Pickpocketing is quite bad in Italy – even in the off-peak seasons. As soon as I arrived to Venice and jumped on the Vaporetto, a poor girl had her wallet and passport stolen. Seeing that was enough to make me super cautious for the rest of the trip. Moral of the story: don’t wear a backpack in these touristy cities (or otherwise maybe keep a lock on it!) I kept my day backpack on my front while travelling, and then during the day I had a small bag that I kept in front of me and held onto.
  • If you can stay in accommodation with a kitchen (hostels, Airbnbs etc.) to cook your own food, this will save you a lot of money! In the end, we were quite disappointed with the food, so we bought pasta, sauce, salads and fruit to cook ourselves which cost just a few euros and tasted better than most restaurant food we had!


Italy 3 Weeks Pinterest Pin

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  • Reply
    January 11, 2018 at 9:39 pm

    Such an easy read Soph -I looooved it. I am so upset that you didn’t enjoy the food as much as planned. I fell in love with all the pizza and pasta. Some of the best I had was when I couch surfed in Venice. My host made me pasta evvveery day and it was out of this world. I can’t wait to get myself to Amalfi but I definitely think I will have to fork out the prices to go in summer when it’s bustling.

    Safe travels beautiful <3

    • Reply
      January 12, 2018 at 9:15 am

      Aw thanks girl!! Yeah I think I just might of had high expectations!! It just wasn’t worth the money we paid for it. That being said, I had some awesome pizza and other meals 🙂 Definitely need the locals to show you the good food hey! Hope you get to Amalfi one day – it was absolutely stunning. I’ll come with 😉

  • Reply
    Nano @ Travel With Nano B.
    January 15, 2018 at 5:56 am

    This is such a wonderful and helpful post. I absolutely love Italy and even though I have been a few times, I cannot wait to go back to explore more. Cinque Terre and Positano are no.1 on my list for next time. xx

    • Reply
      January 15, 2018 at 11:16 am

      So glad you’ve found it handy! Those were some of my favourite places too, so I’m sure you’ll fall in love with them! I’d love to get back there and see some of the smaller towns one day!

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