A Tuscany winter break

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Florence, Italy (January 2026)

Ever had one of those holidays where you were really looking forward to it and then, for whatever reason, things didn’t go as you hoped, and you ended up being disappointed?

The first time I visited Firenze (Florence), the capital of Tuscany, I was 21 and backpacking on a tight budget. It was wintertime – January 1992. I was travelling with a friend from Uni, and we’d met some other girls in the youth hostel we were staying at, which made for a great time, with lots of laughs. I have fond memories of touring museums, browsing markets and exploring its narrow cobbled streets. We also splurged one night and ate in a restaurant, where I was scolded by a group of young soldiers at the next table for picking up my knife to cut my spaghetti.

Fast forward to January 2026, and I found myself back in Firenze, excited to be returning, as my memories made this one of my top 5 favourite cities. This time my travelling companions were my hubby, and daughter, “Miss 18”. It was the first time visiting for them – fair to say, they weren’t as enthusiastic as me, they weren’t sure what the hype was about, and to be honest, I’m not sure they would have chosen this city to visit if I hadn’t insisted. Over the next 5 nights and 4 days, I planned to convince them of Tuscany’s charm, make it a trip they wouldn’t regret, and hoped the experience would be as memorable as mine had been all those years ago.

First impresssions

It started off well. We caught a train from Milan, where we’d spent a couple of nights; before Milan we’d had 2 magnificent nights in Freiburg im Breisgau in The Black Forest. After arriving at the train station, Firenze Santa Maria Novella, around 2 pm on Sunday afternoon, hubby was busting for a toilet, but the only one in the station needed coins, so he had to buy some gum from a nearby newsstand. After he relieved himself, I found a cash machine to withdraw cash for the €90 city tax, which our accommodation provider said needed to be left, in cash, in the key lockbox of our apartment that day- the cash machine exchange rate was ridiculously expensive! Then we navigated ourselves to the correct exit and found a taxi to take us to our accommodation. My research had informed me that taxis all accept credit cards, but I did see a warning that some drivers prefer cash. As we arrived at our accommodation, I asked to pay by card, and the young lady driver said she preferred cash – surprise, surprise! Luckily, we had enough cash to pay the €14 for our journey.

Our accommodation

Our two-bedroom apartment at Domus Plaza was in a great spot, just near the majestic Santa Maria de Fiore – the famous one you see in all the pictures of Firenze. It was so close in fact, that from our bedroom windows we could see the Duomo, much to our excitement.

Even though I knew to expect this from the reviews when I’d booked, you never really know if the views are going to be as described until you get there – as I once discovered in Polignano di Mare, which had promised sea views (they weren’t false claims, but you had to climb 4 flights of narrow stairs and go onto the rooftop to see the views across many other houses).

The apartment I’d booked for 5 nights was small, but nicely decorated, and the master bedroom I shared with hubby was spacious, with a small table and two chairs, a wardrobe, and plenty of space for suitcases.

By comparison, Miss 18’s room was a tiny box-sized bedroom, with only enough room for a single bed and wardrobe. Each bedroom had a TV, with the ability to log into your personal streaming channels.

Unfortunately, there was no TV in the communal area, which wasn’t very spacious, and also had no sofa. There was just a small round dining table with 2 chairs and 2 high stools near a bench attached to the wall by the door, part of the L-shaped tiny kitchenette. It didn’t make it conducive for hanging out there together as a family. There was one bathroom, but that was ok (we’d been spoiled in our last two apartments in Milan and Freiburg, having two bathrooms). The kitchenette was fine for our stay, as I wasn’t planning on cooking. It was good enough to make tea/coffee, and had a small stovetop and microwave, which would come in handy later. There was no washing machine, which was a shame. We’d already been away for 4 nights and had only brought hand luggage with us, since it was cheaper for our flights between Europe and the UK, and more convenient for travel by train. We would need to do a little bit of washing while we there.

Exploring Firenze

After we’d looked around our cute apartment and dumped our bags, I was keen to start exploring outside immediately. The sun was shining, the sky was a beautiful blue, and from the taxi window to our accommodation, I sensed a Sunday afternoon vibe, with lots of people out walking around the cobbled streets. However, Miss 18 didn’t want to go out just yet. She wasn’t feeling well and wanted to stay in her room to rest. I wasn’t too phased by her decision to stay in, and giving her some space wasn’t a bad thing.

Hubby and I ventured outside, headed around the corner, then walked up the main street: Via del Corso. There were lots of shops to browse, and although it was a sunny afternoon, I could see lights hanging across the narrow pedestrianised street, which I was looking forward to seeing at night. We kept walking until we reached the Piazza della Repubblica. It was a busy square, with lots of people milling around, a musician busking, traders selling those lit-up things that shoot up in the air and fall back down, and there was a carousel nearby. We sat on a bench nearby to soak it all in, and so hubby could rest, as he was recovering from a torn Achilles tendon from a few weeks earlier, which had flared up due to all the travelling and walking the last few days.

Deciding we were a bit peckish, having not eaten lunch, we spotted a few restaurants nearby and randomly chose one called Vineria del Re. As we entered, we were pleased to see others seated inside, indicating it wasn’t a bad choice. We were seated by the window, and we ordered a couple of drinks, a coffee for hubby and an Aperol Spritz for me. Then we shared a quattro formaggi (4-cheese) pizza, which was delicious.

After eating enough to keep us content until dinnertime, we walked back to our apartment past the Duomo, which now looked quite spectacular against the blue sky background, as the late afternoon sun hit the cream-coloured tiles. It was very photogenic, so we paused for a while to admire the beautiful structures, enjoy the atmosphere, and, of course, take a few photos.

When we got back to the apartment, I spent a while researching where to eat dinner, while hubby watched an old movie on TV in our bedroom, and Miss 18 lay on her bed looking at her phone. It was a shame to be in separate rooms, but let’s face it, there was nowhere else to lounge, and Miss 18 probably wanted some space. When asked what they felt like for dinner, Miss 18 took some convincing to join us, and was very specific about what she felt like (lasagne), so I had to make sure the menu would satisfy her; and hubby didn’t want to walk too far, as his injured Achilles was giving him grief. I found a place around the corner, Lo Scudo, which had an appealing menu and great reviews. As we entered, I was a bit worried about it being empty, but after we ordered cocktails, the place soon filled up (I forgot how late they eat out in Italy). Importantly, the service was great, and the food and drinks were delicious. As the night wore on, we couldn’t help noticing that almost all the other diners were young Americans, we presumed college students on their winter break vacation.

Full to the brim, we strolled back the short distance to our apartment, detouring briefly by one of the little supermarkets nearby to pick up some limoncello for a nightcap.

Going downhill but making the most of it

Monday is not a good day to be a tourist in Italy, as most museums are closed. I knew this, though, and that was one of the reasons I had booked 5 nights in Firenze. That, plus it was a good base for taking day trips to other places in Tuscany – I’d loosely planned a day trip to Pisa and also to Sienna. I didn’t mind having a quietish Monday as the last few days had been busy with travelling and sightseeing, and I knew my accompanying family would also be happy with the reprieve.

After an awful night’s sleep, thanks to a mattress that was like a marshmallow, noisy neighbours, and some reflux due to my overindulgence the night before, I woke around 9 am. I told my family they could have a lazy day if they wanted, though I wanted to go out for a walk, which they were welcome to join me on. I didn’t really expect them to join me – I know them well. By the time we all finished taking turns with the one bathroom, it was 11:30 am. As I stepped outside the apartment, I popped my head around the corner to admire the majestic Duomo, noticing some clouds coming across the blue skies. Then I followed the GPS on my iPhone to walk a short route I’d planned, in a large rectangle, which would take me around some of the popular touristy sites of Firenze.

My first stop was Piazza della Signoria, where I paused under patchy, overcast skies to reacquaint myself with the beautiful fountain, statues and architecture of the buildings surrounding the square in front of the Palazzo Vecchio (Old Palace), the city’s town hall. There were faint images in my memory banks, though they had been fading over the last 34 years, each time I’d thought of Firenze since my last visit. It hit noon, nearby bells chimed, and I browsed more of the statues around the piazza and in the nearby courtyard of Palazzo Vecchio.

The sun started to reappear through scattered clouds and I headed south towards the River Arno, and past the Uffizi Gallery, which was closed since it was Monday. As I reached the north bank, I could see the Ponte Vecchio in the distance, reflecting on the green river.

I strolled along the side of the river towards the bridge, admiring the perspective of the enclosed arches as I got closer to the bridge. Then, I walked across the bridge and back again, looking in some of the jewellery shop windows along the way, not brave enough to go inside.

Content I’d seen enough of the bridge, next, I walked north on Via Por Santa Maria until I reached Mercato del Porcellino, a covered marketplace selling scarves and leather goods, like handbags, jackets and other items.

There at the edge of the marketplace, I found the Fontana del Porcellino, the famous bronze boar fountain. It’s traditionally good luck to rub its shiny snout (polished from all the years of tourists rubbing it), place a coin, and watch it drop through the grates below. There was something so familiar about it. I knew I had been here before, but hadn’t been able to recall it straight away, until standing there in front of it. Memories slowly came back to me, of standing in that same spot 34 years earlier with my friends, rubbing its snout for good luck.

After browsing a few nearby shops, I headed back to the apartment, continuing up the same road and turning right down Via del Corso, stopping to peer down some side alleys and browse inside a few more shops along the way.

Once at the apartment, I found hubby had been doing some handwashing while I was out. He was happy enough, he’d been washing in between resting and watching the streaming services I’d logged into the night before. He wasn’t complaining, for a change.

I managed to convince Miss 18 to come back out with me in search of food and with a promise of only some brief exploration, and insistence there weren’t many crowds (she sometimes gets overwhelmed in busy and noisy places). Together we walked the same route I’d just done, but in reverse. This was her first time out in Firenze, since she’d not joined hubby and me the day before. We stopped in a couple of shops and bought some clothes on sale, then browsed Piazza della Repubblica and some nearby stands where we each bought a scarf. Moving on to Mercato del Porcellino, we checked out some handbags, but didn’t buy any, as they were a bit outside our budget.

In search of food next, we found a busy, little sandwich takeaway shop near the Ponte Vecchio, called Carpe Diem, and bought some lunch to take back to the apartment.

Then we walked to Ponte Vecchio, where I explained the history of the medieval bridge, famous for its goldsmiths and jewellery shops. We walked briefly across the bridge, pausing at the halfway mark, to admire the river views.

We finished our little walking tour back along the side of the river, past the (still closed) Uffizi, and arrived back at our apartment, where we enjoyed our tasty, but extremely filling, sandwiches. I didn’t get the feeling she was enjoying herself that much on our little sightseeing tour, apart from the shopping, but I put this aside, and accepted that at her young age, she wasn’t as interested as I was, about the history and culture of this charming, foreign city.

After another rest at the apartment, and not being one for sitting around when I’m travelling, I managed to convince hubby to come out for a walk with me in the late afternoon. This time we walked in a different direction, to check out Mercado Central, which I’d read was a large food market, with eateries. I’d enjoyed one we’d visited a few years ago in Madrid, and imagined this would be a larger version. Unfortunately, by the time we got there, it looked all closed up, contrary to what my Google app said. It was Monday after all. We found the San Lorenzo leather district, though, and looked in a couple of stores where I saw a really nice leather jacket I liked. I decided not to buy it straight away, and to sleep on it, figuring I could always come back another day since we were there for a few days. Sneakily, I walked hubby back to the apartment the long way, detouring past Ponte Vecchio again (3 times in one day for me) – he had no clue I’d taken him the long detour. I said I wanted to show him some sites on the way back, and he limped along with me, though we paused in a couple of stores along the way, like this crazy sweet store we found, and Legami, which was full of quirky items.

We also stopped briefly at an (empty) Irish pub in Piazza della Signoria, so he could enjoy a pint of his favourite Kilkenny, but I must admit, I felt a bit bad by the time we got back to the apartment, as he was in a bit of pain by then.

I spent the next couple of hours in the apartment making plans for the next few days and booking tickets – train tickets to Pisa the next day and tickets for the Accademia Gallery to see Michaelangelo’s David on Thursday.

Later that evening, around 8pm, hubby and I went to Il Sasso di Dante for a light meal. Miss 18 stayed in the apartment, as she wasn’t hungry, still full from the big lunch she’d eaten. Close to our apartment, in a small courtyard across from the Duomo, the service was great, and our meals were delicious. Yet, the cozy restaurant was empty. I don’t know how restaurants survive on nights like that. They had at least 3 people working there. On our way back to the apartment, we stopped for gelato and brought some back for Miss 18, which made her happy.

Day trips

A great bonus of staying in Firenze is that it’s a fantastic base for visiting other places in Tuscany for day trips. There are a few destination options, either as self-tours or taking organised tours through a booking company like Viator. On Tuesday, I’d planned for us to go to Pisa, and on Wednesday, I was hoping to visit Sienna. Both were places I had visited on my Tuscany trip 34 years earlier, but again, would be new experiences for hubby and Miss 18. I looked up a few organised trips, but because my travelling companions were so ambivalent, and hubby was not confident of being able to walk far, I thought self-tours might be safer.

Being January, low season for tourists, meant we could be flexible, making decisions and booking tickets pretty much the night before. This was fortunate because Pisa turned out to be a disappointment, so much so, that I almost canned the Sienna day trip idea altogether.

Pisa – our winter day trip from Florence to Pisa began with high expectations but unravelled into disappointment due to poor weather, limited food options, walking difficulties, and a lack of nearby attractions. Despite an extraordinary acoustic performance in the Baptistery and the beauty of the leaning tower and cathedral, our visit ended early, leaving me reflecting on unmet hopes and an underwhelming experience overall. Read about it here.

Our disappointing day was topped off, when we returned to Firenze and discovered there was a taxi strike, so we had to walk back to our apartment. Hubby was complaining most of the way, limping in pain, and the 15-minute walk was too much to bear – for any of us. Nobody wanted to go out for dinner that night, still full from lunch, although I’m sure I could have squeezed in a light meal like the one I’d enjoyed the night before.

I ended up going for a walk on my own, where the sight of the Duomo all lit up cheered me up. Then I found the Basilica di San Lorenzo and Medici chapels, before discovering loads of street markets in the San Lorenzo neighbourhood that had not been there the night before. My spirits were lifted.

On my way back to the apartment, I went to the supermarket and bought some microwave pasta meals, in case we wanted to eat later. It was actually quite yummy. Our day ended on a quiet note, watching TV and, for me, reflecting on the day’s events and reconsidering the plans for the next day.

Sienna – Miss 18 decided she wasn’t interested in going to Sienna and I was concerned whether hubby could manage more walking after our disappointing visit to Pisa the day before. His knee had gone out in sympathy for his achilles due to all the awkward limping. I’d said to him the night before, I’d still like to go to Sienna and didn’t mind if he wanted to stay behind with Miss 18. As much as I’d like him to come, I’d understand if he wasn’t up to it and would be prepared to go on my own. I said I’d leave it up to him to decide by morning. Fortunately, he decided to join me, on the condition we catch a taxi to the station after a quick trip to a pharmacy to stock up on anti-inflammatories. I was happy with that – it’s always nicer to share an experience with someone rather than doing it on your own. It turned out to be a lovely day. Stay tuned and I’ll write about it separately.

Final charms of Florence

The rest of our time in Florence was along the same themes as the last few days – mixed with highs and lows.

We had a fabulous meal out all together on our 3rd night, after hubby and I got back from Sienna. Having spent the day by herself, Miss 18 was happy to join us as we went to a restaurant across the road, La Vetreria. We ended up having our best meal in Firenze. We weren’t sure of our choice of restaurant at first, since there was scaffolding up outside, but the waiter was awesome – attentive and friendly. He recommended some menu items for us, without being too pushy or salesy, which turned out to be amazing. The food was incredibly delicious, and we all had a happy night together, with lots of laughs.

On our 4th and last full day, everyone was knackered, especially hubby’s knee. I planned a route for myself, and at 10 am, set off on a long walk on my own, enjoying my own company and pace. First, I walked across a different bridge up to Michaelangelo Pizzale. It was quite a climb, but manageable for me and definitely worthwhile for the 180º views across Florence at the top.

After enjoying those amazing views, I headed back down the hill in a different direction, through the old city walls I’d spied from the top, and Porta San Miniato, an old medieval gate, built in 1320.

I followed my Google maps through back streets up another steep hill to find Galileo’s house. It was a nice-looking house from the outside, with motifs on the outside walls, but those steep hills to get there were seriously not worth the effort, people!

My next plan was to head to the Gucci museum in Piazza della Signoria. I’d read inconsistent reviews, some negative, but I thought I’d still check it out. I paid my €8 entry fee and followed the stairs up to the displays. As I went through a Loafers exhibition, I saw videos of runway scenes being played on large screens; then came into a large room of mannequins displaying various items of clothing through the decades. Next, I found a room full of bags, on floor-to-ceiling, wall-to -wall mirrored shelves. Another flight of stairs up, I found two more rooms, one full of luggage pieces, the other filled with scarves and a caleidoscope film display showing various scarf designs, which you could stand inside and take a selfie with. This experience, overall, became a highlight for me, though was marred by a little sadness, as I couldn’t see myself ever being able to afford to buy something from their store. I had a quick look in the sales boutique on the ground floor on my way out, and perhaps could have afforded a book, but it was a poor consolation, so I left empty-handed, other than for the experience. (Don’t worry, I ended up buying some Gucci perfume duty-free on my way home as a souvenir).

On my way back to the apartment, I stopped down a side street to find a hidden gem Tuscan sandwich bar called I’ Girone De’ Ghiotti, recommended by a friend, Alistair. It was hard to choose from their extensive menu, and I eventually bought a couple of porchetta sandwiches to take back for lunch. They were absolutely delicious and hugely filling.

In the afternoon, I insisted on all three of us heading to the Santa Croce church, which housed the tombs of Michelangelo, Galileo, and Dante. I thought the others would appreciate the significance, given their scientific minds, and Miss 18’s interest in art when she was at high school. It was another glorious church, with lots of tombs to look at. Well, I thought so. Hubby enjoyed it almost as much as me; Miss 18 not so much – her attention span lasted about 15 minutes, which was a shame considering the entry fee wasn’t exactly cheap.

Afterwards, I asked if we could have a look in some nearby leather shops since I had read this was the best place to buy authentic Florentine leather. Big Mistake. We found the leather-making school after a longer-than-expected detour. It was underwhelming, with not much to see, and very expensive to buy anything in their sales rooms. The stores on the nearby streets were also expensive, and didn’t have the same nice jacket I’d spotted a few days ago in San Lorenzo. All I had achieved was irritating hubby and Miss 18; it had started to drizzle again, and hubby’s knee was hurting. I looked up my app to get a taxi or uber but it said it would take longer to drive than to walk back to the apartment, so we made our way back on foot, with a very cranky hubby.

I had bought tickets for Accademia Gallery for 4:30pm, and we had about an hour spare, so Miss 18 and I left hubby at the apartment and fast walked back to San Lorenzo where I’d seen the jacket I wanted. We found it, and it was on sale, less than half price, reduced from €420 to €190 – bargain! I tried it on, and tried to bargain with the sales guy for cash, which I’d gotten out of a machine on the way, but he wasn’t prepared to budge – waste of time that was. I ended up buying the jacket, and we fast-walked back to the apartment to collect hubby and make our way to the Accademia Gallery.

On the way to Accademia, hubby and Miss 18 had an argument, which ended up in a stand-off outside the entrance to the Gallery. This had been building for a few days, as they were each getting on each other’s nerves. It occurred after I’d scanned the tickets with security, with Miss 18 turning around and walking halfway back down the street, refusing to come inside with us. Luckily, I changed her mind – after I put a guilt trip on her about the €20 ticket, which I had bought for her. Once inside the security area, she walked off on her own, not wanting to share any more space with her dad. I tried not to let it spoil my experience, as hubby and I wandered around. We were there to see David in all his glory, but there were other sculptures, equally as impressive, and they were a bonus. In and out in 45 minutes, we rejoined Miss 18 in the gift shop at the exit. I think we spent almost as much time there browsing the souvenirs as we did browsing the sculptures inside!

On our way back to the apartment we stopped at a supermarket, so Miss 18 could pick up another microwave pasta meal for dinner – she wasn’t in the mood to join us out at a restaurant that night. I was fine with that, as her mood would have brought the evening down for hubby and me.

On our last night in Firenze, hubby and I had one more nice meal out, despite being without Miss 18. It ended up being a funny experience, and close to being another grave disappointment. We’d picked another restaurant close to our apartment. Our dinner started out fine, as we enjoyed our tasty bruschetta and slightly underwhelming antipasto for starters. Then the mains came out. I had ordered Rib Steak Daviola, thinking it sounded nice, not realising how spicy it would be – too hot for me to enjoy; hubby had ordered a fillet steak with “Balsamica” sauce, not realising how sweet it would be, and not enjoyable for him at all. We looked at each other, not sure what to do, then I suggested swapping – the best idea, as we thoroughly enjoyed each other’s meals! The waiter looked confused when he returned to clear our plates and asked if everything was ok. He visibly relaxed when we explained what had happened, and he could see we were laughing. After sharing a tiramisu for dessert, the waiter brought complimentary limoncellos for us both. I noticed he hadn’t brought any to the other diners we’d been seated near, and wondered why we got special treatment? We certainly weren’t complaining.

That was our last night in Firenze, ending with ups and downs – typical of the way our whole trip had been.

My tips
  • Florence is a city where you need to be willing and able to tour on foot, in order to experience its full charm and see all the sites. I realised through this experience that not everyone likes, or is able, to do a lot of walking. If you have any ailments or mobility issues that prevent you from walking, you might want to reconsider Florence.
  • Select your travelling companions carefully. If they don’t share your tastes and interests, or don’t have a spirit for adventure and exploring, be prepared to do things on your own. I thought I was doing something nice by taking our teenage daughter, but in hindsight, I think she would have had a better time if she’d been older, and with her friends.
  • Book advance tickets if you can, especially the galleries and museums, even in low season. When we turned up at Accademia, we were able to walk straight in, but we still observed a line queuing up outside.
  • Low season is the best time to travel – I’ve said this before, and I’ll say it again. Travelling in winter or low season really is the best time to travel, to avoid crowds, long queues, and enable some flexibility and spontaneity in your experiences.
  • Restaurants are aplenty – reservations aren’t necessary in winter / low season, but do check reviews to be sure to have a great experience. We were lucky all the restaurants we chose had great food and service, though I highly recommend La Vetreria for dinner if you are near the Duomo; and for a traditional Tuscan sandwich, do find I’ Girone De’ Ghiotti, and order one of their porchetta options.
  • Cash is not necessary unless you intend to catch a taxi and want to please the driver, or want to buy something from one of the stands selling touristy items. You can risk it, though, as most places accept cards now, and there are many touristy stands that do accept cards.
My regrets
  • Not going inside the Duomo or Uffizi galleries. We ran out of time, and its recommended not to try doing too much in one day. I was fortunate to have seen these sites last time in Firenze, however, don’t remember them clearly. I regret not going back for a second time to refresh my memory.
  • A cooking class was advertised on Via Del Corso and I walked past a couple of times and saw it running. I almost booked in, but again, ran out of time. From the reviews, it looked like a great experience.
  • We saw lots of walking tours in different languages. If I’d had more time and been on my own, I would have opted for one. If you have the time, patience and want to learn more about the city sites and history, consider joining one.
  • On social media, I’d seen lots of short videos of ladies buying a glass of wine in the street, handed through a secret, little window. I was tempted to try this and thought I saw one while on one of my walks, but as I was on my own at the time, and it was early in the day, it didn’t seem right. It looked like it might have been a fun experience to try.
  • A day trip to a place I hadn’t already been to would have been great. Sienna was worth visiting again, and I chose Pisa for the benefit of hubby and Miss 18 because the leaning tower is so iconic, I thought it should be experienced by them once in a lifetime. However, given their reactions and the overall disappointing experience at Pisa, I wish I had selfishly picked an alternative destination that I hadn’t visited before, like Cinque Terre or San Gimignano.

Author: Tash

Travel blogger from Australia

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