The Ultimate 2 Week Guide To Italy

I had only been to Italy once before and that was back in the early 2000’s when I visited Venice with my parents and Nan. I had always planned to go back but it never seemed to be high up on my list as I always wanted to travel further afield sooner.

As Europe is only a short flight for me, so I thought I could do that at anytime. It was only when we had the invite for my God brother’s wedding which would be in Bergamo, that we decided to travel around Italy’s cities for my mums 60th birthday as well.

A 2 WEEK GUIDE TO ITALY | EXPLORE THE BIG CITIES

DAY ONE – 4TH SEPT

Before we flew to Milan, we did a bit of last minute packing and was picked up by taxi to Heathrow T5. The rain was bad, I was glad we were leaving for some lovely Italian sunshine.

We had some food at the airport, before our lunchtime flight. Once we landed in Milan, we received the news that Giorgio Armani had sadly passed away, as I was looking at the Emporio Armani sign above the airport terminal. We caught a taxi from the airport to our apartment which took about 30 minutes to get to our apartment.

Once we had checked in and freshened up, we headed out to explore the area around our apartment to get used to everything. We then headed out to dinner which we had booked a table at Panigacci. It’s a lovely quirky restaurant with a Brazilian chef, so there is that added flare into the dishes.

I ordered my first Aperol Spritz of the trip we had breads, dips and cold meats and a mixed plate of Bruschetta to start with. The coffee infused salmon bruschetta was amazing! I then ordered a king prawn linguine as my main and finished off with a tiramisu (of course!).

DAY TWO – 5TH SEPT

We had a fairly early morning, catching the tram near our apartment to Milano Centrale Train Station. We needed to get the train to Bergamo for my God brothers wedding. As we waited for our train, we got breakfast at a little cafe run by a Thai family but they did traditional Italian coffees and pastries. The food was really yummy and they made me a fresh orange juice.

The train took around 50 minutes and the station was only a short walk to our apartment which was right next to the Atalanta Store. Once we had checked in, we quickly freshened up and had a little explore around the city. We stopped for a bit of lunch and ordered a couple of pizzas at a lovely cafe called Balzer, which is known for it’s sweet pastries and cakes.

We then headed back to the apartment to shower and get ready for the pre wedding gathering in Citta Alta. Citta Alta is the old part of the city that is surrounded by the 16th-century Venetian Walls and lined with medieval cobbled streets. At the gathering, we had a couple of drinks and there was small plates of food to eat in the middle and it was lovely to catch up with everyone and meet some new people.

After the gathering, we headed out for dinner which we went to a restaurant my God brother Dean recommended called Da Mimmo. You wouldn’t know it was a restaurant, as the entrance bit is filled with lots of antiques and a statue of armour. It looks more like an antique shop or museum. We had a table in the covered garden area which was lovely as it was a lovely humid night. I ordered a tonic water and their bucatini pasta with tomatoes and basil.

DAY THREE – 6TH SEPT

It was the day of my God brothers wedding. We got up fairly early to have breakfast, so we had enough time to get ready for the wedding. We had breakfast at a lovely bakery type cafe down the road from our apartment called Tresoldi and had some pastries.

Once we were done with breakfast, we headed back to the apartment to get ready. We had an 11:15am mini bus pick up to take us to the wedding venue. It was about a 40 minute drive from Bergamo and right on Lake Iseo. It was an absolutely stunning day, super hot and sunny.

As we arrived at the venue, we had photos taken in the entrance before joining everyone else for drinks and canapes. We then headed over the bridge, which went directly over the road and onto the lakeside platform for the wedding ceremony. The grooms arrived on a speed boat (very James Bond-esque) and came over the bridge to begin the ceremony which was done in both English and Italian.

It was so hot, everyone was baking in the sun and we didn’t realise how sun burnt we were until the next day. We then headed to the manor house for a full spread buffet before our sit down meal. There was also a DJ, ice cream vendor, dessert station and a few games at the end of the night. We got the mini bus back to our apartment at around 1am, so it was a very long day.

NAVIGATE YOUR WAY AROUND ITALY…

DAY FOUR – 7TH SEPT

We had quite a nice lay in as we had a late night, before heading out to brunch. We had brunch at a cafe called Bar Haiti which is in the middle of the city centre. I ordered their Cheese and Tomato panini and an orange juice. Getting a cooked breakfast in Europe isn’t common, so it was nice to have something other than a pastry and that was slightly different for once.

After brunch, we walked up to Citta Alta – you can take the funicular as well – but it was such a lovely walk. Once we reached the top, there was a huge castle wall with lovely views of Bergamo below. We had a little walk around the city, looking at all the shops and corners we could find. It was quite hot so we stopped for a drink at the restaurant and bar we had the pre wedding gathering at.

It is called Il Dispensario and is themed like a medicine dispensary with massive jars filled with alcoholic drinks around the bar. They do a good beer on tap which my brother and Dad loved. I had really got into the lemon soda they have in Italy, so I had a bottle of that.

After our drinks, we walked to the funicular station which took us to the top of San Vigilio. We walked around the streets and got to Castello San Vigilio, it is an old medieval castle that was used to protect the city from neighbouring villages and towns. We could see Atalanta’s stadium, the airport and the sea from the viewpoint at the top. It was a lovely place to relax and shade from the sun, and lots of locals love hanging out there as well.

We headed back down to the bottom using the funicular and stopped at a cafe for a nice cold drink and some gelato. On our way back to the apartment, we stopped at the Atalanta Store to do some shopping, I got a couple of casual tops to wear.

Once we got back to the apartment, we got ready and headed out for dinner. We caught the bus from outside of our apartment up to the top of Citta Alta and had dinner at Dai Gustosi Rosy. We ordered bruschetta to share and then I ordered a Delicata Pizza (that had tomato sauce, mozzarella, salmon, courgettes and cherry tomatoes on it), I also had a Aperol Spritz. After dinner, we walked down and caught the funicular to the city centre and stopped at a bar for drinks called Bobino Bar.

DAY FIVE – 8TH SEPT

We stopped for breakfast at our favourite cafe for the last time and headed to the station back to Milan with all our luggage. Once we had dropped our bags off at the apartment, we headed out to the city to do some exploring. We walked around the shopping district and stopped at a cafe for some drinks and muffins as we were getting hungry.

We then walked around to the Duomo and designer shopping gallery. Dad was booking tickets for the Duomo and then realised he had booked them for the wrong day.

We came across this really nice restaurant called Obica Cusani (they have multiple restaurants around Europe) , which is famous for it’s cheese especially mozzarella. They didn’t have any tables free yet, so we had a drink at the bar area before a table because available. We sat down and ordered a couple of dishes which actually turned out to be too much food but we managed to finish it all. I ordered their Beetroot Hummus and Focaccia with tomatoes and basil. It was delicious food!

After lunch, we did a bit more walking and exploring and came across the Lindt shop so of course we got a few bags of our favourite chocolates and then explored the grounds of Sforzesco Castle and the Arch of Peace which are free entry and really interesting to explore.

It was time for our Duomo di Milano tour, so we headed to find the ticket office to get the tickets changed, this is when they told me my shorts were too short and I needed to cover up. I had to buy this weird shawl thing to cover up my legs. We got into the Duomo and explored the outside areas first before heading into the main cathedral. After our tour, we stopped at Caffe Spadari and had drinks, I ordered a Hugo cocktail which I had never had before.

We then caught the metro to Navigli which is their riverside section of the city that is very quirky and modern. There are lots of riverside bars and restaurants and lots of cool vinyl shops and craft beer bars. We had dinner at La Proscuitteria which is famous for it’s charcuterie boards filled with meats and cheeses.

I ordered a salad which was new potatoes, salad leaves, mozzarella, sun dried tomatoes and balsamic drizzle. It was really yummy and nice to have something a little less heavy for dinner. We walked around the riverside for a bit before stopping at a craft beer bar called Navigli Craft Beer, before heading back to the apartment.

DAY SIX – 9TH SEPT

We had a nice late rise and got breakfast at Panzera before catching the train to Florence. We ordered a set breakfast menu of our choice which came with cooked eggs, bread, a pastry and a hot drink and juice that we shared around. It was a lovely big breakfast which set us up for the rest of the day. We had a 12:30 train to Florence from Milano Centrale.

We arrived in Florence, around 2pm and checked into our apartment. It was a lovely big apartment, with huge bedrooms and it kind of felt like a haunted house with it’s antique furniture and chandelier in the hallway. After dropping off our bags and freshening up, we took a walk around the city to get the feeling of the area and see what’s around us.

It was a very humid night and we found a restaurant with an outside eating area to sit down at called Trattoria. I ordered their pan fried sea bass with potatoes and broccoli and then finished with a chocolate cheesecake. My brother had booked to play padel with some locals so he didn’t have dinner with us. After dinner, we walked back to this craft beer place we had found called Art17 Birreria for some drinks whilst we waited for my brother to come back.

I had a local sour beer which was really nice. We had a few drinks there standing outside in the street, watching what was happening around us. We then had a nightcap at an Irish pub down the street from our apartment called O’Hara’s Pub.

DAY SEVEN – 10TH SEPT

It was my mums birthday, so we got ready for breakfast before heading out in the rain. It was luckily the only day of rain we had, but it was still very humid. We walked to the cafe we wanted to try called Simbiosi which is known for using organic ingredients and does lots of different dishes for breakfast and brunch like smashed avocado toast and pancakes.

After breakfast, we explored the city a bit more in the rain. Walking to the main shopping area, the Duomo, we then walked to Hard Rock Cafe and stopped for a drink. After that we then came across iris Gallery, Mum and Dad got a picture of their eyes taken and then we decided to get a whole family one done for the dining room.

We then walked past Uffizi Gallery, Piazza della Signoria, Neptune’s Fountain and Ponte Vecchio Bridge. After that, we stopped at Signorvino for a drink overlooking the river. We ordered a plate of deep fried vegetables to share with our drinks.

We walked down past the river and back to our apartment, to get changed before heading out to dinner. We booked a table at Trattoria I Fratellini which is famous for it’s Florentine Steaks. The experience was so unique, you get to watch the steak being cooked and sliced, displayed and finished off with salt. We ordered their signature potatoes that are cooked with salt and baked so they are nice and crispy.

After dinner, we walked a bit more and came across a French Market that was going on outside of Piazza di Santa Croce, we then stopped for a drink at the restaurant down a street opposite that has one of the very few functioning Wine Window’s in Florence. It’s called Osteria San Fiorenzo.

DAY EIGHT – 11TH SEPT

We had quite an early morning to catch the train to Pisa. It’s only 40 minutes by train from Florence, so it’s perfect for a day trip. We got breakfast at Bar Centrale to take away with us as it’s only a short walk to the train station. We got to Pisa around 12pm and walked from the station straight to the centre. Once we arrived in the centre, we took lots of pictures of the tower and walked around the cathedral and found somewhere to have lunch. We then got tickets to visit the cathedral and the mausoleum.

We then got the train back to Florence at around 4pm. We then showered and got changed ready for dinner, it was our final day with Ross before he flew home. We booked a table at Osteria Cancello Dei Macci which was only a short walk away from our apartment.

The decor was so lovely inside and the food and service was faultless. Our waiter was full of character and telling us about his family being half from Bosnia and was helping us decide what to order. I ordered their squid ink pasta which isn’t something I would normally go for but it was absolutely delicious.

DAY NINE – 12TH SEPT

In the morning, we had a slightly later start and we got breakfast at around 10am. We had breakfast at a little cafe locals love going to, I had a salmon and cream cheese croissant and a glass of orange juice. We then got drinks at Coffee Mantra which is a really quirky and small coffee bar that locals love. After our drinks, we then explored more of the city where the main shopping area is and found Fontana del. Porcellino and then stopped at the Fiorentina Store and I got their latest home shirt for my collection.

It was early evening, and we found a really cool bar that had seating outside and it also has it’s own record shop upstairs. The service was a little slow but we eventually got our drinks. It was quite a warm evening so it was nice to sit outside with a cold drink. After our drinks, me and my dad went to the record shop to check out what they had.

We then went back to get changed and went out for dinner at Floretina. It’s quite a small family run restaurant with only a few tables but it was great service and food. I ordered their tuna salad and spinach and goats cheese ravioli.

After dinner, I wanted some gelato and found a shop just down the street from the restaurant called RivaReno. The queue was out the door because it was filled with American students who didn’t know what to order. I ordered a cone of chocolate and banoffee pie ice cream which was absolutely amazing! My favourite gelato so far!

DAY TEN – 13TH SEPT

It was quite an early start as we caught the train to Siena for another day trip. We got breakfast to takeaway again at Bar Centrale to have on the train. Once we arrived at the station, we had to take the escalators through the shopping mall to get into the city. There was a long walk up a hill to get to the walled entrance of the city that was filled with lots of quirky shops and restaurants.

Siena is a city in central Italy’s Tuscany region, is distinguished by its medieval brick buildings. The fan-shaped central square, Piazza del Campo, is the site of the Palazzo Pubblico, the Gothic town hall, and Torre del Mangia, a slender 14th-century tower with sweeping views from its distinctive white crown. The city’s 17 historic “contrada” (districts) extend outward from the piazza. Siena and Florence have a sort of mutual rivalry, after Florence took over Siena and they had to fight their way for freedom.

Once we arrived in the main palazzo, we stopped for a drink and could see barriers being set up in the center opposite the clock tower. We took a walk a little further and came across lots of decorations being put up and massive long tables being set up. There was a celebration going on where the 17 districts came together. There were young boys dressed in their traditional medieval outfits with drums and flags that would parade into the center with their family and friends and drum together.

Each contrada or district is represented by an animal or object and each district was responsible for a certain type of job like a baker or potter. During the war with Florence, they would rely on each other to survive and produce products to share around. They then paraded into the center in front of a massive crowd to display their flag catching abilities before celebrating together with a massive banquet. We then got tickets to explore the Duomo di Siena which is absolutely stunning

We explored a little more and stopped to buy some traditional cake called Panforte. It’s quite a dense cake made with cinnamon and nuts and can have other flavourings also. After that, we made the long walk back to the train station, but we decided to get the bus instead which worked out cheaper and was a lot quicker. We were absolutely knackered from all the walking so stopped at the first good restaurant we came across for dinner called Ristorante Lo Scudo, ironically was at the very end of our street from our apartment.

I will write up a separate food guide for Italy soon.

DAY ELEVEN – 14TH SEPT

It was our final morning in Florence and we had quite an early start. We had to pack our suitcases and leave the apartment before 8am. Our train to Rome was booked for 9am and before then we got breakfast at a lovely boutique hotel we had come across, called Glimpse Hotel. They have a cafe which is accessible for everyone and walk-ins from the street.

I ordered their smoked salmon and cream cheese bagel and a glass of orange juice. After breakfast, we walked to the station and got on our train. We had booked business class seats which gives us an area to store our suitcases, comfy seats and a snack and drinks during our journey. It’s so much better than getting a train in the UK, I can tell you that for sure!

At around 11am, we arrived in Rome and tried to catch the bus to our apartment. Although, it wasn’t easy and the bus we wanted didn’t seem to be there. Instead, we caught a taxi that dropped us off right at our apartment door so we could check in and offload our suitcases. Our apart hotel was lovely, it was a collection of apartments grouped together and was all newly decorated. It was very clean and very nicely done. The lady who checked us in Maria, was lovely and very helpful.

Once we had checked in and freshened up, we headed out to explore Rome and the area around us. We were so lucky and the Pantheon was literally 5 minutes from our apartment. We stopped to get some gelato and then get some lunch, which we got a pizza to share. I got an interesting flavour called American Cookie and paired it with a scoop of Nutella flavoured gelato. We stopped at Trevi Fountain for a little bit whilst we had our gelato and it was so busy, we could barely see it.

We then stopped for a nice cold drink at A Casa Tua as it was SO hot. It was nice to get out of the sun for a bit and relax before walking to the Colosseum ruins and The Wedding Cake, also called Victor Emmanuel II Monument. We then walked down Via del Corso, which is a famous shopping street in Rome until we came to the Roma Store. I really wanted to get a top but even the unnamed third kit top was about €150. We then headed back to the apartment to shower and get changed before heading out to dinner.

It took us a little while to find the restaurant we wanted as Dads satnav wasn’t playing ball. Eventually we made it to the restaurant which is called Come Na Vorta. There are a quite a few around Rome and even Italy. They make fresh pasta at the front of the restaurant and you can also book onto classes and learn how to make it yourself. We ordered a meat and cheese charcuterie board and also some focaccia and shared it around. I then ordered a Tricolore pizza (tomatoes, basil and mozzarella) which was eventually too much for me, so I took the leftovers back to the apartment.

We then stopped in the square of the Pantheon and found a lovely restaurant with outdoor seating and ordered some drinks. I ordered a Pina Colada and the waiter brought out some slices of cake and biscuits which was really nice of him.

DAY TWELVE – 15TH SEPT

It was our final full day in Rome, so we had breakfast early at Giolitti. It’s a very old fashioned and traditional patisserie that has been around since 1890 and has lots of pastry choices and hot drinks. I ordered a Pan au Chocolat and some orange juice.

We then headed out to explore starting at Neptune Fountain before heading to Vatican City and St Peters Basilica. It was absolutely chaotic there as it’s such a popular tourist attraction. We tried to book tickets to go inside but there was none left and there were people outside trying to sell tickets but they aren’t to be trusted. They will scam you and make money off you, so please be careful and avoid them at all costs.

We walked around the outside of the Vatican Walls and St Peters Basilica taking it all in from the outside instead. It was getting quite horrible and our feet were hurting, so we decided to stop for cold drinks and something to eat whilst we rested.

We did quite a bit of walking, taking in all the streets and sights along the way. We then came across this really awesome and quirky street called Via Stora that has lots of cool shops down it. One of them was called The Guitar Bag. It is run by a lovely lady called Maria, who had dreamed up her ideal business at the age of 16 as she was so obsessed with music but couldn’t play any musical instrument – to utilise guitar straps and turn them into fashion.

She now runs her boutique shop in Rome selling and creating bags with guitar straps inspired by famous musicians. You can choose your style of bag, strap type and design or pick from one already created. I bought one inspired by Amy Winehouse which is a black satchel bag and plain black strap with a material front, made from recycled material from Tuscany. The closure on the bag is made to represent a guitar pick and you can swap the bag straps out for any design you want.

After exploring the shops, we then walked a little further before I stopped to get a strawberry and raspberry frappe before heading back to the apartment. Once we went back to the apartment, we showered and got changed before heading out for dinner. We booked a table at Osteria da Fortunata, luckily we booked as it was so busy and can get really hard to find a table.

They were even telling people it would be 30 minutes before a table was ready. We ordered Fritto Misto which is a mixed range of deep fried vegetables before our mains. I had Arrabbiata pasta which is a little spicy but lovely tomato pasta. Our waiter was very good at recommending things to try and was a lovely character.

DAY THIRTEEN – 16TH SEPT

It was our final morning so we packed up our suitcases and bags and placed them in the storage room. We then headed out to get breakfast. I had an awful nights sleep as I was suffering from a really bad sore throat, I think it was COVID. When we stopped for breakfast I couldn’t really each much and only had a plain croissant. I stopped at a pharmacy and bought some throat sweets as I forgot to pack some.

We then walked to Trevi Fountain quite early so we could get a chance at taking good pictures and throw a coin. There was a little bit of a queue but it wasn’t too bad and we weren’t waiting for very long. There were a few people trying to push in, but we held our group so that they had to go to the back. We hung around the fountain for a little bit taking in the sights and snapping loads of photos and videos.

By mid-day, we decided to start walking towards The Spanish Steps and eventually came across the Lazio Store on route, so we stopped there for a little bit to see what they had in the shop. It was only a short walk from there and then we arrived at The Spanish Steps, which has been filmed in quite a few famous movies.

It was so hot and climbing those steps was near on impossible but we eventually reached the top and looked in the lovely little church at the top. I found out that my brothers friends who had been travelling around the world for a year for their honeymoon where in Rome of all places, so we arranged to meet up for lunch before we headed home later in the day.

We walked back from the steps which only took us 10 minutes and met up with them at a lovely restaurant for a drink. They ordered a pizza to share and it was so lovely to catch up and hear all about their travels. Around 1pm, we then walked to the Colosseum but found it impossible to get in so we only walked around the outside and took in the sights and saw some of the ruins.

It was around 2pm and we decided to stop for a late lunch and early dinner before our evening flight. We stopped at Trinity College Pub which is an Irish pub we came across that does really good food. I ordered their quinoa salad which was lovely, I did struggle to eat all of it as I was still feeling delicate with my sore throat. After lunch, we explored some nearby shops before walking back to the apartment to get our cases. We then had a 6 o’clock taxi to take us to the airport before our flight home.

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OUR ACCOMMODATION IN ITALY

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What would you like to do in Italy? What was your favourite city? Let me know in the comments below.