Under the Tuscan Sun: Five days in the heart of Italy
Ever since I watched the film Under the Tuscan Sun (and have subsequently read it), I’ve been enamoured by Tuscany. I first visited when I was 10 and have been lucky enough to have visited since on multiple occasions. However, every time I go, I’m reminded of the special and unique charm of this region of Italy, and exactly just why I love it so.
This trip was one that I planned for my friend’s birthday. With a flight leaving London City on a lovely June morning, we were greeted with the most beautiful views upon departure (there really is something special about flying out of LCY for an avgeek like me). A mere 2 hours later, we were landing into Florence, the jumping off point for this trip to Tuscany.
Having landed into FLR around 11:30, and with a train leaving for Siena booked for 14:10, there was only one thing for it for our first refreshment on Italian soil. At Christmas time just gone, I’d discovered the magic (and perhaps gimmick) of a wine window, but gimmick or no gimmick I loved it. My favourite – Osteria Belle Donna was only a 10-minute walk from the tram stop that took us from the airport to the city, and so that’s where we headed. I love the whole notion of these wine windows. A non-pretentious aperitivo or glass of wine is served through a non-assuming hole in the wall, where tourists and locals alike can perch on a pavement putting the world to right with their drink of choice. Having become synonymous with an Aperol Spritz in recent years, it was the order of choice, and we spent a relaxing few hours in the Tuscan sun, settling into the slower pace of Italian life.
A quick swing by the Duomo later (no matter that I spent significant time here in December, the magnificent façade of this building still takes my breath away), and it was time to catch our train to Siena. Italian trains are something of a marvel to me (coming from the UK where train cancellations and expensive fares are something of the norm), and our train was calm, spacious, affordable and on time. An hour and a half later having filled my head with EuroPop tunes watching the rolling countryside speed, we arrived into Siena.
The walk up to the city from the train station is one to be remembered… not for the historic architecture, but for the escalators. Situated high up on the hills, I lost count of the number of travelators and escalators we scaled before reaching the walls of this city, but you felt as though you were travelling up through to the clouds to some form of higher land.
We had perhaps an hour or so before we could check into the AirBnB I’d booked for this trip, and after an early start and nothing to fuel us except for a couple of spritzes, it was more than time for lunch in the Piazza Del Campo, plus I was eager to get the sightseeing underway, having only got around 48 hours in Siena before moving on to our second stop.
Nestled in the heart of Siena, Piazza del Campo is one of Italy's most beautiful and distinctive public squares. Its unique shell-shaped design and warm brick paving create a welcoming space where locals and visitors gather to relax, enjoy a coffee, and soak up the city's rich history. Surrounded by elegant medieval buildings and overlooked by the impressive Torre del Mangia, the piazza comes alive twice each summer when it hosts the famous Palio horse race, making it a place where centuries-old traditions continue to thrive.
For us, it was the perfect toasted focaccia and double espresso spot. We were also subject to a sudden rain shower which this part of Italy can be known for. However, this didn’t stop the local teens and children playing all manner of ball games in the square. Not long after, it was time to find our accommodation, situated just a two-minute stroll from the Duomo.
With it being a Friday night, I was keen for us to head out to soak up the atmosphere, and I really wanted to find somewhere with a sunset view over the city and the Tuscan hills. Fortezza Medicea proved to be the perfect spot. Perhaps a 20-minute walk from the historic city centre, and certainly uphill (I wouldn’t bother packing any shoes other than a pair of trainers and comfy sandals), the Fortezza is clearly the spot where locals head for their evening Passagio or for the more sports enthusiastic, a light run in the golden glow of sunset. Although it took us approximately 30 minutes to find our way up to the top of the fort, once there the view did not disappoint. Beautiful deep reds, purples and oranges bathed the light golden fields, and terracotta roofs almost shone as they soaked up the last of the heat of the day. Perhaps even better, a small bar located in the corner of the Fort, served aperitivos to live entertainment, which I could absolutely imagine becoming routine if one were to live here.
Dinner beckoned shortly after the sun sank below the horizon, and for our first night we fancied something simple and filling. Pizza ticked that box for me, and portions were most certainly generous. One final spritz later, it was time to head to bed ready for a full day of sightseeing.
Day 2 started with a pastry, juice and coffee at a local café in the city centre, before we made our way to the Siena Duomo. I’d bought tickets well in advance knowing that top attractions in Italy can sell out months prior to your visit. Siena's Duomo is a breathtaking masterpiece of striped marble, intricate mosaics, and soaring Gothic architecture. Just a short walk away, the Facciatone offers a glimpse of the city's grand ambitions - this monumental unfinished facade was meant to expand the cathedral into one of Europe's largest. Climb to the top for sweeping views across Siena's terracotta rooftops and the rolling Tuscan countryside beyond. Both are well worth a visit and earmarking several hours of your time in Siena for.
Having had a sufficient dose of culture, it was absolutely time for a refreshment and the conveniently placed Roxy’s bar (at the exit of the Facciatone) was the perfect lunch stop. I had the obligatory spritz and local cheese and ham sandwich before we headed for a walk through Piazza Del Campo and the Northern side of the city.
Throughout the afternoon, I could have sworn I heard ceremonial drumming, and this got persistently louder and more dramatic as the afternoon went on. If you’ve seen the film Under The Tuscan Sun (or read the book for that matter) you’ll know the iconic scene, where the young Polish boy, in their bid to show Tuscan pride, learns to throw the flag for the local Tuscan town festival. However, distracted by his love, loses sight of the flag and ends up being hit on the head with said flagpole. So, I knew that flag throwing was somewhat of a thing in this part of Italy and was often accompanied by drumming. I decided to go hunting for the drumming in the hope that I might find a spectacle to entertain me for the afternoon. It didn’t take long, but 20 minutes later, I found a rehearsal for a festival, and spent an hour watching the flag throwing progress, sat by the most beautiful fountain with colourful fish.
After a quite exciting afternoon, it was time to head out for dinner and drinks. Dressed like an Aperol (in my favourite colour, orange) we sat by the Duomo, sipping our spritz, before finding a comfortable, local Osteria for a Ragu and glass of wine to round off the night.
The following morning, it was time for a quick coffee and pastry, before leaving the stunning city of Siena, for our next stop on our Tuscan tour. A short hour and 20 coach journey through the rolling Tuscan Hills, lies the gorgeous city of Arezzo, our home from home for two nights. Coincidentally, this happened to be the first Sunday of the month, in which the whole town appears to become a market, which Tuscans from near and far descend upon in the hope of stumbling across a treasure or two. After grabbing an ice cream to perk up after the journey, it was rather pleasant to meander through the crowds of shoppers, thinking about all of the things I’d like to somehow carry back to the UK.
We found our way to Piazza Grande – famous for the film La Vita E Bella (or Life is Beautiful to you and I) for a birthday lunch for my friend, watching the world go by. We checked into another AirBnB, Gatto Storpio (check it out on my insta, it’s a fab place to stay if you’re in Arezzo for a few nights). First on the sightseeing list for Arezzo was Basilica di San Francesco, which happened to have free entry being the first Sunday of the month. The Basilica di San Francesco in Arezzo is one of those places that quietly steals your breath. Step inside the Bacci Chapel, and suddenly you’re surrounded by Piero della Francesca’s radiant fresco cycle, The Legend of the True Cross. The colours feel almost sun‑lit, the geometry crisp, the storytelling serene. It’s a space where Renaissance brilliance meets monastic calm, making it one of Tuscany’s most rewarding artistic detours.
The usual evening routine then resumed, consisting of a couple of spritzes to celebrate the birthday girl’s day, followed by the meal of the trip at a local Osteria. Thinly sliced beef, topped with truffle, and white Tuscan beans, rounded off with Tiramisu. If you’re in Arezzo, check out Antica Osteria l’Agania… you won’t regret the feel of the local charm.
The following morning, I headed out of the AirBnb down to the local café where locals gathered with their morning papers and espresso cups. I grabbed a couple of pastries to take back to the patio of our apartment, to enjoy in the morning June sunshine.
We then headed off to the amphitheatre of Arezzo - one of those spots that’s just fun to stumble into. It’s a big, sun‑soaked Roman oval tucked right into the city, and even though only parts of it remain, you can still totally picture the crowds and chaos it once held. Wander around the arches, sit on a worn stone step, and let the place do its thing. Right next door, the Archaeological Museum has cool finds dug up from the site, so it’s an easy double‑stop if you’re already in the area. Super chill, super atmospheric, and a nice break from the busier Tuscan highlights.
A short stroll away was the second stop of the day. The Cathedral of Arezzo has this calm, slightly dramatic vibe that hits you as soon as you walk in. Its tall Gothic columns pull your eyes upward, and the soft light makes the whole place feel a bit dreamy. Don’t miss the Piero della Francesca fresco tucked inside, it’s small but gorgeous, like a quiet bonus round after the big Renaissance sights around town. Just outside, the Cathedral Gardens are perfect for a breather: leafy paths, city views, and plenty of benches where you can flop down with a gelato and watch Arezzo go by. It’s one of the easiest, most relaxed combos in the city, art, architecture, and a chill green space all in one stop.
Lunch was next on the agenda, and I’d seen the perfect spot on social media for incredible sandwiches. Antica Bottega Toscana will make your sandwiches fresh in front of you, giving you time to explore the local produce on display in this gorgeous gem in Arezzo. We took our sandwiches to a bar in the Piazza to enjoy with a spritz and gelato, basking in the afternoon sunshine.
Evening rolled around with the now regular routine of a spritz in the square kickstarting us off, before we walked back up to the cathedral for sunset. Head to the West side of the cathedral for the most stunning views of the sun setting over the rolling countryside. Breathtaking and worth every second of pausing to take in the view. We then strolled back to the square for dinner, where I enjoyed a traditional wild boar ragu, and local chianti.
All too soon, the final day of our Tuscan adventure arrived, so after a quick breakfast, we headed to the train station to catch our train to Pisa, via Florence. I was craving a pizza and a spritz and the pizza in Pisa did not disappoint. Accompanied with fans that circulated water regularly to cool the crowd down, and photo frames of local currencies around the world, this spot had charisma and character aplenty.
At 14:30 we promptly skipped over to the leaning tower, which was the main purpose of our visit and day to Pisa. You can’t take your bags up the leaning Tower, so do leave time to lock them in the lockers (for free!). The Leaning Tower is world famous, and in my opinion, rightfully so. You wander into the bright green Piazza dei Miracoli and, boom, there it is, tilting like it’s trying to photobomb the cathedral next door. The tower’s white marble pops against the sky, and everyone around you is either laughing, taking the classic ‘holding it up’ photo, or just staring at how delightfully odd it looks. Climbing to the top is a fun, slightly wobbly experience, and the view over Pisa’s rooftops is worth every step. It’s touristy, sure, but in the best way: a quick, joyful stop that never fails to make you smile.
After swinging by the cathedral (making a count of three for this trip to Italy!), a final spritz stop and a gelato for the road, we picked our suitcases up from the locker drop off and headed on the tram to the airport (you can buy tickets at the station, and it’s well signposted!).
Five days under the Tuscan sun reminded me exactly why this part of Italy has such a hold on my heart. From slow mornings with espresso and pastries to sunset spritzes overlooking rolling hills, every moment felt like a gentle pause from real life. Tuscany has a way of wrapping you up in its rhythm, the food, the art, the landscapes, the people, and this trip was the perfect blend of nostalgia, celebration, and discovery. Whether wandering Siena’s medieval streets, soaking up Arezzo’s Renaissance charm, or laughing beneath Pisa’s iconic tilt, it was a journey stitched together by simple pleasures and unforgettable views. I already can’t wait to go back.
My Top 5 list for a Tuscan tour:
1. Sunset at Fortezza Medicea: Golden light, locals strolling, and aperitivos with a view that feels straight out of a film.
2. Siena Duomo & Facciatone: Striped marble, sweeping panoramas, and Gothic drama at its finest.
3. Basilica di San Francesco, Arezzo: Piero della Francesca’s frescoes glowing in perfect Renaissance calm.
4. Arezzo Cathedral & Gardens: Quiet beauty inside, leafy serenity outside, the ideal mid‑day breather.
5. The Leaning Tower of Pisa: Playful, iconic, and surprisingly magical when you’re standing right beneath it.
For more pictures from our Tuscan Adventure check out my gallery here
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