Tuscany Travel Guide – One Week Itinerary

Tuscany is one of those places that actually looks exactly like it does in the photos. In fact it looks better, the postcards, Instagram posts and brochures, really do not do this place justice at all. It needs to be seen to be believed. The rolling hills glistening with sunlight, miles and miles of lush vineyards and the most beautiful architecture and ancient towns, what is not to love about this magical county in Italy. Not to mention the fact it probably has. what I think, the best food and wine in the world, pasta, truffles and red wine, what more do you need?

We stayed in a villa nothing short of amazing in the south of Tuscany, approximately a 1 hour drive from Sienna and 3 hours from Pisa airport and I could not recommend it enough. From the picture perfect, story book setting, to the generous and kind hospitality of the family who owned it. If you’re visiting Tuscany in a group, Villa La Valiana is an absolute must stay place. With four bedrooms, all with an en suite, multiple outdoor seating areas, huge heated pool, a vineyard as the back garden and the most perfect balcony to watch the sunset, it is everything you could want and more.

Here’s what we got up to during our relaxed week in Tuscany and my tips for enjoying this Italian county.

Day 1 – Arrival and Pisa

We flew into Pisa, landing at lunchtime and thought it would be silly not to visit the iconic Leaning Tower. Just a 10 minute drive from Pisa airport, we jumped into a rather erratically driven taxi through the narrow streets of Pisa and arrived at the tower. What we didn’t realise is the Leaning Tower is actually part of a complex of three stunning buildings in total. The Piazza del Duomo and Cattedrale di Pisa are the other two buildings in the same area and equally as intricate and beautiful to explore. These were pretty quiet to wander around as many tourists were interested in the tower only. You can buy tickets to head up the Leaning Tower, but this needs to be booked in advance, sadly there was no availability on the day for us.

Of course you can’t visit Pisa without the classic photo. Don’t worry, you will not be alone, everyone is attempting the same feat and some people were very creative. I’d recommend getting there for sunrise on a weekday for an empty Leaning Tower photo for the gram.

If you’re looking for a bite to eat around Pisa, head slightly further afield form the main tower area. It is an incredible tourist trap with bottles of water costing nearly 4 euro and cheap cafe’s charging 15 euro for a basic Margarita pizza. There are much nicer, more authentic, not to mention cheaper Italian restaurants if you move away from the tower. As we were short on time and wanted to get to our sumptuous villa, we decided to wait it out and let the hanger commence.

After we had filled our boots with photos of the tower and taken in the delights of the other gorgeous buildings, we took a taxi back to the airport, collected our hire car and set off to the villa.

From Pisa to the Montepulciano region it takes around 3 hours, but stock up on snacks and water and you’ll be fine. It’s an incredibly scenic route, twisting and turning through the rolling hills of Tuscany, I think we saw about 50,000 cypress trees (those iconic tall and narrow Tuscan trees) on the journey alone. You’ll definitely want to stop at many of the adorable villages for a photo shoot or two along the way.

After stocking up at a local supermarket and clearing out their red wine stores, we arrived at the beautiful Villa La Valiana and were greeted by the gorgeous family who own the house. We’re were given the grand tour from the library room where we could find games, to the complimentary homemade apricot tart and wine they had kindly left us and of course the gardens where huge rosemary, basil and bay bushes were growing, along with courgette, cumbers and tomatoes, all of which we were told we could help ourselves to. The place is just out of this world.

Rooms chosen, unpacked and it was time for a delicious home cooked meal in our new dining room, followed by card games and a not so early night.

Day 2 – Montepulciano

A leisurely morning, with breakfast on the terrace followed by a swim in the pool was the perfect way to start our first day in the Tuscan valley. After a long day of travelling the day before a slow and relaxed morning was essential. 

In the afternoon, we took a 20 minute drive to the historic town of Montepulciano.

This stunning town situated on a limestone hill, is often called the “jewel of the 1500s” due to its impressive Renaissance art and architecture. No major building work has happened there since 1580,  so you get a pretty good feel for how it’s ancient inhabitants would have lived. Montepulciano is filled with wine shops (with free wine tastings), bakeries, gelato shops, restaurants, cute balconies, clothing shops, leather goods, potteries and more. Plus, the town does not allow cars through it’s narrow streets, so it’s fabulous to wander through without worrying about being run over. There’s a car park at it’s entrance just make sure you have some change.

There are some amazing view points too, once you have ambled through the cobbled streets for 10 minutes of so , you’ll find many alleyways going off to the left which give you access to some pretty fabulous views of the Tuscan valley and those famous cypress trees.

If you’re a Twilight fan like myself, this hilltop town may look rather familiar and that is because New Moon (the second film in the series) was filmed here. Remember the Voltari scene with all those people in red capes, Bella racing through cobbled streets, all before stopping Edward revealing his true, sparkly vampire self? Yep, all filmed in Montepulciano.

You can spend a whole day walking around and exploring, we were here for 3 hours and definitely didn’t see everything. After hitting 10,000 steps and gelatoed out, we headed back to the villa to catch the last rays of sun by the pool and enjoyed another delicious meal on the balcony just in time for the sunset.

Day 3 – Chill Day

Today was Tom’s, brother’s birthday, so as Brits abroad do, we cracked open the fizz at 11am and didn’t stop until the wee hours of the morning. Luckily today was one of the hottest days, perfect for lounging around the pool and not walking through hilltop towns.

In the evening, we had pre-booked a private chef to come in to cook us a four course meal. It was organised by the owners of our villa and we pre-selected what we would like to eat. They opened up the doors to the private dining room and restaurant standard kitchen INSIDE the villa, which was simply amazing. We enjoyed tempura veg, beef tartare, roast pork, steak, seafood linguine and creme brulee. What’s more, there was no washing up, as the wonderful chef and kind staff took care of everything. It was the most perfect evening.

Many villas in the area offer this service and I couldn’t recommend it enough if you’re celebrating a special occasion.

Day 4 – Cortona

With slightly tender heads, we took a trip to another delicious hilltop town called Cortona. This place is similar to Montepulciano just on a larger scale and equally stunning. Again you could wander the cobbled streets for hours.

 I also found one of my favourite shops here, Santa Maria Novella. This tiny perfumery, only has two shops in the UK, both of which in London. I love it so, because on mine and Tom’s second anniversary we went to this tiny and quaint, yet beautiful AirBnB cottage in Wales. When we walked in, we were hit by this glorious smell, which turned out to be potpourri, and after contacting the owners we found out it was from Santa Maria Novella. Seeing that it couldn’t be purchased online, the last time we were in London, we stocked up on two bags. So you can imagine our delight, wandering through the tiny streets of Cortona and seeing a Santa Maria Novella shop! Of course we stocked up again, treated ourselves to some fancy soap and Tom got a rather delicious aftershave.

We enjoyed some well deserved wine in the main square in the shade, to people watch and recharge, then headed back to the villa, so the designated drivers could enjoy some wine too.

Day 5 – Lake Trasimeno and Castiglione del Lago

From the balcony of our villa we could see a lake and discovered it was Lake Trasimeno where the town of Castiglione del Lago sat. We embarked on the half an hour drive there and took our mozzy spray as recommended by the villa hosts for using around the lake. 

This town is lovely and in a more built up area in comparison to Cortona and Montepulciano, it didn’t feel as historic when we first got there, but still very pretty nonetheless. However, Castiglione del Lago had the advantage of a fantastic ancient fortress, which you can walk through and climb to get great views over the lake. If you want to go up it costs 7 euro, definitely worth it.

We of course enjoyed more gelato then headed back to our villa.


Day 6 – Sienna

When you say you’re going or have been to Tuscany, many people associate the region with one of the most popular towns, that town being Siena.

Siena is like all the other hilltop villages but on a much larger scale and it’s much busier and touristy, however it does have some sublime, grand features.

Siena’s heart is its central piazza known as Il Campo, known worldwide for the famous Palio run here, a horse race run around the piazza two times every summer. Apparently 4,000 people descend into the square and those who own a balcony overlooking the square charge thousands to those wishing to enjoy the best seats in the house. The Duomo of Sienna is simply beautiful, along with the adjoining museum. There’s also the fabulous Palazzo Pubblico and its tower, Torre del Mangia, which you can climb to see stunning birds eye views of Siena and beyond. 

I’d recommend nabbing a table in the main square (Il Campo) to enjoy a rather pricey glass of wine, people watch until your hearts contents and plan out what you next wish to see in this historic town. Siena has quite a modern feel as it houses the university of Siena, which is a newly built building and cars can also drive through the centre so it’s a great mix of ancient history and modernity.

If you love truffles like me (not the chocolate kind) you’ll find an abundance of truffle shops here. You’ll smell them before you see them, I was in my element and stocked up on many varieties.

After an indulgent day tasting truffles and drinking red wine, we headed back to the villa for, you guessed it, more wine.

Day 7 – Wine Tasting and Vineyard Dinner

We knew we couldn’t visit Tuscany and leave without visiting a working vineyard and enjoy a wine tasting, so on our final day we did just that. Turns out our villa was luckily a short walk from a nearby vineyard, which offered tours of their cellars, grapes and finished with a wine tasting lunch. It’s called Avignonesi and is simply amazing. All of their wines are certified vegan and they offer such fantastic knowledge about all their wines, plus we were the only one’s on tour, so we enjoyed a very personalised service. We tottered back to the villa to enjoy a vineyard of our own.

On our final night we enjoyed dinner in the villa vineyard, prepared for us by the loving hosts. We enjoyed delicious canapes on the balcony, before devouring homemade pesto pasta, followed by a huge BBQ and finished with homemade baked cheesecake. They paired every course with a sumptuous wine, as the hosts are trained sommeliers and they even prepared a veggie option for me which was so thoughtful.

Enjoying our final night watching the sunset over the vineyard, dining under the stars with great food and even better company was the perfect end to our Tuscan holiday.

Have you been to Tuscany? What did you do? Where did you stay?

You can book your very own stay at the stunning Villa La Valiana here.

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Tuscany travel guide one week itinerary


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About The Style Parcel

Welcome, The Style Parcel is a blog dedicated to all things lifestyle. Featuring beauty product reviews and time-saving tips, detailed travel guides, such as Sri Lanka itineraries, fitness inspiration with easy to do at home workouts, foodie recipes for quick meals on the go, interior tips and much, much more. Based in Manchester, UK, I’m a fashion marketing graduate and Marketing Coordinator by day, lifestyle blogger by night.