I consider Toscana one of the most beautiful regions in Italy and that´s already a big thing to say. Let´s not forget that when it comes to Italy, we are talking about Rome, Milano, Cinque Terre, The Vatican, Pompeii, Pisa, the Italian lakes, and so on. Therefore, the stakes are initially high when you find yourself in a position to choose your epic vacation spot in Italy.
So, what is so special about the holidays in Tuscany? Is it about those romantic panoramas with endless fields and hilltop hamlets? Charming little towns with cobbled streets? The most exquisite flavors of the local food&wine? That deeply-nostalgic and profound feel of Bertolucci or Fellini movies? – I don´t have an exact answer to this myself, but must admit that at this point I´m already sold and planning my next Toscana getaway asap.
Romantic Holidays in Tuscany
Let´s face it: every time you might search for The Most Romantic Vacation Ideas Around the World you’ll eventually come across Toscana. But you know what? In my experience, holidays in Tuscany really lived it up to their international fame. Even though I traveled there with my husband, at the same time I could totally imagine myself being Frances Mayes in Under the Tuscan Sun (check the full list of my favorite romantic travel movies) and finding love, peace, and a bit of adventure in this charming Italian province. For me, the most romantic place in Italy is not Venice, it is Tuscany.
Toscana in 3 days
Our holidays in Tuscany were a lot like that one weekend in Malta or an ambitious Icelandic Ring Road Drive in 5 days: not quite enough to explore the region fully, but yet enjoyable, revealing, and leaving us both (me and my husband) with itchy feet to come back for more. I´ve already complained to you that my husband has a 9 to 5 job and we often just don´t have all the time in the world to make those long trips. But I guess, it´s totally relatable, right? The only thing we can do is to make the most of our busy schedules and try to live our lives to the fullest the best way we can.
Also read: Expat Story – Italy Through American Eyes
So, I believe 5-7 days would be a better fit for the holidays in Tuscany, but that Taste of Toscana, you can savor it even in 3 days. Plus, we didn´t plan to make a stop in Florence, as both of us have previously been in the city. So if it´s your first vacation in Tuscany, add a few days in Florence to your Toscana itinerary.
Also, gourmets might combine sightseeing during your holidays in Tuscany with food or wine tours. You should have heard that Toscana is one of the world’s top popular wine regions, home to the Sangiovese grape. How about a glass of Brunello di Montalcino or Chianti Classico under the Tuscan sun?!
How to get there?
The best travel choice is to fly to Pisa of Florence. Rome could also work, but you’d need to drive a few extra hours ( based on my previous experience with public transport in Italy, I´ve initially decided to rent a car for our holidays in Tuscany).
Where to stay in Tuscany?
One of the best parts of our holidays in Tuscany was our stay in a very local family-owned villa, called La Canonica Di Fungaia (near Monteriggioni and Siena). After traveling to Italy quite a few times, I´ve recently come to the conclusion that for some reason hotels there have never worked for me. They almost always ended up being a disappointment in terms of price, quality, and expectations. Unlike staying with the Italian family.
Also read: Your Perfect Italian Vacation – Como, Garda or Maggiore?
The local cordiality and the warmly-loud Italian mentality, especially outside of the big cities, is an experience itself. You end up bringing back home more than a bottle of Limoncello – you enrich yourself with this unique cultural experience. Not to mention those delicious home-made breakfasts full of local specialties or some useful travel tips you could get from your hosts. And yes, Italians know how to win you over when it comes to food!
When to visit Tuscany?
Even though we traveled to Tuscany in July, so it was not in the offseason, it felt quite relaxed in terms of tourists and overcrowded places. We´ve only realized it was a touristy destination in Pisa: I bet you can easily imagine thousands of people reunited for that famous picture of supporting/pushing or whatever else they were doing with Leaning Tower of Pisa. But it´s one of the top Italian Landmarks – there´s no way around it.
Crowds were honestly my biggest concern after our last trip to Liguria over the Easter holidays (still don´t know how I managed not to develop both claustrophobia and agoraphobia at the same time).
Although, next time I´d probably revisit Toscana in Spring or early Autumn.


Let’s jump into the details and discuss all the wonderful places we visited during our 3-day Tuscany Road Trip. For sure, we wouldn´t be able to see that much, if not traveling by car. Even though navigating around all the mountain curves in Tuscany can´t be named one of the most relaxing driving experiences ever, but after that Masca drive in Tenerife, curves just don´t scare me anymore.
3 Days in Tuscany: Itinerary
While our flight was from Valencia to Pisa, we immediately rented a car and headed to Siena, leaving the famous Leaning Tower of Pisa for the end of our holidays in Tuscany.
Day 1: Siena – San Gimignano
Siena is a beautiful town to start your Toscana adventure. Don´t miss Piazza del Campo, Torre del Mangia, and Duomo di Siena or The Siena Cathedral, one of the most famous landmarks in Italy. In Siena, we´ve also had a nice lunch in Osteria da Divo, a cave-like restaurant lit up with candles. Quite a start for the romantic holidays in Tuscany.
After lunch, we headed to San Gimignano, definitely one of the most charming medieval towns in the whole of Europe. San Gimignano has been the UNESCO World Heritage Site since 1990. We mostly enjoyed a simple stroll through the historic center: tall towers, cobbled streets, and tiny cafes, tasty dishes. Don´t miss Torre e Casa Campatelli, The Bell Tower, Duomo di San Gimignano. For dinner, we´ve shared a delicious pasta with truffles at Perucà.


Day 2: Pienza, Montalcino, Montepulciano
Val d’ Orcia is everything you expect to see when traveling to Tuscany. This was actually my favorite part about our holidays in Tuscany. Visiting 3 small towns in one day felt a bit brief, but I really wanted to check all of of them and to pick favorites Pienza, Montalcino, Montepulciano.
Although, I was mostly excited to walk the street of Montepulciano ( The Twilight Saga fans would know why), but Pienza was probably the small town I liked the most. In Montepulciano, the central square was closed for reforms, so it honestly let us down a bit with the views.




Day 3: Volterra – Pisa
First thing in the morning we left our cozy La Canonica Di Fungaia near Monteriggioni and headed towards Pisa, while making a brief stop in Volterra.
Volterra is often called the Etruscan city and if you´re into the history and archaeological sites, then it´s a place to be. While the Roman Theatre impressed me less than the one in the Spanish city of Tarragona, it was still a must-stop. Don´t miss Piazza dei Priori, Palazzo dei Priori, Cathedral of Santa Maria Assunta, Porta all´Arco. We didn´t go to The Volterra Museum of Torture and the Etruscan Museum Mario Guarnacci, but these are the other populat touristy locations in Volterra.

After visiting Volterra and having lunch there, we drove to Pisa and spent an evening in the city. I don´t regret not leaving a full day for Pisa, because this was the moment when the romance with Toscana actually came to its end for us. If places packed with tourists don´t kill the magic for you, I honestly envy you.
I mean, you can´t leave Italy without crossing off your bucket list the Leaning Tower of Pisa. But would I make a stop in Pisa during my next holidays in Tuscany? – Probably, not (unlike Florence though). Yes, you can never expect to have places like The Eiffel Tower in Paris, The Colosseum in Rome, or one of the most beautiful cathedrals in Spain, Barcelona´s Sagrada Familia, entirely for yourself. But some places are worth the hype for me, while others are just meant to be visited once.

This post is linked up with The Weekly Postcard and Feet Do Travel
Loving all of the photos – this location looks absolutely beautiful!
Heather xoxo
Thanks, Heather!
The pictures are awesome hun and you look fabulous.
xoxo
Lovely
Thank you, Lovely!
Wow such breath-taking photos ♥ Have a nice day!
https://leraseyo.blogspot.com
Thanks, Valeria! Have a great day too!
what a lovely lovely place! it looks so beautiful and i feel like i want to pack my bag right now and travel there x
It is a magical place indeed!
Oh man, I can’t wait to visit Tuscany and these stunning pictures only made me want to go more… Glad to know you had a great time there!
Thanks for stopping by! I´d love to visit again myself – Tuscany is stunning!
Tuscany is probably one of the most charming destinations on my bucket list and I really hope to explore it one day, Anna. Your itinerary seems awesome and I’ll definitely put it to use when planning my trip there. When would it be the best time of the year to explroe Tuscany?
Thanks, Lydia! Next time I´d probably travel there in September/ first weeks of October!
Tuscany landscapes are so beautiful, we have to go back to Italy just to experience it 😀
In love with the vibes here!
Wishing you a lovely day
xx
Patricia & Miguel
http://www.freeoversea.com
Thank you, Patricia and Miguel!
Absolutely gorgeous!! Love these photos!
-Kate
Thanks so much, Kate!
I only spent a couple days in Tuscany as part of a two-week tour of Italy. I would love to go back and see more. I am also going to take your advice and try to stay in more family-owned places. I would like to see more of the small towns. Thanks for sharing on #TheWeeklyPostcard.
Italy is one of these countries you can travel back forever: I´ve been so many times and still haven´t seen even half of the things I planned!
I visited Tuscany as part of a coach tour through Italy. Sienna was lovely, but alas I never made it to Pisa! Looks like my own love affair with Italy and Pizza will continue when I return! Pinned #feetdotravel
I also have to come back: so many Italian gems to discover yet!
Sienna is such a beautiful old city! I was disappointed about Pisa. I haven’t heard about Val d’ Orcia, but it looks like it’s a wonderful place to visit, ill include it on my list the next time I visit Italy! #theweeklypostcard
Thanks for stopping by, Liana Katrina! Val d’ Orcia is absolutely charming!
This looks such a beautiful part of the world, would love to get there one day! 3 days is definitely not enough but some great information here. #feetdotravel
Thank you, Paul and Carole! Hope you´ll get a chance to visit soon!
I’ve read a number of posts of Siena and San Gimignano – they look so beautiful in pictures! I’ve never been to Siena and I would love to the next time I return to Italy. Pisa didn’t impress me much either, I prefer Florence instead. Love your photos! #TheWeeklyPostcard
Thanks so much, Kat! Both Siena and San Gimignano won´t disappoint you, as well as Val d’ Orcia!
I’ve never been to Tuscany – or Italy for that matter – but it sure looks idyllic. I’m heading there for my first time and am over the moon excited. Beautiful photos! #theweeklypostcard
Thank you, Jill! Enjoy your trip!
Ah yes, Anna, you’ve reminded me of a sensational week in Tuscany a few years ago. We stayed in an olive farm & their oil was TDF! Montestigliano if you ever get a chance was awesome. We also managed a chef table experience at the famous Butcher of Panzano. An experience like none I’ve had before. Thanks for the stroll down memory lane. 🙂
Thanks for the advice: will include Montestigliano into my Italian list and a chef table experience at the famous Butcher of Panzano sounds awesome!!!
Pinning for future travel planning! I do want to go back to Italy, and this region calls to me!Sienna is at the top of my list. I love the photo of the narrow street, tall brick buildings. So “Italian”!
This region of Italy is absolutely charming, calls to me as well!
Ah, I miss Italy! I visited Siena a few years ago and absolutely loved it. Your post made me want to go back there again. #TheWeeklyPostcard
Thanks, Anda! Same here: it´s one of these destinations I always enjoy traveling back to!
We have been there a few times and can’t wait to go again. It is so pretty and the pizza isn’t bad either 🙂 #TheWeeklyPostcard
Same here, can´t get enough of Italy!
Nice and Perfect looking outfit..
Thank you, Varuna Jithesh!
Wonderful photos and information. Tuscany is on my bucket list and you have found a wonderful place I would love to visit. Great day trip ideas. I pinned this for later use. Thanks for sharing!
Thanks, Stephanie! Hope you´ll get a chance to visit soon – it´s absolutely gorgeous!
Such a beautiful place! Love your photos. 🙂
Thanks, Emese!
Great post. San Gimignano is one of my favourite places in Italy. Still dreaming about those delicious truffles! #TheWeeklyPostcard
Such a beautiful place! I can´t forget a truffle pasta I had there myself lol
Great choices! I love Tuscany so much, I think I could live there. However, I have never been to Pisa. I may just keep it that way!
Tuscany looks like such a beautiful region! In all of the photos I’ve seen, it looks so laid back and a slower pace of life! This looks like an incredible road trip! Pienza looks adorable! What a beautiful place! And of course, I’d love to visit Pisa! Hopefully, we’ll be able to travel again soon and I can start planning a visit. Thanks for the great guide!
Tuscany really is so romantic! I visited during a family trip, but would love to revisit with someone special and see more of these small and quaint towns. I loved San Gimignano and Siena. 🙂
Tuscany looks like a dream trip, I love the views and the beautiful old buildings, what a remarkable place to visit. I think anywhere that isn’t as easily accessible from an airport always has a shot of being less touristy than the big cities, but good to know there are options to get there
I can’t wait to plan a trip to Tuscany! All of the villages look so beautiful and the landscape is amazing. Thanks for all of the tips!