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 and 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.
- This post contains affiliate links from which I earn a commission (at no extra cost to you). For more info, please read my disclosure. As an Amazon Associate, I earn from qualifying purchases.
Honestly, 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.
Romantic Holidays in Tuscany
Let´s face it: every time you 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 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 San Michele (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.
The local cordiality and the warmly loud Italian mentality, especially outside of the big cities, is an experience in 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 homemade 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 the 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, 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.
Unique Siena experiences and day trips:
- Cathedral Complex Pass with Audio Guide (check availability)
- Guided City Tour with Cathedral Skip-the-Line Entry (check availability)
- Siena Horseback Adventure in the Tuscan Countryside (check availability)
- From Siena Chianti Countryside E-Bike Tour w/ Lunch & Wine (check availability)
- From Siena Chianti and Castles Tour with Wine Tastings (check availability)
Visiting San Gimignano
After lunch, we headed to San Gimignano, one of the most charming medieval towns in the whole of Europe.
San Gimignano has been a 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, and Duomo di San Gimignano. For dinner, we´ve shared a delicious pasta with truffles at Perucà restaurant.
Unique San Gimignano experiences and day trips:
- Torre Grossa and Duomo Tickets (check availability)
- San Gimignano Tour in a family winery with wine tasting (check availability)
- San Gimignano Romantic Vineyard Lunch (check availability)
- San Gimignano Campatelli Home and Tower Visit (check availability)
Day 2: Pienza, Montalcino, Montepulciano
Visiting Val d´Orcia
The region of Val d’Orcia is everything you expect to see once 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 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.
Unique experiences to book:
- Montalcino Vineyard Picnic with a Bottle of Wine (check availability)
- Montalcino Brunello Wine Tasting & Lunch in a Tuscan Castle (check availability)
- Montepulciano Wine Tasting and Cellar Tour (check availability)
- Montepulciano Historical Cellars Guided Tour & Wine Tasting (check availability)
- Pienza Palazzo Piccolomini & Palazzo Borgia Entrance (check availability)
- Pienza Dairy Farm Tour with Pecorino Cheese Tasting (check availability)
- Movie Sets Tour in Valdichiana Senese & Val d’Orcia (check availability)
Day 3: Volterra – Pisa
A 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 popular stops in Volterra.
My impressions of Pisa
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 an 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. Yes, you can never expect to have places like The Eiffel Tower in Paris, The Colosseum in Rome, or Barcelona´s Sagrada Familia, one of the most beautiful cathedrals in Spain, entirely for yourself. But some places are worth the hype for me, while others are just meant to be visited once.
Unique experiences to book in Pisa:
- Leaning Tower and Cathedral Skip-the-Line Tickets (check availability)
- Pisa Food Tour (check availability)
- Pisa Self-Guided Tour by Bike (check availability)
- Pisa All-Inclusive Guided Tour with Optional Leaning Tower (check availability)
For more ideas to plan your epic Italian vacation check my Pinterest board – Italy Travel Tips and Destinations.
- Accommodation: For short stays, I usually book via Agoda, Booking, and Hotellook
- Tours&excursions: My favorites for guided tours are GetYourGuide and Viator
- City breaks&sightseeing: Go City helps to avoid multiple entry fees and paper tickets
- Travel Insurance: find the best trip insurance plans via VisitorsCoverage, EKTA, and Insubuy
- Flights: To find the best deals I like WayAway and Aviasales
- Airport Lounge: Get independent airport lounge access worldwide via Priority Pass
- Train&bus tickets: Currently, I book via RailEurope, Omio, and Busbud
- Car rental: To find the best deals I use Rental Cars, Discover Cars, and GetRentalCar
- Transfers: For individual transfer services I like Kiwitaxi
- For Foodies: Eatwith is great for finding culinary experiences with locals
- Cruise Reviews: To find the best cruise offer I check out Cruise Critic
- Suitcases&Luggage: To eliminate problems of early arrivals/late departures I find helpful Radical Storage
- Compensation for delayed/canceled flights: AirHelp is useful for all flight cancellation or delay claims
- To avoid roaming fees I use Airalo eSIMs around the world
- Budget-friendly stays: Check Hostelworld to find the best deals around the world
- Events: To find the best offers I use Ticketmaster and TicketNetwork
- Renting Bikes: to find motorcycles, scooters, quads, and bicycles I use BikesBooking
- Package Tours: head to CheapOair, Expedia UK, Tourhub, and loveholidays
- For Bloggers: To monetize my blog I use Travelpayouts