Tuscany
The one that holds up for a long stay with a mixed group.
Country
Italy
Best Months
May, June, September, October
Best For
Families, Couples, Multi-generational, Foodies
Tuscany works for two weeks in a way most places do not, because there is enough to do that nobody is bored and enough space that nobody is on top of anybody. Chianti sits between Florence and Siena and is the obvious base. Val d'Orcia further south is emptier, more photographed and further from everything.
It is a farmed landscape rather than a scenic one, which is why it repays a slow week. The cypresses were planted, the terraces were built, the woods are managed. Understanding that changes what you look at.
The case against is that you are inland. If the holiday is built around swimming, this is the wrong region and the coast is a drive.
Tuscany
Highlights
Chianti between Florence and Siena for a first visit
Val d'Orcia for emptier roads and longer views
Florence, Siena and Arezzo all reachable as days out
A working agricultural landscape, not a scenic one
Spring and autumn beat high summer for heat and crowds
Book it
Things to do in Tuscany
The Florence Pottery Experience: Factory Tour & Masterclass
Hi, my name is Matteo, and I grew up surrounded by clay, watching my father and grandfather shape ceramics by hand. Florence is full of incredible things to see, but there is an Italy beyond the tourist routes that is worth discovering. We are right there. Montelupo Fiorentino is where Florence's ceramics have been made for over 700 years. When you visit us, you step into the daily life of a pottery family. You meet my father Salvatore, who has been at the wheel for 50 years, and the artisans who hand-paint every single piece — it gives you a whole new appreciation for handmade things. If something catches your eye, you can also order custom-made pieces directly from the factory! After the visit you get into it yourself, sit at the wheel, and make something with your own hands. We are proud to enrich the Italy trip of the people who come to us, so they can say they did not only visit Italy — they explored it, understood its traditions, and left with something they created themselves.
Farm To table Experience on an organic hilltop estate in Tuscany
For a day you will get away from the crowds, heat, noise and queues. Enjoy a day of nature, incredible views, friendly people, great food and wine! Our experience starts in Florence Santa Maria Novella Central Station where you will meet and we will help you buy the train tickets to San Miniato. The train ride to San Miniato will take 40 minutes. The name of our farm is Agriturismo Tenuta Chiudendone. Upon arrival, we'll walk around the estate so you can see our vineyard and olive grown. We'll visit the gardens to gather ingredients for our lunch, which we'll prepare together. You'll find out how traditional Tuscan cuisine is simple, fresh, and delicious. Depending on the season, we might pick grapes, olives, wild asparagus, wild herbs, or even hunt for prized white truffles in autumn. PLEASE NOTE ! THIS EXPERIENCE IS ONLY FOR EXTROVERTED SMILING PEOPLE
The Cooking Lab - Authentic Food Experience
I have a real passion for quality food and I am impatient to share it with new people. Cooking and eating all together is such a good experience that I don't want to keep it just for me! I'm realy enthusiastic for the genuine italian cuisine since childhood and I look forward to meet new "lovers" every day!
UFFIZI Private Tour in Florence Italy
Unlock centuries of Italian genius with an exclusive private tour of Florence’s legendary Uffizi Gallery — home to some of the most extraordinary masterpieces ever created. Accompanied by an expert guide, you’ll journey through the stories and passions that shaped the world of art forever. Stand face-to-face with Botticelli’s “Primavera” and “The Birth of Venus,” two icons of beauty that continue to captivate hearts centuries later. Uncover the mystery behind Michelangelo’s only panel painting — and why he ultimately chose marble over canvas. Marvel at Leonardo da Vinci’s “Annunciation” and hear the tale of his “Adoration of the Magi.” As you wander through this maze of masterpieces, your guide will bring to life the saga of the powerful Medici family — the patrons who made Florence the cradle of the Renaissance. This isn’t just a museum visit — it’s a journey through time, passion, and genius. Experience art as it was meant to be seen: up close, personal, and unforgettable.
Brunello Wine Tour and Val D'Orcia Landscape
I was born and raised here in Tuscany and I know the best wine maker but the key is small wineries with high quality where they will call you by name and not by number.... Private experience for real. My English is quite good which will maximize your experience and that is very important. Also this tour as all of my tour are fully CUSTOMIZABLE..... is your tour..
Montalcino: Renowned Tuscan Olive Oil Mill Tour & Tasting
Tuscany’s Most Popular Olive Oil Tour – Discover a World-Renowned Producer Step inside one of Tuscany’s most celebrated olive oil mills and discover the secrets of world-class Extra Virgin Olive Oil. This 1.5-hour immersive experience includes: a short historical introduction, a visit to our state-of-the-art production area, and a guided professional tasting. Taste ultra-premium EVOO paired with warm Tuscan bread and local specialties while learning how to select, use, and store high-quality olive oil. Our award-winning Brunera – Ultra Premium EVOO by Frantoio di Montalcino has earned Gold Medals at major international competitions worldwide. After the tour, enjoy exclusive access to purchase directly from the producer. Perfect for food lovers, couples, and families visiting Tuscany.
Prices, durations and ratings are Viator's, shown as Viator published them on 2026-08-25. They change. Booking goes to Viator, not to us, and we earn a commission at no extra cost to you.
Getting There
Florence Airport (FLR) and Pisa Airport (PSA) both serve the region, with Pisa offering more low-cost options and Florence better connections to premium carriers. Rome Fiumicino (FCO) is 2.5-3 hours by car. A hire car is strongly recommended for exploring the region - distances between towns are short but public transport is limited.
Insider Tip
Base once and radiate. Tuscan distances look small and the roads are hill roads. Two bases in a fortnight, not five.
Guides
Tuscany guides
How to tell whether a holiday listing still exists
We opened and read 1,621 venue websites across six destinations. Here is what we found, what it means for anyone booking anything, and the five checks that catch most of it.
When to go to the Mediterranean, month by month
September water is warmer than June water almost everywhere, and it is the single most useful thing nobody tells you.
How we source these guides, and why it changes what we will tell you
Every venue we name has been checked against its own website with the date recorded. Here is the method, what it costs us, and the things it stops us saying.
FAQ
Tuscany questions
Is a car necessary in Tuscany?
Yes. The countryside is the destination and public transport connects towns rather than the places between them. Take the smallest car you are comfortable in: the hill roads and the village streets were not laid out for anything large.
What is the difference between Chianti and Val d'Orcia?
Chianti sits between Florence and Siena, so it is the practical base for a first visit, with both cities reachable as day trips. Val d'Orcia is further south, emptier, more dramatically photogenic and further from everything. Chianti for convenience, Val d'Orcia for the longer views.
Can you swim in Tuscany?
Not conveniently. This is an inland region and the coast is a real drive from Chianti or Val d'Orcia. If the holiday is built around getting in the sea, Tuscany is the wrong choice and the book says so.