Home to beloved towns such as Florence and Siena, the Tuscany region is a staple when exploring wine in Italy. And, as most travelers know, a trip to Italy simply is not complete without delicious wine. When travelers envision their trips to Italy, many know they want to visit vineyards and drink delicious vino. However, they may not know the best places to do so. In this guide, you can discover the best sites and wineries in Tuscany.
While we love Florence, the lesser known Tuscan towns just have a certain charm about them that make your vacation unforgettable. After a walking tour of Florence and a visit to the Uffizi Gallery, a visit to Tuscany’s hideaways is a perfect addition to your vacation.
San Gimignano
You can find countless charming towns and villages tucked away in the hills of Tuscany. Among the best towns in Tuscany is San Gimignano, a small town in the province of Siena. Perched atop a hill, San Gimignano looks like a medieval city from below. Its tall towers appear as medieval skyscrapers, coining the city’s nickname “Medieval Manhattan.”
Here you can explore a host of landmarks. We recommend visiting Piazza del Duomo, where you can find Palazzo Communale and Torre Grossa. Palazzo Communale is a beautiful municipal palace in the center of San Gimignano with a tall tower protruding from the top. This tower, Torre Grossa, is the tallest of the towers in San Gimignano. You can even climb it to get a beautiful lookout over the city.
After exploring the alluring town, stop into a bar to get a glass of the local goods: Vernaccia wine. With a fruity and revitalizing flavor, this wine has a DOCG designation, meaning it’s among Italy’s purest wines. This particular wine is the only white wine in Tuscany of this rank.
Tuscan Wine in the Chianti Region
Chianti isn’t just the name of a wine, it’s a magnificent wine producing region in Tuscany. Here, you can find miles of rolling hills and some of the finest red wine in Italy. The Chianti region produces seven different types of wine, each produced in a different section of the region.
The most famous strain of Chianti wine is Chianti Classico. For a wine to classify as Chianti, it must be produced at least 80% from Sangiovese grapes. To perfectly enjoy your Chianti wine, you can’t go wrong with a delicious meal to accompany.
If your perfect afternoon consists of leisurely wine tasting and a delicious spread of authentic food, you’re in luck. Our Chianti wine outing, you will be able to tour a family-owned vineyard, sip tasty wine and enjoy a fantastic Italian lunch. If you’re more into a solo wine adventure, you can check out towns such as Greve, San Casciano in Val di Pesa, Castellina in Chianti, and Barberino Val d’Elsa.
Brunello di Montalcino Wine
Looking to live it up while on vacation? Brunello di Montalcino is one of the more expensive red wines. This type of wine becomes pricy due to its concentration of Sangiovese grapes. While Chianti wine must be at least 80%, Brunello di Montalcino is produced 100% using Sangiovese grapes.
You can taste the authentic nectar in the region of Montalcino, located in the Siena province. With high tannin and acidity, Brunello wine reaches its peak taste after about a decade. Now, that’s a fine wine.
Things to do in Montalcino
This captivating town tucked away in the Siena province got its name from the beautiful oak trees once native to the area. Because Montalcino is situated on a hill, you can enjoy some of the best views in Tuscany during your visit.
If you’re visiting Montalcino, not just for the wine, there a few historical landmarks to explore. Discover the Fortress of Montalcino, which dates back to the 14th century. The fortress serves as the last fortress of the province of Siena’s resistance to the Medici family. You can also visit the Duomo di Montalcino, a beautiful church with a neoclassical structure and facade.
Tours of Chianti and Florence
Top-Rated Experience
Florence Day Trip to Tuscany: Siena, San Gimignano & Winery Lunch
Planning a day in Tuscany’s countryside can be tricky, with winding roads, remote villages, and countless wineries to choose from. With a 3-course lunch and 5 wine tastings, allow us to take the guesswork out of your Tuscan experience. Start in Florence, drive through Siena’s rolling hills, walk the medieval streets of San Gimignano, and tour a family-run Chianti winery. Along the way, learn the stories behind Chianti’s renowned wines and soak in the charm of Tuscany’s most stunning landscapes.
Planning to hit all of Florence’s highlights in one day can be a lot to manage. We’ll take care of every detail so all you have to do is enjoy the experience. With skip-the-line access, insider stories, and a charismatic guide who knows the city inside and out, you’ll see everything from Michelangelo’s David and the Florence Duomo to Ponte Vecchio and masterpieces by Caravaggio and Botticelli at the Uffizi Gallery. Experience Florence with all the must-sees, and none of the stress.
When visiting Tuscany, most people decide to stay in Florence. Not to worry though, making a day trip from Florence to Chianti is quite easy. On our Chianti wine outing, you will not have to worry about transportation to Chianti or choosing the best vineyards to visit. If staying within Florence is more your style, check out our Florence evening food tour to explore Florence’s best wine and cuisines.
Find the best places to stay
Where To Stay in Florence
Florence has a small historical center packed with iconic landmarks to explore. Plan where to stay in the best neighborhoods in this beautiful city.
Sean is a co-founder and owner of The Tour Guy and its subsidiary The Roman Guy. He studied finance and statistics, but that is his "Dr. Jekyll" side! His "Mr. Hyde" is in love with travel, art, history, and culture. Sean has read libraries of historical text and believes that all internet content should come from books. A practice he follows!
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