A Taste of Tuscany
- Tony Elvin
- May 24
- 6 min read
Earlier this month we had the opportunity to return to Tuscany on unfinished business .. exploring Siena and Montalcino.
We had previously explored Tuscany from our base in Lucca over ten days visiting Pisa, Florence, Volterra and San Gimigiano. We didn't have time to see Siena or Montalcino and had fallen in love with the sweeping landscapes and wonderful wines of Tuscany, so pledged to return and do a bit more.
Below we'll offer a run down on Tuscan wines and detail some recommendations from our experiences:
Tuscany: Rockstar Wine Region
When it comes to wine, Tuscany isn’t just another pretty vineyard—it’s the rockstar of Italian wine country. Think rolling hills bathed in golden sunlight, centuries-old stone villages, and a glass of ruby red Chianti in hand. This iconic region has become the poster child for what great wine (and serious wine vibes) should look like. But what exactly makes Tuscany so special?
Chianti: More Than Just a Red
You can’t talk Tuscany without talking Chianti. This wine is the region’s pride and joy—made primarily from Sangiovese grapes, Chianti is all about bright cherry flavors, earthy notes, and a dry, food-friendly style. There are different subregions too, like Chianti Classico, Chianti Rufina, and Colli Senesi, each adding their own twist to the classic.
The Little Black Rooster
And if you’ve ever noticed the little black rooster on a bottle of Chianti Classico, you’ve already met the Gallo Nero—the iconic symbol of the Chianti Classico consortium. Legend has it that centuries ago, when Florence and Siena were battling over borders, they agreed to send knights riding out at dawn—when the rooster crowed—to meet wherever they crossed paths. The clever Florentines starved their black rooster so it would crow earlier, giving their knight a head start and more territory. Moral of the story? Never trust a hungry rooster or a Florentine! Having spent the weekend in Siena, they're still salty about it!
Super Tuscans: Rebels With a Corkscrew
In the 1970s, a few bold winemakers in Tuscany decided to colour outside the lines. They ditched the strict DOC regulations and started blending Sangiovese with international grapes like Cabernet Sauvignon and Merlot. The result? Smooth, powerful, age-worthy wines that couldn’t legally be labeled as Chianti—so they called them Super Tuscans (well Robert Parker did).
These rebels may have broken the rules, but they also redefined Tuscan wine. Today, names like Sassicaia and Tignanello are legends in the wine world, and Super Tuscans have carved out their own prestigious category.
Montalcino: Brunello Royalty
Head south and you’ll find Montalcino, home of the regal Brunello di Montalcino—a wine made from 100% Sangiovese (known locally as Sangiovese Grosso or "Brunello"). These wines are bold, structured, and built to last decades. With strict aging requirements (at least 5 years!), Brunello is the crown jewel of Tuscany, the kind of wine you open to celebrate life’s biggest moments. The wines we tasted in Montalcino were among the best we've tasted from the region.
Montepulciano: Not What You Think
Confused by the name? You’re not alone. Vino Nobile di Montepulciano comes from the town of Montepulciano, but it’s made mainly from Sangiovese (called Prugnolo Gentile here)—not the Montepulciano grape from Abruzzo. These wines are a bit softer and more accessible than Brunello, offering elegance and complexity with a slightly gentler price tag.
The Tuscan Magic
What ties it all together? Tuscany’s secret is its combination of climate, soil, grape varieties, and people who live and breathe tradition—with just enough rebellious spirit to keep things exciting. Whether you're sipping a rustic Chianti, a sleek Super Tuscan, or a majestic Brunello, you're tasting history, passion, and a little bit of Tuscan sun in every drop.
🍷 Where to Go: The Greatest Hits
Chianti Classico Region Between Florence and Siena, this is ground zero for classic Tuscan reds. Towns like Greve, Panzano, and Radda are full of scenic wineries and family-run estates. It's ideal for first-timers.
Montalcino Home to the bold and age-worthy Brunello di Montalcino. This area is a bit pricier and more exclusive, but totally worth it for a splurge day.
Montepulciano Offers a more laid-back vibe and slightly more affordable tastings than Montalcino. Try Vino Nobile di Montepulciano at charming hilltop wineries with postcard views.
Bolgheri (on the Tuscan Coast) If Super Tuscans are on your bucket list, this is the spot. The famous Sassicaia hails from here, along with many other world-class blends.
💸 How Much Does Wine Tasting Cost?
Basic Tastings: €10–€20 per person for 3–5 wines.
Mid-Range Tastings: €25–€40, often includes a cellar tour and small bites (think bread, cheese, olive oil).
Premium Tastings: €50+ for high-end wines like Brunello, Super Tuscans, or vertical tastings (same wine from different vintages).
Some tastings are waived if you buy wine.
👉 Tip: Book in advance—especially at smaller, family-owned wineries. Walk-ins aren’t always available.
🚗 Getting Around: Don’t Drink and Drive
Tuscany’s winding roads are stunning but not ideal for tipsy navigation. Your best options:
Hire a driver: Great for a group—expect to pay €250–€500/day for a private wine tour.
Join a wine tour: Budget-friendly group options from Florence or Siena.
Stay on a wine estate: Many agriturismi (farm stays) offer tastings right where you’re sleeping. Maximum wine, zero logistics!
Designated Driver: I'm very lucky, Lucy enjoys driving between wine estates, won't trust my driving abroad and will use a spitoon whilst tasting, as long as we can park the car back at the hotel and head into town for her to catch up later. That's the deal.
🧀 What to Expect at a Tasting
Tastings are often relaxed, guided by passionate winemakers.
You’ll usually taste 3–6 wines, starting with young reds and ending with the bold stuff.
Many tastings include extras: olive oil, salami, aged pecorino, or even full lunches.
🎭 Opera
Tuscany isn't just famous for wine and there are some incredible experiences you just shouldn't miss whilst you're there.
City Opera—both Florence and Siena offer some wonderful opportunities to catch Opera performances with well know popular classics at around €30 per head.
The Puccini Opera Festival—in Torre del Lago, is amazing! It is the only opera festival in the world entirely dedicated to Giacomo Puccini. It takes place every summer (July and August) in a large open-air theatre by Lake Massaciuccoli. The festival offers performances of Puccini's best-loved operas, like La Bohème, Tosca, Madama Butterfly, and Turandot. Tickets from just €21. https://www.invitationtotuscany.com/guide/italy/tuscany/lucca/the-puccini-opera-festival
Bocelli on his home turf—Andrea Bocelli performs annual concerts in his hometown of Lajatico at the Teatro del Silenzio, an outdoor Tuscan amphitheater. Expect to pay €120+. https://www.teatrodelsilenzio.it/en/events/
Something different in Lucca—The Lucca Summer Festival offers an eclectic mix of classical music and rock bands with tickets from €50. When we stayed in Lucca we pitched up in a bar just outside the concert, listening to a fantastic Sting concert for free and spending the money on Chianti and Brunello. https://www.luccasummerfestival.it/home
🍇 Extra Tips
Ask questions—winemakers love sharing their story.
Buy what you love—most estates can ship internationally, in many cases for free.
Dress smart-casual—no need for stilettos, but leave the flip-flops at home.
Bring cash and a card—some smaller places still don’t accept cards and it's good to be able to give a small tip.
Vin Santo—make sure to try some of the local dessert wine, usually served with Biscotti that you can soak in the rich, sweet Vin Santo.
Our trip:
Accomodation
We stayed at the Villa Il Castogne a winery and hotel near Siena which offers tastings, tours of the vineyards and many other experiences on-site. A taxi into Siena cost approx €25.
Accomodation and Tasting
We also visited the San Felice Winery and Resort, which unfortunately had no availability for our stay, likely due to the culmination of the Giro d'Italia cycle race that weekend. The tasting hosted by Julia was excellent and the accomodations looked incredible. The San Felice resort encompasses the whole little village and will set you back a little more than Il Castogne as this is a five star hotel. Worth a visit just for a tasting.
Tasting in Montalcino
We tasted Montalcino in a Medievel Fortress at the top of Montalcino, the Enoteca la Fortezza. They had all the top Montalcinos, Super Tuscan's and Chiantis and it was a fantastic experience.
Tasting in Siena
Our favourite tasting in Siena was by far and away was at the Enoteca Sotto al Duomo which sits adjacent to the Battistero di San Giovanni Battista Church. Diletta was a wonderful host and can tell you everything you ever wanted to know about Tuscan wine.
Dining in Siena
We really enjoyed dining at the Zest Ristorante & Winebar on the steps of the Costa di Sant'Antonio. Probably the best Lasagne I've ever eaten, an excellent wine list and very friendly service.
Sightseeing in Siena
You must not miss Siena Cathedral. Make sure you do the full visit of the whole complex, you won't be disappointed. We recommend going along at 10am and booking your tickets in person if you want to avoid their awful and confusing ticket purchasing website which had everyone confused.
Palazzo Pubblico is an incredible square in the heart of Siena. You'd actually struggle to miss it. For terrific views of the city and surrounding Tuscan landscapes, climb the Torre del Mangia.
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