Montepulciano Wine Tour From Florence
A day trip out of Florence trades the Renaissance crowds for the golden hills of the Val d'Orcia, where two of Tuscany's greatest reds are poured in the towns that make them. You taste Brunello in Montalcino, wander the pecorino-scented lanes of Pienza, and finish with a glass of Vino Nobile in Montepulciano itself. Prefer to compare a few options first? Have a look at our full lineup of guided wine trips before you commit.
About This Day Trip at a Glance
Roughly 12 hours, door to door, with an early-ish start from Florence.
Roundtrip air-conditioned coach with onboard wifi, so nobody has to drive or navigate.
Two seated tastings included: Brunello di Montalcino and Vino Nobile di Montepulciano.
Small guided group, relaxed enough to ask the guide real questions along the way.
Live commentary in English (other languages vary by departure).
Meet at a central Florence departure point; no hotel hunting or car park stress.
Check Live Availability & Prices
Dates sell out fast in spring and autumn, when the Val d'Orcia is at its best. Check current departures and lock in your seat below.
Why Book a Montepulciano Wine Tour From Florence
Montepulciano sits about 115 kilometres south of Florence, close to a 90-minute drive on its own. Trying to reach it, plus Montalcino and Pienza, by public transport in a single day is a genuine headache, and driving means one person stays sober while everyone else tastes. A guided day trip solves both problems: someone else handles the wheel and the winding backroads while you look out the window at cypress-lined ridges.
The other reason is depth. Rather than a single stop, this loop threads together three of the Val d'Orcia's most famous towns and pairs them with the two reds they are known for. You get context from a guide who knows which fortress to climb and where the good pecorino is, so the day feels less like ticking boxes and more like being shown around by a knowledgeable friend.
What You'll See and Taste
The route is built around big views and two serious glasses of wine. Here is what fills the day:
- Montalcino's pentagonal fortress, worth the short climb for a sweeping look over the vineyards below
- A seated Brunello di Montalcino tasting at a working winery, poured where the grapes actually grow
- Pienza's tidy Renaissance streets, famous across Italy for their aged pecorino cheese
- A Vino Nobile di Montepulciano tasting in the town that gives the wine its name
- Long, open views across the Val d'Orcia, a UNESCO-listed landscape of rolling hills and lone cypress trees
- Time to wander medieval lanes, buy local food, and slow down between tastings
What's Included (and What Isn't)
What's Included
- Roundtrip transport from Florence by air-conditioned coach with wifi
- Live guide and commentary through Montalcino, Pienza and Montepulciano
- Brunello di Montalcino tasting at a winery
- Vino Nobile di Montepulciano tasting
- Free time in each town to explore and shop for local food
Not Included
- Lunch and any extra food or drink you buy along the way
- Additional wine purchases or bottles to take home
- Gratuities for your guide and driver
- Hotel pickup and drop-off (meet at the central departure point)
A Typical Day, Hour by Hour
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8:00 AM
Depart Florence
Meet your guide at the central departure point and settle in for the drive south, watching the Tuscan countryside open up through the coach windows.
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9:45 AM
Montalcino & Brunello tasting
Arrive in Montalcino, climb the pentagonal fortress for the view, then sit down for a tasting of Brunello di Montalcino at a local winery.
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12:15 PM
Pienza
Roll on to Pienza, a compact Renaissance town famous for pecorino. Stroll the panoramic walls and pick up some cheese to take with you.
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1:00 PM
Lunch & free time
Break for lunch on your own, whether that's a proper sit-down meal or a picnic of pecorino, bread and cured meats bought nearby.
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3:00 PM
Montepulciano & Vino Nobile tasting
Head into Montepulciano, wind up its steep main street, and finish the wine part of the day with a tasting of Vino Nobile di Montepulciano.
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5:00 PM
Return to Florence
Reboard the coach for the ride back, arriving in Florence in the early evening after a full loop through the Val d'Orcia.
Important Things to Know Before You Go
This is a long, rewarding day, and a little planning makes it smoother:
- It's a full day with an early start, so plan a relaxed evening beforehand rather than a late night out in Florence
- The hill towns are steep and paved with cobbles, so comfortable, grippy shoes matter more than style
- Two tastings add up; pace yourself, drink water, and make sure you eat a real lunch
- What to bring: water, sun cover, a light layer, and cash for lunch and cheese, as small shops may not take cards
- What to leave behind: heavy bags and rigid plans, since the day flows better when you let the guide set the rhythm
Insider Tips for the Florence Day Trip
A few things that make the difference between a good day and a great one:
- Go in late May to June or late September to October, when temperatures are kind and the light on the hills is at its best
- If you can time it, late September into October is vendemmia, the grape harvest, and the wine towns feel especially alive
- Skip a full Florence lunch and instead build one in Pienza from fresh pecorino, bread and local salami
- Brunello is the more powerful, longer-aged red; ask your guide to point out how it differs from Vino Nobile as you taste both the same day
- Carry cash, since small producers, cheese shops and casual lunch spots often prefer it to cards
- In July and August it gets genuinely hot, so pack a hat and refill your water bottle whenever you can
Where This Tour Takes You
Who This Tour Is For
This day trip is a strong fit if you:
- Want to taste Brunello and Vino Nobile without renting a car or planning routes
- Like the idea of pairing wine with medieval towns and big countryside views
- Are visiting Florence and can spare one full day for the Tuscan hills
- Enjoy a guided pace with free time built in, rather than a rigid schedule
Not ideal for
- Travellers with very limited time who only have a half day to spare
- Anyone who struggles with steep, cobbled streets and repeated climbs
- Non-drinkers looking mainly for a wine-focused experience
Frequently Asked Questions
How far is Montepulciano from Florence?
Montepulciano is roughly 115 kilometres south of Florence, about a 90-minute drive. Because this tour also loops through Montalcino and Pienza in the Val d'Orcia, it fills a full day, which is exactly why a guided coach makes more sense than trying to piece it together yourself. You can compare the timing of other departures on our tours page.
What's the difference between Brunello and Vino Nobile?
Both are Sangiovese-based Tuscan reds, but Brunello di Montalcino is made entirely from a local Sangiovese clone and aged longer, giving it more power and structure. Vino Nobile di Montepulciano uses at least 70 percent Prugnolo Gentile, another Sangiovese clone, is aged a minimum of two years, and was one of Italy's first DOCG wines back in 1980. Tasting them the same day makes the contrast easy to appreciate.
Do I need to rent a car for this tour?
No. The tour includes roundtrip coach transport from Florence with onboard wifi, so you can taste at both wineries without anyone having to stay sober to drive. If you would rather start from the capital instead, see our Montepulciano wine tour from Rome.
Is lunch included?
Lunch is not included, which leaves you free to eat where you like. Many travellers build a picnic in Pienza around its famous pecorino cheese, or find a casual spot during the free time. Bring some cash, as smaller places may not take cards.
Can I do a more in-depth cellar visit instead?
If you want to go deeper into how the wine is made rather than covering three towns, look at our Montepulciano wine tasting and cellar tour, which focuses on the cellars themselves rather than a full Val d'Orcia loop.
What Recent Travellers Say
Doing Montalcino, Pienza and Montepulciano in one day sounded rushed, but it never felt that way. The Brunello tasting alone was worth it, and having a driver meant we could actually enjoy both wines.
We based ourselves in Florence and this was the highlight of the trip. The Val d'Orcia views are unreal in October, and buying pecorino in Pienza was a lovely surprise.
Great value for a full day. The guide explained the difference between Brunello and Vino Nobile so clearly that I finally understood what I was drinking. Comfortable coach and easy from Florence.