Dreaming of doing a wine tour from Florence? Here’s what to know before you go : from affordable group tours through Siena and San Gimignano to luxe Chianti experiences with private tastings and stunning vineyard views. Let’s start planning your Florence wine tours!
There’s something about Tuscany that feels like stepping into a painting.. From Florence, it only takes an hour before the city fades into rolling vineyards, winding roads, and rustic stone farmhouses, and suddenly, you’re in wine country.
During my last trip to Florence, I knew I couldn’t leave without experiencing that world for myself. So I did what any indecisive traveler does: I booked two very different wine tours. One was an elegant, small-group experience : think family-run wineries, generous pours, and endless views of Chianti. The other was a lively, budget-friendly day trip that blended culture and wine, with stops in Siena, San Gimignano, and Monteriggioni.
Both promised Tuscany. Both delivered something entirely different.
In this post, I’ll share what each tour was really like – from the private, slow-paced experience to the larger, social one – and help you decide which wine tasting tour from Florence fits your style, your budget, and your idea of the perfect Italian day.
Read More // Read these 12 things to know before visiting Florence !
Don’t forget to check out all of my Italy blog posts to make the most of your visit!
Why Take a Wine Tour from Florence
If you’re staying in Florence, you’re already perfectly positioned to explore some of Italy’s most iconic wine regions. The Tuscan countryside begins just beyond the city limits : a patchwork of vineyards, olive groves, and medieval villages that looks straight out of a dream.
The beauty of joining a wine tasting tour from Florence is how effortless it makes the experience. No need to rent a car or navigate winding rural roads, you can simply hop on a comfortable bus or van, sip your way through Chianti, and let someone else handle the driving.
Most tours blend wine with a bit of culture. You might wander Siena’s Piazza del Campo, climb San Gimignano’s medieval towers, or stroll through Monteriggioni’s fortified walls before heading to a local winery for tastings and homemade snacks. Each stop adds something to the story of Tuscany; the rhythm of village life, the taste of freshly pressed olive oil, the way light hits the vineyards in late afternoon.
Whether you’re a casual wine drinker or a dedicated enthusiast, there’s something special about tracing the journey from vine to glass right where it all begins. Tuscany doesn’t just serve wine; it invites you to slow down and savor it.
The Two Wine Tours I Tried
When it comes to wine tasting tours from Florence, there’s something for every type of traveler. Some focus on a deep dive into winemaking and intimate tastings, while others offer a full Tuscan experience : a mix of charming towns, scenic drives, and a glass (or three) of Chianti along the way.
I decided to experience both ends of the spectrum. My first tour was a luxury-style, small-group Chianti wine tour, visiting two boutique wineries near San Gimignano. The second was a budget-friendly full-day trip through Siena, San Gimignano, and Monteriggioni : a lively, culture-packed adventure that still ended with a glass of red overlooking the hills.
Here’s a quick look at how they compare:
| Tour | Price | Duration | Type | Highlights |
|---|---|---|---|---|
| Tuscany Wine Tour: 2 Wineries & San Gimignano | €190 | Full day | Small group / Luxe | Two wineries, up to 7 wines, Chianti & Vernaccia tastings, olive oil and balsamic tasting, visit to San Gimignano |
| Siena, San Gimignano & Monteriggioni Tour | €65 | Full day | Large group / Budget-friendly | Visits to three medieval towns, wine and balsamic tasting in Chianti, scenic countryside drive |
Both tours offered the beauty and flavor Tuscany is known for, but in very different ways. One felt like a quiet afternoon spent among vineyards, chatting with winemakers. The other, like a whirlwind journey through the best of Tuscany, lively, social, and surprisingly affordable.
My Experience #1: Semi-Private Chianti Wine Tour (€190)
This was the first tour I booked, and it ended up being the perfect introduction to Tuscany. I wanted something centered on wine tasting – less sightseeing, more time among the vineyards – and this small-group Chianti experience was exactly that.
We met just outside Porta Romana in Florence on a crisp February morning, and I was relieved to see it wasn’t a big bus tour, just a handful of us, including a few other solo travelers. By the end of the day, we were sharing stories, travel tips, and plenty of laughs over glasses of Chianti. It’s the kind of tour where you instantly feel part of the group, even if you arrive alone.
The drive into the Chianti wine region was straight out of a postcard: winding roads, cypress-lined hills, and sunlit vineyards. Our guide – warm, funny, and clearly passionate about Tuscan wine – shared bits of history and local culture along the way.
The first stop was a family-run winery near San Gimignano. We sampled everything from crisp Vernaccia to full-bodied Super Tuscans, paired with homemade olive oil and balsamic vinegar. It wasn’t just about tasting, we actually learned how to swirl, smell, and recognize the notes in each glass.
After lunch, we headed to a second estate just a few kilometers away, with views that honestly looked painted. Three more wines awaited, including a Chianti Colli Senesi and a light, summery rosé. Between the tastings and the scenery, time seemed to slow down in the best way.
We wrapped up the day with a visit to San Gimignano, where I wandered its medieval streets and treated myself to the gelato world champion (yes, it’s as good as everyone says).
If you want a slower-paced, wine-focused day that feels personal and relaxed, this tour delivers.
Best for: Solo travelers, couples, and small groups who want to dive deeper into Tuscany’s wine culture.
Highlights:
- Two boutique wineries and up to 7 wine tastings
- Olive oil and balsamic vinegar sampling
- Visit to San Gimignano
- Friendly small-group atmosphere
THE DETAILS
Price | €190 per person
Reservation | You can book your tour here.
My Experience #2: Budget-Friendly Group Tour (€65)
A few days later, I joined my second wine tasting tour from Florence, this time, one of those big, budget-friendly day trips that combine Tuscany’s highlights into a single whirlwind adventure. It promised medieval towns, stunning countryside views, and, of course, a bit of Chianti at the end.
This one felt very different right from the start. The bus was full, and most people were traveling with partners, friends, or family. As a solo traveler, I’ll admit it felt a little intimidating at first. There was that awkward moment of figuring out where to sit, and I caught myself feeling like the odd one out for the first hour or so. It’s not that anyone was unfriendly, it’s just the nature of big-group travel.
Once we hit the road though, the Tuscan countryside worked its usual magic. The guide was upbeat and knowledgeable, sharing stories about the region as we rolled through green hills and vineyards. Our first stop was Monteriggioni, a small walled village perched on a hill, followed by Siena, where we had free time to wander around the Piazza del Campo and admire its gothic charm.
By the time we reached San Gimignano, I’d settled into the rhythm of the day. I wandered its narrow cobblestone streets, revisiting a few spots I’d discovered earlier in the week, and couldn’t help but notice how different it felt seeing it in a bigger crowd, less intimate, but still beautiful.
The day ended at a Chianti winery, where we gathered around long wooden tables for a tasting of local reds, olive oils, and balsamic vinegar. It was lively and fun, with the buzz of conversation in half a dozen languages. The setting was lovely, but it wasn’t quite as personal or detailed as my first tour.
Still, for the price, it was incredible value: three historic towns, postcard-worthy scenery, and a taste of Tuscany in one day.
Best for: First-time visitors, couples, or groups of friends who want to see a lot of Tuscany without spending too much.
Highlights:
- Excellent value for a full-day experience
- Visits to Siena, San Gimignano, and Monteriggioni
- Wine, olive oil, and balsamic tasting in the Chianti region
- Free time in each town
THE DETAILS
Price | €65 per person
Reservation | You can book your tour here.
Private vs. Group Wine Tours : Which Should You Choose?
After doing both, I realized that choosing a wine tasting tour from Florence really comes down to what kind of experience you want, and the kind of traveler you are.
The private-style Chianti tour felt slow, personal, and beautifully immersive. It was the kind of day where you could really connect with your guide, chat with winemakers, and soak in the scenery without rushing. The small group size made it easy to meet people (especially as a solo traveler), and the entire experience felt relaxed and intentional, like the day had room to breathe.
The budget-friendly group tour, on the other hand, was full of energy and offered way more variety. You get three towns, a ton of photo stops, and a snapshot of Tuscany’s highlights all in one go. But it’s also more structured, more crowded, and a little less flexible, ideal if you want to see a lot, but not necessarily if you’re hoping for quiet vineyard moments.
Here’s a quick breakdown to help you decide:
| Feature | Private / Small Group Tour | Budget / Large Group Tour |
|---|---|---|
| Price | Higher (€190) | Affordable (€65) |
| Group Size | 6–10 people | 40+ people |
| Vibe | Relaxed, social, immersive | Busy, energetic, more sightseeing |
| Focus | Wine tasting and local culture | Variety: towns, history, landscapes |
| Flexibility | More personal and slower pace | Fixed schedule |
| Best For | Solo travelers, couples, wine lovers | First-timers, friends, travelers on a budget |
If you’re dreaming of quiet vineyards, long tastings, and connection, go for the smaller group. But if you’d rather cover as much of Tuscany as possible in a single day – and don’t mind a crowd – the group tour gives you a great overview without stretching your budget.
In short: the first tour made me feel Tuscany, while the second let me see Tuscany. Both are worth it, just in different ways.
What to Know Before You Go
No matter which wine tasting tour from Florence you choose, a little prep makes the experience even better. Tuscany might look effortlessly magical, but a few small things can make a big difference in how your day unfolds.
Timing matters : Spring through early fall (April to October) is ideal, vineyards are lush, skies are clear, and many wineries are at their most active. If you’re lucky enough to visit during harvest season in September, you’ll catch Tuscany at its most vibrant.
Dress for comfort : Most tours include walking through towns and vineyards, so wear comfy shoes and bring a light jacket. Countryside weather can shift quickly. Sunglasses and sunscreen are a must, especially in summer.
Eat breakfast before you go : Wine tastings can start earlier than you’d think, and trust me, sipping Chianti on an empty stomach is not the move. Some tours include snacks or lunch, but it’s best to start the day with something solid.
Bring water (and maybe a tote bag): You’ll want to stay hydrated, and if you fall in love with a particular bottle (which you probably will!), a small bag helps keep it safe for the trip back.
Book in advance : The best Tuscany wine tours fill up fast, especially on weekends and during peak season. Booking early means better choices for group size, timing, and route.
Don’t stress if you’re not a wine expert : Both tours I joined were super welcoming to beginners, guides explained everything in a way that made it approachable and fun. You don’t need to know wine terminology to enjoy the experience.
Final Thoughts : Take a Wine Tour From Florence
Tuscany has a way of reminding you to slow down, to let a glass of wine, a golden sunset, or a quiet hilltop village be enough. Taking these wine tasting tours from Florence gave me two completely different but equally memorable versions of that feeling.
The private Chianti experience was all about connection, to the land, the people, and the slower rhythm of the countryside. It felt personal and grounded, and I loved that as a solo traveler, I never felt out of place.
The budget-friendly group tour, on the other hand, offered that classic postcard version of Tuscany : Siena’s gothic beauty, San Gimignano’s towers, and vineyard views for miles. It was busier, sure, but still worth every moment for how much it packed into one day.
In the end, both showed me why Florence is the perfect gateway to Tuscany: you can step out of the city and, within an hour, be surrounded by vineyards, cypress trees, and the kind of light that makes you fall in love with Italy all over again.
So, whichever you choose – a luxe escape or a lively day trip – go with an open mind (and an empty memory card). Tuscany will take care of the rest.
Don’t forget to check out all of my Italy blog posts to make the most of your visit!
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➡️ Save this if Québec City is on your holiday list
What’s YOUR pick for Canada’s most magical Christmas city? Or is Quebec City the winner for you too? 👇
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➡️ Swipe through to see exactly how I’d spend a fall weekend in Belleville, from morning coffee to dinner plans to the best spots to explore.
📌 Save this for your next Ontario getaway
Which Ontario town should I feature next? 👇
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If you’re looking for something unique, charming, and a little bit quirky, add this to your list immediately.
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Would you try an alpaca sleepover… or is that a hard no for you? 👀👇
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Last year, I did my very first Ontario Awards and you guys loved it so much that I had to bring it back this year! 🙌
Some winners stayed the same (because let’s be honest, a few spots are just forever Ontario classics)… but there are also a few new faces on the list 👀, and a bunch of new categories to include even more of my favourites from this past year.
➡️ Swipe through to see all the winners!
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Which spot do you think deserves a trophy next year? 👇
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📍 Add Haliburton to your fall bucket list, before winter fully moves in.
Have you ever visited Haliburton? Do you agree with me?
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