Heading to Tuscany and want to know more about wine tasting culture and how organizing a wine tasting in Tuscany or Italy works? Start by not being intimidated or stressed about the process. Tuscans are super-welcoming and relaxed people so you’ll do fine.
Visiting vineyards is not about “who you know,” it is simply about wearing a smile and being well-mannered.
How to Plan a Great Wine Day in Tuscany

Before I had a family and tons of responsibility, I used to join many of my customers on wine tours to Tuscany because it was an opportunity to tour Tuscany and drink wine. We would even hire helicopters to jump around from one remote location to another.
One high-end customer kept asking, “Can you get us into this vineyard!? What about that vineyard!?” I couldn’t understand why he was so nervous about “getting in.” I kept replying, “yea, no problem,” and the day went well.
Tuscans work hard to produce great wine and love watching the reactions of people who drink it. They are wonderful people who want you to see their beautiful properties and drink their incredible wines just as bad as you do. Follow my advice and you’ll be welcome to any vineyard you like.
Step 1:
What Type of Wine Drinker are You?
There are a few different types of wine drinkers and to keep things simple I will name three.
The Casual Wine Lover
- Adores wine and is excited about visiting a vineyard.
- Wants to learn more about wine.
- Purchases a bottle or two at each vineyard they visit.
- 95% of people fall into this category.
The Wine Enthusiast
- A lot of knowledge on different types of wines produced.
- Familiar with many different wine regions, varietals, and are particular to certain producers.
- Can easily hold a conversation with the wine producer.
- Likely to ship 3 to 12 bottles back from each vineyard they visit shipping most back home.
- About 4% of wine drinkers fall into this category.
The Wine Connoisseur
- Plans their trips around visiting wine regions that have had a stellar year.
- Have contacts at the major vineyards and may communicate with them regularly.
- Vineyards likely remember these people and might even have them on a special list.
- Spreads their efforts out from region to region but has a particular favorite varietal or producer.
- Holds wine for years if not decades before consuming.
- Have a home wine cellar fit to store wine at varying temperatures with a catalog.
- purchase anywhere from 12 to 100 bottles shipping most to their home cellar.
- Represent the remaining 1% of wine drinkers
Which Are You?
It is very likely you are a Casual Wine Lover or a Wine Enthusiast. Both can benefit from this article if they have never been to Tuscany or have been to Tuscany but feel like it could have been done better.
If you are a Wine Connoisseur, email us at [email protected] if you’d like to find niche producers that your friends won’t know about.
Step 2:
Pick Your Destination in Tuscany
Tuscany is a large region so don’t expect to see the entire area. Pick a sub-region with a large number of producers, ideally a place whose wine you have drunk in the past, and start there. Not sure where? Here are some of our favorite areas.
- Montalcino & Val d’Orcia (near Siena & Pienza)
- Bolgheri (Sassicaia)
- Greve in Chianti (Chianti & Tignanello)
- San Gimignano (Between Siena & Florence)
I personally would pick one of these areas and stay one to two nights. You could stay at a vineyard or in a town. The advantage of staying at a vineyard is it is awesome to stay at a vineyard. Staying in a town, like San Gimignano, offers a little more variety and nightlife. After a long day of indulging in the nectar of the gods, it is fun to stumble around a castle city.
That said, a long day of wine-tasting can leave you feeling like a long day of skiing. Tired and ready for bed!
If you want me to pick for you, I would pick Montalcino if you are ready to rent a car (no drinking and driving) and sleep there a few nights. Otherwise, consider staying near or in Florence and doing a day trip!
Tours of Chianti & Florence

Top Rated Experience
Chianti Day Trip from Florence with Vineyard Lunch
Want to have an epic experience in Tuscany? Remove the guesswork and logistics by joining us on a day trip to Chianti from Florence including Siena. Transportation, lunch, and lots of wine included!





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Best Selling Tour
Florence in a Day Combo Tour with David & Uffizi
This tour is your best value in Florence. See Michelangelo’s David statue in the Accademia Gallery with a licensed guide and the Uffizi Gallery. It also visits the Florence Cathedral (outside), Baptistry Doors, Ponte Vecchio, and more. All your admissions are included to skip the lines and visit these great museums with an English speaking guide.





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Step 3:
Build Your Itinerary
Your structure for the day can be pretty simple. The good news is that most wine tastings don’t start until after 10 am so you shouldn’t have to get up early. This structure assumes you are either renting a car and traveling with someone willing to restrain themselves from over-indulging or hiring a driver.
10:00 am: First Wine Tasting – I will spit or not finish most samples on my first tasting. It can make for a long day.
11:30 am: Second Wine Tasing – Pick a vineyard that also has a restaurant. This way you can finish this tasting and sit down to lunch.
12:30 am: Lunch
2:30 pm: Scenic Stop – Even connoisseurs of wine will mix in a little walking around to keep the blood flowing and prepare you for your final tasting.
4:00 pm: Last Call – Normally vineyards will close their “enoteca” or wine shop at 4:30 or 5pm. Scheduling your last tasting at 4 or 4:30 will ensure you get three good tastings in.
From there, you’ll want to do some walking around and ideally get some dinner around 6:30 or 7 pm. Many of these “lazy” Tuscan towns start dinner around 6 or 7 and close pretty early unlike big cities such as Rome.
Step 4:
Pick Your Vineyards
Picking the right vineyards is important but don’t feel like you have to be so incredibly prepared. I normally have one very consistent vineyard that I absolutely must visit scheduled. For Montalcino, it might be Poggio di Sotto, Le Chiuse, or Casanova di Neri. From there I will fill in the blanks as I go.
You can ask the vineyard you are currently at things like, “What vineyards have done well with this vintage (year)? These people all know each other and will send. you in the right direction.
Step 5:
Follow Tasting Etiquette
Tuscans are fun people and aren’t going to scoff at you if your pinky isn’t out like some neighboring countries may. That said, there is a bit of etiquette involved.
Call Ahead
Calling 15 or 20 minutes ahead makes a big difference. I normally call myself, but you can always ask the vineyard you are leaving to call for you. Most are happy to do so. Showing up unannounced is not against the law – many smaller producers will be happy to receive you, but I try to avoid it as a courtesy.
Always Buy Something
I normally won’t ask how much wine tastings cost because I always buy wine. For this very reason, I normally am not charged for the tasting. If I find something I like, I will make a larger purchase but at least a bottle or two. In a place like Montalcino that could run you a pretty penny. You could pay 25€ a low-end Brunello to 150€+ bottle for a riserva.
Don’t worry, every vineyard sells something called a “Rosso di Montalcino”. It just means “red from Montalcino”. It’s a reasonably priced but delicious bottle of wine that can go for as little as 8€ to max 18€ for special blends. Pick up one of two of these at a minimum if nothing strikes your fancy. That said, if I don’t like any wines and the vineyard does charge for the tasting I will just pay for the tasting and not purchase bottles.
Ask Questions
Wine producers take great pride in their work. You should ask a lot of questions and you will find yourself paying for fewer tastings.
Ask to Explore the Grounds
The wine business is a lucrative one and many properties reflect that. You should most definitely soak in their estate but always ask to be polite.
From here, you should have everything you need to plan a killer wine tasting in Tuscany. We’ve added some more Tuscany info below which will hopefully help!
Useful Information On Visiting Vineyards in Tuscany
How to Get to Wine Regions with Mass Transport
We don’t recommend trying to visit vineyards by bus. It takes a lot away from the experience. That said, we won’t stop you from trying!
San Gimignano: You can get here by train, by bus or by car. The ride will take you about three hours from Rome and one and a half hours from Florence with public transportation. Take Italo or Trenitalia fast trains from Rome to Florence. From Florence Santa Maria Novella Station, take bus 131 to Poggibonsi. From there, take bus 130 to San Gimignano
Montalcino: You can get here by train, bus or by car. The ride will take you about 5 hours from Rome and two hours from Florence with public transportation. Take Italo or Trenitalia fast trains from Rome to Florence. From Florence Santa Maria Novella station, take Regional train to Siena. From Siena take bus 114 to Montalcino.
Chianti Region: You can get here by train, by bus or by car. The ride will take you about three hours from Rome and one hour from Florence with public transportation. Take Italo or Trenitalia fast trains from Rome to Florence. From Florence Santa Maria Novella station, take bus 365 A to Greve in Chianti.
What kinds of wine are made in Tuscany?

These are the types of wines you will find: Vernaccia, Chianti, Brunello, Rose Sparkling (spumante) Super Tuscan and dessert wine.
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.
Chianti: 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.
Brunello di Montalcino: This is one of the more expensive red wines. This type of wine becomes pricey 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.
Our tours of vineyards in Tuscany

With our Chianti wine outing, you will be able to tour a family-owned vineyard, sip tasty wine and enjoy a fantastic Italian lunch. With The Tour Guy, you can experience two different, amazing tours that both offer delicious wine options.
Tuscany Wine Tour from Florence with Farm to Table Lunch
On this small group tour, you can take a day trip through the Chianti Hills and stop at one of our favorite places for wine tasting in the region. Your driver will take you to explore the village of San Gimignano and visit an organic farmhouse in the heart of Chianti. After all, if you visit Florence without the chance to sample the local nectar, did you really experience the magic of Tuscany?
Wine Day in the Chianti Hills from Florence
You can also enjoy our private wine day in the Chianti Hills tour from Florence, a custom-made trip to enjoy the best of the local wines. With beautiful views, charming villages, and a private driver, it is truly one of the best ways to experience a Tuscan vineyard.
Luxury Helicopter Tuscan Wine Day From Italy
On this extravagant adventure from Rome, travel by helicopter to the rolling hills of Montalcino. After admiring the stunning views from above, enjoy a leisurely day of wine tasting, farm to table lunch and an opportunity to buy some of the best wines in Italy.
Tours of Chianti & Florence

Top Rated Experience
Chianti Day Trip from Florence with Vineyard Lunch
Want to have an epic experience in Tuscany? Remove the guesswork and logistics by joining us on a day trip to Chianti from Florence including Siena. Transportation, lunch, and lots of wine included!





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See Prices

Best Selling Tour
Florence in a Day Combo Tour with David & Uffizi
This tour is your best value in Florence. See Michelangelo’s David statue in the Accademia Gallery with a licensed guide and the Uffizi Gallery. It also visits the Florence Cathedral (outside), Baptistry Doors, Ponte Vecchio, and more. All your admissions are included to skip the lines and visit these great museums with an English speaking guide.





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See Prices
Here is Where to Stay in the Most Popular Destinations
Rome, Florence, Venice, and the Amalfi Coast & Capri
Hello , going to Tuscany region Mid Oct and want to visit some wineries and stay in small villages for two weeks..Need advice on and possibly day tours
Ciao David! Thanks for checking out our blog. I recommend checking out our Tuscany Day Trip from Florence with Farm to Table Lunch. Contact our travel experts at 888-290-5595 for more info!
With the wine tours, will there be free time to just walk around and take pictures alone or is the while day with everyone at all times?
Ciao Jennifer! You can absolutely take time to walk around and take pictures alone. You will spend a few hours at the vineyard and will also have free time in San Gimignano.
I have a large group (about 13) staying at a Villa near Cortona. Would you do any custom tours for part or all of the group where you would pick us up and drop us back off at our Villa?
Hi Janice! Yes, we do! Please call our Travel Experts to plan a custom tour!