A private wine tour in Tuscany is the one day in Italy when nobody in your party has to drive, check a timetable or leave early: a car collects you in Florence, the hills do the rest, and the cellar doors open for your group alone. We compared the two private tours from Florence that travelers rate highest. Private Wine Tour Tuscany: Chianti Wineries with an Expert English Driver is rated 4.9 across 64 reviews, from about $918 per group. Brunello and Nobile, Wine Lover Tour Montalcino and Montepulciano is rated 4.9 across 102 reviews, from about $896 per group.
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The verdict
The two prices look almost the same. However, they are not the same deal. The Brunello and Nobile tour includes lunch and the wine tastings; the Chianti tour does not. On the Chianti day, the listing puts lunch with five wines at Poggio Amorelli at €70 per person and the tasting at Castello di Gabbiano at €35 per person, paid on the day. As a result, a couple pays about €210 on top of the booking.
That makes the Montalcino and Montepulciano tour our pick for a private wine tour in Tuscany: one price for the day, 98 of 102 reviews at five stars, room for up to eight people, and the two most famous red wines of southern Tuscany, Brunello di Montalcino and Vino Nobile di Montepulciano.
Choose the Chianti tour if you want a shorter drive, a Mercedes with Wi-Fi and a driver-host who is known for arranging the moments around the wine. For example, two reviewers describe how the owner helped organize their marriage proposal at a winery, down to the flowers and the photographer.
Good to know before you book
The Chianti tour is the one reviewers used for it. Both proposal reviews describe the owner-driver arranging privacy at the winery, flowers and a photographer, at sunset for one of them. However, none of that is in the listing’s inclusions, so it is something you ask for when you book, and pay for separately. So write to the supplier through Viator before you confirm, and agree what will be arranged and at what cost.
I have done both days. For a first visit to Tuscany, I send people south to Montalcino and Montepulciano: one price, lunch included, and the Val d’Orcia on the way. However, if you are planning to propose, the Chianti day is the one to look at, but write to the owner before you book and agree every detail and its cost. Tony lives in Rome and works as a guide across Italy.
Which one is for you?
Take Montalcino and Montepulciano if
- You want one price that covers the guide, the driver, lunch and the tastings.
- You are more than four: this tour takes up to eight in an air-conditioned minivan.
- Brunello is the wine you came for, and the Val d’Orcia is the Tuscany you have in mind.
- You like small family wineries where you meet the people who make the wine.
Take the Chianti tour if
- You are two to four and want a car to yourselves, with a driver rather than a guide on foot.
- You want less time on the road: Chianti starts just south of Florence.
- You are planning a proposal or another surprise and want a host who helps set it up.
- You want to end the day at Piazzale Michelangelo, above Florence.
Who should skip both
Travelers who do not drink wine, and solo travelers: at about $900 per car, a private day only makes sense shared. Instead, a small-group day costs a fraction, and our Montalcino Brunello wine tour compares the group options. Also, if you are not staying in Florence, check first: the Chianti tour picks up only in Florence city, and the Montalcino tour within the Florence urban area.
What each price covers
Brunello and Nobile, Montalcino and Montepulciano
Included: pickup and drop-off at your hotel in the Florence area, a private guide and driver, an air-conditioned minivan, live commentary, lunch and the wine-tasting fees at two wineries. Start at 9:00. The route passes through the Val d’Orcia and Pienza, with about 30 minutes each in Montalcino and on Piazza Grande in Montepulciano.
Not included: gratuities, souvenirs and extra drinks. Vegetarian and gluten-free lunches on request. Also, the tour runs in all weather.
Private Chianti wineries tour
Included: an English-speaking driver, a Mercedes with Wi-Fi, bottled water, pickup and drop-off in Florence, and a stop at Antinori nel Chianti Classico to see the winery’s architecture from outside. In addition, a larger Mercedes van is offered for about $1,143 per group.
Paid on the day: lunch at Poggio Amorelli, with three courses, five wines, olive oil, balsamic vinegar and a cellar visit, listed at €70 per person; the tasting and cellar visit at Castello di Gabbiano, €35 per person; and any tasting at the Antinori wine bar. The day also stops in Panzano in Chianti and ends at Piazzale Michelangelo.
Side by side
| Montalcino and Montepulciano | Chianti wineries | |
|---|---|---|
| Rating | 4.9 from 102 | 4.9 from 64 |
| Five-star reviews | 98 (96%) | 61 (95%) |
| Price | from about $896 per group (up to 8) | from about $918 per group (up to 4) |
| Lunch and tastings | Included | About €105 per person, paid on the day |
| Length | About 9 hours, from 9:00 | About 8 hours |
| Wines | Brunello di Montalcino, Vino Nobile di Montepulciano | Chianti Classico |
| With you all day | Private guide and driver | English-speaking driver |
| Pickup | Hotels in the Florence urban area | Florence city only |
| Wheelchair accessible | Yes, collapsible wheelchairs with assistance | Yes |
| Booked ahead, on average | 81 days | 48 days |
| Cancellation | Free up to 24 hours before | Free up to 24 hours before |
What travelers say
On Montalcino and Montepulciano
It was harvest season, and we were delighted to see grapes being harvested and processed. Maurizio entertained us with his description of how he farms grapes, the 3 harvests, and his method for making wine.
Chris_S, October 2025, via Viator
Our private car was excellent, clean and spacious for our family of four. Our guide, Dario, was pleasant and did an excellent job taking us to two amazing locations to experience the Brunello area.
Caesar_I, August 2025, via Viator
On the Chianti wineries tour
I wanted to pull off a proposal at sunset and Jon Luca set everything up and recommended a photographer and privacy with the winery and flowers. Definitely a day to remember.
Cameron_D, September 2024, via Viator
Gianluca (owner operator) went above any beyond to help me plan my engagement proposal (organizing with 2 wineries, photographer, flowers etc.)! He helped make the experience unforgettable for me and my fiancé.
Stephen_M, June 2024, via Viator
Reviewers of the Montalcino tour keep returning to the small family wineries and the owners who show them around; reviewers of the Chianti tour to the driver and the freedom of not driving between tastings. Finally, fall is harvest time, and it shows in the reviews: September and October bring the grapes in, and with them the busiest weeks in the cellars.
More in Tuscany
For a different morning in the same hills, compare truffle hunting in Tuscany and horseback riding in Tuscany. In the city, a Florence cooking class and the Florence food tour keep the theme going.
For more at this level, see our guide to luxury experiences in Italy, and our private tours in Italy compared.
Questions travelers ask
How much is a private wine tour in Tuscany?
On October 1, 2026, Viator listed the private Montalcino and Montepulciano tour from about $896 per group of up to 8, with lunch and tastings included, and the private Chianti tour from about $918 per group of up to 4, with lunch and tastings paid on the day, listed at about €105 per person.
Chianti or Montalcino: which is better for a first visit?
Chianti is closer to Florence and greener; Montalcino and Montepulciano are farther south, in the open landscape of the Val d’Orcia, and make fuller-bodied reds. So if you want the classic picture of Tuscany with cypress-lined roads, go south; if you want a shorter day, stay in Chianti.
Can a private wine tour help with a proposal?
Two reviewers of the Chianti tour describe the owner arranging privacy at a winery, flowers and a photographer for their proposal. However, these are not listed inclusions: ask the supplier through Viator before booking, and agree the details and cost.
Do these tours pick up outside Florence?
The Chianti tour picks up and drops off only in Florence city. The Montalcino tour picks up at hotels in the Florence urban area. So if you are staying in the countryside, ask the supplier before booking.
When is the best time for a wine tour in Tuscany?
Fall, for most wine lovers: the harvest runs through September and October, and reviewers describe seeing the grapes picked and pressed. Therefore, book early for those months: Viator shows the Montalcino tour is booked 81 days ahead on average.
Can I cancel?
Both offer a full refund if you cancel at least 24 hours before the start, as shown on Viator on October 1, 2026. Check the terms again when you book.
Book Montalcino and Montepulciano for the fullest day at one clear price; book Chianti for a shorter drive, a car for two to four and a host who can help with a surprise.
Editorial assessment by Italy2Love, October 2026. Inclusions and exclusions, prices paid on the day, meeting points, itineraries, prices, ratings, review counts and cancellation terms read on both Viator product pages (product codes 15786P4 and 107856P30), October 1, 2026. Reviews quoted with attribution to their authors and to Viator. Next review April 2027, or sooner on any change to either option.