Brunello di Montalcino is made around a single hill town south of Siena, in the landscape of the Val d’Orcia. On Viator, two well-reviewed days reach it from different bases. From Siena, a small-group wine day for eight, with two wineries and lunch, is rated 4.9 across 1,025 reviews, from about $220. From Florence, a coach day adds Pienza and Montepulciano with two tastings, rated 4.7 across 1,521, from about $107.
Italy2Love is a Viator affiliate. Bookings are completed on Viator, not on this site, and we earn a commission on bookings made through our links — at no extra cost to you. Prices and availability shown on Viator are the ones that apply.
The verdict
The small-group day from Siena is the wine lover’s choice: eight guests at most, two Brunello wineries with cellar visits and tastings, lunch included, and stops at the Sant’Antimo abbey and Montalcino’s fortress. 973 of 1,025 reviews are five stars.
The coach day from Florence is the sightseeing choice for about $113 less: free time in Montalcino, Pienza and Montepulciano, a Brunello tasting in Montalcino and a Vino Nobile tasting with cheese in Montepulciano, and a stop at the Vitaleta chapel. Lunch is not included, the group is a coach, and the day is long.
Our pick depends on where you sleep and what you came for: wine and a small table, from Siena; three hill towns in one day, from Florence.
The coach tour from Florence lasts about eleven and a half hours, and one reviewer wished for more time in Montepulciano. From Siena, one reviewer noted about an hour and a half of driving to the first winery. Both tours serve wine only to travelers aged 18 and over.
Which one is for you?
Take the small-group day from Siena if
- You are staying in Siena or nearby.
- Wine is the point: two Brunello wineries with cellar visits.
- You want lunch included and at most eight people.
- Reviews matter: it is rated 4.9 from 1,025 travelers.
Take the coach day from Florence if
- You are based in Florence and want the Val d’Orcia in one day.
- You want Pienza and Montepulciano as well as Montalcino.
- You want to spend about $107 rather than $220.
- A long day and a large group do not bother you.
What each price covers
The small-group day from Siena, from about $220
Included: a local guide, lunch, visits to wine cellars with tastings and an air-conditioned vehicle. The itinerary lists the Sant’Antimo abbey and the fortress of Montalcino.
Not included: gratuities and hotel pickup. The tour is not advised for travelers with heart problems or other serious medical conditions.
The coach day from Florence, from about $107
Included: a coach with wifi, a tour leader, free time in Montalcino, Pienza and Montepulciano, a Brunello tasting at a Montalcino wine cellar and a Vino Nobile tasting with cheese at a Montepulciano winery.
Not included: lunch, gratuities, hotel pickup and attraction tickets. A vegetarian option is available if requested at booking, and the tour may run with a multilingual guide.
Where each one starts
- From Siena: the steps of the red-brick San Domenico church, in Piazza San Domenico.
- From Florence: the tours and news kiosk at the Piazzale Montelungo bus terminal, 5 to 10 minutes on foot from Santa Maria Novella station; look for the fuchsia jackets.
Side by side
| From Siena | From Florence | |
|---|---|---|
| Rating | 4.9 from 1,025 | 4.7 from 1,521 |
| Five-star reviews | 973 (95%) | 1,260 (83%) |
| Price | from about $220 | from about $107 |
| Length | 9 hours | 11.5 hours |
| Group | Up to 8 | Coach, up to 45 |
| Wineries | Two, Brunello | One Brunello, one Vino Nobile |
| Lunch | Included | Not included |
| Towns | Montalcino, Sant’Antimo | Montalcino, Pienza, Montepulciano |
| Cancellation | Free up to 24 hours before | Free up to 24 hours before |
What travelers say
On the small-group day from Siena
This was our very best day of our two week tour of Italy.
Tanya_B, September 2026, via Viator
we enjoyed all the wines/wineries including the delicious lunch!
Jackie_R, September 2026, via Viator
On the coach day from Florence
The three towns we visited were beautiful and different.
David_L, September 2026, via Viator
Views were amazing but wished we could have had more time in Montepulciano.
Kari_G, September 2026, via Viator
The Siena day is almost unanimously five stars. The Florence coach day scores well for value and logistics; its critical reviews are mostly about how little time each town gets.
How a Montalcino day fits a Tuscany trip
If you are in Florence, the closer wine country is Chianti: compare the Chianti wine tour and the Tuscany day trip to Siena, San Gimignano and Pisa. In Siena, pair Montalcino with a Siena food tour.
Every wine region is compared in our wine tours in Italy by region; for the landscape, see the Tuscany guide.
Questions travelers ask
Which Montalcino wine tour should I book?
For wine and a small group, book the day from Siena, rated 4.9 from 1,025 reviews on Viator, from about $220 with lunch (checked September 2026). From Florence, the coach day to the Val d’Orcia starts from about $107 and adds Pienza and Montepulciano.
Can you visit Montalcino as a day trip from Florence?
Yes. The coach day from Florence lasts about eleven and a half hours and includes free time in Montalcino, Pienza and Montepulciano, with two wine tastings.
Is lunch included on a Brunello wine tour?
On the small-group day from Siena, yes. On the coach day from Florence, lunch is not included.
How many wineries do you visit?
Two on each tour: two Brunello cellars from Siena; one Brunello cellar in Montalcino and one Vino Nobile winery in Montepulciano from Florence.
Can I cancel a Montalcino wine tour?
Both offer free cancellation up to 24 hours before the start.
Book the day from Siena for Brunello, lunch and a small group; book the coach day from Florence for three Val d’Orcia towns at half the price.
Editorial assessment by Italy2Love, September 2026. Inclusions and exclusions, itineraries, group sizes, meeting points, prices, ratings, review counts and cancellation terms read on both Viator product pages (product codes 5493MONTALCINO and 6367P16), September 2026. Reviews quoted with attribution to their authors and to Viator. Next review March 2027, or sooner on any change to either tour.