In this guide
💡 The Short Version: Tuscany’s hill towns are a coach-tour day from Rome. Montepulciano is 3¼ hours each way by Intercity and bus, and Trenitalia sells no journey from Rome to Pienza or into the Val d’Orcia, the valley of cypress-lined farms and hilltop villages below it. The Tuscany and Montepulciano day tripad (from £84.85, 11 hours) takes in Montepulciano and Pienza with lunch at a vineyard and a Brunello di Montalcino tasting. Florence and Orvieto, by contrast, are easy by train on your own.
Why a tour
Trenitalia’s times and fares, searched on 30 September 2026 for Tuesday 13 October.
| Destination | Fare each way | Quickest by train |
|---|---|---|
| Montepulciano (town centre) | From €20.50 | 10:15 Intercity to Chiusi-Chianciano Terme, then an Autolinee Toscane bus: 3 hours 15 minutes, arriving 13:30 |
| Siena | From €34.70 | Frecciarossa and a regional train, one change: 3 hours 35 minutes |
| Pienza | None | No journey from Rome on Trenitalia |
- Montepulciano on your own gives you about four hours in the town: the last good connection back leaves Montepulciano Centro at 17:35 and reaches Termini at 21:35. The 8:20 regional train and bus (arriving 12:15, from €17.40) is cheaper and slower.
- A tour puts two or three towns, lunch and a wine tasting into the same 11 or 12 hours, door to door from Rome.
Tours from Rome
Prices are GetYourGuide’s lowest “from” price on 30 September 2026.
Montepulciano and Pienza, with a vineyard lunch
From £84.85 · 4.7 stars from 3,450 reviews · 11 hours
Rome: Tuscany and Montepulciano Day Trip with Lunch and Winesad visits Montepulciano and Pienza, then stops at a vineyard for lunch and a tasting of Brunello di Montalcino, the red wine of Montalcino. It is the most reviewed of the tours on this page.
Montepulciano and Montalcino, with a sommelier lunch
From £92.57 · 4.6 stars from 238 reviews · 12 hours
From Rome: Tuscany, Montepulciano Tour with Wine and Lunchad goes to Montepulciano and Montalcino, with lunch led by sommeliers and a visit to a 13th-century wine cellar.
Civita di Bagnoregio and Pienza
From £84.85 · 4.7 stars from 152 reviews · 11 hours
Rome: Tuscany Day Trip with Vineyard Lunch and Wine Tastingad starts across the footbridge into Civita di Bagnoregio, the hilltop village in Lazio, then lunches at a family-run winery and ends with free time in Pienza. It suits anyone who wants Civita and Tuscany in one day; for Civita with Orvieto instead, see the Orvieto day trip.
Siena and San Gimignano
From £212.56 · 4.7 stars from 55 reviews · 10 hours
From Rome: Siena and San Gimignano, Tuscany Wine One-Day Tourad goes further north, to Siena and San Gimignano, with a wine estate visit and tasting. At more than twice the price of the Montepulciano tours, it is for anyone set on Siena.
What you see
Montepulciano
Every tour above stops here except the Civita one. It is the only one of these hill towns you can reach from Rome and leave the same day by public transport, by the Intercity and bus above.
Piazza Grande in Montepulciano. Photo: Sailko, Wikimedia Commons, CC BY-SA 4.0.
Pienza
Pope Pius II decided in 1459 to rebuild his birthplace as a planned Renaissance town, and the architect Bernardo Rossellino laid out Piazza Pio II with the cathedral and the Piccolomini and Borgia palaces round it. UNESCO calls it the first place where Renaissance town planning was put into practice, and listed its centre as a World Heritage Site in 1996 (whc.unesco.org, 30 September 2026).
A street in Pienza, looking out over the Val d’Orcia. Photo: Eric Kilby, Wikimedia Commons, CC BY-SA 2.0.
The Val d’Orcia
The valley below Pienza and Montalcino is Siena’s old farming hinterland, redrawn in the 14th and 15th centuries: chalk plains with steep hills rising out of them, a fortified village on each, and avenues of cypress trees marking the farms and roads. It has been a World Heritage Site since 2004 (whc.unesco.org, 30 September 2026).
A cypress avenue in the Val d’Orcia. Photo: Enrico Pighetti, Wikimedia Commons, CC BY 2.0.
Before you book
- Wine: every tour here includes a tasting.
- The day is long: 10 to 12 hours, door to door from Rome.
- Florence instead? Florence is 1 hour 36 minutes by Frecciarossa and needs no tour; see the Florence day trip.
Tuscany is one of the day trips from Rome, compared there with Pompeii, the Amalfi Coast, Orvieto and Tivoli on travel time and cost. For what to book in Rome itself, see what to book before you go.
Common questions
Can you do a day trip to Tuscany from Rome?
Yes, on a coach tour. Tours from Rome to Montepulciano and Pienza, with lunch at a vineyard and a wine tasting, take 11 to 12 hours and were from £84.85 on GetYourGuide on 30 September 2026. By public transport, Montepulciano is 3 hours 15 minutes each way by Intercity to Chiusi and a bus, and Trenitalia sells no journey from Rome to Pienza.
Can I get to Montepulciano by train from Rome?
Only with a bus for the last leg. Trenitalia sells Roma Termini to Montepulciano Centro as one ticket: the 10:15 Intercity to Chiusi-Chianciano Terme and an Autolinee Toscane bus, arriving at 13:30, from €20.50. The last good connection back leaves at 17:35 and reaches Termini at 21:35.
How far is Siena from Rome by train?
There is no direct train. The quickest takes 3 hours 35 minutes with a change, a Frecciarossa and a regional train, from €34.70; regional trains only take 3 hours 42 minutes with two changes, from €21.05 (Trenitalia, searched 30 September 2026 for a Tuesday in October).
