Cornelius Amann
October 06, 2026
5/5
Tuscany: a slow week in the Val d'Orcia
7 days from Florence with one hotel in Montepulciano for six nights: Pienza, Siena on a weekday, Montalcino, a village walk, a pasta class, Bagno Vignoni and a free day.
7 days · Round trip from Florence · up to 12 guests
Cypresses in the Val d'Orcia, the valley below Montepulciano and Pienza Photo: Iaia quark, CC0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Continua_-_cypresses_(no_watermark).jpg)
The facts
At a glance
- Length
- 7 days, 6 nights
- Start and end
- Round trip from Florence
- Group size
- 7 to 12 guests
- Activity level
Easy
Mostly easy walking on steep, paved hill-town lanes, 3 to 5 km a day. One optional 7 km walk on gravel roads with roughly 150 to 200 m of climbing (both villages sit at about 500 m, with a dip into the valley between) on day 4, with the van following so you can stop or skip it. Drives are 20 minutes to 2 hours.
- Meals included
- 6 breakfasts, 2 lunches, 2 dinners
- Room of your own
- + CAD 750 (estimated price)
- Season
- April to June and September to October
Highlights
Why this trip
- Unpack once: six nights in one central hotel in Montepulciano
- Pienza's wall walk over the Val d'Orcia in the early evening, after the day visitors leave
- Siena on a weekday morning with a local guide, Duomo and Piccolomini Library included
- A morning walk on white roads from Pienza to Monticchiello, with lunch in the village
- A pasta class making pici, then dinner on what you made
- A Brunello lunch at a Montalcino wine estate and the Abbey of Sant'Antimo
- A soak in a thermal pool at Bagno Vignoni
- A whole free day, with an optional day out to San Gimignano at no extra charge
What makes this trip different
Free time is part of the plan
Free time and choices are marked on the days they fall.
Solo without the penalty
A room of your own is + CAD 750 (estimated price).
Day by day
Itinerary
Tap any stop on the map to open that dayClick any stop on the map to open that day
Florence, then south to Montepulciano
Central Florence (or Florence Airport, FLR) to Montepulciano
- Lunch in Florence and welcome dinner
- Stay in Montepulciano
- Drive about 2 h
Morning
We meet at 11 am in central Florence; if you land at Florence Airport (FLR) that morning, a driver brings you in (land by about 9:30 am).
Afternoon
Your See Sight Tours guide walks the group from the Duomo past Piazza della Signoria and over the Ponte Vecchio to a sit-down lunch in the Oltrarno, the quieter bank of the Arno. Mid-afternoon we drive south, about two hours and 125 km on the A1 and then country roads, to Montepulciano, the hill town on the ridge above the Val d'Orcia that is home for the next six nights. You unpack once.
Evening
There is time to settle in and walk the main street, the Corso, before a welcome dinner in town, where the guide runs through the week, the walk on day 4 and the free day. If you want Florence's museums, arrive a day or two early; we can suggest how to book the Uffizi and the Accademia.
Included
- Meeting in central Florence, or a transfer from Florence Airport (FLR) if you land that morning
- Guided walk from the Duomo over the Ponte Vecchio
- Sit-down lunch in the Oltrarno
- Drive to Montepulciano
- Welcome dinner
Free time: Late afternoon free to settle in
Activity: About 1.5 km on foot in Florence, flat.
Montepulciano's cellars and Pienza at golden hour
Montepulciano, then Pienza and back
- Breakfast
- Stay in Montepulciano
- Drive about 45 min
Morning
A slow first morning on foot from the hotel. With a local guide we walk up to Piazza Grande, the town's high square, with the cathedral, the Palazzo Comunale and the long view south over the valley, then go underground into one of the old wine cellars cut beneath the palazzi for a visit and a tasting of Vino Nobile di Montepulciano.
Afternoon
Lunch is yours on the Corso. After a rest we drive twenty minutes west to Pienza, the town Pope Pius II had rebuilt around 1459 to 1462 as a model Renaissance centre, now a UNESCO World Heritage site. Walk the lane along the southern wall for the classic view over the Val d'Orcia, step into the cathedral on the square, and taste pecorino di Pienza, the sheep's cheese the town is known for.
Evening
We stay into the early evening, when the day visitors have gone and the light turns warm on the hills.
Included
- Guided walk of Montepulciano with a local guide: the Corso and Piazza Grande
- Wine cellar visit and Vino Nobile tasting
- Pienza: Piazza Pio II, the cathedral and the wall walk
- Pecorino tasting in Pienza
Easier option: Ride the van to the top of town and walk only the level parts of Pienza.
Free time: Lunch and early afternoon free in Montepulciano
Activity: Montepulciano is steep: the Corso climbs about 100 m from the lower gate to Piazza Grande. About 4 km on foot today.
Siena on a weekday
Montepulciano to Siena and back
- Breakfast
- Stay in Montepulciano
- Drive about 2.5 h
We go to Siena on a weekday on purpose, when the streets are full of people who live there rather than weekend crowds. The drive is about an hour and ten minutes each way, about 130 km there and back, through the Crete Senesi, the bare clay hills between the Val d'Orcia and the city. We are in the centre by about 9:30 am. A local guide takes us through one of the contrade, the city's seventeen neighbourhoods that race each other in the Palio, down into the shell-shaped Piazza del Campo below the Torre del Mangia, and into the Duomo, with its striped marble, the inlaid floor and the Piccolomini Library. Entry is included.
Afternoon
After the tour the day is yours: lunch where you like, the climb up the Facciatone for the view, or the Pinacoteca. We drive back in the late afternoon. On the two Palio days, 2 July and 16 August, and the days around them, we move Siena to another weekday.
Included
- Siena with a local guide: a contrada, Piazza del Campo and the Duomo
- Duomo entry, including the Piccolomini Library
Optional experiences
- The Facciatone viewpoint or the Torre del Mangia (pay locally)
Free time: Lunch and the afternoon free in Siena
Activity: About 5 km on foot on steep, paved lanes.
A morning walk between villages, then a pasta class
Pienza to Monticchiello on foot, then back to Montepulciano
- Breakfast, lunch and dinner
- Stay in Montepulciano
- Drive about 1 h
Today is a walk, not a drive. We start from Pienza at about 8:30 am, before the heat, and follow white gravel roads and farm tracks south-east to Monticchiello, a small walled village of stone houses above the valley. Both villages sit at about 500 m, so the route dips into the valley and climbs back: about 7 km and two and a half hours with stops for photos of cypresses and farmhouses. The van follows, so anyone can stop at any point.
Afternoon
Lunch is a sit-down meal in Monticchiello, then the van takes everyone home for a free afternoon: sleep, read, or walk down to the church of San Biagio below Montepulciano.
Evening
In the late afternoon a local cook teaches the group to make pici, the thick hand-rolled pasta of this part of Tuscany, with a sauce or two, and we eat what we made together for dinner with local wine.
Included
- Guided walk from Pienza to Monticchiello
- Sit-down lunch in Monticchiello
- Pasta class with a local cook, with dinner and wine
Easier option: Ride the van to Monticchiello and walk its lanes, or walk only the first 3 km out of Pienza.
More active option: Walk on from Monticchiello to Montepulciano, about 10 km more, with the guide.
Free time: Afternoon free
Activity: About 7 km on gravel roads with roughly 150 to 200 m of climbing, most of it the last stretch up to Monticchiello; good shoes and a hat.
Montalcino, a Brunello lunch and the hot springs
Montepulciano to Montalcino, Sant'Antimo and Bagno Vignoni, then back
- Breakfast and lunch
- Stay in Montepulciano
- Drive about 3 h
We drive about an hour west, roughly 55 km, past San Quirico d'Orcia and the cypress-ringed Vitaleta chapel, where we stop for photos, to Montalcino, the walled hill town that gives its name to Brunello di Montalcino.
Afternoon
Walk up to the 14th-century fortress and its view over the vineyards, then go down to a family wine estate for a cellar visit and a long sit-down lunch with Brunello and Rosso di Montalcino. On the way back we stop at the Abbey of Sant'Antimo, a Romanesque church in a valley of olive trees ten minutes south of Montalcino. The afternoon ends at Bagno Vignoni, where a medieval square holds a large pool of hot spring water instead of a piazza; you cannot bathe in it. Below it, the Parco dei Mulini, where the hot water runs down the cliff past old mills, is free to walk, and your entry to a thermal pool in the village that is open to visitors is included. Soak until late afternoon, then it is 35 to 40 minutes home. About 140 km of driving in all.
Included
- Photo stop at the Vitaleta chapel
- Montalcino and the fortress viewpoint
- Wine estate visit and Brunello lunch
- Abbey of Sant'Antimo
- Bagno Vignoni and entry to a thermal pool
Easier option: Skip the fortress walk and wait in a café on the square.
Free time: Evening free in Montepulciano
Activity: Light walking. Bring a swimsuit and flip-flops for the thermal pool.
A free day in the Val d'Orcia
Montepulciano, at your own pace
- Breakfast and dinner
- Stay in Montepulciano
A whole day with nothing planned, because a week in one place should feel like one.
Afternoon
Sleep late, have a long breakfast and spend the day as you like: a weekly market in one of the nearby towns, a long lunch in a trattoria, a bike ride, or just a chair and a book. Your guide is around in the morning to help you book anything, from a horse ride to a second winery or a massage. For anyone who wants one more hill town, the guide and van go to San Gimignano for the day, about an hour and three quarters each way, for its medieval towers, the Collegiata frescoes and the view from the Rocca; it costs nothing extra, and you can choose that morning.
Evening
Everyone meets again in the evening for a farewell dinner in Montepulciano, the last night in the hotel you have stayed in all week.
Included
- Farewell dinner in Montepulciano
Optional experiences
- Day out to San Gimignano with the guide and van (about 3.5 hours of driving in total, no extra charge)
- E-bike hire, horse riding, a second winery or a spa treatment (pay locally)
Free time: The whole day is free
Back to Florence
Montepulciano to Florence (Santa Maria Novella station or Florence Airport, FLR)
- Breakfast
- Drive about 2 h
Morning
A last breakfast in Montepulciano, then we leave at about 9:30 am for the two-hour drive back north to Florence, 125 km on country roads and the A1, with a coffee stop on the way.
Afternoon
We drop off at Santa Maria Novella station in the city centre, which has trains to Rome, Venice and Milan, by about midday, and at Florence Airport (FLR) about twenty minutes later. Book a flight leaving after about 3 pm, or stay on in Florence; we can suggest a central hotel if you want a few more nights. If you are flying from Pisa or Rome instead, the fast trains from Santa Maria Novella take about an hour to Pisa and about an hour and a half to Rome. Your guide sees the group to the station and the airport before saying goodbye.
Included
- Drive to Florence
- Drop-off at Santa Maria Novella station or Florence Airport (FLR)
Activity: Book flights leaving Florence after about 3 pm.
- Florencestart
- Montepulciano6 nights
- Florenceend
- Overnight stop
- Day trip
- By boat or train
Wildlife and weather: Spring brings green wheat and poppies in the Val d'Orcia; September and October bring the grape harvest. July and August are hot, so the walk starts earlier and is shortened. Some wine estates and restaurants close or shorten hours from November to March.
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Before you book
Right for you?
Good for you if you want
- Travellers who want to unpack once and slow down
- Food and wine lovers who also like a morning walk
- First-timers to rural Tuscany who do not want to drive themselves
- Solo travellers who want company at dinner without a busy schedule
Not for you if you want
- Travellers who want to see Florence's museums on the trip (arrive early or stay on)
- Step-free access: hill towns mean steep cobbled lanes and steps
- Those who want a new town every night or a full schedule every day
Book flights after we confirm your seat.
6 nights
Where you'll stay
Your hotels are named in your trip confirmation.
- Montepulciano6 nights
One price
What's in the price
Included
Accommodation
- 6 nights in one central hotel in Montepulciano
- Rooms shared, or your own for a supplement
Transport
- Meeting in central Florence, or a transfer from Florence Airport (FLR) on the morning of day 1
- Drop-off at Santa Maria Novella station or Florence Airport (FLR) on day 7
- Our own air-conditioned van and driver for every day out
Your guide
- A See Sight Tours guide for the whole trip
- Local guides in Montepulciano and Siena
- A local cook for the pasta class
Activities
- Florence: a walk from the Duomo over the Ponte Vecchio
- Montepulciano: guided walk and a wine cellar visit with a Vino Nobile tasting
- Pienza: the town and wall walk, with a pecorino tasting
- Siena: guided walk, a contrada, Piazza del Campo, the Duomo and the Piccolomini Library
- The walk from Pienza to Monticchiello
- Pasta class making pici
- Montalcino and the fortress viewpoint, a wine estate visit and Brunello lunch
- The Abbey of Sant'Antimo
- Bagno Vignoni and entry to a thermal pool
- Optional day out to San Gimignano with the guide on day 6
Meals
- 6 breakfasts
- 3 lunches: Florence, Monticchiello and a Brunello lunch in Montalcino
- 3 dinners: welcome, the pasta class dinner and a farewell dinner
- Wine with the tastings, the Brunello lunch and the pasta class dinner
Not included
- International flights to and from Italy
- Travel insurance
- Visa or ETIAS fees, if they apply
- Lunches and dinners not listed (3 lunches and 3 dinners are on you)
- Drinks other than the wine listed
- Tips
- Optional activities on the free day, such as e-bike hire, horse riding or a spa treatment
- Museum entries in Florence and San Gimignano
- Personal expenses
Extras
- Room of your own
- CAD 750 (estimated price)
When you can go
Dates and prices
Pick your start date when you request to book. We check that date and confirm it in your quote.
Prefer to travel without a group or guide? Ask us about arranging hotels, transport and city tours for you to travel independently.
Before you book
Booking terms
Nothing is charged now. Full terms and the cancellation schedule come with your quote, before you accept.
Business addresses
See Sight Tours Trips (USA): 3172 N Rainbow Blvd, Las Vegas, NV 89108, United StatesSee Sight Tours Trips (Canada): 5305 50 Avenue, #1091, Red Deer, AB T4N 4B6, Canada+1-888-961-6584Guest reviews
What guests say
Reviews from guests on our day tours.
Jane
October 06, 2026
5/5
Susan
October 06, 2026
5/5
Tom L
October 05, 2026
5/5
MandL83
October 05, 2026
5/5
Darren O
October 05, 2026
5/5
Good to know
Questions
What does the price include?
Six nights in one central hotel in Montepulciano, 6 breakfasts, 3 lunches and 3 dinners, Florence meeting and drop-off, our own van and driver, a See Sight Tours guide all week, local guides in Montepulciano and Siena, the Siena Duomo, cellar and pecorino tastings, a Brunello lunch, the pasta class and a thermal pool at Bagno Vignoni.
Are all meals included?
No. You get 6 breakfasts, 3 lunches and 3 dinners, including a Brunello lunch and the pasta-class dinner. Three evenings and the lunches on days 2, 3 and 6 are free on purpose, so you can eat where you like in Montepulciano and Siena; your guide suggests places and books tables.
How big is the group?
The small-group trip runs with 7 to 12 guests, so the whole group fits around one table at lunch and in one van, and everyone can hear the guide in Siena's narrow lanes.
Who leads the trip?
A See Sight Tours guide is with the group from the Florence meeting to the drop-off on day 7. Licensed local guides lead the walks in Montepulciano and Siena, and a local cook runs the pasta class. We name your guide when we confirm your dates.
Why stay in one hotel all week?
Because packing every morning is the most common complaint about Italy tours. Montepulciano is within 20 to 70 minutes of Pienza, Siena, Montalcino and Bagno Vignoni, so every day out ends back at the same hotel, and you can walk to dinner each night.
How fit do I need to be?
Fairly fit for hill towns. Expect 3 to 5 km a day on steep, cobbled lanes. The day 4 walk is about 7 km on gravel roads with roughly 150 to 200 m of climbing, and the van follows, so you can ride to Monticchiello instead or join part of the way.
I am travelling solo. What does a single room cost?
A room of your own is from CAD 750 more for the six nights, shown before you book with no surprise later. If you would rather share, ask us when you request to book and we will tell you whether another solo traveller can share with you on that departure.
When is the best time to go?
April to June and September to October. Spring has green fields and poppies, September and October the grape harvest. July and August are hot, so the walk starts earlier. We avoid Siena on its Palio days, 2 July and 16 August.
Can I book my own dates?
Yes. The private version runs for your party only, on a date you choose, with your own guide and vehicle. If you would rather travel independently on your own dates, ask us from the dates section and we can quote the same hotel, tastings and transfers without a guide.
How does booking work?
Pick a departure and send a request to book. We confirm availability and your price within 24 hours. Nothing is charged until then, and you can ask us anything before you accept.
Do I need a visa for Italy?
Canadian, US, UK and Australian passport holders do not need a visa for a stay of up to 90 days in the Schengen area. ETIAS, the EU's travel authorisation, is not yet in operation; the EU will announce a start date ahead of launch, and we confirm the rules when you book.
Can we swim in the hot springs at Bagno Vignoni?
Not in the famous square, whose old pool of spring water is for looking at only. Your entry to a thermal pool in the village that is open to visitors is included, so bring a swimsuit; we confirm which pool and its hours with your final itinerary.
See Sight Tours has been providing travel services across North America since 2006. Operating in 20 cities across Canada and the USA, the company specializes in small group tours that offer personalized, high-quality experiences for travelers.
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