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Tuscany and Umbria: Chianti, the Val d'Orcia and Assisi

9 days from Florence: three nights in a Chianti village for San Gimignano and Siena, two in Pienza for the Val d'Orcia, two in Spello for Assisi, then Orvieto and a last night in Florence.

9 days · Round trip from Florence · up to 12 guests

The facts

At a glance

Length
9 days, 8 nights
Start and end
Round trip from Florence
Group size
7 to 12 guests
Longest drive
4 h on day 8No drive day is longer than 4 hours.
Activity level

Moderate

Gentle walking of 2 to 3 hours most days on cobbles, paving and sloping lanes, because every town on this trip is built on a hill. Longer walks on farm tracks are optional: about 4 km into Monteriggioni, 6 km from Volpaia to Radda, 9 km across the Val d'Orcia and 13 km from Assisi back to Spello. Each has a shorter alternative or a seat in the van, and the longest day in the van is about 3.75 hours, just under our 4-hour cap and split by a half day in Orvieto.

Meals included
8 breakfasts, 4 lunches, 3 dinners
Room of your own
+ CAD 1,240 (estimated price)
Season
April to June and September to October

Highlights

Why this trip

  • San Gimignano at 8:45 am, before the coaches, then a walk on Monteriggioni's 13th-century walls
  • Three nights in one Chianti village, with a vineyard walk, a cellar visit and a long lunch at a family wine estate
  • Volpaia and Radda, the Chianti hamlets coach tours drive past, with an optional 6 km walk between them
  • Siena with a local guide who knows the contrade, then the back roads of the Crete Senesi to Pienza at sunset
  • A Val d'Orcia day: a field walk from Pienza, a Brunello tasting in Montalcino, Bagno Vignoni and dinner in walled Monticchiello
  • Montepulciano's rock-cut cellars, lunch in Cortona and two nights in Spello, ten minutes from Assisi and much quieter
  • Assisi's Basilica of San Francesco at 8:30 am and Orvieto's Duomo early, soon after it opens
  • Michelangelo's David at the 8:15 am opening on the last morning in Florence

What makes this trip different

  • Short drives, all published

    Every drive is listed day by day, and none is longer than 4 hours.

  • 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 1,240 (estimated price).

Day by day

Itinerary

The longest drive is 4 h, on day 8.

CHIANTIVAL D'ORCIAUMBRIATUSCANYLake Trasimeno1234FlorenceDays 8 to 9Greve in ChiantiDay 1Castellina in ChiantiDays 1 to 4Radda and VolpaiaDay 3San GimignanoDay 2MonteriggioniDay 2SienaDay 4PienzaDays 4 to 6MontalcinoDay 5Bagno VignoniDay 5MontepulcianoDay 6CortonaDay 6SpelloDays 6 to 8AssisiDay 7OrvietoDay 8

Tap any stop on the map to open that day

Florence to Chianti on the Chiantigiana

Florence Airport or Santa Maria Novella station to Greve in Chianti, then Castellina in Chianti

  • Welcome dinner
  • Stay in Castellina in Chianti
  • Drive about 1.5 h
A row of old wooden wine barrels with faded red ends and a copper funnel, set on a plank against a stone wall
Photo: David MacSpadden, CC BY 2.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Museo_del_vino_(Greve_in_Chianti).jpg)

Your driver meets you at Florence Airport (FLR) or at Santa Maria Novella station, the easier arrival if you come by train from Rome or Pisa. We confirm the latest arrival time and the pick-up times with your final itinerary. Your See Sight Tours guide rides with the group from the first pick-up. We leave the city on the Chiantigiana, the old SR222 road, which climbs south through olive groves and vineyards into the Chianti Classico hills. The first stop is Greve in Chianti, about 45 minutes out, where the arcaded, triangular Piazza Matteotti is lined with butchers, wine shops and cafes: time for a coffee, then a short walk to the forecourt of the San Francesco museum, where terracotta urns and a cypress frame the vineyard hills. Another half hour brings us to Castellina in Chianti, one of the three towns of the medieval Chianti League, where we stay three nights, so you unpack once for the whole Chianti and Siena part of the trip.

Evening

Before dinner, walk Via delle Volte, an arched passage tunnelled along the town walls, then we sit down together to a welcome dinner.

Included

  • Pick-up at Florence Airport (FLR) or Santa Maria Novella station
  • A stop in Greve in Chianti and Piazza Matteotti
  • Welcome briefing with your guide
  • Welcome dinner in Castellina in Chianti

Free time: Early evening free in Castellina before dinner

  1. Florencestart
  2. Castellina in Chianti3 nights
  3. Pienza2 nights
  4. Spello2 nights
  5. Florence1 night
  • Overnight stop
  • Day trip
  • By boat or train
Print itinerary

Wildlife and weather: April to June and September to October bring mild walking weather; the vines are green in spring and the grape harvest runs from about mid-September to mid-October. July and August are hot, often in the mid-30s C, and Siena's Palio fills the Campo on 2 July and 16 August. Winter is quiet and cool, with some estates closed.

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Before you book

Right for you?

Good for you if you want

  • Travellers who want Tuscany's hill towns and wine country without changing hotel every night
  • Wine and food lovers who want to taste with the people who make it
  • Walkers who like a gentle morning walk, with a longer option on farm tracks
  • First-timers who want San Gimignano, Siena and Assisi early, before the crowds
  • People who want Umbria as well as Tuscany on one trip

Not for you if you want

  • Step-free access: every town is on a hill, with steep lanes and steps
  • Travellers who want several days in Florence: this trip gives it one evening and a morning
  • A cycling holiday: the walks are on foot
  • Anyone who wants nightlife: the bases are small towns that go quiet after dinner

Book flights after we confirm your seat.

8 nights

Where you'll stay

Your hotels are named in your trip confirmation.

  • Castellina in Chianti3 nights
  • Pienza2 nights
  • Spello2 nights
  • Florence1 night

One price

What's in the price

Included

Accommodation

  • 8 nights: 3 in Castellina in Chianti, 2 in Pienza, 2 in Spello, 1 in central Florence
  • Hotels of at least a 3-star-plus standard, in or at the edge of each old town, named when we confirm your dates
  • Rooms shared, or your own for a supplement
  • Local tourist taxes

Transport

  • Pick-up at Florence Airport (FLR) or Santa Maria Novella station on day 1
  • Drop-off at Florence Airport (FLR) or Santa Maria Novella station on day 9
  • Our own air-conditioned minibus and driver for the group for the whole trip
  • The van to and from Monticchiello for dinner on day 5

Your guide

  • A See Sight Tours guide with the group for the whole trip
  • Local guides in San Gimignano, Siena, Assisi and Spello, and at the Accademia in Florence

Activities

  • Greve in Chianti: a stop in Piazza Matteotti
  • San Gimignano: guided walk and the Collegiata
  • Monteriggioni: the walkway on the walls
  • Volpaia and Radda in Chianti
  • Chianti Classico estate: vineyard and cellar visit with a tasting
  • Siena: guided walk, the Duomo and the Piccolomini Library
  • The Crete Senesi back roads
  • Pienza: field walk to the Pieve di Corsignano and a pecorino tasting
  • Montalcino: Brunello estate visit and tasting
  • Bagno Vignoni
  • Montepulciano: cellar visit and Vino Nobile tasting
  • Cortona: guided walk
  • Assisi: the Basilica of San Francesco with a local guide, and Santa Chiara
  • Spello: guided walk, the Baglioni Chapel and an olive oil tasting
  • Orvieto: the Duomo and the Chapel of San Brizio
  • Florence: an evening walk, and the Galleria dell'Accademia at opening

Meals

  • Breakfast daily (8)
  • 4 lunches: the Chianti Classico estate, Montalcino, Cortona and Orvieto
  • 4 dinners: a welcome dinner in Castellina, Monticchiello, Spello and a farewell dinner in Florence
  • Tastings of Chianti Classico, Brunello, Vino Nobile, pecorino and olive oil

Not included

  • International flights to and from Italy
  • Trains to Florence before the trip or from Florence after it
  • Travel insurance
  • Visa or travel authorisation fees, if any apply to you (such as ETIAS once it starts)
  • Meals not listed (lunches on days 2, 4, 7 and 9 and dinners on days 2, 3, 4 and 6 are on you)
  • Drinks, except at the tastings and the estate lunch
  • Tips
  • Optional activities, such as the Torre Grossa, the Torre del Mangia and the Pozzo di San Patrizio
  • Shipping wine home
  • Personal expenses

Extras

Room of your own
CAD 1,240 (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+1-888-961-6584

Guest reviews

What guests say

Reviews from guests on our day tours.

Cornelius Amann
October 06, 2026
google

5/5

Parminder did a great job guiding us around, giving us tips & teaching us the history of the falls. A great experience!

Jane
October 06, 2026
gyg

5/5

Good views of the surrounding area of Halifax in a comfortable minivan

Susan
October 06, 2026
gyg

5/5

June was brilliant- made good contact beforehand and really attentive and knowledgeable. Made me feel like I was special- something only experience can do. Thank you June.

Tom L
October 05, 2026
tripadvisor

5/5

Our host was very knowledgeable, friendly and even provided some humor.

MandL83
October 05, 2026
tripadvisor

5/5

Peter was a very good guide, giving us insight into the various parts of the Park, including parking lot congestion details, trail and viewing location suggestions.

Darren O
October 05, 2026
tripadvisor

5/5

Excellent morning spent with my guide Nancy. Very knowledgeable and friendly. Thoroughly enjoyed my trip

4.7/5 from 38,601 guest reviews

Good to know

Questions

What does the price include?

Eight nights in hotels in Castellina in Chianti, Pienza, Spello and Florence, breakfast daily, 4 lunches and 4 dinners, a long lunch at a Chianti Classico estate and tastings of Brunello, Vino Nobile, pecorino and olive oil, our own minibus and driver, transfers in Florence, local tourist taxes, your See Sight Tours guide throughout with local guides, and every entry in the day plan.

How big is the group?

The small-group trip runs with 7 to 12 guests. That is small enough to reach hamlets like Volpaia and Monticchiello in one minibus, sit at one table at the wine estate and hear the guide in a crowded Siena street, where many Italy tours of 16 to 29 people split up or wait their turn.

Who leads the trip?

A See Sight Tours guide travels with the group from the Florence pick-up to the last morning at the Accademia. Licensed local guides join in San Gimignano, Siena, Assisi, Spello and Florence, and the wine makers and cellar hosts lead their own tastings. We name your guide when we confirm your dates.

How fit do I need to be?

Moderately fit. Most days are 2 to 3 hours of gentle walking on cobbles and slopes, because every town is on a hill. The longer walks, from 4.5 to 13 km on farm tracks, are optional, and each has an easy version or a seat in the van. Assisi on day 7 is the steepest town.

I am travelling solo. What is the single supplement?

A room of your own is from CAD 1,240 more, about 17 percent of the trip price, shown up front with no surprise at checkout. If you would rather share, tell us when you book and we check whether another solo guest on your date would like to share a twin room for the whole trip.

When is the best time to visit Tuscany and Umbria?

April to June and September to October. The walking weather is mild, the vines are green in spring and the grape harvest runs from about mid-September to mid-October. July and August are hot, often in the mid-30s C, and Siena's Palio fills the Campo on 2 July and 16 August.

How does booking work?

The small group starts from CAD 7,295 per person sharing, with taxes, and private trips from CAD 13,130. Pick your start date and request to book; we confirm your place within 24 hours and no payment is taken until we do. Prices are indicative until your dates are confirmed.

Can we travel privately or on our own dates?

Yes. The private version is 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 quote the same hotels, estates, drivers and local guides for you.

Do Canadians or Americans need a visa for Italy?

No visa is needed for a tourist stay of up to 90 days in the Schengen area with a Canadian or US passport valid for at least three months after you leave. The EU's ETIAS travel authorisation is expected to start in late 2026; we tell you if your dates need it.

Which airport should I fly into for this trip?

Florence Airport (FLR) is closest, about 20 minutes from the city, but has fewer long-haul connections. Many travellers fly into Rome and take the fast train to Florence's Santa Maria Novella station, about an hour and a half, or into Pisa, about an hour away. We pick up at the airport or the station.

I do not drink much wine. Is this trip still for me?

Yes. Tastings are small pours served with food, and the visits are as much about the vineyards, cellars and families as the glass. Non-drinkers are welcome at every tasting, the estates serve water and soft drinks, and our driver does all the driving. Pecorino and olive oil tastings are part of the trip too.

Can I combine this trip with the Amalfi Coast?

Yes. Our Amalfi Coast and Capri trip starts in Naples, about three hours from Florence by fast train, so the two fit back to back. Ask us when you book and we arrange the nights and the train between them, in either order.

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