Cornelius Amann
October 06, 2026
5/5
Women-only Tuscany and Umbria: Chianti, the Val d'Orcia and Assisi
9 days for women only from Florence, with a female guide: three nights in a Chianti village, 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 Chianti hills from the San Francesco museum terrace in Greve in Chianti Photo: Anna.Massini, CC BY 4.0, via Wikimedia Commons (https://commons.wikimedia.org/wiki/File:Museo_san_francesco_greve_in_chianti_-_il_piazzale.jpg)
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 1,265 (estimated price)
- Season
- April to June and September to October
Highlights
Why this trip
- A slow first evening in Castellina in Chianti: check in, rest, then a short briefing and a light supper with your female guide
- San Gimignano at 8:45 am, before the coaches, then a walk on Monteriggioni's 13th-century walls
- A vineyard walk and a long lunch at a family Chianti Classico estate, chosen where we can among estates run by women
- Siena with a local guide, a woman where one is available, then the Crete Senesi back roads 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, then a home-cooking evening with local women in Spello
- 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 1,265 (estimated price).
Day by day
Itinerary
The longest drive is 4 h, on day 8.
Tap any stop on the map to open that dayClick any stop on the map to open that day
Florence to Chianti, an easy first evening
Florence Airport or Santa Maria Novella station to Greve in Chianti, then Castellina in Chianti
- Light welcome supper
- Stay in Castellina in Chianti
- Drive about 1.5 h
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, and your See Sight Tours guide, who is a woman, rides with the group from the first pick-up. We confirm the latest arrival time and the pick-up times with your final itinerary. We leave the city on the Chiantigiana, the old SR222 road, which climbs south through olive groves and vineyards into the Chianti Classico hills. There is one stop, about 45 minutes out, in Greve in Chianti: a coffee under the arcades of the triangular Piazza Matteotti and, for those who want it, a look at the old barrels in the small wine museum. Another half hour brings us to Castellina in Chianti, where we stay three nights. Nothing else is planned: check in or walk Via delle Volte, the arched passage along the town walls. At about 6:30 pm your guide runs a short briefing on the week, what to wear in churches, how rooms are shared and how the days are paced, over a light supper close to the hotel, and we finish early.
Included
- Pick-up at Florence Airport (FLR) or Santa Maria Novella station
- A coffee stop in Greve in Chianti and Piazza Matteotti
- Welcome briefing with your guide
- Light welcome supper in Castellina in Chianti
Free time: Free from check-in until the 6:30 pm briefing
Activity: Arrive by about 1 pm to join the group transfer; later arrivals are met and join the supper.
San Gimignano before the coaches, then Monteriggioni
Castellina in Chianti to San Gimignano, then Monteriggioni and back
- Breakfast
- Stay in Castellina in Chianti
- Drive about 2 h
Morning
We leave at 8 am so we walk into San Gimignano at about 8:45, well before the day-trip coaches that fill its two main streets from mid-morning. The town grew rich on the Via Francigena pilgrim road and the saffron trade, and of the dozens of towers its merchant families built, 14 still stand; its centre was listed by UNESCO in 1990. With a local guide, a woman where one is available, we climb from Porta San Giovanni to Piazza della Cisterna and its 13th-century well, then step into the Collegiata, whose walls are covered in 14th-century frescoes of the Old and New Testaments. From about 11 am the time is yours: climb the Torre Grossa, taste Vernaccia, the town's white wine, or find a quiet stretch of wall.
Afternoon
Lunch is your choice in town. In the early afternoon we drive half an hour to Monteriggioni, a tiny walled village that Siena fortified between 1213 and 1219, and walk the walkway along its walls, past the towers Dante compared to giants.
Evening
We are back in Castellina by about 4 pm, and the evening is free.
Included
- San Gimignano with a local guide (a woman where available): Porta San Giovanni, Piazza della Cisterna and Piazza del Duomo
- The Collegiata and its frescoes
- Monteriggioni and the walkway on its walls
Optional experiences
- Climb the Torre Grossa, San Gimignano's tallest tower (paid locally)
Easier option: Skip the Monteriggioni wall walkway, which is reached by steep steps, and wait in the village square with a coffee.
More active option: Walk into Monteriggioni on the Via Francigena from Abbadia a Isola, about 4 km on farm tracks with the walls in view, while the van meets you at the gate.
Free time: Free from about 11 am, and for lunch, in San Gimignano; evening free in Castellina
Activity: About 2 hours on foot in San Gimignano on paving and short, steep slopes.
Volpaia, Radda and a long wine lunch
Castellina in Chianti to Volpaia and Radda in Chianti, then a Chianti Classico estate
- Breakfast and lunch
- Stay in Castellina in Chianti
- Drive about 1.5 h
A slow day in the heart of Chianti Classico, the hills between Florence and Siena whose wine carries the black rooster seal. We drive about 20 minutes up a winding road to Volpaia, a fortified hamlet of stone houses at about 600 m, still gathered around its castle keep, with views over the vines and woods towards Radda. Few coaches come up here. From Volpaia we go down to Radda in Chianti, once the seat of the medieval Chianti League, and walk its main street past the Palazzo del Podestà, its front studded with the stone coats of arms of former governors, while the shops open.
Afternoon
Late morning we reach a family wine estate, chosen where we can among the Chianti estates run by women winemakers and confirmed with your dates, for a walk through the vines and the cellar with the people who make the wine, then a long lunch at their table: Chianti Classico poured with local salumi, pecorino, pasta and olive oil from their own trees.
Evening
The afternoon is free: a swim if your hotel has a pool, a nap, or an evening walk around Castellina.
Included
- The hamlet of Volpaia
- Radda in Chianti with your guide
- Vineyard and cellar visit at a family Chianti Classico estate (woman-run where we can confirm one), with a tasting
- Long lunch at the estate
Easier option: Ride the van from Volpaia down to Radda and have a coffee in the piazza while the walkers come down.
More active option: Walk from Volpaia down to Radda on country tracks and lanes, about 6 km and mostly downhill, with your guide.
Free time: Afternoon and evening free in Castellina
Activity: An easy day: about 1 hour on foot in Volpaia and Radda, or about 2.5 hours with the walk between them.
Siena, then south through the Crete Senesi
Castellina in Chianti to Siena, then through the Crete Senesi to Pienza
- Breakfast
- Stay in Pienza
- Drive about 2 h
We pack up and drive half an hour south to Siena, park outside the walls and walk in at about 9 am. With a local guide, a woman where one is available, you see the city the Sienese know: the 17 contrade, the districts that race each other in the Palio twice each summer, each with its own church, fountain and animal emblem; then the shell-shaped Piazza del Campo, sloping down to the Palazzo Pubblico and the Torre del Mangia. We go into the striped marble Duomo, with its inlaid marble floor (fully uncovered only at set times of year), and the Piccolomini Library, painted by Pinturicchio. Siena's historic centre was listed by UNESCO in 1995.
Afternoon
After the tour, lunch and an hour or two in the city are yours. In the mid-afternoon we drive south on back roads through the Crete Senesi, bare clay hills of grey and gold with lone farmhouses and rows of cypress, stopping where the light is good. We reach Pienza, our base for two nights, in the late afternoon, in time to walk the lane along its walls as the sun lowers over the Val d'Orcia.
Included
- Siena with a local guide: a contrada, Piazza del Campo and the Palazzo Pubblico
- Siena Duomo and the Piccolomini Library
- The Crete Senesi back roads, with photo stops
- Sunset walk along Pienza's walls
Optional experiences
- Climb the Torre del Mangia over the Campo (timed tickets, paid locally)
Easier option: Sit out the middle of the walking tour at a cafe on the Campo and rejoin the group at the Duomo, a short walk uphill; the van meets everyone outside the walls.
Free time: Lunch and early afternoon free in Siena; evening free in Pienza
Activity: About 2.5 hours on foot in Siena, on sloping streets and stone paving.
Val d'Orcia: Pienza, Montalcino and Bagno Vignoni
Pienza to Montalcino and Bagno Vignoni, then Monticchiello for dinner
- Breakfast, lunch and dinner
- Stay in Pienza
- Drive about 2 h
The Val d'Orcia, listed by UNESCO in 2004, is the landscape of cypress avenues, wheat fields and farmhouses on low hills that Renaissance painters made famous.
Morning
We set off on foot at 8:30 am from Pienza, the village Pope Pius II had rebuilt from 1459 as an ideal Renaissance town, and walk down through the fields to the Romanesque Pieve di Corsignano and back up, about 5 km in the cool of the morning.
Afternoon
Late morning we drive 35 minutes west to Montalcino, on its hill above the vineyards of Brunello, for lunch together in town and then a visit and tasting at a Brunello estate. On the way back we stop at Bagno Vignoni, where the village square is a Renaissance pool of steaming thermal water (for looking, not bathing). Back in Pienza in the late afternoon, we taste pecorino di Pienza, the sheep's cheese the town is known for, with a cheesemaking family (a woman-run dairy where we can confirm one), and the rest of the afternoon is yours.
Evening
In the evening the van takes us ten minutes to Monticchiello, a walled hamlet most visitors drive past, for dinner together.
Included
- Morning walk from Pienza to the Pieve di Corsignano
- Montalcino and lunch in town
- Brunello di Montalcino estate visit and tasting
- Bagno Vignoni and its thermal-water square
- Pecorino tasting in Pienza
- Dinner in Monticchiello
Easier option: Skip the walk down to the Pieve and stroll Pienza's lanes and cathedral square instead; the van leaves for Montalcino from the town gate.
More active option: Walk about 9 km on white gravel roads from Pienza past the Cappella di Vitaleta to San Quirico d'Orcia, where the van collects you on the way to Montalcino.
Free time: Late afternoon free in Pienza before dinner
Activity: About 5 km on gravel farm tracks, with a steady climb back up to Pienza; Montalcino's lanes are steep too.
Montepulciano's cellars and Cortona, into Umbria
Pienza to Montepulciano and Cortona, then Spello in Umbria
- Breakfast and lunch
- Stay in Spello
- Drive about 2.5 h
A 20-minute drive east brings us to Montepulciano at about 9 am, before the day visitors. The town runs along a ridge at about 600 m, and its Renaissance palaces sit on cellars cut deep into the rock, where Vino Nobile di Montepulciano ages in big oak casks. We walk up the Corso to Piazza Grande, with its unfinished cathedral facade, then go underground with a cellar host for a visit and tasting.
Morning
Late morning we cross the Val di Chiana to Cortona, about 45 minutes away, a hill town of Etruscan origin with views down to Lake Trasimeno.
Afternoon
Lunch is together in town, followed by a walk to Piazza della Repubblica and the cathedral and some free time in the lanes. In the afternoon about an hour and a quarter, past Lake Trasimeno and Perugia, brings us into Umbria and to Spello, a small walled town of pink and white stone on the slope of Monte Subasio, our base for two nights.
Evening
Spello is a quarter of an hour from Assisi but has none of its crowds, and the evening is yours to find a table in a quiet piazza.
Included
- Montepulciano with your guide: the Corso and Piazza Grande
- Cellar visit and Vino Nobile tasting in Montepulciano
- Cortona with your guide: Piazza della Repubblica and the cathedral
- Lunch in Cortona
Easier option: The van drops you at the top of Montepulciano by Piazza Grande, so you skip the climb up the Corso.
Free time: Some free time in Cortona; evening free in Spello
Activity: Montepulciano's Corso climbs steadily for about a kilometre; Cortona is steep from the gate to the cathedral.
Assisi early, cooking with women in Spello
Spello to Assisi and back
- Breakfast and dinner
- Stay in Spello
- Drive about 30 min
We are in Assisi by about 8:30 am, an hour or more before the tour coaches arrive, when the upper town is quiet and the light is soft on the pink stone. With a local guide, a woman where one is available, we visit the Basilica of San Francesco, begun in 1228, two years after the saint's death: the lower church, with his tomb, and the upper church, lined with the frescoed cycle of his life traditionally attributed to Giotto. Assisi and its Franciscan sites were listed by UNESCO in 2000. Then we walk the length of the town to the Roman Temple of Minerva and on to the Basilica of Santa Chiara, built for Saint Clare, who founded the order of Franciscan nuns.
Afternoon
Lunch and the early afternoon are yours. Back in Spello, a local guide walks you through the Roman gates and into Santa Maria Maggiore for Pinturicchio's frescoes in the Baglioni Chapel.
Evening
In the evening we cook with local women hosts, confirmed with your dates: you roll strangozzi, the hand-cut Umbrian pasta, taste their olive oil and sit down together to eat what you made.
Included
- Assisi with a local guide (a woman where available): the Basilica of San Francesco, upper and lower churches
- The Temple of Minerva and the Basilica of Santa Chiara
- Spello with a local guide: the Roman gates and the Baglioni Chapel in Santa Maria Maggiore
- Home-cooking evening in Spello with local women hosts, confirmed with your dates, with an olive oil tasting and dinner
Optional experiences
- A Sagrantino tasting in Montefalco, about 25 minutes from Spello, in the early afternoon instead of the guided Spello walk (arranged on request, paid locally)
Easier option: Take the van back to Spello after lunch and rest before the cooking evening; at the cooking evening you can watch and eat rather than cook.
More active option: Walk back from Assisi to Spello on a stretch of the Via di Francesco, about 13 km on tracks and lanes along the lower slopes of Monte Subasio, in time for the cooking evening.
Free time: Lunch and early afternoon free
Activity: Assisi is steep from end to end: about 3 hours on foot on sloping paving. The basilicas ask for covered shoulders and knees and silence inside.
Orvieto, then Florence
Spello to Orvieto, then north on the A1 to Florence
- Breakfast, lunch and dinner
- Stay in Florence
- Drive about 4 h
The longest day in the van: about 300 km and three and three-quarter hours of driving, just under our 4-hour cap and split by a half day in Orvieto.
Morning
We leave Spello at 8 am, pass below Todi and reach Orvieto, built on a cliff-edged plateau of volcanic tufa, when the Duomo opens in the morning. Its facade is covered in gold-ground mosaics and carved marble reliefs of the Bible stories, and inside, the Chapel of San Brizio holds Luca Signorelli's Last Judgement frescoes, painted around 1500. With your guide you walk the medieval lanes to Piazza del Popolo, and there is time to look down the Pozzo di San Patrizio, a 16th-century well with two spiral staircases that never meet.
Afternoon
After lunch together we drive about two and a quarter hours north on the A1 motorway to Florence, arriving in the mid to late afternoon at a central hotel, with time to rest.
Evening
In the early evening your guide walks you past the Duomo and Brunelleschi's dome, through Piazza della Signoria and onto the Ponte Vecchio as the lights come on along the Arno, and we end the trip with a farewell dinner.
Included
- Orvieto with your guide: the Duomo and the Chapel of San Brizio
- Lunch in Orvieto
- Evening walk in Florence: the Duomo, Piazza della Signoria and the Ponte Vecchio
- Farewell dinner in Florence
Optional experiences
- The Pozzo di San Patrizio in Orvieto (paid locally)
Easier option: After the Duomo, wait at a cafe in Piazza del Duomo instead of walking the lanes to Piazza del Popolo, and in Florence skip the evening walk and meet the group at dinner.
Free time: A short rest at the hotel in Florence before the evening walk
Activity: Florence's centre is closed to most traffic, so the van stops at the edge and your bags go on to the hotel; the last few minutes are on foot. The Florence evening walk ends at the restaurant, and the guide walks the group back to the hotel.
David at opening, then home
Florence: the Accademia, then Florence Airport or Santa Maria Novella station
- Breakfast
- Drive about 15 min
Morning
On the last morning we are at the Galleria dell'Accademia for its 8:15 am opening, with timed tickets booked, so you stand in front of Michelangelo's David, carved from a single block of marble between 1501 and 1504, before the queues build along Via Ricasoli. A local guide also shows you his unfinished Prisoners, figures half freed from the stone, which line the hall leading to the statue. By about 10 am we are back at the hotel, and transfers leave from late morning for Florence Airport (FLR), about 20 minutes away, or for Santa Maria Novella station, where fast trains reach Rome in about an hour and a half and Pisa in about an hour. The Accademia is closed on Mondays, so we set departures so that this morning never falls on one. If you want more time in Florence for the Uffizi, the dome climb or the Oltrarno, ask us and we add nights at the same hotel.
Included
- Galleria dell'Accademia at opening with a local guide and timed tickets
- Drop-off at Florence Airport (FLR) or Santa Maria Novella station
Activity: Book a flight from Florence after about 1:30 pm, or from Rome Fiumicino after about 5 pm.
- Florencestart
- Castellina in Chianti3 nights
- Pienza2 nights
- Spello2 nights
- Florence1 night
- Overnight stop
- Day trip
- By boat or train
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
- Women travelling solo who want company, with roommate matching if they ask for it
- Women who want to meet the women who cook, make wine and guide here, not only see the sights
- Travellers who want Tuscany's hill towns and wine country without changing hotel every night
- 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
Not for you if you want
- Mixed groups or couples: the dated small group is for women only (the regular Tuscany and Umbria trip is mixed)
- 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
- 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
- Twin rooms shared with another guest, roommate matching on request, or your own room 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 female 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, women where licensed women guides are available
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 a home-cooking evening with local women hosts (confirmed with your dates), with 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 light welcome supper in Castellina, Monticchiello, the home-cooking evening in 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 1, 2, 4, 7 and 9 and dinners on days 2, 3, 4, 6 and 9 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 1,265 (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?
Eight nights in hotels in Castellina in Chianti, Pienza, Spello and Florence, breakfast daily, 4 lunches and 4 dinners including a home-cooking evening with local women in Spello, a long estate lunch and tastings of Chianti Classico, Brunello, Vino Nobile, pecorino and olive oil, our own minibus and driver, Florence transfers, tourist taxes, your female See Sight Tours guide throughout and every entry in the day plan.
Who can join a women-only trip?
Any woman, travelling alone or with friends; the minimum age is confirmed when you book. The dated small group is for women only, guests and lead guide alike. Drivers, winemakers and some local guides may be men. If you want to travel with a partner, book the regular Tuscany and Umbria trip, which follows the same route.
How big is the group?
The small group runs with 7 to 12 women. That is small enough for one minibus to reach hamlets like Volpaia and Monticchiello, to sit at one table at the wine estate and in the Spello kitchen, and to hear the guide in a crowded Siena street.
Who leads the trip?
A female 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 we ask for women guides where they are available. 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 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'm travelling solo. Do I have to pay a single supplement?
Only if you want a room of your own, which is from CAD 1,265 more, about 17 percent of the price, shown up front. If you would rather share, ask for roommate matching and we pair you with another solo woman on your date where one is booked. If no match is found, we tell you before you pay and you choose.
What should I wear in Tuscany and Umbria as a woman?
Whatever you would wear at home in the street; Italy is relaxed about it. Churches are the exception: Assisi, Siena and Orvieto ask for covered shoulders and knees and do turn people away, so carry a light scarf and wear a skirt or trousers below the knee on those days. Bring shoes with grip for steep stone lanes.
Is Tuscany safe for women travelling without a partner?
Yes, most women find it easy. The small towns on this trip are quiet after dinner. The usual problems are pickpockets in Florence crowds and at stations and occasional comments from men in the cities, which locals ignore. Your guide is with the group every day and walks you back to the hotel after the Florence farewell dinner.
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 7,445 per person sharing, with taxes, and private trips from CAD 13,400. Send your preferred dates as an enquiry. We check availability and provide the final quote, itinerary and booking terms before you accept. No payment is taken when you send the request. 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; you can ask for a female guide. If you would rather travel independently on your own dates, ask us from the dates section and we quote the same hotels, hosts, 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 not yet in force; we tell you if your dates need it.
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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