Florence, Italy · Siena, San Gimignano, Chianti & beyond
Tuscany Tours from Florence
Medieval towers, cypress roads, a long lunch among the vines: the hill towns
of Tuscany are an hour from Florence. Here are the best-rated ways to see them in a
day, compared honestly.
Independent guideNot a tour operator; we compare so you book the right day out
~70 kmFlorence to Siena
4 stopsSiena, Chianti, San Gimignano, Pisa
14 towersStill standing in San Gimignano
€20Leaning Tower climb, official
~75 minSiena by bus, if you go alone
Sep-OctHarvest season, softest light
Tours & Tickets
Choose your Tuscany tour from Florence
Booked through Viator: instant confirmation, mobile voucher and free
cancellation up to 24 hours before departure. Ratings are Viator & Tripadvisor figures as of September 2026.
Small group10 hours
Small-Group Siena & San Gimignano with Winery Lunch
★ 4.9(1,848 reviews on Viator & Tripadvisor)
Instant confirmationMobile ticketFree cancellation to 24h
Two hill towns at a gentler pace, in a minivan or minibus of up to 25 rather than a full coach: a guided walk in Siena, a sit-down lunch of seasonal Tuscan dishes and red wines at a family winery, then free time in San Gimignano. Back in Florence around 6 PM.
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Small group, max. 25, minivan or minibus with Wi-Fi
Guided walk of Siena + free time
Winery visit and lunch paired with local red wines
Free time in San Gimignano; Monteriggioni walls on the way
Optional Siena Cathedral visit with a guide (€15, not on Sundays)
Tuscany Day Trip: Siena, San Gimignano, Pisa & Winery Lunch
★ 4.9(24,087 reviews on Viator & Tripadvisor)
Instant confirmationMobile ticketFree cancellation to 24h
The classic one-day sweep of Tuscany from Florence: a guided walk through Siena and its cathedral, a farmhouse lunch with wine tasting in the Chianti hills, free time among the towers of San Gimignano, and Pisa’s Field of Miracles at the end of the day.
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Coach from Florence + English-speaking guide all day
Guided walking tour of Siena with a local city guide
Farmhouse lunch with 4 wine tastings (lunch options)
Val d’Orcia Day Trip: Montalcino, Pienza & Montepulciano
★ 4.7(1,521 reviews on Viator & Tripadvisor)
Instant confirmationMobile ticketFree cancellation to 24h
The postcard Tuscany of cypress roads and rolling hills, south of Siena: a Brunello tasting in a Montalcino cellar, pecorino and Renaissance streets in Pienza, a stop at the Vitaleta chapel and a Vino Nobile tasting with cheese in Montepulciano.
How the best-selling day trip from Florence runs. Timings are typical; the order can change with traffic and opening hours.
1Leave Florence
Meet by Santa Maria Novella station and roll south through the Chianti hills. Your guide sets up the day on board.
7:45 AM
2Siena on foot
A local guide walks you through the contrade to the shell-shaped Piazza del Campo and the striped Duomo, then free time for a coffee.
~2 hours
3Lunch among the vines
A working Chianti farm: a stroll through vineyard, olive grove and cellar, then a long Tuscan lunch with four wines.
~2 hours
4San Gimignano
The medieval Manhattan: 14 stone towers, cobbled squares and the gelato everyone talks about, at your own pace.
~1.5 hours
5Pisa at golden hour
The Field of Miracles: cathedral, baptistery and the Leaning Tower, climbable with the upgrade. Back in Florence in the evening.
~1 hour
Piazza del Campo, SienaA long lunch in the Chianti hillsThe towers of San GimignanoPisa’s Field of Miracles
Plan Your Trip
Plan your Tuscany day from Florence
Getting out of the city, choosing a tour style, timings and what to pack - one tab each.
On a tour: coaches and minibuses leave from beside Santa Maria Novella station (SMN) or the Piazzale Montelungo bus terminal, a 5 to 10 minute walk away; private tours collect you at your hotel.
Siena by bus: Autolinee Toscane route 131R takes about 65 to 75 minutes and stops at Piazza Gramsci, a short level walk from the Campo. The train takes about 90 minutes and arrives below the walls.
Pisa by train: regional trains from SMN take about 50 to 80 minutes; the tower is a 20-minute walk from Pisa Centrale.
San Gimignano: train to Poggibonsi, then bus 130 or 133 up the hill, 1.5 to 2 hours in total. More in Tuscany without a car.
Coach tours (up to 40 to 50 people): the cheapest way to see the most, from about $76 to $107 with tastings.
Small groups (up to 25): quicker on and off, more time in the towns and a proper sit-down lunch; from about $174.
Private tours (up to 8): door-to-door pickup and your own pace; from about $460 per booking.
Wine-first tours: half-day Chianti tastings from about $104, or a full wine safari with lunch; see the Chianti guide.
Most full-day tours leave between 7:45 and 8:45 AM and are back in Florence between 6 PM and 8 PM.
Do not book an onward train out of Florence before 9 PM on a tour day; traffic back into the city can be slow.
Siena Cathedral closes to visitors during services, and some tours skip the interior on Sundays.
Summer afternoons in the hill towns are hot: the morning stop (usually Siena) is the most comfortable.
Comfortable shoes: reviewers count about 20,000 steps, many of them uphill on cobbles.
Covered shoulders and knees for the cathedrals in Siena and Pisa.
Water, a hat and sunscreen from May to September; a light rain layer in spring and autumn.
A photo ID, and some cash for gelato, cathedral entry or shipping wine home.
Worth knowing about along the way
€20Leaning Tower climb251 steps, timed tickets · minimum age 8, book ahead or take the tour upgrade
€5-8Siena CathedralWalk-in ticket, €8 while the marble floor is uncovered (27 Jun to 31 Jul, 18 Aug to 15 Nov 2026) · some tours sell a guided visit for more
2 Jul & 16 AugPalio di SienaThe bareback horse race round Piazza del Campo · huge crowds, book early
Sep-OctGrape harvestVendemmia in the Chianti hills · the busiest, most beautiful weeks at the wineries
FreeMonteriggioni wallsA tiny walled village built from 1213 on the Via Francigena, on several tour routes
UNESCOVal d’OrciaWorld Heritage landscape since 2004 · Pienza, Montalcino and the cypress roads
Where Tours Start
Tuscany tour meeting points in Florence
Next to Santa Maria Novella station
Piazza della Stazione 27, 50123 Firenze
The classic day trip checks in at 7:45 AM by the taxi stand outside Santa Maria
Novella station, where the guide holds a Walkabout Tours sign. Several other group
tours, including the small-group and Val d’Orcia days, meet at the Piazzale
Montelungo bus terminal, 5 to 10 minutes’ walk north of the station. Your
voucher always names the exact spot.
Arrive 15 minutes early; late arrivals are not refunded
Tuscany from Florence - everything else worth knowing
When to go, the small things reviewers wish they had known, where else to head, and the cancellation fine print.
April to June: green hills, poppies in May, long days and pleasant walking weather.
July and August: hot (often above 35°C) and the busiest time; the Palio fills Siena on 2 July and 16 August, and many local businesses close around 15 August.
September and October: the sweet spot - the grape harvest, golden fields and softer crowds.
November to March: quiet and cheap, with shorter days; some wineries and farm restaurants close, so check what a tour includes.
Pick a tour with lunch included: reviewers call the farmhouse lunch the highlight, and it is cheaper than eating in the towns.
An hour in San Gimignano feels short to many people. If that is your favourite town, choose a small-group tour or go on your own.
Want to climb the Leaning Tower? Book the tour option with tower tickets; children under 8 are not allowed up.
Wineries ship bottles home; ask before you carry six bottles round Pisa.
Driving yourself? Historic centres are ZTL zones with camera fines; park outside the walls.
Val d’Orcia - the cypress-and-hills postcard, with Pienza, Montalcino and Montepulciano: our guide.
Chianti wine country - between Florence and Siena, half a day is enough: wine tours compared.
Lucca - Renaissance walls you can cycle round, often paired with Pisa.
Cinque Terre - five cliff villages on the coast of Liguria, about 2.5 hours away: see the coast option.
Volterra and Cortona - quieter Etruscan hill towns, best with a car or a private driver.
The Viator tours on this page cancel free up to 24 hours before departure, with instant confirmation and mobile vouchers.
Book-now-pay-later is offered on most listings at checkout.
Tours run in all weather; rain is not a reason for a refund, so check the forecast before the 24-hour cut-off.
Missing the check-in time usually means no refund and no reschedule; allow for queues at the station.
The hills south of Florence have been painted for 600 years. Go and see the originals.
4.9★★★★★24,087 reviews Classic Tuscany day trip · Viator & Tripadvisor, September 2026
5 ★89%
4 ★8%
3 ★2%
2 ★<1%
1 ★<1%
★★★★★
This was a lovely tour. Adela was our guide and she was so fun and knowledgeable! You will see Siena, have lunch and a wine tasting on a Tuscan hillside, and visit San Gimignano and Pisa. A small warning: this tour is not recommended for those with mobility issues. You will walk about 20,000 steps and many of them are uphill!
★★★★★
My husband and I aren’t typically “tour” people, but this tour was a fantastic way to experience a lot of Tuscany in a relatively short amount of time. It is definitely a get-on-a-tour-bus type of experience, so it’s good to know that going in. Mano was our guide, and he was incredibly knowledgeable, kind, and funny.
★★★★★
We thoroughly enjoyed our tour. Miri was an excellent guide, and Ali an excellent driver. We received interesting information about each place, and Tuscany in general. We covered a lot of ground, and enjoyed each of our stops, and beautiful winery lunch.
★★★★★
It’s three visits to three very cool places, but there is an hour drive in between which could make it very hectic. Lea our tour guide was very knowledgeable, and very good about keeping us on track. If you want to spend any time in any of the places, you actually don’t have a lot of time.
★★★★★
Our tour guide David was great. He was informative and kept the group engaged. Everything was planned well. A lot of walking but it was good. The wine tasting and lunch was great and a break from the hectic tour.
★★★★★
Be prepared to walk... a lot, but it’s worth it. They organized it so Pisa would be last and the sun would shine on the buildings. The food was great. If you are expecting a lot of time at each location, you should consider just taking separate day trips from Florence to each location.
All quotes are from verified Viator bookings of the classic day trip, lightly trimmed and shown with the reviewer’s own star rating. Rating and breakdown as shown on Viator & Tripadvisor in September 2026.
Prefer the Sea?
The Cinque Terre also works as a day from Florence
Strictly speaking it is in Liguria, not Tuscany, but the five cliff villages are
Florence’s other great day trip - and a coach saves a complicated train connection.
Cinque Terre Day Trip from Florence (Hike or Pisa)
★ 4.8 (8,929 reviews) · 13 hours · from $58
The coast instead of the hills: a coach from Florence to the Cinque Terre national park, time in Vernazza, Monterosso and Riomaggiore, an optional cliff-path hike or boat ride (April to October), and an optional stop at the Leaning Tower on the way home.
Same operator as the classic day tripMinimum age 8
Florence is not next to Tuscany, it is the heart of it: the regional
capital sits an hour from Siena, San Gimignano and the Chianti vineyards. The
question is not whether to get out into the hills but how - on a coach, in a small
group, with a private driver or by bus and train - and how much of the day you want
to spend on the road. Here is the honest version.
What a day tour actually covers
The classic loop links four very different places. Siena is the great Gothic rival
of Florence, built round the sloping, shell-shaped Piazza del Campo where the Palio
is run twice a year. Between Siena and Florence lie the Chianti hills, where the
black-rooster Chianti Classico is made and where most tours stop for a farm lunch.
San Gimignano, on its hill to the west, kept 14 of its medieval tower houses and
looks it. Pisa, an hour further on, adds the Leaning Tower and the white marble
Field of Miracles. Further south, the Val d’Orcia - Pienza, Montalcino,
Montepulciano - is the rolling, cypress-lined landscape on every calendar, a
UNESCO World Heritage site since 2004 and a separate day.
The Chianti hills between Florence and Siena: most day tours stop here for lunch and a tasting.
Tour or DIY: the honest math
On your own, Siena is easy: the 131R bus takes about 75 minutes and costs under
€10 each way, and Pisa is about an hour by regional train for around €9.
One town per day works well that way. What public transport cannot do is link the
hill towns and a winery in one day: San Gimignano alone takes a train and a bus, 1.5
to 2 hours each way, and farm estates have no buses at all. That is the gap the
tours fill. The classic day trip from about $100 covers the
coach, a guide, a Siena walking tour and the four-stop route, with a farm lunch and
wine on the lunch options; the budget version from about $76 drops the lunch and
Pisa. Against DIY fares of about €20 return for a single town, the premium
buys three extra places and zero logistics. A rental car is the other answer, but
the historic centres are camera-enforced ZTL zones, and whoever drives cannot join
the tasting.
The one thing reviewers warn about: these are walking days.
Expect around 20,000 steps, a lot of it uphill on cobbles, and not much time to rest.
If anyone in your group has limited mobility, a private tour with door-to-door
transport is the kinder choice.
Which tour for which traveller
First time in Italy and one free day: take the classic
four-stop day and accept that it is a highlights reel. Hate crowds or want a
proper lunch: the small-group Siena and San Gimignano day
drops Pisa and gains time. Photographers and anyone who has seen the pictures: the
Val d’Orcia trip. Wine first, towns second: a
Chianti wine tour. Families with young children:
note that the Leaning Tower does not admit under-8s, and a private driver makes
naps possible.
The Val d’Orcia, south of Siena: the Tuscany of postcards is a separate, longer day.
When to come
April to June and September to October are the best months: warm days, cool
evenings, and in autumn the vendemmia, the grape harvest. July and August are hot and
crowded, and the Palio on 2 July and 16 August packs Siena solid. Winter tours run
with fewer people, but some farm restaurants close and it is dark by 5 PM.
Making a day of it
Book the tour for your first free day in Florence rather than your last, so a
weather change leaves room to move it within the 24-hour free cancellation. Eat a
proper breakfast, since lunch comes after Siena. Do not plan an onward train that
evening. And if one day leaves you wanting more, that is the point: the
3 and 5-day itineraries show how to come back
and stay.
Montepulciano’s steep main street: hill towns reward slow walking and comfortable shoes.
For a first visit, the classic full-day loop of Siena, San Gimignano, a Chianti winery lunch and Pisa is the most-booked Tuscany tour from Florence, rated 4.9 from over 24,000 reviews. Prefer fewer stops and a smaller group? The small-group Siena and San Gimignano day with a winery lunch is calmer. For the rolling-hills postcard, pick the Val d’Orcia day trip; for wine first, a Chianti wine tour.
Is a day trip to Tuscany from Florence worth it?
Yes. Florence is the capital of Tuscany, and Siena, San Gimignano and the Chianti hills are all within about an hour by road. A day tour removes the hardest part - hill towns are awkward by public transport and the historic centres are closed to traffic - and fits three or four places into one day. The trade-off is time: expect about an hour in each town. If you want to linger, see the 3 and 5-day itineraries.
How many days do you need for Florence and Tuscany?
Plan at least 3 full days in Florence itself, then 1 day trip for the highlights or 2 to 3 nights in the countryside to slow down. Five days total works well: three in Florence, one on a day tour to Siena and San Gimignano, one in the Val d’Orcia or Chianti. A week lets you base yourself in a farmhouse and explore by car.
How can I travel from Florence to the Tuscan countryside without a car?
The bus is the best DIY option to Siena (about 75 minutes, dropping you near the centre), and regional trains run to Pisa (about an hour) and Lucca. San Gimignano takes a train to Poggibonsi plus a local bus, about 1.5 to 2 hours. Wineries and Val d’Orcia villages are hard without wheels, which is why most visitors use a tour. Full routes: Tuscany without a car.
What is the prettiest town in Tuscany?
San Gimignano, with 14 medieval towers still standing, is the one most people picture. Pienza and Montepulciano in the Val d’Orcia win for views, and Siena’s shell-shaped Piazza del Campo is the most beautiful square in the region. The classic day tour covers Siena and San Gimignano; the Val d’Orcia trip covers Pienza, Montepulciano and Montalcino.
Can you do a day trip from Florence to San Gimignano?
Yes, easily. It is about 60 km away, just over an hour by car. On your own it is a train to Poggibonsi and bus 130 or 133 up the hill, 1.5 to 2 hours each way and about €10.50. Most Siena day tours include San Gimignano with 1 to 1.5 hours of free time. Details in our Siena and San Gimignano guide.
Is it better to stay in Florence or Siena?
For a first trip, stay in Florence: it has the art, the fast trains and the departure point for nearly every tour. Siena is smaller, quieter and more medieval, and a good base for the Chianti and Val d’Orcia by car. Many travellers split the stay: Florence first, then two or three nights in Siena or a countryside agriturismo.
What is the best time to visit Tuscany?
April to June and September to October: mild weather, green or golden hills, and the grape harvest from mid-September. July and August are hot (often above 35°C) and busy, and around 15 August many local businesses close. Winter is quiet and cheap but some wineries close and days are short. Siena’s Palio horse race runs on 2 July and 16 August.
Is Tuscany closer to Rome or Florence?
Florence is in Tuscany: it is the regional capital, so the hill towns are an hour away. Rome is in Lazio, about 1.5 hours from Florence by high-speed train. Southern Tuscany (Val d’Orcia, Montepulciano) sits roughly halfway and is reachable from Rome too, but Florence is the natural base for tours.
How far apart are Florence and Pisa?
About 85 km. Regional trains from Santa Maria Novella take roughly 50 to 80 minutes and cost around €9; Pisa Centrale is a 20-minute walk from the Leaning Tower. The classic Tuscany tour ends in Pisa, and a half-day Pisa trip runs from about $45.
Can I use Uber in Tuscany?
Only in a limited way. In Florence the Uber app mainly books licensed taxis, and in the countryside there is no ride-hailing at all. For hill towns and wineries, book a tour, a private driver or a rental car, and remember that historic centres are restricted traffic zones (ZTL) with automatic fines.
Is Tuscany expensive to visit?
It is mid-priced for Western Europe. Group day tours from Florence start around $45 for Pisa and $76 to $107 for a full day with tastings; lunch with wine at a farm is often included. DIY public transport costs about €20 return per town. Entry fees are modest: €20 to climb the Leaning Tower, €5 to €8 for Siena Cathedral at the ticket office.
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Instant confirmation and free cancellation up to 24 hours before
departure on the tours below. Summer and harvest dates fill first.
Small group10 hours
