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Handpicked experience · Florence

Highlights of Tuscany with Lunch in a Chianti Winery

Florence, Italy

12 HoursDurationFlorenceLocationShow Mobile Voucher or PrintedConfirmationJoin-in GroupTypeEnglish, SpanishGuide

What you do

Four Tuscan towns in one day, including a cathedral that was never finished because the plague arrived, and the rooster legend that decided where Chianti begins.

Highlights

  1. 01

    See the fields of vineyards and wineries that will definitely make a wine lover's heart throb.

  2. 02

    Visit the beautiful town of Siena and walk down ancient streets.

  3. 03

    At the Pisa Cathedral is where you'll also find the famous Leaning Tower.

  4. 04

    The Leaning Tower of Pisa was constructed for more that 200 years.

  5. 05

    A guided walk through Siena with commentary

  6. 06

    Photo stops and wide views across the Tuscan countryside and towards San Gimignano

  7. 07

    A traditional Tuscan lunch with wines at a Chianti estate

  8. 08

    Pisa's principal monuments, as time allows

  9. 09

    A professional guide working in English and Spanish throughout

Stops · 7

SienaOn the route
San GimignanoOn the route
ChiantiOn the route
Chianti wineryOn the route
PisaOn the route
Tuscan countrysideOn the route
FlorenceOn the route

Overview

This is a highlights day across Tuscany in the literal sense: four places in twelve hours, joined by a good deal of road. Each stop has one thing that genuinely earns the stop, and this describes what those things are.

It is a sampler, and the last stop may go

Said first because it is the commonest complaint. Something over five hours of this day is spent in the vehicle, and lunch takes another substantial slice. That leaves roughly an hour in the first town, less in the second, and whatever remains at the end. The final stop is offered subject to time, which means it is the one cut when the day runs late. If it is the reason you booked, choose a different itinerary.

Siena's cathedral was never finished

The best thing in the first town, and most people walk past it. In the 1330s Siena set about turning its cathedral into the largest church in Christendom, the existing building becoming a mere transept of something enormous. Then the plague arrived in 1348 and killed between half and two-thirds of the city. Work stopped and never resumed. The wall of the intended nave still stands, its window openings framing nothing but sky, and you can climb it. Standing on top of an unbuilt cathedral is a strange and specific experience.

The square is a written constitution

Look down, not up. The great sloping shell-shaped piazza is paved in brick divided by nine strips of stone, and those nine are not decorative: they stand for the Nine, the merchant council that governed the city for most of a century and laid the square out. A committee wrote its own membership into the floor.

The horse can win without the rider

That square is a racecourse twice each summer. Earth is laid over the paving, seventeen city wards compete on ten horses, and the race lasts about ninety seconds. The rules are older than those of most sports and stranger: jockeys ride bareback, almost anything is permitted between riders, and a horse finishing first wins even if it threw its rider on the way round. The wards are not clubs — each has its own church, museum, fountain and flag, and you are born into one.

The towers were a competition the council had to stop

In the second town, families built stone towers against each other as pure display of standing, and there were once more than seventy. Fourteen survive. The escalation ended only when the commune legislated that no private tower could rise above the one on the town hall, the medieval equivalent of a planning rule aimed squarely at showing off.

And they were paid for by saffron

Not by wine, which surprises people. The wealth came from crocus fields around the town, whose saffron was traded across Europe as currency, dye and medicine. When plague and shifting trade routes broke that market, the town stopped growing and stayed as it was, which is precisely why it looks the way it does now.

Why there is a black rooster on the bottle

The story behind the label you will meet at the winery. Florence and Siena, tired of fighting over the boundary between them, agreed to settle it by sending a rider from each city at first cockcrow, the border fixed wherever they met. Florence chose a black rooster and starved it, so it crowed well before dawn and its rider set off in darkness. They met almost at the walls of Siena. Whether or not it happened, the bird is on every bottle of Chianti from the historic zone, whose boundaries have been legally defined since a Medici edict of 1716.

What is not covered

Admission is separate everywhere, which matters most at the first stop, where the cathedral and the climb both charge. Carry cash.

Choose your option

Open it to pick a date and work out the price.

Options are being loaded — the desk can quote you directly in the meantime.

What's included

What the fare covers, and what to budget for separately.

IncludedIn the fare
  • ✓An English and Spanish-speaking guide
  • ✓The guided walking tour of Siena
  • ✓A traditional Tuscan lunch served with wines from the region
Not IncludedBudget separately
  • —An audio guide
  • —Admission to any attraction
  • —Other personal spending
  • —Tips and gratuities

Good to know

The practical detail, and the answers people actually ask for.

Practical

  • Duration12 Hours
  • PickupNo Pickup
  • TypeJoin-in Group
  • GuideEnglish, Spanish
  • VoucherShow Mobile Voucher or Printed
  • CancellationFree cancellation up to 24 Hours before

Frequently asked

Do we definitely visit all four places?

Not necessarily. The final stop is offered subject to time, which makes it the one dropped when the day runs late. If it is your main reason for booking, choose a different itinerary.

How much of the day is driving?

Something over five hours across the four towns and the return, with lunch taking another substantial slice. That leaves roughly an hour in the first town and less in each of the others.

Why is Siena's cathedral unfinished?

Because the plague arrived in 1348, in the middle of a project to turn the existing church into the transept of the largest cathedral in Christendom. It killed between half and two-thirds of the city, work stopped, and the wall of the intended nave still stands with its windows opening onto sky.

What do the stone strips in the square mean?

They divide the brick into nine segments for the Nine, the merchant council that governed Siena for most of a century and laid the square out. The government wrote its own membership into the paving.

Can a horse win the Palio without its rider?

Yes. Jockeys ride bareback, the race lasts about ninety seconds, and a horse that crosses first still wins having thrown its rider on the way. The competing wards are not clubs; each has its own church, museum and flag, and you are born into one.

Why are there so few towers left?

There were once more than seventy and fourteen survive. They were built by families competing for standing, and the escalation only stopped when the commune forbade any private tower from rising above the one on the town hall.

What is the black rooster on the wine?

A legend about fixing the border between Florence and Siena by sending riders at first cockcrow. Florence starved a black rooster so it crowed early, and its rider got almost to Siena. The historic zone has had legally defined boundaries since a Medici edict of 1716.

From · per personOn request