Quick Facts

Date
Monday, 18 December 2023 — Day 8 of 14
Tour
Full-day guided coach tour from Florence, around 12 hours door to door
Region
Tuscany, Italy
Covers
Siena, Poggio ai Laghi winery, San Gimignano, Pisa
Good for
A long but easy day — most of it is coach travel, not walking

A Day Through Tuscany

We joined a full-day tour to explore Tuscany, setting off from Florence in the morning under clear blue skies. The coach ran about twelve hours door to door, with Siena, a winery, San Gimignano and Pisa all in one loop.

As the city slowly gave way to open countryside, the landscape changed into rolling hills, vineyards, and quiet roads. The sunlight felt softer here, and everything seemed to move at a slower pace.

Siena – A City That Holds Its Past

Our first stop was Siena, a medieval city that feels almost untouched by time. It has kept most of its original street plan, and its historic centre is built on the same hills it was founded on in the Middle Ages.

We walked into Piazza del Campo, a wide, shell-shaped square built in the 13th and 14th centuries, where the famous Palio horse race takes place twice a year. Twice a year, in July and August, ten of the city's seventeen historic contrade race bareback horses around the square's edge, in a race that lasts less than 90 seconds but carries centuries of rivalry behind it. Standing there, it was easy to imagine the crowds, the energy, and the traditions that continue today.

Siena's Palazzo Pubblico and Torre del Mangia bell tower The Palazzo Pubblico and the Torre del Mangia, rising over the square.
A tour group gathered in a Siena square beside a statue, a tall Christmas tree and a bank building with the Monte dei Paschi sign The tour gathers in a neighbouring square, by the Monte dei Paschi building.

The tall Torre del Mangia rises 87 metres over the square. It was completed in 1348 and, according to local legend, is named after its first bell-ringer, nicknamed "Mangiaguadagni" (roughly "eat the profits") for spending his wages on food rather than work. Nearby, Siena Cathedral surprised us the most. Inside, the black-and-white striped marble columns and intricate ceilings made every corner feel detailed and intentional: quiet, but impressive in its own way.

Siena Cathedral's black-and-white striped marble interior
Inside Siena Cathedral: black-and-white striped marble columns and carved ceilings.

A Pause at the Vineyard

Next, we stopped at a local winery, Poggio ai Laghi, surrounded by vineyards stretching under the Tuscan sun.

Before lunch, we joined a short wine tasting where we were shown how to taste properly: observing the colour, gently swirling the glass, and slowly sipping to notice the different notes. It made the experience feel more thoughtful, less about drinking and more about understanding what was in the glass.

Lunch was simple but memorable: fresh pasta paired with the wines we had just learned about. Each one had its own character, shaped by the land and the seasons.

Meanwhile, our daughter sat beside me, gently reminding me not to drink too much and half-serious that I might get tipsy. It became a small running joke at the table, one of those moments that made the day feel more personal.

We also met a mother and daughter from South Korea on the tour. As the day went on, we started helping each other take photos, small interactions that turned strangers into familiar faces, even if just for a day.

A four-glass wine tasting flight beside a board of bread, cured meats and cheese
A four-glass tasting flight, with bread, cured meats and cheese.
Wine glasses and a charcuterie board at the winery tasting Local wines and a charcuterie board, served with the tasting.
The winery shop, shelves of local wines and gift baskets tied with red ribbon The winery shop, with local wines and gift baskets.
Family Travel Tip

Most Tuscany day tours build in a winery stop like this one. Ask in advance about a kid-friendly option at the tasting. Ours simply skipped pouring for our daughter and let her sit in on lunch, which worked well and meant nobody felt left out.

San Gimignano – The Town of Towers

In the afternoon we arrived at San Gimignano, often called the Town of Fine Towers. At its medieval peak it had around 72 of them, built by rival noble families as both a status symbol and, during feuds, a place to retreat into. Fourteen survive today, enough to define the skyline. The town has been a UNESCO World Heritage Site since 1990.

We wandered through the stone streets, stopped for gelato at Gelateria Dondoli, a shop that has won world gelato championships, and simply enjoyed the atmosphere.

Walking through the Porta San Giovanni gate into San Gimignano's walled old town Through Porta San Giovanni, into the walled old town.
A view over the Tuscan countryside from San Gimignano's walls The countryside, seen from the walls.
San Gimignano's medieval fortress walls
The medieval walls, their stone worn smooth over centuries.
A girl eating gelato outside Gelateria Dondoli in San Gimignano Gelato from Gelateria Dondoli, said to be among the best in the world.
A Christmas tree in the square in front of San Gimignano's Duomo, with a visitor beside it A Christmas tree in front of the Duomo.

As we left San Gimignano, the journey continued through the Tuscan countryside.

From the bus window the scenery slowly unfolded: rolling hills, scattered farmhouses, and long stretches of vineyards glowing under the soft light. Tuscany has a kind of beauty that doesn't try too hard. Morning, afternoon, or evening, it feels different each time, and always just as beautiful.

Pisa – Seeing It for Real

Our final stop was Pisa, reached as the light began to fade.

Standing in front of the Leaning Tower of Pisa, I had a strange but familiar feeling. We have all seen it countless times in photos, but seeing it in real life felt completely different: more real, more detailed, and somehow more impressive. The tower leans because its foundation sits on soft, unstable ground. Construction began in 1173 and took almost two centuries, and builders compensated for the lean floor by floor, which is why the tower has a slight banana curve. Around it, the cathedral and baptistery completed the scene as the sky slowly turned to evening.

We took our last photos of the day there, holding onto the moment a little longer before heading back.

A woman in a dark jacket looking up at the Leaning Tower of Pisa at night, the tower lit against the sky The Leaning Tower at night, lit against the dark sky.
Family selfie in front of the Pisa Baptistery at dusk A family selfie in front of the Baptistery at dusk.
The Piazza dei Miracoli lit up after dark, the Leaning Tower and cathedral glowing
The Piazza dei Miracoli, lit up after dark.
A Baroque cherub statue in Pisa's old town at night
A Baroque cherub in the old town, seen at night.

A Day to Remember

It was a long day, but one that never felt heavy.

The sunlight, the views, the places, and the people we met along the way all came together naturally. Tuscany felt calm yet full of life: quiet landscapes, rich history, and simple moments in between. It is one of the most beautiful regions we have seen, and a reminder that Italy holds many different kinds of beauty, each in its own way.