Walk & Discover: Florence & Tuscany

Arrive at the airport for your flight to Pisa. On arrival we transfer by coach to Florence, where we stay for three nights, with breakfast, at the four-star Grand Hotel Mediterraneo.

Today we discover Oltrarno, a charming and less-explored side of Florence south of the Arno River. We cross the Ponte Vecchio, the landmark bridge over the river, and walk through the medieval quarter of San Niccolò. We are mere minutes away from the old town centre, but San Niccolò’s remarkably preserved 13th-century walls, narrow cobbled lanes and charming yellow-hued buildings are reminiscent of a small Tuscan village. It’s a conducive environment for creative souls, evidenced by the many galleries, artists’ workshops and taverns.

We begin our gentle ascent up the hills, passing elegant villas with olive gardens, and wind our way through a lush park. Before long we reach Piazzale Michelangelo, where we are rewarded with panoramic views of Florence and the rolling hills beyond. After some time to take it all in, we continue along a cypress-lined street to San Miniato al Monte, a splendid church built between the 11th and 13th centuries. At this height, the views are even more spectacular – look out for the Duomo and Palazzo Vecchio.

Our descent takes us through leafy streets to Porta Romana, the best-preserved gate of the city’s ancient walls. From this imposing gate, Via Romana leads straight to the historic centre of Florence. However, we veer off the beaten path to Oltrarno, which literally means ‘across the Arno.’ Locals outnumber tourists and grand buildings give way to more humble homes, making this the perfect place to end today’s walk.

There is plenty to see and do, such as visit the magnificent Pitti Palace and resplendent Boboli Gardens. Or you could return to the old town centre to visit the Uffizi gallery, once a private collection belonging to the Medici family. Botticelli’s Birth of Venus is just one of the countless masterpieces on display. We recommend that you purchase tickets in advance – for details, visit the official Uffizi website.

After breakfast we leave for the delightful city of Lucca, birthplace of composer Puccini. Be sure to visit the ancient cathedral and its venerated wooden crucifix, known as the Holy Face of Lucca. You may wish to wander under your own steam along the city’s medieval ramparts.

Forming a perfect ring around Lucca, the thick walls have been transformed into a tree-lined park, which offers stunning views of the city’s towers and churches on one side and the Apuan Alps on the horizon. It’s an easy walk that’s just 2.5 miles long.

Then we take the short drive to Pisa, whose most famous gems are on display in the Piazza dei Miracoli – the ‘Square of Miracles’. The Leaning Tower, one of the world’s most recognisable silhouettes, is your introduction to the rest. The decoration in the cathedral is breathtakingly detailed and its nave is where Galileo is said to have formulated his pendulum theory. Then there’s the baptistry, a fascinating blend of Romanesque and Gothic architectural styles.

We end the day back at our hotel. Relax or discover more of Florence’s lively restaurants and street cafés, it has an ambience you’ll love any time of the year.

After breakfast we explore the rural Tuscany made famous by Renaissance paintings, literature, films and travel posters – a truly memorable landscape of undulating hillsides, vineyards, ochre-coloured valleys, terracotta-tiled farmhouses and pencil pines. The Chianti region is renowned as the symbol of Tuscany and one of the best ways to get a taste of it is on a walk. Today you have a choice between a Green or a Blue walk.

We begin in medieval Greve, a jewel of Chianti and birthplace of explorer Giovanni da Verrazzano, who discovered the Hudson Bay in New York. The main square’s elegant palaces are reminders of the town’s illustrious past and today house restaurants, bars and food shops. Leaving Greve behind, we find ourselves almost immediately immersed in Chianti’s gorgeous landscape.

We follow cypress-shaded country roads, which wind through hypnotic rows of vineyards and silvery olive groves set against gently undulating hills so typical of Tuscany. Along the way we see Monte San Michele, the highest mountain in Chianti, often covered with snow in winter.

The Blue walk follows a similar route to the Green walk but continues further through the Tuscan hills, giving us more time to enjoy the atmosphere and unforgettable views.

Later we drive to the four-star Hotel Il Piccolo Castello, where we stay for the next four nights, with breakfast and dinner. Situated in its own grounds close to the walled hilltop town of Monteriggioni, the hotel provides a relaxing base from which to explore. It has a spacious lounge, bar and restaurant serving authentic Tuscan food.

After breakfast we take the short drive to glorious Siena for an enriching guided tour of its treasures. Not only was it the capital of the Republic of Siena during the 12th and 13th centuries, but it was also one of the richest cities in the world. It’s a jewel of Italian Gothic and medieval architecture that’s been preserved to a remarkable degree and is justifiably a UNESCO World Heritage site.

The city centres on the main square, the Piazza del Campo, an architectural work of art. Formed in a half-moon shape, it’s lined by tall, striking buildings whose gracious and varied facades have a unique charm. With its abundance of pavement cafés, it’s the perfect place to sit and enjoy a glass of wine or a coffee and reflect on the city’s sheer beauty.

Siena is equally famous for the Duomo, one of Italy’s most intricate and fascinating cathedrals. The exterior is built from black and white marble, and the west facade offers a particularly fine example of workmanship. The interior is even more breathtaking, with splendid stained-glass windows and paintings and sculptures by leading artists, including the young Michelangelo.

Impressive as it is today, in the 14th century the Duomo was set to become the largest church in Christendom had plans for an additional nave gone ahead. The Black Death put paid to its construction, though, as two-thirds of the population perished, and the city fell into rapid decline. Little was built thereafter but even less was demolished, leaving a wonderfully preserved city for us to appreciate today.

The afternoon is then yours to shop, people-watch or further explore before returning to your hotel for dinner.

During today’s walks, you’ll discover the enchanting area around picturesque San Gimignano. You have a choice of a Green or a Blue walk.

The Green walk follows part of the ancient Via Francigena pilgrim route, which in medieval times connected Canterbury to Rome. The picture-postcard sights of sand-coloured stone buildings, vine-clad hills and vibrant flowers will delight as we ramble our way to San Gimignano.

The longer walk takes us around San Gimignano, with the impressive skyline of its towers in front of us. We hug the ridges of the gentle Tuscan hills, pausing to admire the spectacular views. The colours you’ve seen in countless oil paintings come alive in the golden fields of barley, oat and ancient wheat, and in the green of the woods, olive groves and vineyards.

We reconvene in San Gimignano, where you may wish to stop by the award-winning Dondoli gelateria to reward yourself with a scoop or two of its mouth-watering flavours.

Today you have a free day to do as you please. Just a few miles away are two utterly charming hilltop settlements, Monteriggioni and Colle Val d'Elsa. Lovers of literature may recall Monteriggioni in the Divine Comedy, the chef-d'œuvre of Tuscan poet, Dante Alighieri, who compared the ring of giants surrounding the abyss to the town’s monumental towers.

There are plenty of boutiques to browse, as well as a 13th-century church that wouldn’t look out of place in a film set in the Middle Ages! The sleepy village of Colle Val d’Elsa is best-known as the birthplace of sculptor and architect, Arnolfo di Cambio, whose tremendous works of art include the Palazzo Vecchio and the old basilica of the Duomo in Florence, and funerary monuments for several popes and cardinals.

Both hilltop gems can be reached by local bus, but if you’re feeling energetic, you can wander along pleasant walking paths from the hotel. Should you prefer to stay in, why not catch up on some reading by the hotel pool or take a stroll through its enchanting Italian garden.