Tour Overview

Tuscany embodies the very essence of Italy - centuries of heritage, exquisite art and architecture, beautiful scenery, an enviable climate, great food and wine - and so much more. Florence, together with lesser-known gems such as Lucca and San Gimignano, offer perfectly preserved architecture and artistic treasures.

Arguably the finest city of the Renaissance, Florence owes its great riches to the commercial boom that emerged after the Dark Ages. Political power at the time was in the hands of just a few families, in particular the Medicis, who married into most European royal families, including our own. Architects, artists and sculptors flocked to the city to be engaged by nouveau riche patrons. Gradually grand residences, churches and palaces were filled to bursting point with magnificent works of art.

You'll also experience extraordinary San Gimignano, a superbly preserved enclave famous for its immense stone towers and dramatic skyline. Siena is another wonderful Tuscan city on our tour, guarded behind impressive walls. At its heart is Piazza del Campo, one of Europe's most attractive squares.

Then there's Lucca, one of Italy's most graceful towns, with a historic quarter nestling inside outstandingly preserved Renaissance walls. To the south of Lucca is Pisa, a city famed around the world for a tower that seems to defy gravity, yet it has so much more to offer. Wander a little way from the Square of Miracles and you discover the city's maze of tiny streets and intimate piazzas.

The Tuscan countryside really is picture-postcard Italy and a rambler's dream. Gently undulating biscuit-coloured hills often covered with vineyards flow and disappear into the distance, inviting further discovery. Punctuated by isolated farmhouses, unchanged for centuries, and studded by tall cypress trees, this beautiful landscape yields a rich harvest of food and wine.

The local cuisine is simple and uses the finest local ingredients. Thick soups, grilled meats, fresh vegetables, pecorino cheese, olive oil, garlic and herbs are all part of the typical Tuscan table. To complement the food, Tuscany also produces some of Italy's best-known wines, such as Brunello di Montalcino, Vin Santo and, of course, Chianti.

Embodying the excitement and romance of Italy, Tuscany is stylish, justifiably proud of its heritage, vibrant, expressive-?¦ and absolutely unforgettable.


Discover a less-visited ‘other side’ of Florence on an urban trek with a local guide Explore the breathtaking Tuscan countryside on a guided walk through the renowned wine region of Chianti Savour the spectacular scenery around the hilltop village of San Gimignano on a guided walk See Pisa’s incredible Leaning Tower and explore the medieval walled city of Lucca Marvel at the medieval splendour of Siena on a tour led by a local guide Return flights from a selection of regional airports, plus hotel transfers Seven nights in four-star accommodation, inclusive of all local taxes, with breakfast and four dinners The services of our experienced and insightful tour manager throughout A specialist guide to accompany you on all walks Selected departures in September and October 2019

Places You'll See



Day 1
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. Access into the city centre couldn’t be easier, as the hotel enjoys an enviable position on the banks of the Arno River, close to Piazza Santa Croce. All rooms have air-conditioning, Wi-Fi, satellite television, safe and hairdryer. The hotel has a choice of international and Italian cuisine plus a lounge and American bar.

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. Duration: 3 hours (4.1 miles) Altitude gain: 349 feet Terrain: urban

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 an easy or a moderate walk. Easy walk Duration: 2 hours (3.1 miles) Altitude gain: 472 feet Terrain: country roads Moderate walk Duration: 3 hours (5.2 miles) Altitude gain: 781 feet Terrain: country roads 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 moderate walk follows a similar route but continues further through the Tuscan hills, giving us more time to enjoy the atmosphere and unforgettable views. No trip to this region is complete without a visit to a local winery, for a tasting of the local fine Chianti wines followed by a light traditional lunch. 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, it was 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 an easy or a moderate walk. Easy walk Duration: 2 hours (3.1 miles) Altitude gain: 569 feet Terrain: country paths The easy 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. Moderate walk Duration: 3 hours (5.5 miles) Altitude gain: 770 feet Terrain: country paths 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. Both walks conclude 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 mouthwatering 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.

Transfer to the airport for your return flight.

What's Included

  • icon


  • icon

    Bed & breakfast plus 4 dinners

The price of this holiday is per person based on two people sharing a room. Single rooms are available at the relevant supplement. The price includes: five nights’ accommodation with breakfast; all tours as mentioned; airport departure taxes; return flights and hotel transfers; all coach travel as mentioned; the services of a Riviera Travel tour manager and an expert local walking guide.

Your Peace of Mind Options

  • icon
    Low Deposit

    Riviera Travel requires a deposit of 20% to secure a place on this tour, and the final balance is not due till 56 days before departure..

  • icon
    Secure payments

    All payments to TourHub are deposited into an externally regulated Trust account.

Dates & Availability