Small group tour Wine tour of Tuscany Italy

4 nights/5 days

Radda in Chianti • Montalcino • San Gimignano

A glorious 4-night wine tour of Tuscany for a small group of up to 14 people accompanied by an experienced wine and food expert, discovering the land and the variety of the wines of Tuscany, in particular Chianti and Brunello.
Holiday price guide

Available on selected dates, as specified below, from £2,890 per person.

Luxury wine tour of Tuscany for small groups of up to 14 people


Radda in Chianti • Visit Isole e Olena • Visit the Castello di Volpaia • Visit the estate of Col d’Orica • Visit Fattoria Poggerino • Visit Felsina Berardenga • Montalcino • San Gimignano • Visit il Colombaio di Santa Chiara

Day by day

British Airways flight departs London Heathrow at 13.05, landing Pisa at 16.15. Your wine tour manager, Cindy-Marie Harvey, is waiting to greet you at Pisa airport for the private mini coach transfer to our hotel located in the very heart of Chianti, in Radda-in-Chianti. After checking into our hotel on the main winding road of this delightful hilltop village, we dine together at the hotel’s restaurant, where a Tuscan menu will be paired with a selection of regional wines as your introduction to the many styles of wine that the Sangiovese grape can produce.

After breakfast, we head to our first visit in the Chianti Classico classification, Isole e Olena. Widely revered as one of the best wine makers in Italy, Paolo de Marchi hails originally from Piemonte, but moved to Tuscany many vintages ago. His passion for attention to detail in the vineyards and in the cellar is reflected in his iconic wines including the ground breaking Cepparello. We taste a selection of these seductive wines at the cellar surrounded by his immaculately tended vines. Our lunchtime appointment is at the nearby estate, Castello di Monsanto, where the Bianchi family are producing lovely, appealing Chianti wines with a great ability to age. The family bought the Villa and grounds in the 1960s, (having fallen in love with the property when visiting it for a wedding!) and today have 56 hectares of Sangiovese, but also some plantings of Chardonnay and Cabernet. We taste their wines over lunch at their beautiful estate. After our leisurely lunch, we return to Radda-in-Chianti, where there is free time for the rest of the afternoon to explore this peaceful village. The main street, unsurprisingly, has several wine shops, but also a couple of leather shops with soft Italian leather bags and shoes to tempt! Or simply, relax with a glass of wine and a book, enjoying the views of the rolling Tuscan countryside. This evening, we are invited to the hilltop hamlet of Castello di Volpaia, which dates from the 11th century and is one of the best preserved mediaeval villages in Tuscany. The Stianti family continue to produce both wine and olive oil using an ingenuous system of production hidden away so not to disturb the beauty of the village. We will be welcomed by the charming owner, Giovanella Stianti, into her private residence for dinner, where we will taste her wines paired with a Tuscan menu.

Breakfast first and then this morning, we head south from the Chianti classification towards Montalcino. After the dense Chianti forests, the land opens out south of Siena to the wide, rolling hills of the Crete Senesi. As we draw closer, the skyline is dominated by Monte Amiata, a dormant volcano which rises to almost 2000 metres. Our visit is to the estate of Col d’Orcia, which belongs to the Count Francesco Marone, of a noble family originally from Piemonte, but who own this estate in Tuscany and also one in Chile. The estate is named after the Orcia river which runs along the south west side of the appellation. They have been instrumental in the experimentation taking place in the region and their attention to detail shines through in the purity and elegance of their wines, which we taste over lunch at the estate. Much of the produce on the menu is grown on the property. After lunch, we call in to the mediaeval small town of Montalcino, dominated by its clock tower and fortress, and which remains barely untouched since the Middle Ages. The flagstones of the narrow streets invite a post-prandial stroll passing numerous wine shops or perhaps simply relax in the beautiful Liberty-style Café with an affogato. From here it’s about an hour and a half bck to the hotel, with time to freshen up before our evening tasting. This evening, our visit is to an estate located a short distance of just 15 minutes from the town walls of where we are staying in Radda. Fattoria Poggerino is a boutique, family-run winery, following organic principals of viticulture. The owner and winemaker, Piero Lanza, is passionate about allowing the fruit flavours of his vines to show through in the wine without the over dominance of oak. We taste their wines this evening at the cellar, with a simple supper of local cheeses and hams. We return to the hotel after supper.

After breakfast, we visit the Castello di Brolio, a dramatic castle featuring mediaeval, romanesque and neo-gothic architecture. It is on the border between the ancient states of Florence and Siena and featured in many of the on-going battles for territory between these warring neighbouring cities. The wine estate is one of, if not the, oldest in Italy dating back to 1141, but it was in 1872 that the Baron Ricasoli wrote down the original blend of Chianti. After a visit to the Castle, we taste a selection of their attractive wines in their modern cellars. Just 35 minutes later, we reach the award-winning estate of Felsina Berardegna on the southern side of Chianti Classico, where the terroir gives a rounded, deep style of Chianti, with rich plum and dark chocolate notes. They also produce single varietal olive oils from four varieties made in the Veronelli style. Following a visit to the historical cellar, we taste their alluring wines and oils over lunch at the property. Returning to Radda late afternoon, there will be some time to relax before we saunter through the old mediaeval gallery to a local wine bar for a tasting of wines from other Tuscan classifications such as the crisp white Vermentino from the Tuscan Coast through to non-Sangiovese based red wines, such as Syrah or Merlot followed by a rustic Tuscan supper, to show how very food-friendly these wines truly are when paired with the local produce. It’s just five minutes on foot from the hotel, so an easy walk back.

We check-out of the hotel after breakfast and leave the vineyards of Chianti behind, and make our way to one of the most iconic of Tuscan towns, San Gimignano. The vineyards of the classification here are mostly planted with the white Vernaccia grape variety, which we discover during our visit to Il Colombaio di Santa Chiara. This estate makes three styles of Vernaccia di San Gimignano, which are fascinating to compare and contrast during our tasting. The profile of San Gimignano has long dominated the skyline in this part of Tuscany thanks to its towers; striking in size, number and state of preservation. In mediaeval times, there were 72 towers within the 13th century walls of this hilltop town, though today only 14 towers remain. Listed as a UNESCO World Heritage Site, it is a delight to explore the narrow streets, lined with artisanal shops of ceramics, print and local foodie specialities such as saffron, wild boar salami and of course wine! There is free time over lunch for you to explore this picturesque town before we depart for the return transfer to Pisa airport, about one and a half hours’ away, before the flight to Pisa leaving at 17.00 hrs and arriving at 18.20 hrs.

Terms and conditions

This tour is based on 14 people participating. If there are fewer than 14 participants we may modify the tour (smaller coach but the visits would remain the same). We do reserve the right to alter the itinerary if we cannot be accommodated at any of the venues for any reason closer to the date of departure.


Please note that this part of Tuscany in based on a series of hilltop villages. Our hotel is in the centre of the small village Radda-in-Chianti, but as traffic is not permitted in the centre, there is a short but steep walk from the car park to the hotel each day (your luggage naturally will be transferred for you by van). At San Gimignano, there is a 7-minute steep walk from the car park to the actual village. All the estates we visit are working cellars and there is an inevitable amount of standing around during visits, so if you have any issues with mobility, please do call to discuss the suitability of this tour. Please ensure you wear suitable footwear both for the cellars, vineyards and also the steep cobbled streets of the Tuscan hilltop towns of Radda and San Gimignano.

Your tour leader

Cindy-Marie Harvey tells us that having discovered a love of Pinot Noir at an early age, she seemed destined for a life in the wine trade. However, her love of languages led her to work in Italy. After living in Piemonte for five years, discovering the delights of Nebbiolo and white truffles, she returned to the wine trade in the UK. She has spent the last 20 years planning and escorting wine tours to all the main wine regions of the world, from South America to Burgundy and Bordeaux. She now shares her passion for food and wine on her own website, Love Wine Food Ltd as well as in her own kitchen where she is often found surrounded by recipe books in Italian, French or Spanish. She looks forward to sharing her passion for the region of Tuscany with you.

From about Prices per person
6 June 2022 £2,890
19 June 2023 £2,990
Single room supplement £250

Holiday Code SGWT03

Luxury wine tour of Tuscany for small groups of up to 14 people

From about Prices per person
6 June 2022 £2,890
19 June 2023 £2,990
Single room supplement £250

Holiday Code SGWT03

Our prices include ● Scheduled flights with British Airways London Heathrow to Pisa return, Euro traveller. Club upgrade available on request at a supplement.
● Transport from Pisa airport in a small luxury coach for a maximum of 14 people, with one piece of luggage per person.
● English-speaking tour guide with knowledge of the wine and food of Tuscany.
● Four nights’ bed and buffet breakfast in double or twin rooms at the Palazzo Leopoldo, Radda-in-Chianti.
● One dinner at the Palazzo Leopoldo on day one, with wine pairings.
● Other meals included as follows: Lunch with wine on day two, dinner with wine on day two, lunch with wine on day three, simple supper with wine on day three, lunch with wine on day four.
● Entrances and wine tastings as mentioned in the itinerary
● Concierge service and Expressions Holidays regional helpful hints

Our prices do not include ● Early check-in or late check-out at any hotels (although we can arrange this on request at additional cost)
● Any other services not mentioned above, such as transfers and meals not mentioned
● Personal holiday insurance. This is essential and cover should be in place from when you book the holiday.
● Local tourist tax, usually between Euros 1 and 3 per person per night, and payable locally to the hotel

Additional information Supplement Single use of double £250 per person
Deposit payment £400 per person

Luxury wine tour of Tuscany for small groups of up to 14 people

Expressions Holidays includes these hotels in this small group touring holiday.
Hotels included in this tour
Palazzo Leopoldo

Palazzo Leopoldo is a 4-star hotel in an excellent location in the centre of Radda. Original architectural features such as frescoes and cotto tiles offer a slice of Tuscan history in an excellent spot to explore wine country.

Double or twin room

From about Prices per person
6 June 2022 £2,890
19 June 2023 £2,990
Single room supplement £250

Holiday Code SGWT03

Luxury wine tour of Tuscany for small groups of up to 14 people

Highlights of Tuscany

Famous vineyards producing wines of Chianti Classico, Brunello di Montalcino, Vino Nobile di Montepulciano. Alabaster is produced in Volterra. Gold and silver are worked in Florence and the Ponte Vecchio is lined with jewellery shops. Marbled paper and stationery is a speciality of Florence. Ceramics and hand-painted majolica from raw terracotta from Impruneta to the glazed pottery of Siena are to be found throughout Tuscany. Lucca has traditionally produced silk and hand-woven fabrics. Leather goods including shoes, handbags and belts are to be found from market stalls to designer shops such as Gucci and Ferragamo. Interesting markets include the Mercato dell' Antiquariato which sells furniture from antiques to bric-a-brac in Arezzo on the first weekend of every month, in Pisa on the second weekend and in Lucca on the third weekend. The 'wild' Maremma is known for its long-horned white cattle and cowboys (butteri) and natural springs including Saturnia.

Cultural highlights of Tuscany

As birthplace of the Renaissance, Tuscany contains a wealth of treasures: Giotto`s Campanile and Brunelleschi`s Dome in Florence, the Tombs of Galileo and Michelangelo in Florence`s Santa Croce, Botticelli`s `Birth of Venus` and `Primavera` and the portraits of the Duke and Duchess of Urbino by Piero della Francesca in the Uffizi, Michelangelo`s `David` in the Accademia, the architecture of the Piazza della Signoria in Florence, `The Tuscan Maremma` painting by Giovanni Fattori in the Palazzo Pitti in Florence, the Piazza del Campo in Siena, `The Legend of the Cross` frescoes by Piero della Francesco in Arezzo, `The Creation` fresco by Bartolo di Fredi in the Collegiata in San Gimignano, Romanesque church of the Collegiata in San Quirico d`Orcia, 14th Century Fortezza of Montalcino, Renaissance masterpiece of the church of Madonna di San Biagio at Montepulciano, the abbey-church of Sant`Antimo, mediaeval Lucignano and the towers of San Gimignano, the Etruscan Museum in Cortona.  

Festivals in Tuscany

Many of Tuscany`s festivals resound with the flamboyance of the Renaissance and keep Tuscans and visitors alike in touch with the region`s rich history. Others are linked to Tuscany`s hearty traditions of eating and drinking. The most famous is Siena`s Palio which takes place on 2 July and 16 August each year. Others include the Sagra del Tordo (Festival of the Thrush) in Montalcino on the last Sunday in October when there is an archery contest and charcoal-grilled thrush are a delicacy. In Florence, Calcio in Costume (a football match played in mediaeval costume) takes place in June. Pisa has the Giocco del Ponte (Game of the Bridge), a mock battle in Renaissance dress also held in June. Viareggio celebrates Carnival on Shrove Tuesday with a huge display of flamboyant floats. In May and August Massa Marittima holds the Falcon Contest.  

Gastronomy in Tuscany

Simple country food is at the heart of Tuscan cooking. Regional dishes include Bruschetta (bread or ciabatta toasted and rubbed with garlic, olive oil and salt), Ribollita (bean, cabbage and bread soup), Pasta with hare or wild boar sauce, Porcini mushroom and truffle dishes, Bistecca all Fiorentina (thick cut of sirloin and fillet beef), Cantucci (almond and honey biscuits) served dipped in Vin Santo, Panforte (chocolate, nut and spice cake). Pecorino cheese made from sheep's milk. Local wines include the white Vernaccia di San Gimignano and the Bianco di Pitigliano. Famous reds include Chanti Classico, Brunello di Montalcino and the Vino Nobile di Montepulciano. Vin Santo made from semi-crushed grapes left for several months is an excellent dessert wine.

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