Tailormade tour Explore southern Tuscany rail-drive tour Italy

8 nights /9 days

Swiss Alps • Florence • Chianti • Cortona • Candeli

This touring holiday of southern Tuscany by rail and car includes rail travel with an overnight stop in either Zurich or Lausanne on the outward journey, then one night in Florence before collecting a hire-car to use to tour Chianti, southern Tuscany, and returning to a stop on the banks of the Arno outside Florence. You return by train to Milan and then by overnight sleeper train to Paris, or with another overnight stop in northern Italy or Switzerland, with the final leg by Eurostar.
Holiday price guide

Available year-round subject to the opening period of the hotels, from £2,530 per person.

Luxury rail-drive tailormade touring holiday to southern Tuscany


Overnight in either Zurich or Lausanne • Swiss Alps • Florence • Chianti • Visit San Gimignano • Visit Chianti wine towns • Visit Siena • Visit Arezzo • Cortona • Visit Perugia • Candeli

Day by day

Start your rail holiday by departing London on an early morning Eurostar to Paris. Following a change of station in Paris, you then continue to Lausanne or Zurich by TGV train which reaches 198 mph. Arrive early evening and spend one night here.

Spend the first part of the morning looking around, depending on how late you want to arrive in Florence, before boarding the Eurocity train to Milan. You change trains in Milan and continue to Florence by high-speed train arriving in the evening. On arrival in Florence you will met at the station and transferred to your hotel for one night.

Collect your hire-car and drive out of Florence into the Chianti. The drive is about 55 miles and takes about an hour and a half. We recommend that you take the country route south from Florence, heading through the wine villages of Greve, Gaiole and Radda in Chianti. These towns are charming with wineries you can visit but take time to gaze at the vista of the Tuscan countryside. Spend two nights in the Chianti area enjoying the surroundings of vineyards, gently rolling hills and the turrets of Siena in the distance.

Enjoy a day at leisure to explore with your hire car, perhaps venturing into Siena, or driving to the fortified town of San Gimignano.

Your destination today is a charming hotel in the vineyards and countryside just outside the historic, Etruscan town of Cortona. It takes a little over an hour to cover the 42 miles, but you may want to take a detour to visit the town of Arezzo, whose hill-top cathedral features painted vaulted ceilings and a 15th century fresco of Mary Magdalene by Piero della Francesca.

Your day at leisure at your hotel near Cortona can be spent relaxing in the hotel’s gardens or visiting the wine estate of the hotel owners. Cookery lessons can also sometimes be arranged here. Another option is to drive south from Cortona to nearby Umbria and visit Lake Trasimeno or the cathedral city of Perugia.

Today you can take your time driving north with your destination being in the village of Candeli, set on the banks of the River Arno, just outside the city of Florence for your final night in Italy. Your hotel is an historic building with its grounds alongside the River Arno. The hotel has a shuttle service to take you into Florence, otherwise have a relaxing last night’s dinner at the hotel itself.

You have most of the day free before needing to return your car in Florence in good time to board the train from Florence to Milan, before changing to the Thello sleeper service to Paris.

You arrive into Paris Gare de Lyon just after 10am and after an easy change of stations in Paris, complete your rail journey by travelling on the Eurostar back to the UK, arriving at lunchtime.

Holiday price guide From £2,930 per person based on two people sharing a double room including first class rail travel.
From £2,530 per based on two people sharing a double room including second class rail travel.

Holiday Code ITRD01

Luxury rail-drive tailormade touring holiday to southern Tuscany

Holiday price guide From £2,930 per person based on two people sharing a double room including first class rail travel.
From £2,530 per based on two people sharing a double room including second class rail travel.

Holiday Code ITRD01

Our prices include ● Second-class travel on all trains, with standard class on Eurostar (first and standard premier can be booked at a supplement)
● Double sleeper compartment on Thello sleeper train with one night on board
● Hire of a Group B car from day 3 to day 9
● 1 night’s bed and breakfast in a Standard double at Hotel Angleterre et Residence in Lausanne or at the Romantik Hotel Europe in Zurich
● 1 night’s bed and breakfast in a Classic double at Hotel Helvetia and Bristol in Florence
● 2 nights’ bed and breakfast in a Classic double at Castel Monastero in Chianti
● 2 nights’ bed and breakfast in a Classic double at Relais Il Falconiere near Cortona
● 1 night’s bed and breakfast in a Classic double at Villa la Massa near Florence
● 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 except breakfast at hotels
● 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
●Supplements for alternative routes
●Transfers in Lausanne, Zurich and Paris

Luxury rail-drive tailormade touring holiday to southern Tuscany

Expressions Holidays includes these hotels in this touring holiday as suggestions, but they can be substituted by others in the same region, if you have a preference to stay elsewhere.
Hotels included in this tour
Lausanne or Zurich
Hotel Angleterre et Residence

Hotel Angleterre et Résidence is a charming, traditional, Swiss-style, 4-star hotel in a prime location. Delicious cuisine, exceptional service and immaculate grounds offer guests a truly relaxing and indulgent experience.

Standard double room

Romantik Hotel Europe

The Romantik Hotel Europe in Zurich is a charming, boutique, family-run hotel with 39 rooms just two minutes’ walk from the shores of Lake Zurich and by the Opera House.

Standard double room

Hotel Helvetia Bristol

Helvetia & Bristol is a charming boutique 5-star hotel in an excellent central location. Exquisite fine-dining cuisine and luxurious accommodation make it an ideal spot to recuperate after enjoying the delights of Florence.

Classic double room

Castel Monastero

Castel Monastero is a luxurious village-resort with superb facilities. Sympathetically renovated from an ancient hamlet and monastery, this hotel blends original architectural features with excellent cuisine and service in order to create an authentic Tuscan experience.

Classic double room

Il Falconiere

Il Falconiere is an exclusive, charming country hotel in a beautiful rural location. Cuisine is certainly the main focus of this hotel, with a Michelin-starred restaurant, cooking classes, vineyard tours and wine tastings on offer.

Classic double room

Villa La Massa

Villa la Massa is an enchanting 5-star Renaissance villa in the midst of glorious countryside, yet only fifteen minutes from Florence. Gourmet cuisine, stunning grounds and rustic, elegant accommodation afford guests a truly relaxing and restorative retreat.

Classic double room

Holiday price guide From £2,930 per person based on two people sharing a double room including first class rail travel.
From £2,530 per based on two people sharing a double room including second class rail travel.

Holiday Code ITRD01

Luxury rail-drive tailormade touring holiday to southern Tuscany

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.

Luxury rail-drive tailormade touring holiday to southern Tuscany

Highlights of Florence

The markets in Florence are great for browsing for leather bags and shoes, but be prepared to haggle the price, as these markets are now really geared up for tourists and you can end up paying more than you need to. Fiesole can be reach by train or bus and has lovely views of the city. The Boboli gardens are an enchanting place to spend a few lazy hours and can be reached on foot over the other side of the River Arno from the main sites. Hire a car and visit Siena, Lucca, San Gimignano, Chianti, Montepulciano, Perugia and many more fascinating mediaeval towns nearby.

Cultural highlights of Florence

The Duomo, The Battistero, Uffizi Gallery, Accademia Gallery, the mausoleum of the Medici family in the Medici Chapel, Ponte Vecchio, Palazzo Pitti, The Piazza della Signoria.

Festivals in Florence

There are a wide range of fashion shows held in Florence in January, which can make finding hotel availability difficult during the show period. Otherwise, Florence holds any wonderful festivals throughout the year including the Scoppio del Carro or the explosion of the cart on Easter Sunday, which is really a firework display, but the atmosphere is tremendous. Calcio in Costume in June is a fun spectacle and a slightly different take on ‘Calcio’ or football! Alternatively, in September there is the Festa della Rificolana where children carrying candlelit lanterns converge on the Piazza della Santissima Annunziata to celebrate the eve of the birth of the Virgin Mary. The most notable festival in the area however, is of course the Palio in Siena, just south of Florence and easily reachable by train, which takes place in July and August. Early booking is essential.

Gastronomy in Florence

Florence is famous for its food, namely Bistecca alla Fiorentina and many grilled meats and game dishes, but of course it is the centre of the Chianti wine producing region and thereby has access to some of the most prestigious wines from Chianti and the hearty reds of Southern Tuscany. Olive oil is also in abundance here and is used with everything, from cooking to dipping and even tasting!

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