Tailormade tour Tuscany to the Amalfi Coast fly-drive tour Italy

12 nights/13 days

Chianti Classico • Frascati • Positano on the Amalfi Coast

This is a luxury 12-night fly-drive touring holiday from Tuscany to the Amalfi Coast. Visit the quintessential but contrasting landscapes of Italy. You travel from the rolling, green hills of Chianti and its wealth of architectural treasures, to the heart of Italy where you stay outside Rome among the Castelli Romani, before reaching the dramatic cliffsides of the Amalfi Coast, clad with Byzantine-style houses cascading to the sea, interspersed with lemon trees and vibrant bougainvillaea.
Holiday price guide

Available year-round subject to the opening period of the hotels, from £4,220 per person.

Luxury Italy fly-drive tailormade holiday from Tuscany to the Amalfi Coast


Chianti Classico • Visit wineries • Visit Siena • Frascati • Visit Tivoli and the Villa d’Este • Visit Anzio, Landriana or Ninfa • Positano on the Amalfi Coast

Day by day

It is worth arriving in Pisa early in the day to allow time in the famous historical city after collecting your hire-car. Visit the Torre Pendente, or ‘leaning tower,’ which has become somewhat iconic for the city, but do not neglect the many other sites of historical importance. Take the time to visit the Duomo, which dates back to 1064, the triple-spired Chiesa di Santa Maria della Spina, and explore the Museo Nazionale di San Matteo and its vast collection of medieval artworks. From Pisa, begin the drive south to San Felice, immersed in the Tuscan countryside, dotted by the Chianti vineyards and gold-stone hilltop villages. Your hotel, the Borgo San Felice, is a traditional Italian hamlet in its own right, having converted, one by one, the original houses into the luxurious and interesting hotel that stands there today. Situated conveniently between Florence and Siena, it is an excellent base for exploring the two cities that have been, for so long, in direct competition with each other. The qualities of the larger city of Florence are internationally renowned, with its beautiful cathedral and baptistery, many churches, and the monastery that contains a wealth of Florentine paintings. Siena, on the other hand, bears considerably more evidence of this competition. Its aspirations can be most obviously seen in the Piazza del Duomo, which was originally intended to be an extension of the Duomo itself. The colourfully tiled floor of the Piazza and the grand free-standing archway are all that remains of Siena’s plans. Artistically, one of Siena’s greatest assets is the baptismal font in the cathedral’s baptistery, decorated with relief panels by Donatello, Ghiberti, and Jacopo della Quercia. On the 2nd of July and 16th of August, the semi-circular Piazza del Campo hosts a medieval horserace called the ‘Palio’, in which one horseman from each of the 17 districts competes. The nearby village of San Gimignano is another testament to Italian inspiration and aspiration, with its plans to become a larger cultural centre evident in the high-reaching towers that rise above the many village squares. Or drive out to Volterra, a brooding village of tall, austerely serene buildings that line exceptionally narrow streets, encircled by deep ravines. Back at your hotel, dine in one of the two restaurants, both offering the best food that Tuscany has to offer. One afternoon take part in a cookery lesson and receive the best Tuscan souvenir available: the ability to cook the regional cuisine at home. The wines produced on the hotel’s estate can be tasted after a tour of the extensive wine cellar, or alongside an evening meal.

Your journey takes you south allowing you time perhaps to stop to visit Orvieto, perched on a rocky outcrop and its striking cathedral or Hadrian’s Villa at Tivoli to the east of Rome. You stay near Frascati for two nights. Explore the village of Frascati, the most famous of the Castelli Romani - villages famous for being the favourite retreats of city-dwelling Romans seeking fresh-air and relaxation - and taste the Frascati white wines. Be sure to try the Amaretti biscuits that originated here, or the Cesanese dry red wine that can be tasted at a nearby winery. Visit Frascati’s two most beautiful gardens, the Giardini della Landriana and the Giardino di Ninfa, or the Villa Aldobrandini, originally built for the nephew of the Pope. Plan your visit for around the 23rd of June to witness, or take part in, the Sagra della Lumaca, an outdoor snail feast, or in October to enjoy the Sagra del Vino. Venturing further out into the countryside of Latium, why not visit the cliff-side village of Anticoli Corrado, the almost inaccessible Saracinesco, or the medieval citadel of Zagarolo. Palestrina is built on the site of the Sanctuary of Fortuna Primigenia, the greatest Hellenistic temple in Italy, and therefore makes a highly interesting afternoon excursion. Perhaps visit Fiuggi, the site of the famous Acqua di Fiuggi that rises out of several natural springs and feeds the village’s spas. Michelangelo himself was said to have come to Fiuggi, seeking the water, to relieve the stress of painting the Sistine Chapel. Fiuggi itself is a town dominated by ornate hotels and tree-lined boulevards, but the Borgo Medievale di Fiuggi is a complex network of small palaces, craftsmen’s houses, churches, squares, and alleyways dating back to the 16th century. In the evenings, return to your hotel, peruse the art in the noble rooms, wander through the hanging gardens, and relax in the grand and peaceful ambience.

Your third destination on this touring holiday is the hillside town of Positano, one of the prettiest of the towns dotted along the Amalfi Coast. During the day, navigate Positano via the winding stairways, perhaps in a pair of their speciality sandals. Walk along the Sentiero degli Innamorati from the Spiaggia Grande to Fornillo beach for a spectacular view of the coastline and a rewarding relaxing endpoint. Be sure to visit the secret hamlet of Nocelle, tucked away on the Monte Pertuso hillside. Walk to Nocelle from Agerola for a gentle, downhill stroll that takes you past more breath-taking views across the Amalfi Coast and the island of Capri. For a longer day trip, drive along the Amalfi coast, through the white and terracotta towns, to Amalfi itself. While here, explore the many monuments, such as the Byzantine Duomo di Sant’ Andrea Apostolo, fronted by 57 stone steps that take you up to its three main arches. From the top of these steps in the atrium, the views across Amalfi and the sea are exceptional. The picturesque main square sits just below it, surrounded by small cafes and pretty buildings. Wander between the towering, climbing houses of the Vagliendola, or watch the Amalfi musical under the curved roof of the Antichi Arsenali, or old shipyards. From here, perhaps walk across the hilltops to the artistic village of Ravello to listen to a classical music concert on the terraces of Villa Rufolo, or venture out into the Valle delle Ferriere, with its old steps, waterfalls, bridges, forests, and beautiful abandoned buildings. Spend your evenings in the restaurant of the Hotel Poseidon, indulging in the specialities of Neopolitan Cuisine, such as mozzarella, fresh seafood, gelato, and sfogliatella pastries, finished off, of course, with limoncello made from Amalfi lemons. In the summer, dinner can be eaten under a pergola on the terrace. The hotel’s wine cellar offers the best wines of the Campania region, all available to drink alongside the delicious flavours of the Amalfi Coast.

On your final day in Italy, drive north to Naples for your return flight, and depending on the time of your flight, perhaps stopping off in Pompeii. Uncover the secrets of the ancient ruins, so well preserved by the volcanic rock, under the brooding glare of Vesuvio. You return your hire-car at Naples airport before taking your flight back to London.

Special offers for this holiday>

Thank you. We had an amazing holiday. Really appreciate the work put in to give us the trip of a lifetime!
Mrs H, Jan 2023

Holiday price guide Prices from £4,220 per person based on two people sharing a double or twin room.

Holiday Code ITFD04

Luxury Italy fly-drive tailormade holiday from Tuscany to the Amalfi Coast

Special offers for this holiday>

Thank you. We had an amazing holiday. Really appreciate the work put in to give us the trip of a lifetime!
Mrs H, Jan 2023

Holiday price guide Prices from £4,220 per person based on two people sharing a double or twin room.

Holiday Code ITFD04

Our prices include ● Scheduled flight with British Airways from London to Pisa, returning from Naples to London
● Hire of a Group B car for the duration of your holiday
● Five nights’ bed and breakfast in a Classic room at the Villa le Barone in Chianti
● Two nights' bed and breakfast in a Classic room in the Paggeria at the Park Hotel Villa Grazioli in Frascati
● Five nights’ bed and breakfast in a Standard room with garden view at the Hotel Poseidon, Positano
● 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

Additional information Driving times for this touring holiday
Pisa to San Felice 2 hours 5 minutes
San Felice to Frascati 2 hours 30 minutes
Frascati to Positano 3 hours
Positano to Naples 1 hour 20 minutes

Luxury Italy fly-drive tailormade holiday from Tuscany to the Amalfi Coast

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

Special offers

Call to make your booking and save an extra £50 per adult Call us instead of emailing us when you are thinking of booking a holiday and save an extra £50 per adult (in addition to any special offers that might be available). We want to talk to you to discuss your requirements and a phone call is usually the best way for you to define what you want enabling us to respond more accurately. We want to talk to you and you save an extra £50 per adult.

Thank you. We had an amazing holiday. Really appreciate the work put in to give us the trip of a lifetime!
Mrs H, Jan 2023

Holiday price guide Prices from £4,220 per person based on two people sharing a double or twin room.

Holiday Code ITFD04

Luxury Italy fly-drive tailormade holiday from Tuscany to the Amalfi Coast

Highlights of the Amalfi Coast

A drive along the Amalfi coast from Positano to Amalfi offers stunning and breath-taking scenery. Visit the Emerald Cave near Vettica Minore by boat. Enjoy the superb view of the coast from the 13th Century Gothic Villa Rufolo in Ravello (we offer garden tour holidays of the Amalfi Coast and Capri including a visit to Villa Rufolo). Spend a full day visiting the awe-inspiring site of Pompeii, visiting the remains of the villas containing both vibrant and delicate frescoes. Herculaneum is nearby and also worth visiting. The Greek site of Paestum has outstanding Doric temples. In the resort of Amalfi stroll along the Via Genova and the Via Capuano taking in the typical architecture of Campania with the flower-covered balconies, narrow alleyways leading to fountain-filled little squares. Take the chairlift on Capri to Monte Solaro or walk to the Migliara Belvedere for a view of the lighthouse. On Ischia visit the beaches of Citara and Maronti and enjoy a morning's walk to Monte Epomeo for panoramic views of the coast. Well worth visiting is the often-forgotten island of Procida between Naples and Ischia, with its vines and fishing, flat roofed white houses and atmosphere most characteristic of the region in bygone days. Visit Vietri for ceramics as well as stalls of lemons, garlic and peppers.

Cultural highlights of the Amalfi Coast

The House of the Vettii at Pompeii, the baroque Palazzo Reale at Caserta, Villa Jovis in Capri, the Doric temples of Paestum, Michelozzo`s tomb of Cardinal Rinaldo Brancaccio in the 14th Century church of Sant`Angelo, and in Naples: `Modesty` by Antonio Corradini in the Cappella Sansevero, the Gothic church of San Lorenzo Maggiore and the Majolica tiles in the cloisters of the 14th Century Santa Chiara.

Festivals on the Amalfi Coast

The Ravello music festival June to July, the festival of San Costanzo on 14 May on Capri, the festival of Sant`Antonio in Anacapri on 13 June, the festival of Madonna della Liberta in Marina Grande in September, Lo Sbarco dei Saraceni in Positano on the second Sunday in August.

Gastronomy of the Amalfi Coast

Neapolitan cuisine is now famous the world over for its use of tomatoes, pizza, mozzarella cheese, dried pasta and lemons. Local specialities include Mozzarella in Carrozza, Panzanella alla napoletana, Pasta alla sorrentina (with scamorza cheese and tomatoes), Sartu (an elaborate rice pie stuffed with meats, sausages, mushrooms etc), Timballo di Maccheroni (also elaborate with maccheroni baked in a pie and a sauce of chicken livers, mushrooms and black truffles), Carciofi ripieni alla napoletana (baked stuffed artichokes), Coviglie (a mousse-like dessert), Sproccolati (sun-dried figs on sticks) and Sfogliatelle (breakfast pastries). The region produces a number of excellent red and white wines. The most famous white is called Lacrimi Christi, from vines grown on the slopes of Mount Vesuvius. Taurasi from Avellino is a full-bodied red. Capri, Ischia and Sorrento all produce their own local wines.

Luxury Italy fly-drive tailormade holiday from Tuscany to the Amalfi Coast

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 Italy fly-drive tailormade holiday from Tuscany to the Amalfi Coast

Highlights of Latium

There are a number of places nearby that are worth visiting: The hot springs at Tivoli and Fiuggi. The Alban Hills and the 13 hilltop towns surrounded by vineyards and elegant villas of the Roman aristocracy over the years, including the summer palace of the Pope at Castel Gandolfo. Visit mediaeval Anguillara on Lake Bracciano north of Rome. Explore the countryside of the Ciociaria region near Anagni (the name of the region comes from the bark clogs worn by the locals until about twenty years ago). Ostia Antica now inland was once ancient Rome's trading port and the ruins offer a fascinating insight into the Roman way of life. The region north of Rome is very rich in Etruscan remains -visit the necropoli at Tarquinia and Cerveteri. Great monasteries were founded around Rome, especially at Subiaco and Montecassino. The best beaches on the Lazio coast are to be found between Sabaudia and Gaeta. From the town of Bolsena take boat trips to the islands of Bisentina and Martana on Lake Bolseno. Visit the Island of Ponza off the coast near San Felice Circeo.

Cultural highlights of Latium

The gardens of the Villa d`Este at Tivoli. Hadrian`s Villa at Tivoli. Villa Lante near Viterbo. Palazzo Barberini in Palestrina which houses a 1st Century BC mosaic depicting the Nile in flood. The Byzantine frescoes in the crypt of the 11th Century Basilica of Santa Maria in Anagni. The Palazzo Farnese by Vignola at Caprarola. The 13th Century Italian Gothic church of Santa Maria Maggiore at Ferentino. 17th Century frescoes by Domenichino in the chapel at Grottaferrata.

Festivals in Latium

Spring is the main season for festivals in Latium. Genzano holds the `Infiorata`, Marta has the `Barabbata`. In the autumn there is the `Sagra dell`uva` grape festival in Marino. The influence of Rome is obvious in this area, supplemented by either proximity to coast or country.  

Gastronomy in Latium

Sage, rosemary and bay are used extensively to season. Specialities of the region include Spaghetti alla carbonara, Suppli (croquettes made with rice, meat and mozzarella), Carciofi alla giudia (artichokes fried crisp in olive oil and sprinkled with lemon juice), Saltimbocca alla romana (veal with ham and sage), Torta di ricotta. Frascati is the best-known white wine of the region although similar wines made from the Trebbiano grape include Colli Albani and Castelli Romani. Very few red wines are produced, but the best is Torre Ercolana.

Luxury Italy fly-drive tailormade holiday from Tuscany to the Amalfi Coast

Highlights of Umbria

Shop for ceramics in Gubbio, truffles and cooked meats from Norcia. Dramatic landscapes of the Monte Sibillini and one of Europe's highest waterfalls called the Cascate delle Marmore near Terni. One of Italy's beauty spots is the Fonti del Clitunno south of Trevi. See carpentry and woodworking in Todi. Visit the wine museum in Torgiano. Forests of holm oak near Spoleto. Antique fair in April and a national craft fair in August and September in Todi.

Cultural highlights of Umbria

A mixture of religious and secular art and architecture makes Umbria fascinating. The cities of Perugia and Assisi are great centres but the smaller towns of Gubbio, Todi, Spoleto and Spello are also of outstanding interest. Highlights of the region include the Fontana Maggiore in the Piazza IV Novembre in Perugia. Perugia`s Galleria Nazionale containing works by Perugino and Pinturicchio. Gattapone`s Palazzo dei Consoli in Gubbio and his Ponte delle Torri in Spoleto. The `Adoration of the Magi` by Perugino in the church of the Madonna della Lacrime in Trevi. Frescoes by Matteo da Gualdo in the Pinacoteca of Gualdo Tadino. `San Sebastiano` by Luca Signorelli in the Pinacoteca at Citta di Castello. Frescoes by Giotto and Lorenzetti in the Basilica of St Francis in Assisi.

Festivals in Umbria

Perugia has a jazz festival in the summer and the Sagra Musicale music festival held in its churches in September. Orvieto holds concerts in August and has a firework display on the 15th. Spoleto`s Festival of the Two Worlds, a world-class cultural event, takes place June and July. Spello holds its Infiorata in June when the streets are decked with flowers. Foligno holds jousting in September during its Giostra della Quintane.

Gastronomy in Umbria

Umbria's gastronomy is very much a product of its earth and waters: Mushrooms and truffles flavour many dishes, Game and wild boar, Trevi produces black celery, olive oil and black truffles, Pecorino cheese from Torgiano, Todi offers Panzanella, dried bread soaked and marinated in sliced tomato, basil, onion and olive oil, Sweet macheroni with walnuts, Salami and sausages are a regional speciality, Trout from the rivers and perch from Lake Trasimeno, Strangozzi and Bici are local pasta, often flavoured with porcini and truffles. Umbria produces some high quality robust red wines near Torgiano (Rubesco produced by Lungarotti for example) and Orvieto is known for its white wine.

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