Tailormade tour Romantic Interludes Italian fly-drive tour Italy

9 nights/10 days

Portofino • Chianti classico • Porto Ercole

Italy is probably the most romantic country in Europe, a country where romance is not only in the beautiful landscapes, buildings, and atmosphere, but a way of life. This touring holiday includes a stay at three very romantic and yet very places, two on the dramatic Italian coastline, and one amid the grey-green hills and vineyards of Chianti country in Tuscany, from where you can see the towers of Siena in the distance. This itinerary is ideal as honeymoon or special occasion, or just a marvellous holiday. You can use this luxury fly-drive touring holiday exactly as it is or let us help you to adapt it to suit your own tastes and budget.
Holiday price guide

Available year-round subject to the opening period of the hotels, from about £4,270 per person.

Luxury fly-drive tailormade touring holiday Italy's Romantic Interludes

From your arrival in Italy, this fly-drive touring holiday takes you first to the picturesque fishing village of Portofino on the Ligurian Riviera. One of the best hotels in Italy, the Belmond Hotel Splendido takes full advantage of the rugged verdant landscape, set in an enviable position high above the village, and nestled into the side of the green mountainside of the Portofino peninsula. The ideal place to relax, with large luxurious suites painted in a neutral palate, to contrast the vibrant emerald of the hills and the deep turquoise of the sea outside your window. Enjoy dining at the hotel’s superb restaurant which boasts magnificent sea views and relax in the large outdoor heated swimming pool. Leave the small fishing village of Portofino for the Tuscan region of Chianti Classico. Here you are within a short driving distance of the romantic cities of Florence and Siena, and small, historic towns, such as Volterra and San Gimignano. From inland Tuscany, drive across the rolling landscape, through Grosseto and the less well-known but rural landscape of the Maremma, towards the Tuscan coast, to Orbetello, where you cross over a short stretch of water onto a small island, the Argentario. The last stay on this touring holiday is at the Pellicano, near Porto Ercole. On the south side of the island, this exclusive hotel, in a secluded cliffside location, is an intimate idyllic retreat that pampers and pleases. Spend a few days relaxing on the private beach, playing tennis or enjoying a spa treatment. Your return your hire-car to Rome Fiumicino for the flight back to London.

Highlights

Portofino • Chianti Classico • Visit wineries • Visit Siena • Visit San Gimignano • Drive across the Maremma • Argentario peninsula • Porto Ercole

Day by day

You arrive at either Milan Malpensa or Genoa airport and collect your hire-car. Spend the next three nights in the exclusive hillside Belmond Hotel Splendido on the shore of the Ligurian Riviera. A favourite haunt of names such as Elizabeth Taylor and Richard Burton, Humphrey Bogart, Liza Minnelli and Winston Churchill, this hotel offers some of the most highly regarded service and one of the most luxurious experiences in Italy. During the day, ramble between the olive and cypress trees you can see lining the hills from your hotel room and into the Monte di Portofino natural park. Several peaceful walks take you up to the modest summit, while another trail will lead you to the Semaforo Nuovo lighthouse. The fishing port itself offers the same feel of exclusivity of the Hotel Splendido, perhaps first instilled in the village by the visiting painters who were fascinated by the quiet radiance of the sea and the green hills. Walk along Portofino’s streets to discover the small boutique shops, some selling the famous Genoa lace, or drop in to the Church of Sant Giorgio to view the relics of Portofino’s past. Castello Brown has some of the best views across the port, and from here you can walk to the Faro lighthouse, with its magnificent views over the Gulf of Tigullio and the pine forest. Rise early on your second day in Portofino for a invigorating run on the water in the hotel’s very own speed boat, feeling the spray of the sea on your skin and appreciating the view of the village from the water. Spend your evenings sipping inspired cocktails in one of the portside bars. We specifically recommend La Gritta American Bar and the Scafandro American Bar, both a favourite with Portofino’s A-list guests.

Have one last breakfast on the terrace under the sub-tropical canopy at the Splendido, before beginning your journey south along the coast and then inland to Chianti country. The Borgo San Felice, a traditional Tuscan hamlet, is a neat collection of red-roofed houses, surrounded by its own fields and vineyards. As part of the Chianti wine region, small wineries are open for wine-tasting sessions, including the Agricola San Felice. Nearby Siena is perhaps most famous for its long-standing competition with Florence. This fly-drive tailormade tour, placing you so conveniently between the two cities, will let you make up your own mind about which is the most charming. In Siena, the old city walls contain a town that is half taken up by olive groves and gardens. The part of the town occupied by buildings, however, truly is an architectural and historical delight. Home to the tallest secular tower of mediaeval Italy, the Palazzo Pubblico is home to the seat of the city council, as well as a vast collection of beautiful Sienese art. The original weathered mythological relief panels from the Fonte Gaia can also be found here, while the fountain itself is now adorned with faithful copies. The Piazzo del Duomo, however, tells the most interesting story. Its free-standing marble arch is all that remains of Siena’s plan to extend the original Duomo di Siena; the square itself, paved with red and white tiles, was intended to be the cathedral’s interior. The baptistery of the original cathedral lies underground, while the crypts are on ground level. The baptismal font is said to be one of Siena’s finest spectacles, with relief panels carved by the likes of Donatello, Ghiberti, and Jacopo della Quercia. The semi-circular Piazza del Campo exudes the laid-back Tuscan lifestyle, lined as it is with pavement cafés. On the 2nd July and 16th August of every year, the square plays host to the Palio horse race, still carried out as it was in mediaeval times, with one member of each of Siena’s 17 districts competing. The square itself comes alive with enthusiasm and age-old tradition. For an experience of rural Tuscany, drive across the grey-green forested hills into San Gimignano, another small town that once had ideas of greatness. All that remains of its plans seem to be the rising peaks of its square towers, while the rest of its buildings have remained in the mediaeval form.

Your next stop on this romantic touring holiday of Italy is on a small island off the Tuscan Coast. Porto Ercole sits at the base of the Rocca Spagnola and surrounded by the verdant Tuscan countryside. On your journey, consider stopping at Orbetello, the town built on the causeway between the mainland and the island, for a brief tour of the cathedral, built on the site of an Etruscan-Roman temple. Upon arrival at the Il Pellicano, your hotel for the next three nights, make yourself comfortable in your luxury room, and explore the many buildings of Il Pellicano that sit on the slopes of the hillside, and then venture down to the beautifully clear waters of the private beach. Other beaches are available nearby, should you want to sample more of the island’s golden sand, such as the Spaggia della Feniglia, or the rocky Riva del Marchese, perfect for snorkelling. For the best, most atmospheric views of Porto Ercole, wait until dusk, and then walk up to the 16th century Forte Stella, which gets its name from the star-shape of its inner fort. You enter through an archway where the drawbridge used to be and are met with the most spectacular views across the water, the hills, and the town below. Borgo Antico, the old quarter of Porto Ercole, can be accessed only on foot, requiring a brisk walk up the hillside to reach its winding narrow streets, beautiful views, and historic squares. The Piazza Santa Barbara is lined with the arcades of the old Governor’s Palace, and from here it is an 80-step ascent to the Church of Sant Erasmo, still in use today, and claimed by some to be the final resting place of Caravaggio, who is known to have died in Porto Ercole. Explore the hillsides further by seeking out the many hidden caves. To return to modern Tuscany, drive the short distance to Cala Galera, a port specifically built to aid Porto Ercole. It is now an excellent destination for bars, fine-dining, and shopping excursions. Have dinner at Cala Galera, portside in Porto Ercole, or in Il Pellicano’s Michelin-starred restaurant, with its beautiful views of the setting sun across the water.

Leave Porto Ercole today for your return flight from Rome Fiumicino to London.

Holiday price guide Prices from about £4,270 per person based on two people sharing a double or twin room.

Holiday Code ITFD07

Luxury fly-drive tailormade touring holiday Italy's Romantic Interludes

You arrive at either Milan Malpensa or Genoa airport and collect your hire-car. Spend the next three nights in the exclusive hillside Belmond Hotel Splendido on the shore of the Ligurian Riviera. A favourite haunt of names such as Elizabeth Taylor and Richard Burton, Humphrey Bogart, Liza Minnelli and Winston Churchill, this hotel offers some of the most highly regarded service and one of the most luxurious experiences in Italy. During the day, ramble between the olive and cypress trees you can see lining the hills from your hotel room and into the Monte di Portofino natural park. Several peaceful walks take you up to the modest summit, while another trail will lead you to the Semaforo Nuovo lighthouse. The fishing port itself offers the same feel of exclusivity of the Hotel Splendido, perhaps first instilled in the village by the visiting painters who were fascinated by the quiet radiance of the sea and the green hills. Walk along Portofino’s streets to discover the small boutique shops, some selling the famous Genoa lace, or drop in to the Church of Sant Giorgio to view the relics of Portofino’s past. Castello Brown has some of the best views across the port, and from here you can walk to the Faro lighthouse, with its magnificent views over the Gulf of Tigullio and the pine forest. Rise early on your second day in Portofino for a invigorating run on the water in the hotel’s very own speed boat, feeling the spray of the sea on your skin and appreciating the view of the village from the water. Spend your evenings sipping inspired cocktails in one of the portside bars. We specifically recommend La Gritta American Bar and the Scafandro American Bar, both a favourite with Portofino’s A-list guests.

Have one last breakfast on the terrace under the sub-tropical canopy at the Splendido, before beginning your journey south along the coast and then inland to Chianti country. The Borgo San Felice, a traditional Tuscan hamlet, is a neat collection of red-roofed houses, surrounded by its own fields and vineyards. As part of the Chianti wine region, small wineries are open for wine-tasting sessions, including the Agricola San Felice. Nearby Siena is perhaps most famous for its long-standing competition with Florence. This fly-drive tailormade tour, placing you so conveniently between the two cities, will let you make up your own mind about which is the most charming. In Siena, the old city walls contain a town that is half taken up by olive groves and gardens. The part of the town occupied by buildings, however, truly is an architectural and historical delight. Home to the tallest secular tower of mediaeval Italy, the Palazzo Pubblico is home to the seat of the city council, as well as a vast collection of beautiful Sienese art. The original weathered mythological relief panels from the Fonte Gaia can also be found here, while the fountain itself is now adorned with faithful copies. The Piazzo del Duomo, however, tells the most interesting story. Its free-standing marble arch is all that remains of Siena’s plan to extend the original Duomo di Siena; the square itself, paved with red and white tiles, was intended to be the cathedral’s interior. The baptistery of the original cathedral lies underground, while the crypts are on ground level. The baptismal font is said to be one of Siena’s finest spectacles, with relief panels carved by the likes of Donatello, Ghiberti, and Jacopo della Quercia. The semi-circular Piazza del Campo exudes the laid-back Tuscan lifestyle, lined as it is with pavement cafés. On the 2nd July and 16th August of every year, the square plays host to the Palio horse race, still carried out as it was in mediaeval times, with one member of each of Siena’s 17 districts competing. The square itself comes alive with enthusiasm and age-old tradition. For an experience of rural Tuscany, drive across the grey-green forested hills into San Gimignano, another small town that once had ideas of greatness. All that remains of its plans seem to be the rising peaks of its square towers, while the rest of its buildings have remained in the mediaeval form.

Your next stop on this romantic touring holiday of Italy is on a small island off the Tuscan Coast. Porto Ercole sits at the base of the Rocca Spagnola and surrounded by the verdant Tuscan countryside. On your journey, consider stopping at Orbetello, the town built on the causeway between the mainland and the island, for a brief tour of the cathedral, built on the site of an Etruscan-Roman temple. Upon arrival at the Il Pellicano, your hotel for the next three nights, make yourself comfortable in your luxury room, and explore the many buildings of Il Pellicano that sit on the slopes of the hillside, and then venture down to the beautifully clear waters of the private beach. Other beaches are available nearby, should you want to sample more of the island’s golden sand, such as the Spaggia della Feniglia, or the rocky Riva del Marchese, perfect for snorkelling. For the best, most atmospheric views of Porto Ercole, wait until dusk, and then walk up to the 16th century Forte Stella, which gets its name from the star-shape of its inner fort. You enter through an archway where the drawbridge used to be and are met with the most spectacular views across the water, the hills, and the town below. Borgo Antico, the old quarter of Porto Ercole, can be accessed only on foot, requiring a brisk walk up the hillside to reach its winding narrow streets, beautiful views, and historic squares. The Piazza Santa Barbara is lined with the arcades of the old Governor’s Palace, and from here it is an 80-step ascent to the Church of Sant Erasmo, still in use today, and claimed by some to be the final resting place of Caravaggio, who is known to have died in Porto Ercole. Explore the hillsides further by seeking out the many hidden caves. To return to modern Tuscany, drive the short distance to Cala Galera, a port specifically built to aid Porto Ercole. It is now an excellent destination for bars, fine-dining, and shopping excursions. Have dinner at Cala Galera, portside in Porto Ercole, or in Il Pellicano’s Michelin-starred restaurant, with its beautiful views of the setting sun across the water.

Leave Porto Ercole today for your return flight from Rome Fiumicino to London.

Holiday price guide Prices from about £4,270 per person based on two people sharing a double or twin room.

Holiday Code ITFD07

Our prices include ● Scheduled flight with British Airways from London to Genoa or Milan, returning from Rome to London
● Hire of a Group B car for the duration of the holiday
● Three nights’ bed and breakfast in a Classic room at the Belmond Hotel Splendido at Portofino
● Three nights’ bed and breakfast in a Classic room at the Relais Borgo San Felice in Tuscany
● Three nights’ bed and breakfast in a Garden view room at the Hotel Il Pellicano at Porto Ercole on the Tuscan Coast
● 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
Milan to Portofino 4 hours 50 minutes or Genoa to Portofino 60 minutes
Portofino to San Felice 3 hours 20 minutes
San Felice to Porto Ercole 1 hour 55 minutes
Porto Ercole to Rome 2 hours 10 minutes

Luxury fly-drive tailormade touring holiday Italy's Romantic Interludes

About Tuscany

An Expressions tailor-made holiday in Tuscany allows you to appreciate its classical landscape of rolling hills and vineyards dotted with olive and cypress trees, its misty green-grey mountains that are never too far distant, and hill-top towns of rich brown and gold stone houses. This combines with the beauty of the works of art contained in the towns and villages throughout Tuscany to create an inspirational union of the spirit and the senses. There is an intrinsic comfort in the supposed contrast between the delicacy of a Botticelli and the heartiness of Ribollita soup, yet both are typical of this fascinating region. As birthplace of the Renaissance, the impact of Tuscan and particularly Florentine traditions and culture on European heritage is fundamental to our way of life. In addition to the obvious attractions of the scenery of Chianti and the art cities of Florence and Siena, there are the less well-known regions south of Siena with its moon-like landscape of hills, the patchwork vineyards of Montalcino, the coastal marshlands of the Maremma, the spas of Montecatini and Saturnia, the islands of Elba and Giglio, and the Casentino with the source of the Arno and abundant mushroom crops. Wherever you travel on holiday in Tuscany, you will be inspired by the beauty of your surroundings and the way of life, which is quintessentially that of Italy too.

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 fly-drive tailormade touring holiday Italy's Romantic Interludes

About Ligurian Riviera

An Expressions tailor-made holiday to the Italian Riviera incorporates the stretch of coast from the French border in the west to La Spezia in the east. This region has been long famed for its gloriously mild climate, its luxuriant vegetation of vines, olives, lemons, olives, cypress, pines, bougainvillaea and roses, and its colourful fishing villages of gaily-painted shuttered houses nestling on cliff-sides and in coves. To the west of Genoa the road along the coast forms a corniche with fishing villages, resorts and fruit orchards, this part of the coast being known as the ‘Riviera dei Fiori' as its mild climate encourages abundant flowers, notably roses and carnations. To the east of Genoa the coastline of the Ligurian Riviera is more rugged with promontories such as the Portofino peninsula, renowned for its graceful beauty, sheltered coves, wide bays and larger resorts. Inland, seemingly a world removed from the coast are greenish-grey rugged mountains and hill towns, ruined castles and fast flowing streams. There are abundant chestnut woods and remote valleys, caverns and grottoes and interesting little churches. The Ligurian Riviera is a delightful holiday region where the emphasis is on stylish and tasteful rest and relaxation.

Highlights of the Ligurian Riviera

There are numerous places of interest on and around the Ligurian Riviera. Visit the resort of Nervi with the collection of clocks, fabrics, furniture and lace in the Villa Luxoro and its Galleria d'Arte Moderna. Genoa, a busy port and bustling city, also has fine palaces such as the Palazzo Reale and the Palazzo Bianco and the fascinating Steglieno Cemetery, full of elaborate tombs. The wild beauty of the Cinqueterre should be seen from the ancient footpath, the Sentiere Azzurro, which links the coastal villages. The Abbbazia di San Fruttuoso on the Portofino Peninsula can be reached by boat or on foot. In Camogli sea shells adorn the house walls and the castle contains a display of sea creatures. Flower market in Sanremo early mornings. Giardino Hanbury near Ventimiglia. Diano Marino known for its olives and sandy beaches. Visit Andora Castello, inland from Alassio, known as the finest mediaeval building on the western Riviera.

Cultural highlights of the Ligurian Riviera

The 12th Century Church of San Matteo in Genoa, with its striped black and white Gothic facade. The 16th Century Via Garibaldi in Genoa, designed by Cantone. The `Adoration of the Magi` by Joos van Cleve in the Church of San Donato in Genoa. Crucifixion by Van Dyck in the Church of San Michele di Pagana between Santa Margherita and Rapallo.

Festivals in the Ligurian Riviera

Festivals include the Blessing of the Fish in Camogli in May and the Stella Maris procession of boats to the Punta della Chiappa in August. Procession at Montallegro, above Rapallo, is held at the beginning of July. La Spezia holds a `Festa del Mare` on first Sunday in August.  

Gastronomy in the Ligurian Riviera

Local cuisine is influenced by the sea in particular and the mountains to the north. Local specialities include dishes made with pesto for example Trenette al Pesto and Farinata which is a flat bread of chickpea flour and oil, thin like a pancake and eaten as a snack. Pansoti with walnut sauce is a Ligurian speciality of spinach and egg filled pasta with a sauce of nuts, garlic, herbs, ricotta and olive oil.

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