Venice to Southern Italy

Welcome to Venice. This watery wonderland of bridges, towers, piazzas, canals, churches and gondolas – practically unchanged for 600 years – is literally sinking under the weight of its iconic sights. There are no activities planned before tonight's group meeting, so if you arrive early there are plenty of things to keep you busy. Take a walk around the maze of streets behind San Marco Square and begin to understand the complex canal system of Venice. The Grand Canal is a great place to start, as you can stroll over the Rialto Bridge and browse the endless amounts of boutique shops that sell Venetian masks and handmade Murano glassware. After the meeting, why not enjoy dinner with your fellow travel companions at a local restaurant.

After an orientation walk to familiarise you with the city, you are free to venture out and explore Venice. There are only two ways to get around this city – on foot or by boat. Some of the more popular sights include Doge's Palace, the Piazza and Basilica di San Marco, and the Bridge of Sighs. Take the vaporetto (water bus) over to the island of San Giorgio to climb the bell tower for the best view of Venice. No trip here would be complete without a journey down the Grand Canal in a Venetian gondola. It's a common way for visitors to see the major canal routes from an immersive perspective. While away your day in the busy San Marco square and be sure to try the local tiramisu and Italian coffee that's on offer.

There's creativity everywhere, overflowing into the canals; see it in the venetian glass in Dorsoduro or down the streets spreading out from Campo Santo Stefano, lined with unique galleries and small boutiques. Visit the Palazzo Ducale, overflowing with paintings by Italian masters, and contrast it with the modern Guggenheim. Simply enjoy getting lost crossing the hundreds of bridges and uncovering your own slice of Venice. In the evening, perhaps join your fellow travellers for a group dinner at a local restaurant. Venice is famous for its specialities of fresh lobster and squid ink spaghetti dishes, so make sure you give one a try.

Take a train and bus combination south to Assisi, Italy's second-holiest city (approximately 5 hours). Assisi was the home of one of the world's most famous saints and the founder of the Franciscan order – St Francis. Whatever your feelings about religion, it's a place which inspires reverence. Join your group leader on an orientation walk to uncover a plethora of impressive monuments in Assisi, including Piazza Matteotti, the Basilica of St Clare and the Roman temple remains.

Take a short guided tour of the magnificent Basilica di San Francesco (St Francis Cathedral). You'll be led by a member of the Franciscan community, who will explain the life and times of St Francis and the beautiful art inside the church. Construction of the basilica started the day after St Francis's canonisation in 1228, and this imposing building houses the bones of St Francis and four of his followers. In your free time, you could walk four kilometres up a small trail to the top of Monte Subasio, home to the Eremodelle Carceri, a hermitage where Francis came to pray. That activity will work up an appetite for all the pasta you can eat tonight.

Today you'll take the train to the charming nearby medieval town of Spello (approximately 20 minutes), a Roman town that straddles a thin ridge at the base of Mount Subasio – the mountain where St Francis was said to have talked to the animals. It's a place scattered with weathered Roman monuments and known for its wine and rural charm. Two of the local churches feature frescoes by famed Renaissance painter Pinturicchio, who later lent his hand to works in the Vatican and Siena's cathedral. Sample exclusive local wine and regional food specialties here when you lunch at a local enoteca. Mushrooms like tartufo and porcini make up the base of many pasta and risotto dishes, while whole stuffed pig with rosemary is a signature dish of the region.

Return to Assisi in the late afternoon with some free time to further explore this unique town. Walk the via Guila that circles town, and stop by Piazza Santa Chiara – which has a stunning panorama of the Umbrian countryside – and Piazza del Comune, which gives an insight into life here in Roman times. It'll be very hard not to spend the whole evening simply continuing the day's foodie theme and indulge on the region's fabulous food. (B/L)

Take a bus to the medieval hill-top town of Gubbio (approximately 2,5 hours). The streets of Gubbio, the province's oldest town, are filled with stone houses and orange-tiled roofs, set against a mountain backdrop. This is a perfect medieval town, where there are centuries of history around every corner and the right amount of requisite cobblestone streets, gothic palaces and churches. The surrounding countryside is also lush and cool, the reason why many Italians retreat here in the summer months. When you arrive, a good way to get to know the town is to simply wander the 14th and 15th century streets. A trip to Gubbio wouldn't be complete without a lengthy lunch or dinner along one of its narrow streets, so grab an outdoor table at a taverna for truffle-infused dishes. (B)

This morning take a ride with Gubbio's unique cable car – a 15 minute and 1,000 metre high ride to the Basilica of Sant'Ubaldo, which contains the mummified body of the town's patron saint. From up here you can marvel at the amazing vistas of the Umbrian valleys and mountains, plus get a great rooftop view of the town itself. The alternative is a 30-40 minute walk uphill on a gravel road to reach the basilica. Then take a peaceful countryside hike from the top of Mt Ingino to admire the Umbrian landscape and stunning view down to Gubbio (approximately 2-3 hours).

You'll then have some free time to explore the delights of Gubbio as you wish. You can take in the Civic Museum (home to 3rd-5th century BC bronze Eugubine Tablets), the Duomo, or the Palazzo Ducale, whose original wooden study was deemed so exceptional it was shipped off to New York's Metropolitan Museum of Art. Explore the many churches around town, including one on the spot where legend has it that St Francis tamed a wolf that was terrorising the town. Otherwise, simply just relax into the Umbrian pace of life. Enjoy a variety of local cuisine and try one of the dishes that Umbria is famous for – pecorino cheese, game meat and mushrooms all feature on restaurant menus.

Travel by train to Rome (approximately 4 hours), and remember that while here, the best attitude is ‘when in Rome'! Join your leader on an orientation walk around the city, where you see some of the iconic sights such as the Colosseum and Arch of Constantine, the Forum (centre of ancient Rome), the Victor Emmanuel Monument, the Pantheon, Spanish Steps, Via Dei Condotti and Piazza Venezia. Recharge with a slice of pizza and a strong espresso at the Piazza Navona or throw a coin into the Trevi Fountain and make a wish to return to the 'Eternal City'.

No visit would be complete without a trip to Vatican City and St Peter's Basilica. Entry to the Basilica is free and there's a small charge to climb the dome for a panorama over the city. Art-lovers should visit the Sistine Chapel to admire the timeless work of Michelangelo, while history buffs will enjoy a jaunt through the ancient halls of the Pantheon. Rome is packed full of restaurants and trattorias that cater to every taste and budget. Local specialities tend to be quite heavy, and include pastas such as carbonara (egg, cheese and bacon) and amatriciana (tomato, bacon and chilli). Eating in trattorias will give you a chance to sample some Italian wines, with house choices usually very good and affordable.

Today is a free day for you to explore Rome. Crowded with ancient ruins and religious monuments, Rome still pulses to the beat of modern life and is packed with designer shops, restaurants, cafes and exciting nightlife. Walk beneath the Colosseum's arches and marvel at the mighty Pantheon to gain an understanding of the might of Roman civilisation at the height of its power. Saunter through colourful piazzas, share narrow laneways with beeping Vespa's and be awestruck by the history that is revealed around every corner. Or, to escape the heat of the afternoon sun, get lost amid the cool, marbled hallways of the Galleria Borghese and Galleria Nazionale d'Arte Moderna. (B)

Travel by train to Naples (approximately 3 hours), a raucous city that overflows with passion, tradition and gastronomy. Naples was carved out by many empires of the past and by merchants and pirates from across the world: Romans, Phoenicians, Carthaginians, Venetians, Spaniards, Normans and Africans. Its evocative, historical old centre is a World Heritage-listed area and the famous Spanish Quarter is still one of the most densely populated residential areas in Europe. Naples is the birthplace of the pizza, so why not head to one of the many pizzerias and taste what's truly some of the best that Italy has to offer. Head underground to see ancient Napoli Sotterranea, the famous underground city. Later in the afternoon, board a train to the time capsule of Pompeii, in the shadow of Mt Vesuvius (approximately 1 hour). Your accommodation is perfectly located right near the entrance to the archaeological excavation site. (B)

The small picturesque town of 'modern' Pompeii has a wonderful old town square – the perfect place to while away some time with the locals, drinking true Italian coffee and watching the world go by. Most of today though will be spent exploring the ruins of ancient Pompeii on a guided tour. Until 26 August, 79 AD, Pompeii was a thriving Roman trading centre, where ordinary people went about their everyday business, but it was frozen in time when Mount Vesuvius erupted, killing 2,000 people and their homes under a layer of ash. The city was never rebuilt and largely disappeared from people's minds until the 18th century, when the ruins were re-discovered.

Now you can take an unparalleled look back into the lives of ancient Romans and discover how they lived, worked and interacted 2,000 years ago. The finely preserved ruins include villas, temples, theatres and bustling markets. Walk along the chariot-marked streets, visit the magnificent amphitheatre and the ‘Villa of Mysteries'. You can also visit the Roman Forum and basilica, temples, public baths, and the tiny Odeon created for music recitals. The rest of the day is free, but if the ruins piqued your interest, head to nearby Herculaneum, which also holds a wealth of fossilised archaeological finds. (B)

This morning take a bus up the mighty Mt Vesuvius, where you'll meet a local volcanology guide. Ascend to the summit of Mt Vesuvius for staggering 360 degree views over the Bay of Naples and into the steaming crater. Although Mt Vesuvius is still considered to be an active volcano, the last eruption was in 1944 and there's no sign of lava. See first-hand the awesome power of the volcano that engulfed the cities of Pompeii and Herculaneum in 79AD. In the afternoon, travel by private vehicle to the picturesque resort town of Sorrento (approximately 1 hour).

People have been coming to the peninsula and islands of the Sorrento region for at least 2,000 years, and set invitingly atop dramatic cliffs over sparkling, blue waters, it's easy to see why. There are many options in this small seaside town with its fine piazzas, maze of old streets, sidewalk cafes and glamorous shops. The area is also famous for its lemon groves, producing the famous limoncello liqueur. In the evening head out to try some of the best limoncello on offer in Sorrento. (B)

You have a free day to explore this delightful area and the museums, galleries and piazzas of Sorrento. Perhaps stroll along the marina or cool off in the waters of the local small beaches. They're not big on sandy beaches here, so swimming Sorrento-style is via wooden or stone bathing platforms beneath the cliffs. Taking a trip to Capri is also a great option, with a hydrofoil taking you across to the island that was once home to the magnificent holiday palaces of the Roman emperors. Capri's dramatic rocky coastline is pierced by natural grottoes, while in the interior, narrow roads wind through fragrant citrus groves, past villages of flat-roofed white cubist-looking houses with flower-filled gardens, and manicured towns which offer swanky hotels and chic cafes. Here you can take a boat trip to the fairy-tale Blue Grotto (La Grotta Azzurra), where the water shines with an extraordinary blue translucence, a result of refraction of the sunlight outside. Your leader will be of assistance and will have plenty of suggestions of what to do and see today. End the day a very Italian way with a demonstration of Gelato making.

Arrive on the Amalfi Coast after a short journey by private vehicle (approximately 2 hours). The Amalfi peninsula is a land of rocky coasts, cliff-top vistas, azure seas, tiered lemon groves, whitewashed villages clinging to steep cliffs, and bright blue skies. If you're after a relaxing walk with a few cultural highlights, stroll from one side of Amalfi town to the other and pay a visit to the Cattedrale di Sant'Andrea and the Chiostro del Paradiso. If you're after something more active, perhaps embark on a walk through the Valley of Mills where for centuries paper mills were in operation.

Alternatively catch a bus up the Valley of Dragons to reach pretty Ravello. The French novelist André Gide once described this town as being ‘closer to the sky than the seashore'. For centuries, its lofty position and sunny, dry climate has made it an appealing place for writers, artists, musicians and travellers. Ravello also boasts two magnificent villas – the superb 11th Century Villa Rufolo which was once the home of Wagner, and Villa Cimbrone, a sumptuous 19th Century mansion with fabulous gardens and unequalled views over the Gulf of Salerno. Otherwise just laze around on the beaches and in the piazza, gazing back up at the amazingly picturesque part of the world.

Your leader will take you for a half-day hike along the narrow trail of the famous Sentiero Degli Dei (the Walk of the Gods) which, until quite recently, was followed by mules and donkeys as they traversed the dramatic landscape. This path winds its way through unique scenery and boasts unrivalled views along the coast. Walk through forests and fields of wildflowers, olive groves and vineyards, past ancient stone huts and beside sheer walls of granite. Glimpse local farmers tending their crops by hoe and elbow grease, herds of goats feeding beside the trail beside their shepherds, and teams of workmen commuting by mule. The trail ends in picturesque Positano where there will be ample time to explore and maybe take a dip in the sea. Return to Amalfi by ferry which is the perfect way to see the coast from a different perspective. (B)

Today is a free day for you to enjoy more of the region surrounding Amalfi. A great way to see the beautiful Amalfi coastline and take in the sights is to board a boat – there are regular seasonal services between Amalfi, Positano and Capri. (B)

Another day on the Amalfi Coast allows you explore further. It is highly recommended to walk down into the shaded Valle dei Mulini (Valley of the Watermills). Here you will find remnants of Europe's earliest paper mills, strewn among thick foliage fed by the valley's streams. You may pass locals collecting wild mushrooms and stout men carrying half their body weight in lemons on their heads. The path takes you deep into the valley and the entrance to the nature reserve of ‘Valle delle Ferriere' (Valley of Iron). This is one of the most interesting nature reserves of the area and an ideal place for lunch. Or perhaps visit neighbouring Atrani, the best-preserved town on the Amalfi Coast, with narrow little streets and a serene town square. (B)

Travel to Italy's east coast to Trani (approximately 4 hours), known as the 'Southern Pearl', a beautiful town with a sophisticated feel. Once an ancient trading hub, Trani is a delightfully eccentric port with a white cathedral perched on the seawall. The crescent-shaped marina is a great place to relax and watch the world go by. With the stunning seaside cathedral, medieval streets bathed in a rarefied light, and its own, sweet wine, Trani is truly like stepping back into a 1950s movie set. Upon arrival explore the historic centre and its medieval churches on a walking tour with a local guide. The old town points to a time when this was a major port for merchants travelling to the Near East. Later on simply kick back on the waterfront and watch the sophisticates of Puglia clink glasses of Moscato di Trani in cosy bars. (B)

Today is a free day to explore all that Trani has to offer. You might like to visit the dramatic Cattedrale di San Nicola Pellegrino, one of the most beautiful buildings in southern Italy. Begun in 1099, and taking over two centuries to finish, the soft white-pink limestone Norman cathedral is dedicated to the famously foolish St Nicholas the Pilgrim, whose bones lie in the crypt below the church. Inside, it is astonishingly bright and airy, and the simply furnished church is set off by the remains of a 12-century mosaic near the main altar. Outside, closer examination reveals lovely decorative details – look out for the elephant corbels.

You can also head to the castle built by Frederick II, who was the king of Sicily, Italy, Germany, Jerusalem and the Holy Roman Emperor in the 13th century. Maybe explore the medieval Jewish quarter, built in all-white stone, stopping by two fine synagogues along the way: the Scola Nova and the Scola Grande. Fishermen sell the day's catch right in the marina, so maybe taste the freshness by heading for dinner and a glass of wine harbourside. (B)

Head south and delight in the baroque architecture and atmosphere of Lecce (approximately 2.5 hours). Lecce's baroque ornamentation is elevated to dizzying heights, presenting the casual viewer with a feast for the senses. Sumptuous palazzi (mansions), a defensive main square, Roman ruins and magnificent allegories dancing across ornate facades make Lecce a swoon-worthy sight for any traveller. The university gives the town a lively feel, and there are little boutique, antique shops and delicious delis to explore. (B)

Today is a free day for you to explore Lecce. If open perhaps step beneath the city and see the restored Roman amphitheatre excavated in the 1930s. Built in the 2nd century AD, the remarkably intact horseshoe-shaped theatre seated 15,000 people. Overlooking the amphitheatre is the Colonna di Sant'Oronzo, a statue of Lecce's patron saint mounted upon a Roman column. Presented to Lecce from Brindisi, this column once stood at the terminus of the Via Appia that ran from Rome to Brindisi. The fascinating Basilica Di Santa Croce inspires varied reactions – its heavily decorated façade of sheep, dodos, cherubs and monsters is a cacophony to some, while others are drawn to the lavish brilliance. Building began in the 14th century, but it wasn't until the 17th century that the façade was created by artists under Giuseppe Zimbalo. The Renaissance interior is a nice contrast.

For another baroque experience head to the Piazza del Duomo. Used in the past as a defence against invaders, when residents would barricade the narrow entrances, the square's pleasant openness is bordered by a 12th-century cathedral, a 68 metre-high bell tower, a 15th-century Episcopal Palace and an 18th-century Seminario – sunglasses are essential on a sunny day to protect against the dazzle of the white stone. There are museums to browse, over 40 churches dotted around, and a castle to climb to look across the town. In the afternoon meet up with the group again for an aperitivo with local specialties, such as friselle, taralli, puccia, bombette and burrate. (B)

Travel by private transport to Ostuni and explore it's narrow streets before continuing to a local olive oil producer who will show you how the techniques have changed over the millennia. Some of the olive trees here are thought to be close to 3000 years old, and the farm has reputedly been active since Roman times. Your visit will also include an oil tasting. Next up is Alberobello (approximately 4 hours), set in a landscape of olive trees and low walls dotted with unique dwellings. People flock to Alberobello to marvel at the beehive-shaped trulli (singular trullo): small, dry-stone houses built from local limestone in the 14th century. The origins of the buildings are unclear, although its possible the mortar-less dwellings were created to be easily dismantled in a feudal tax-evasion scheme. Either way, the sight of the thick, gleaming walls capped with grey cones and topped with distinct, white, stubby spires is a unique and endearing Apulian experience.

Wander the old town quarter of Rione Monti, where thousands of trulli (and souvenir shops) rise up over the hill, or head over to Rione Aia Piccola and see trulli that are still family dwellings. See religious and mystical symbols on the roofs, the differently shaped spires, and head to the Church de Sant'Antonio, built in the style of a huge trullo. You'll spend the night in your own little bit of local history, staying in restored trulli that will make you feel like a true Alberobello resident. (B)

Transfer by private mini bus to Matera (approximately 1 hour). The extraordinary sight of Matera's old town gives a haunting, bittersweet insight into ancient life. One of the oldest cities in existence, Matera's otherworldly drawcard are the sassi (singular sasso) – stone houses formed from natural grottoes and tufo cliffs overlooking a dramatic gorge. Its resemblance to Jerusalem has attracted film directors of biblical epics, but its dark interiors were the scene of shameful poverty in the mid-20th century. Duck down into the sassi through the knot of staircases and alleyways that snake their way through the limestone ravines, and take a guided tour to appreciate both its ancient and modern history. With over 3,000 habitable caves, some dating as far back as the 8th century BC, the sassi are filled with stunning frescoed rock church complexes, exhibits recreating inhabited caves, and even a contemporary sculpture museum.

There is also an exhibit at the Casa-Grotta di Vico Solitario detailing the sassi's recent history as a place of gruelling poverty – when the city's population expanded uncontrollably, previously unoccupied (and unsuitable) grottoes filled with the poorest citizens, packed with children with high mortality rates. In the late 1950s the Italian government intervened and 15,000 inhabitants were forcibly relocated. The sassi are undergoing extensive restoration, and it's now the one place in the world where you can eat at a restaurant inside a 9,000 year-old dwelling! Tonight you'll stay in accommodation with balconies overlooking the sassi. (B)

This morning is free for you to further explore the narrow alleyways and caves of Matera, before boarding a local train to Bari at around lunch time (approximately 2 hours). Sitting on a small peninsula in the Adriatic Sea overlooking Greece, Bari is the prosperous capital of Puglia. The tangled streets of its old town, Bari Vecchia, conceal Romanesque churches, a riotous market, elegant medieval piazzas and a Swabian castle. The Basilica di San Nicola was built to hold the relics of St Nicholas, which were stolen from Turkey by local Bari fishermen and have made the city a place of pilgrimage since 1087. The relics are also the mainstay of Bari's biggest annual celebration, the Festa di San Nicola. The stone walls are wonderful to walk around, with the sea lapping on one side and the medieval town on the other, while at the end of the Lungomare promenade is great beach to lounge as your Southern Italian adventure comes to an end. Bari is also the perfect place to see out your last night on this trip and have a group meal by the harbour, sampling local limoncello and some of the seafood that the city is famous for. (B)

Your journey will come to an end after breakfast today and you are free to depart at any time. If you would like to extend your stay here we can be of assistance with additional accommodation, subject to availability. Please enquire at the time of booking. (B)