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Benvenuto! Welcome to Puglia – the heel of Italy’s boot. Your adventure kicks off in the coastal city of Bari, where you’ll be met at the airport and transferred to your hotel. You’ll have a welcome meeting at 6 pm tonight to meet your local leader and fellow travellers joining you on your adventure. If you arrive early, why not wander the mazelike Old Town or see the 11th-century Basilica di San Nicola – a key pilgrimage site that holds some of St Nicholas’ remains. You could also pop into a local cornetteria for a decadent Italian croissant. After your meeting, get to know your group over an included dinner, where your local leader will introduce you to Puglia’s cuisine.

Leave the coastline behind as you travel inland by private vehicle to the little town of Alberobello. Set among a landscape of olive groves, the town is famed for its unique beehive-shaped trulli (dwellings built from limestone in the 14th century). Join a local guide for an inside look at the town, wandering through the Old Town quarter of Rione Monti, dotted with thousands of trulli and Rione Aia Piccola. Then, see the Church de Sant’Antonio – a huge cathedral built in the trulli style. For lunch, you’ll join a local woman in an authentic trullo for a cooking demonstration. Watch and learn as she prepares an Apulian meal with ingredients from the local market or masseria (historic agricultural estate). Focaccia, orecchiette (a pasta shape typical of the Apulia region) and bombette (thinly sliced meat rolled up and stuffed with garlic, cheese and parsley) are some of the regional delights that could be on today’s menu. You’ll then visit Polignano a Mare, another gorgeous coastal town popular for its beaches and rugged cliffside dwellings. Return to Bari in the late afternoon, then your trip leader will take you on an orientation walk to help you get your bearings in the city. Discover key landmarks, local eateries and hidden spots you may want to explore during your free evening. The rest of the night is yours to enjoy.

This morning, visit a local olive oil producer on a farm that’s been active since Roman times. You’ll learn how production techniques have changed over the centuries, taste some of the olive oil for yourself and have an included lunch of regional favourites. Then, visit the small city of Ostuni and explore its whitewashed streets flanked with Gothic, Romanesque and Byzantine buildings. From here, travel to the quiet town of Nardo and join an expert local guide for a walking tour through the Old Town, where there are more than a dozen grand palazzos. Tonight, settle into your Feature Stay accommodation – three 13th-century Baronial Palaces, once home to aristocracy from the Kingdom of Naples, which have been converted into a hotel by a local architect. Spend the evening exploring the palaces and grounds that feature artwork and sculptures by local artists. In Palazzo Mignano, you’ll find an excellent onsite restaurant offering Salento cuisine and a panoramic view from the terrace.

Before breakfast, you may like to take a leisurely walk through your Feature Stay’s historic ‘secret garden’. Today, you’ll head to the beautiful city of Lecce. With its ornate baroque buildings, lively university and ancient Roman ruins, Lecce’s narrow streets are a delight to explore. Let a local guide show you hidden corners and share the city’s history with you this morning, ending your guided tour with an aperitivo – the perfect chance to pause and watch local life go by. You’ll also have some free time to explore this historic city on your own before heading back to Nardo. Later this afternoon, you’ll take a private boat trip from Santa Caterina di Nardo to Porto Selvaggio Regional Park. Trace the rocky coastline, taking in views of the Ionian Sea, and explore the pine forest-lined beaches of the Regional Park. Along the way, you’ll make a few stops for swimming and snorkelling (snorkelling gear will be provided). You’ll also pass the sea caves, filled with deep, rippling waters.

Enjoy a final morning at your Feature Stay hotel, sitting back with a coffee and soaking up the scenery. Then, it’s time to say goodbye and travel to Matera – an ancient city on a rocky outcrop. Along the way, stop at a local winery for a wine tasting and lunch before continuing to Matera. Matera is believed to be the third-longest continuously inhabited human settlement in the world. You’ll be exploring the city’s famous sassi houses in depth tomorrow, so this evening, why not take a walk around Matera to discover its churches, traditional restaurants and thousands of years of human history.

Today, dive into Matera’s Old Town, made famous by sassi – more than 3000 stone houses formed from natural grottoes and tufo cliffs, some dating back as far as the 8th century. Join a local guide who will lead you through a labyrinth of staircases and alleyways that cut their way through limestone ravines, dipping in and out of ancient sassi houses as you go. Up until the late 1950s, the sassi were considered the ‘Shame of Italy’ due to the gruelling living conditions and poverty suffered by those who lived here – a result of the city’s rapid population growth. The Italian government intervened, and 15,000 inhabitants were forcibly relocated. Today, the sassi are undergoing extensive restoration, with some dwellings featuring exhibits that recreate inhabited caves. You’ll also visit an ancient underground neighbourhood, made up of houses, streets, cisterns and churches.

Begin the day by driving to the storied town of Pompeii, home to one of Europe’s most well-known archaeological sites – the ruins of Pompeii, caused by the eruption of Mt Vesuvius in AD79. Join a local guide to discover the remains of this once thriving Roman trading centre. After the eruption, the city was covered in a layer of ash and remained undisturbed until the 18th century, when the ruins were rediscovered. Walk among well-preserved villas, temples, theatres, markets and chariot-marked streets as your expert guide helps you to imagine what life here once looked like. You can also visit the Roman Forum and basilica, temples, public baths and the tiny Odeon built for music recitals. Later in the day, travel to the buzzing city of Naples where you’ll join your group for a final dinner and a chance to look back on all you’ve seen on your journey.

This morning, catch a train to Italy’s iconic capital city, Rome. If you arrive early, maybe grab an espresso and hit the streets for a self-guided walking tour. The second half of your adventure begins with another welcome meeting at 6 pm tonight, where you’ll meet your local leader and the new travellers joining you. When the formalities are out of the way, head to dinner at a local restaurant and get to know each other better over some delicious Italian cuisine.

Today, join a private guide for a trip to the Spanish Steps, the Trevi Fountain, the Piazza Navona and inside the Pantheon. Make your way to Campo de Fiori, where a local fresh produce market has been held since 1869. Join your leader for a quick stop at a local bar for a granita (an iced Italian espresso), then have lunch at a classic local restaurant that’s frequented by Romans. In the afternoon, take a guided tour of the Colosseum – one of the Seven Wonders of the World. Then, the evening is free for you to explore at your own pace.

Start your day with an early-access visit to the Vatican Museums with a local guide. You’ll get there well before everyone else, offering a much quieter experience in the Sistine Chapel. After you’ve taken it all in, you’ll head to Monteriggioni – a medieval walled town with over a dozen towers once used to defend Sienese territory from the Florentines. You’ll have time to explore this tiny hilltop spot before arriving at your Feature Stay accommodation near San Gimignano. This country hotel with views of a tree-studded landscape features an outdoor pool and an onsite restaurant. Tonight, indulge in an included gourmet dinner made with local ingredients that pays homage to traditional Tuscan dishes, with a modern twist.

Start the day in San Gimignano – the ‘Town of Fine Towers.’ Explore the medieval Old Town centre and its Gothic and Romanesque architecture with your leader. This region is also renowned for its ancient Vernaccia grapes, which are the basis for one of Tuscany’s finest white wines. Your group will visit a local agriturismo, where you’ll explore the vineyards and sample some of their celebrated wine before enjoying an included lunch featuring regional cheese, fine olive oil and bruschetta. Then, take a private vehicle to the city of Siena, where your leader will show you the most interesting sites on an orientation walk. At the city’s heart is Piazza del Campo – home to the biannual Palio horse race and nearby the Siena Cathedral. Return to your Feature Stay accommodation for another delicious dinner.

Today you’ll visit Pisa. It’s not always possible to climb the Leaning Tower of Pisa due to its precarious state, but as your leader shares the history of this legendary building, you’ll have the opportunity to take a photo from the ground. Your next stop is historic Lucca – one of Italy’s most beautiful but underrated cities – where you’ll take a short walk with a local expert guide along the city’s beautifully preserved Renaissance walls. From here, you’ll take the short journey to Florence where the evening is yours to walk the cobbled streets, eat gelato and soak up the unmistakenly Tuscan atmosphere.

This morning, join a private guided walk of Florence, including a visit to the Galleria dell’Accademia – an art museum renowned for its collection of sculptures, including the iconic statue of David by Michelangelo. You then have a free afternoon to explore at your own pace. Perhaps you’ll visit the Uffizi, which is highly recommended, as it’s one of the oldest galleries in the world. Maybe head to Piazzale Michelangelo for sweeping views of Florence’s timeless skyline and sample some of the culinary delicacies on offer from across Tuscany, with dishes known for their freshness, simplicity and quality. Olive oil, beans and herbs are a feature here.

In the morning, head to the railway station and take a high-speed train to Venice. When you arrive, take an orientation walk with your leader so you can get acquainted with the city’s maze of canals and learn about its unique history. Then, make your way to Palazzo Pisani, which was once home to one of the most powerful Venetian dynasties and now houses the Music Conservatory of Venice. You can also take the stairs to the rooftop for a spectacular aerial view of the city. Venice is renowned for its glass, so end the walk with a visit to a glass-blowing factory to learn about the art of its production. The rest of the afternoon is yours to explore before joining back up with your group in the evening for a Venetian dinner.

With no activities planned for today, your trip comes to an end after breakfast. If you’d like to extend your stay, just speak to your booking agent to arrange additional accommodation.