Panoramic evening cityscape of Polignano a Mare town, Puglia region, Italy, Europe.
Operated by Intrepid Travel

Premium Sicily and Italy in Depth

From
CAD 22,395
Duration
24 days
Countries
Italy
Activity
easy
Group size
Max 12

The adventure

Traverse from top to toe of Italy's 'boot' and explore ancient ruins and iconic sites. Eat your weight in pasta and tuck into giant piazzas as you get lost in Venice and find yourself in the Tuscan countryside. This 24-day trip will take you to all the best spots and teach you all the most important parts of Italian culture – like how to roll pasta like the pros! Visit Mount Etna, as you drive up the northern flank of the volcano and take a walk through the spectacular Valle del Bove. Visit a family-run winery, learn about ancient Pompeii, visit Rome’s famous sites and write home about your three amazing Feature Stays – all with a local leader by your side.

At a glance

Duration
24 days
Route
Palermo → Venice
Countries
Italy
Activity level
easy
Style
Culture & History
Group size
Max 12
Ages
15+
Flights
Not included
Solo travellers
Welcome

Day by day

View of a historic hilltop town surrounded by lush greenery under cloudy skies.
Your journey through

Italy

Day 1PalermoBongiorno! Welcome to Sicily. When you arrive in Palermo, you’ll be met by a local representative for your airport transfer into the city. Your adventure officially begins with a welcome meeting at 6 pm tonight to meet your fellow travellers and local leader. If you arrive early, you might like to get acquainted with the sights and sounds of the old heart of Palermo. Explore the main monuments like the uniquely styled cathedral, or cafe-hop to try the best of Sicily’s sweets. After your meeting tonight, you'll head out for a traditional Sicilian dinner as a group and get to know the city’s beloved cuisine at a great local restaurant.
Discover the vibrant skyline of Palermo, Sicily capturing historic architecture beneath a bright blue sky.Palermo
Bongiorno! Welcome to Sicily. When you arrive in Palermo, you’ll be met by a local representative for your airport transfer into the city. Your adventure officially begins with a welcome meeting at 6 pm tonight to meet your fellow travellers and local leader. If you arrive early, you might like to get acquainted with the sights and sounds of the old heart of Palermo. Explore the main monuments like the uniquely styled cathedral, or cafe-hop to try the best of Sicily’s sweets. After your meeting tonight, you'll head out for a traditional Sicilian dinner as a group and get to know the city’s beloved cuisine at a great local restaurant.
Map showing Palermo
Day 2PalermoEnjoy a free morning to see more of Palermo’s small alleyways and buzzing market squares. In the afternoon, join a walking tour with your local leader to see some of the symbolic places of rebellion and anti-Mafia racketeering like the Teatro Massimo, Cape Market, Piazza della Memoria and Beati Paoli Square. You’ll meet local shop owners who have had the courage to denounce their extortionists and follow the ethical consumer campaign ‘Pago chi non paga’ – a campaign promoted to support those that rebel against the Mafia. Then, delve deeper into the local cuisine and learn how to create Sicilian dishes with the help of a local chef. As locally sourced products are used, the menu may differ depending on seasonality and market availability, but whatever you make, you’ll tuck into for dinner with a glass of local wine.
Aerial shot of a historic piazza in Palermo, Italy with landmarks and urban architecture.Palermo
Enjoy a free morning to see more of Palermo’s small alleyways and buzzing market squares. In the afternoon, join a walking tour with your local leader to see some of the symbolic places of rebellion and anti-Mafia racketeering like the Teatro Massimo, Cape Market, Piazza della Memoria and Beati Paoli Square. You’ll meet local shop owners who have had the courage to denounce their extortionists and follow the ethical consumer campaign ‘Pago chi non paga’ – a campaign promoted to support those that rebel against the Mafia. Then, delve deeper into the local cuisine and learn how to create Sicilian dishes with the help of a local chef. As locally sourced products are used, the menu may differ depending on seasonality and market availability, but whatever you make, you’ll tuck into for dinner with a glass of local wine.
Map showing Palermo
Day 3MarsalaToday, it’s time to say goodbye to Palermo and head towards the small town of Erice. Located more than 750 m above sea level, this beautifully preserved medieval town showcases architectural styles from its varied history. When you arrive, you’ll head to a Genovesi tasting (traditional Sicilian pastries filled with custard or ricotta cream). After, take a cable car back down to the town of Trapani, then continue south towards Marsala – a coastal town where you’ll be staying tonight. Famous for its sweet dessert wines, you might like to use your free evening to go out and enjoy a sip (or two) or, you can simply stroll the marble paved streets as the sun sets.
Stunning view of a historic windmill at Trapani Salt Works, Sicily, with mirror-like reflections.Marsala
Today, it’s time to say goodbye to Palermo and head towards the small town of Erice. Located more than 750 m above sea level, this beautifully preserved medieval town showcases architectural styles from its varied history. When you arrive, you’ll head to a Genovesi tasting (traditional Sicilian pastries filled with custard or ricotta cream). After, take a cable car back down to the town of Trapani, then continue south towards Marsala – a coastal town where you’ll be staying tonight. Famous for its sweet dessert wines, you might like to use your free evening to go out and enjoy a sip (or two) or, you can simply stroll the marble paved streets as the sun sets.
Map showing Marsala
Day 4Mazara del Vallo – AgrigentoThis morning, head east as you stop in the old port of Mazara del Vallo. It’s here that some of the Arab influences in Sicily are most clearly visible. As you stroll through the kasbah (Arab Quarter) you’ll witness the artistic and cultural enrichment brought on by the arrival of Tunisian families in the 70s. Wander the winding lanes and alleyways lined with colourful murals, then continue to Agrigento, stopping at Scala dei Turchi (Stair of the Turks) on the way – this coastline with its white marble cliffs offered protection from the severe winds for the pirates that roamed these waters. Finally, make your way to Agrigento, where you’ll stay in a boutique hotel built in the 13th century and share a meal with your fellow travellers.
Stunning aerial view of a historic church dome amidst urban cityscape by the sea.Mazara del Vallo
This morning, head east as you stop in the old port of Mazara del Vallo. It’s here that some of the Arab influences in Sicily are most clearly visible. As you stroll through the kasbah (Arab Quarter) you’ll witness the artistic and cultural enrichment brought on by the arrival of Tunisian families in the 70s. Wander the winding lanes and alleyways lined with colourful murals, then continue to Agrigento, stopping at Scala dei Turchi (Stair of the Turks) on the way – this coastline with its white marble cliffs offered protection from the severe winds for the pirates that roamed these waters. Finally, make your way to Agrigento, where you’ll stay in a boutique hotel built in the 13th century and share a meal with your fellow travellers.
Map showing Mazara del Vallo
Day 5AgrigentoThis morning after breakfast, travel to the nearby Valley of the Temples. One of the largest archaeological sites in the world, this is where the ancient city of Akragas once stood. Your local guide will bring this classical Greek site to life as you visit the temples of Hera, Herakles, Zeus and Castor and Pollux. Along the way, enjoy views of the landscape and Mediterranean Sea. Return to Agrigento and enjoy a free afternoon. Maybe head to Agrigento's Old Town and wander the narrow alleyways and courtyards or find a local cafe, grab a panino and sit and watch the world go by.
Explore the ancient Temple of Concordia, a classical architectural marvel in Agrigento, Sicily.Agrigento
This morning after breakfast, travel to the nearby Valley of the Temples. One of the largest archaeological sites in the world, this is where the ancient city of Akragas once stood. Your local guide will bring this classical Greek site to life as you visit the temples of Hera, Herakles, Zeus and Castor and Pollux. Along the way, enjoy views of the landscape and Mediterranean Sea. Return to Agrigento and enjoy a free afternoon. Maybe head to Agrigento's Old Town and wander the narrow alleyways and courtyards or find a local cafe, grab a panino and sit and watch the world go by.
Map showing Agrigento
Day 6Modica – Noto – SiracusaToday, say goodbye to Agrigento and hit the road to Siracusa. Along the way, you’ll stop in Ragusa – one of the most scenic towns in all of Sicily. Explore the town and then continue to Modica, which is particularly famous for its chocolate. After tasting some of the local produce, continue to Noto and get acquainted with the city on a guided walking tour. Lesser-known Noto has recently gained a reputation as an architectural jewel and its limestone structures sparkle on a sunlit afternoon. Finally, arrive in Siracusa, where you’ll stay for the next two nights.
Stunning view of the Baroque Cathedral in Modica, Sicily, showcasing intricate neoclassical architecture.Modica
Today, say goodbye to Agrigento and hit the road to Siracusa. Along the way, you’ll stop in Ragusa – one of the most scenic towns in all of Sicily. Explore the town and then continue to Modica, which is particularly famous for its chocolate. After tasting some of the local produce, continue to Noto and get acquainted with the city on a guided walking tour. Lesser-known Noto has recently gained a reputation as an architectural jewel and its limestone structures sparkle on a sunlit afternoon. Finally, arrive in Siracusa, where you’ll stay for the next two nights.
Map showing Modica
Day 7SiracusaThis morning, head out on an orientation walk through Ortigia – a small island just adjacent to the main town of Siracusa. Wandering the narrow streets and laneways will reveal ancient ruins, fountains and trattorias. Return to Siracusa in the afternoon and enjoy a free afternoon to explore. You might like to head to the Greek theatre, Roman amphitheatre and ancient stone quarries of the Neapolis Archaeological Site, see more of the Siracusa town or simply relax at your accommodation.
Scenic view of Ortigia's coastline in Sicily with historical stone buildings against clear blue waters.Siracusa
This morning, head out on an orientation walk through Ortigia – a small island just adjacent to the main town of Siracusa. Wandering the narrow streets and laneways will reveal ancient ruins, fountains and trattorias. Return to Siracusa in the afternoon and enjoy a free afternoon to explore. You might like to head to the Greek theatre, Roman amphitheatre and ancient stone quarries of the Neapolis Archaeological Site, see more of the Siracusa town or simply relax at your accommodation.
Map showing Siracusa
Day 8Mt Etna – CataniaToday, come face-to-face with Europe’s largest active volcano on a daytrip up Mt Etna. At an altitude of approximately 2000 m, you’ll walk into the centre of an extinct crater and visit a lava cave that can be explored with helmets and torches. Walk among the cold lava streams of Piano Provenzana – a former ski resort that has been destroyed during the last big eruption of 2002. After exploring this fiery natural wonder, continue to Catania. The city has a unique energy – an interesting blend of young and old. This afternoon, you’ll get the opportunity to explore both sides of the city by wandering through its grand piazzas and wide roads.
A scenic view of Mount Etna's volcanic terrain in Sicily, featuring red soil and scattered vegetation.Mt Etna
Today, come face-to-face with Europe’s largest active volcano on a daytrip up Mt Etna. At an altitude of approximately 2000 m, you’ll walk into the centre of an extinct crater and visit a lava cave that can be explored with helmets and torches. Walk among the cold lava streams of Piano Provenzana – a former ski resort that has been destroyed during the last big eruption of 2002. After exploring this fiery natural wonder, continue to Catania. The city has a unique energy – an interesting blend of young and old. This afternoon, you’ll get the opportunity to explore both sides of the city by wandering through its grand piazzas and wide roads.
Day 9Taormina – CataniaAfter breakfast today, take a daytrip to the city of Taormina. Start things off with a guided walk, where you’ll notice Greek influence in the architecture. Walk through the back streets, gardens and the world-famous Greek theatre and cathedral. The afternoon is free, so there's plenty of time to explore at your own pace. Have a drink in the Mediterranean sun or dig into some traditional Sicilian pasta before heading back for your final night in Catania. This evening, enjoy a farewell dinner at a local restaurant with your newfound travel friends and group leader.
Scenic aerial view of Taormina, Sicily, showcasing vibrant buildings and lush greenery.Taormina
After breakfast today, take a daytrip to the city of Taormina. Start things off with a guided walk, where you’ll notice Greek influence in the architecture. Walk through the back streets, gardens and the world-famous Greek theatre and cathedral. The afternoon is free, so there's plenty of time to explore at your own pace. Have a drink in the Mediterranean sun or dig into some traditional Sicilian pasta before heading back for your final night in Catania. This evening, enjoy a farewell dinner at a local restaurant with your newfound travel friends and group leader.
Map showing Taormina
Day 10BariCatch an unescorted flight to the coastal city of Bari to begin the next stage of your Italian adventure in Puglia. When you arrive, you’ll be met at the airport and transferred to your hotel. You’ll have another welcome meeting at 6 pm tonight to meet your new local leader and fellow travellers. If you arrive early, why not wander the maze-like 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 new group over an included dinner, where your local leader will introduce you to Puglia’s cuisine.
A stunning drone shot of a lighthouse in an urban coastal cityscape under a clear blue sky.Bari
Catch an unescorted flight to the coastal city of Bari to begin the next stage of your Italian adventure in Puglia. When you arrive, you’ll be met at the airport and transferred to your hotel. You’ll have another welcome meeting at 6 pm tonight to meet your new local leader and fellow travellers. If you arrive early, why not wander the maze-like 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 new group over an included dinner, where your local leader will introduce you to Puglia’s cuisine.
Map showing Bari
Day 11BariLeave the coastline behind as you travel inland by private vehicle to the little town of Alberobello. Set among a tranquil landscape of olive groves, the town is famed for its unique beehive-shaped trulli (dwellings built from limestone in the 14th century). While the origins of the buildings are unclear, one theory suggests the houses were created to be easily dismantled in a feudal tax evasion scheme. Whatever their purpose, the buildings make the Apulia region unlike anywhere else in the world. Join a local guide for an insider’s look at the town, wandering through the Old Town quarter of Rione Monti, dotted with thousands of trulli, and Rione Aia Piccola. Your guide will point out the different shapes of spires and the religious symbols adorning the roofs. Finally, see the Church de Sant’Antonio – a huge cathedral built in the trulli style. You’ll then visit Polignano a Mare to explore another gorgeous coastal town popular for its beaches, rugged cliffside dwellings and bright turquoise waters. Tonight, you’re free back in Bari to find some dinner.
A breathtaking drone capture of a coastal city with a bustling harbor, showcasing beautiful architecture and sea.Bari
Leave the coastline behind as you travel inland by private vehicle to the little town of Alberobello. Set among a tranquil landscape of olive groves, the town is famed for its unique beehive-shaped trulli (dwellings built from limestone in the 14th century). While the origins of the buildings are unclear, one theory suggests the houses were created to be easily dismantled in a feudal tax evasion scheme. Whatever their purpose, the buildings make the Apulia region unlike anywhere else in the world. Join a local guide for an insider’s look at the town, wandering through the Old Town quarter of Rione Monti, dotted with thousands of trulli, and Rione Aia Piccola. Your guide will point out the different shapes of spires and the religious symbols adorning the roofs. Finally, see the Church de Sant’Antonio – a huge cathedral built in the trulli style. You’ll then visit Polignano a Mare to explore another gorgeous coastal town popular for its beaches, rugged cliffside dwellings and bright turquoise waters. Tonight, you’re free back in Bari to find some dinner.
Map showing Bari
Day 12NardoThis 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 enjoy 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 on-site restaurant offering Salento dishes and a panoramic view from the terrace.
Stunning aerial view of Terracina, Italy, showcasing its coastline, cityscape, and Mediterranean Sea.Nardo
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 enjoy 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 on-site restaurant offering Salento dishes and a panoramic view from the terrace.
Map showing Nardo
Day 13NardoBefore breakfast, you may like to take a walk through your Feature Stay’s historic ‘secret garden’ where it seems as if figures from days gone by could walk around the corner at any minute. Today 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. You’ll also have some free time to explore this historic city on your own before heading back to Nardo. Later this afternoon, join your group for a cooking class on traditional Puglia regional cuisine.
Stunning aerial capture of Terracina, Italy showcasing beach, city, and coastline.Nardo
Before breakfast, you may like to take a walk through your Feature Stay’s historic ‘secret garden’ where it seems as if figures from days gone by could walk around the corner at any minute. Today 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. You’ll also have some free time to explore this historic city on your own before heading back to Nardo. Later this afternoon, join your group for a cooking class on traditional Puglia regional cuisine.
Map showing Nardo
Day 14MateraEnjoy 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 some 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.
Aerial view of the ancient stone buildings in Matera, showcasing historic Italian architecture.Matera
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 some 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.
Map showing Matera
Day 15MateraToday, 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.
A scenic view of the ancient stone cityscape in Matera, Italy, under clear skies.Matera
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.
Map showing Matera
Day 16NaplesBegin 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 79 AD. 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 created 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.
A vibrant aerial view of Naples's diverse architecture, capturing the city's essence.Naples
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 79 AD. 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 created 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.
Map showing Naples
Picturesque village by the lake with misty mountains and charming architecture on a cloudy day.
Your journey through

Austria

Day 17RomeThis morning, you will catch a train to Italy's iconic capital city, Rome. If you arrive early maybe grab an espresso and hit the streets. This portion of your adventure begins with a meeting at 6 pm, where you’ll meet your new local leader and fellow travellers. When the formalities are out of the way, get your first taste of Italy with an included dinner at a local restaurant.
The Colosseum stands majestically amidst bustling Rome, an iconic remnant of ancient architecture.Rome
This morning, you will catch a train to Italy's iconic capital city, Rome. If you arrive early maybe grab an espresso and hit the streets. This portion of your adventure begins with a meeting at 6 pm, where you’ll meet your new local leader and fellow travellers. When the formalities are out of the way, get your first taste of Italy with an included dinner at a local restaurant.
Map showing Rome
Day 18RomeFrom ancient monuments to romantic restaurants, Rome is a city of great beauty and diversity. Today, join a private guide for a trip to the Spanish steps, the Trevi Fountain, the Piazza Navona and inside the Pantheon before reaching 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.
Captivating wide-angle shot of Rome's iconic Colosseum with a serene sunset backdrop.Rome
From ancient monuments to romantic restaurants, Rome is a city of great beauty and diversity. Today, join a private guide for a trip to the Spanish steps, the Trevi Fountain, the Piazza Navona and inside the Pantheon before reaching 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.
Map showing Rome
Picturesque landscape of Lake Garda with a distant island under a summer sky.
Your journey through

Italy

Day 19Siena / Monteriggioni / San Gimignano RegionToday you’ll take a private vehicle to the city of Siena, where your leader will show you the most interesting sights 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. Next, visit 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 geatures an outdoor pool and an on-site restaurant. Tonight, indulge in an included gourmet dinner made with local ingredients that pays homage to traditional Tuscan dishes, with a modern twist.
Siena Cathedral with its iconic striped bell tower and dome on a sunny day.Siena
Today you’ll take a private vehicle to the city of Siena, where your leader will show you the most interesting sights 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. Next, visit 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 geatures an outdoor pool and an on-site restaurant. Tonight, indulge in an included gourmet dinner made with local ingredients that pays homage to traditional Tuscan dishes, with a modern twist.
Map showing Siena
Day 20San Gimignano RegionStart the day with a visit to 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. Return to your Feature Stay accommodation for another delicious dinner.
Captivating aerial view of San Gimignano's historic towers lit up at night, Italy.San Gimignano Region
Start the day with a visit to 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. Return to your Feature Stay accommodation for another delicious dinner.
Map showing San Gimignano Region
Scenic view of a tranquil village surrounded by lush greenery in Bornel, France.
Your journey through

France

Day 21Pisa / Lucca / FlorenceToday 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 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.
Explore the beautiful Pisa Cathedral in Italy bathed in warm daylight, showcasing its architectural grandeur.Pisa
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 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.
Map showing Pisa
Stunning aerial view of the rugged Alpine mountains near Salzburg, Austria.
Your journey through

Austria

Day 22FlorenceThis 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. Visiting the Uffizi 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.
Beautiful nighttime scenery of Florence's Arno River with illuminated buildings and bridge reflections.Florence
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. Visiting the Uffizi 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.
Map showing Florence
Day 23VeniceIn the morning, head to the railway station and take a high-speed train to Venice. When you arrive, your leader will take you on an orientation walk 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 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.
A picturesque scene of a boat navigating a Venetian canal with rustic, historic buildings and a small bridge.Venice
In the morning, head to the railway station and take a high-speed train to Venice. When you arrive, your leader will take you on an orientation walk 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 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.
Map showing Venice
Day 24VeniceWith 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.
Discover the charm of Venice's canals, offering a glimpse of historic architecture and tranquil waterways.Venice
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.
Map showing Venice

Discover Italy

A glimpse of the destination you'll explore.

Picturesque landscape of Lake Garda with a distant island under a summer sky.
Overcast day in Tuscan hills featuring cypress trees and traditional stone house.
A picturesque town nestled by cliffs on the Amalfi Coast, Italy.
Picturesque view of Tuscany's rolling hills, vineyards, and Italian villas under a clear summer sky.
Beautiful view of Ponte Sant'Angelo spanning the Tiber River in Rome, Italy under a clear sky.

Upcoming departures

DatesPrice / personAvailability
27 Aug 202619 Sep 2026CAD 26,695Only a few spotsBook my trip
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