The Italian Affair 2024/2025

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1-888-597-3519

905-639-9954

dhtour@dhtour.ca

13 Days / 12 Nights
Availability : April to November
Start: Milan, Italy
End: Rome, Italy

The Italian Affair: 1 nt La Spezia, 2 nts Florence, 2 nts Montepulciano, 2 nts Rome, 1 nt Ariano, 2 nts Lecce, 2 nts Salerno

Italy’s influence is immense.

Markets around the world sell their designer clothing, Renaissance art is found in millions of galleries, and pizza is delivered to almost every street you’ve walked upon.

But on this trip, you forget about the imitations and discover the originals.

You get as close to the Ancient Romans as possible in Pompeii, the city frozen in time; see the inspirations of Michelangelo and da Vinci in Tuscany, and amble through luscious coastlines and mountain-studded landscapes awash with folklore and myths.

Join this journey and discover how this boot-shaped country changed the world.

13 DAYS / 12 NIGHTS / MAX 16 GUESTS

Contact DHTour at 1-888-597-3519 or 905-639-9954 or dhtour@dhtour.ca to book this small group tour The Italian Affair.

Tour Details
Places you explore

Cinque Terre – Imagine five pastel-hued villages perched on the rugged coast surrounded by terraced cliffs and clear deep blue water. It’s Bella Italia at its finest

Pisa – A legendary city with the iconic architectural duo: the spectacular Romanesque Cathedral and the famous leaning tower

Florence – Marvel at the finest collection of Italian Renaissance art and architecture in this fine city

Val d’Orcia – Bucolic Tuscan hills dotted with cypress trees, olive groves and vineyards

Pompeii – Ponder over the everyday life of the Ancient Romans as you stroll through the city that froze in time

Salento Peninsula – The heel of Italy will steal your heart with the turquoise bays of Otranto and Santa Maria di Leuca

Amalfi Coast – Pastel-coloured houses, steep cliffs, azure seas, lemon groves and a lot of glamour: Feel La Dolce Vita at its finest

Mount Vesuvius – Vesuvius may be tame now, but this infamous volcano reshaped the ancient world

Pick Up Location & TIme

Milan  (Google Map)
8:30am – Starhotels Business Palace, Via Privata Pietro Gaggia, 3, 20139 Milano MI, Italy

* If your tours departs on and after 1st April 2025, you will depart from hotel AC SESTO 4*, Milan. (Google Maps)

Drop off Location & Time

Rome  (Google Map)
6:30pm – Hotel American Palace, Via Laurentina, 554, 00143 Roma RM, Italy

Price Includes

  • 12 nights 3/4 star hotel accommodation
  • Daily breakfasts
  • Transport in a 16 seat Mercedes mini-coach
  • Air conditioning as standard
  • The stories and services of an English-speaking driver-guide
  • Train to Cinque Terre as part of the Cinque Terre Card
  • Wine tasting and tour
  • Entrance to Montecassino Abbey
  • Entrance to Vesuvio Volcano Crater
  • Entrance to Pompeii Archaeological Site
  • Ferry ticket for Positano to Amalfi and Amalfi to Salerno

Meals

  • 12 breakfasts
  • 0 lunches
  • 0 dinners
  • 0 teas

Price Excludes

  • Entry fees to visitor attractions/Optional Activities
  • Airfare
  • Transfers
  • Pre / Post hotel nights
  • Driver / Tour Leader gratuity is at your discretion
  • Travel Insurance
What to Expect

Explore in 16 seat mini-coaches, always taking the scenic route, you have great views through large windows, and you’re free to sample the local tipple without worrying about driving. Our driver-guides are famous for their knowledge, facts, quirky stories, history, and fairy-tales. They truly take you beyond the guidebooks and into your adventure. You make your trip your own. We provide the timetable; and you can choose where you want to eat and which attractions you pay to see. So, if you want to skip a castle and read your book by a mountain view, you can.

A good night’s sleep is often needed for a good day of travel. So we’ve hand-picked three-star to four-star hotels in remote coastal villages, bustling towns, and mountain valleys. Your accommodation is included in the tour price.

Most people can comfortably enjoy our tours, but it’s worth bearing in mind that we often include optional short walks in scenic locations. Please also be aware that many of the old European towns are built on steep hills with cobbled lanes, and you may have to carry your own luggage at times.

We’ve arranged experiences for you on your tour. The ‘included activities’ are already booked and paid for as part of your trip, whereas you can purchase ‘optional activities’ while on your tour. You also have free time in many destinations to pick and choose which attractions you visit.

Pack comfortable shoes for walks up to beautiful views. Carry swimwear and a towel for swimming spots. Your holiday’s more fun when you protect yourself from the sun.

Itinerary
The Italian Affair

Day 1Milan - Cinque Terre villages - La Spezia

  • Savour local Italian specialities
  • Spend the afternoon and evening in the stunning pastel-hued villages of Cinque Terre

We leave Milan and head for La Spezia, port town and gateway to the beautiful Cinque Terre. After checking in to your hotel for the night, your guide accompanies you on the short train journey to the first of the seaside towns. From there, you can roam free for the remainder of the afternoon and evening.

Each town has a unique character, so you decide what you’re in a mood for. If you want to see beaches and a seafront promenade, head to Monterosso. Wine lovers should explore Manarola and savour its local wine. And if you want to visit a hamlet with great views, choose one of this fantastic trio: Riomaggiore, Vernazza or Corniglia.

After exploring the Cinque Terre villages, you get on the train back to La Spezia, your base for the night.

Included Activities: Train to Cinque Terre as part of the Cinque Terre Card

Accommodation: Hotel CDH La Spezia or similar, La Spezia

Day 2La Spezia - Pietrasanta - Pisa - Lucca - Florence

  • Pose for that classic photo with the iconic Leaning Tower of Pisa
  • Be impressed with Lucca’s impeccably preserved city walls

Buongiorno! Today is all about discovering the architectural wonders of Northern Italy.

You leave La Spezia in the morning and stop in Pietrasanta where Michelangelo picked out the best marble for his sculptures.

We then travel to Pisa where you can explore the city for a couple of hours. Once a maritime power competing with Genoa and Venice, this city is now famous worldwide for an architectural project which went horribly wrong. Tilting or not, the Leaning Tower of Pisa has beautiful, elaborate Romanesque architecture and fascinating history. Grab your lunch and take in the views of other architectural highlights at Campo dei Miracoli (Field of Miracles).

Next on the list of our Italian delights is Lucca, famous for its completely preserved city walls. Originally founded by the Etruscans, then a Roman colony, the city has gained its wealth through the silk trade. You can see this prosperity in the abundance of graceful buildings and pretty piazzas. With a couple of hours of free time, you can wander along the city walls before you continue your journey further.

All these impressive architectural gems of the day were just a warm-up. Prepare yourself for a real feast for the eyes as you travel to Florence, your base for the next two nights. (B)

Accommodation: B&B Hotel Firenze Laurus al Duomo, or similar, Florence

Day 3Florence

  • Marvel at Florence’s Renaissance masterpieces in the city’s grand galleries
  • Stare in awe at the ornate details of Florence Cathedral

You have a free day in the ‘Birthplace of the Renaissance’ and can decide how you want to spend it.

You can start by following the paths of Leonardo, Michelangelo, Dante and Galileo – stare in awe at the Duomo, the city’s majestic Cathedral that dominates the skyline; see The Birth of Venus and some of the most celebrated treasures at the Uffizi Gallery; and visit Galleria dell’Accademia, to admire Michelangelo’s masterpiece, David.

Man does not live by art alone, so don’t forget to try some of the local specialities. The culinary delights like handmade pasta, pizza, pastries, wine and gelato will help you to regain your strength.

In the afternoon, you could ponder over the Medici’s power and secrets and explore Palazzo Pitti. The grand palace of this influential family is home to some of the greatest treasures of the Renaissance.

For a perfect end to the day, you can visit Boboli Gardens peppered with statues, fountains, ponds and hidden mazes. It’s your second night in Florence so spend the evening soaking up the atmosphere as you explore the bustling squares or excellent restaurants and bars. (B)

* As this is a free day, we would recommend that you book any attractions you are interested in visiting before you depart, to save time and avoid queues

Accommodation: B&B Hotel Firenze Laurus al Duomo, or similar, Florence

Day 4Florence - San Gimignano - Siena - Montepulciano

  • Explore San Gimignano, the city of soaring towers in Tuscany
  • Enjoy your lunch at Siena’s unique Piazza del Campo

It’s time to wave Florence goodbye to go discover the spectacular medieval hill-towns of Tuscany.

As you travel over the green hills of the famous Chianti wine region, you notice the 14 towers of San Gimignano soaring like a medieval Manhattan. Listen to the story of the noble families who got caught up in a race to build the highest tower house. Then enjoy a walk around the well-preserved fortified old centre and sample some of the local delicacies for lunch.

You continue south to Siena, the highlight of the day. This gorgeous red-brick city celebrates Gothic architecture like no one else. The place’s essence centres around the unique shell-shaped Piazza del Campo. It’s here where the bi-annual horse race ‘Palio di Siena’ is hosted. And it’s also where James Bond madly chases his enemy in ‘Quantum of Solace’.

Next, you travel along the country roads, past cypress trees and olive groves to arrive in Montepulciano in the early evening. This hilltop town in rural Tuscany is your home for two nights. (B)

Accommodation: Albergo San Biagio or similar, Montepulciano

Day 5Montepulciano - Pienza - Bagno Vignoni - Montepulciano

  • Stare in wonder at the revolutionary vision of urban space in Pienza
  • Savour Brunello, the famous red wine, in the place it’s bottled

Today you explore the dreamy Tuscan region of Val d’Orcia where time seems to slow down. This area boasts unspoiled beauty and is steeped in history and culture. No wonder it has been declared a UNESCO heritage site.

Start the day exploring Montepulciano on your own before travelling to Pienza. This jewel of urban planning is known as the ‘Ideal City’ and is the fruit of Pope Pius II‘s Renaissance vision. Call it vain or forward-thinking, but in the 15th century the Pope set about transforming his birthplace. And the results are so stunning that UNESCO designated Pienza as a world heritage site.

Then it’s time to try some of the best wines in the world on an included visit to Solaria Winery in Montalcino. This is the home of Brunello, the famous red wine made of a special grape variety with protected status.

We finish today’s exploration of the Val d’Orcia with a visit to Bagno Vignoni, a village renowned for its curative waters. The Etruscans, Romans, pilgrims of the Via Francigena, and the Medici appreciated the hot sulphurous waters here in the past. Today, you can admire this ancient spa and follow the flow of the spring waters across the archaeological park.

After experiencing and savouring the best of rural Tuscany, you arrive in Montepulciano in the early evening for your second night. (B)

Included Activities: Wine tasting and tour 

Accommodation: Albergo San Biagio or similar, Montepulciano

Day 6Montepulciano - Sorano - Sovana - Capodimonte - Rome

  • Travel through the marvelous Maremma region, the home to the mysterious Etruscans
  • Visit the Etruscan Necropolis of Sovana and the Vie Cave

You leave Tuscany in the morning and travel south to the Maremma region. Here, you can get up close to the Etruscan civilisation at the Sovana Necropolis and the Vie Cave. This site forms an impressive road network carved out of tuff during the Bronze Age. Then, you visit Sovana, where you can grab something to eat and absorb the atmosphere of this medieval town before you continue your adventure.

In the afternoon, you continue your journey Capodimonte. This small town is situated on the bank of Bolsena Lake, the largest volcanic lake in Italy. It’s your final comfort stop, so enjoy the charms of this little hamlet before your journey to Rome.

*Please note: This Italian Affair  tour is a combination of two tours: Cinque Terre, Florence & The Flavours of Italy, and Pompeii, The Amalfi Coast & Irresistible Italy. Today you finish the first part. 

Optional Activities: Entrance to the Etruscan Necropolis & Vie Cave

Accommodation: Hotel American Palace or similar, Rome

Day 7Rome

  • Ponder over the past glory of Ancient Rome in the Colosseum
  • Enjoy a gelato by the lavish Trevi Fountain

Haunting ruins, awe-inspiring art, and vibrant street life. This is Rome, the Eternal City.

You have a free day to discover the delights of the city. Why not make the most of your time here and jump on the hop-on hop-off bus?

You can also get a map and follow the trail of the icons of Rome’s heyday. There’s the huge Colosseum; the architecture of the Pantheon; and the Roman Forum, the centre of the religious, political, and social activities.

Once you’ve had a glimpse into the past, focus on the current culinary scene and grab an alfresco table on one of many elegant piazzas. Sit down, relax, and get your taste buds ready for the local delicacies.

Then, you can soak up the atmosphere of this fascinating city. Stroll along the Tiber River and snap photos of the beautiful Castle Saint Angelo, count the legendary Spanish Steps, and unwind with a tasty gelato by the dazzling Trevi Fountain. Toss a coin into the water to make sure you’ll return here and start getting excited for the next part of your tour. (B)

*Please note: This is a free day for you to explore the city at your own pace and there will not be a guide on hand. The second part of the tour begins tomorrow (day 8) – please see tomorrow for more details.

Optional Activities: Ticket for a hop-on hop-off sightseeing bus

Accommodation: Hotel American Palace or similar, Rome

Day 8Rome - Montecassino Abbey - San Pietro Infine - Benevento - Ariano Irpino

  • See the beautiful Abbey of Montecassino tower over its surroundings
  • Discover the ancient history and legends of Benevento

*Please note: This Italian Affair tour is a combination of two tours: Cinque Terre, Florence & The Flavours of Italy, and Pompeii, The Amalfi Coast & Irresistible Italy. Meet your new guide and group in the hotel lobby at 8:15am today, to begin the second part of the tour.

You leave the hustle and bustle of Rome and head south towards peaceful Cassino.

Sitting atop of the mountain, the Montecassino Abbey is a sight to behold. A working monastery and a pilgrimage site, this place was a centre of art, culture, and learning. It was also the scene for a decisive battle near the end of World War II. You have your entrance ticket included and get time to stroll through the cloisters of the monastery and contemplate the turbulent history of war.

Then, you visit the overgrown ruins of San Pietro Infine, before you travel past hilltop villages and mountains to Benevento.

Built on a hill with a stunning background of mountains, this timeworn city has a special aura. It’s filled with memories of the ancient Samnites, Romans, and Longobards. Legends also say witches gather from all over the world by an ancient walnut tree by the local river.

After a day of soaking up the history, legends, and stunning views; you travel south-east to Ariano Irpino your home for the night.

Included Activities: Entrance to Montecassino Abbey

Accommodation: Hotel Incontro or similar, Ariano Irpino

Day 9Ariano Irpino - Trani - Polignano a Mare - Alberobello - Lecce

  • Explore the sun-soaked coast of Apulia
  • Stare in awe at Alberobello’s unique cylindrical, whitewashed buildings called trulli

You wake up in the stunning region of Campania and head south to Trani.

Known as the ‘Pearl of Apulia’, this historic stone-built port and fishing village exudes sophistication. Walk along the promenade in the marina or stroll through the historic centre and admire the medieval churches, cathedral, and historic Jewish quarter.

You travel to Polignano a Mare, a small, idyllic seaside town perched on the edge of cliffs. Enjoy your lunch surrounded by sun-bleached stone buildings and enjoy the Adriatic breeze. You should also try to catch sight of the brave cliff divers disappearing into a small inlet of water.

Just when you thought your day couldn’t get any better, your adventure takes you to Alberobello. With over 1,500 small and rounded white houses, this town looks like it was inhabited by gnomes. These beehive-shaped buildings are called trulli and are so unique to Apulia that they were awarded UNESCO World Heritage status. Take your time to meander around the narrow streets and marvel at the impossibly photogenic nooks.

Feeling that La Vita è Bella, you leave Alberobello and ramble south towards the heel of Italy to Lecce, your base for two nights. (B)

Accommodation: Hotel Eos or similar, Lecce

Day 10Lecce - Otranto - Gallipoli - Lecce

  • Marvel at the Baroque architecture of Lecce, ‘the Florence of the South’
  • Enjoy the stunning vistas of the southernmost part of Italy’s heel

Buongiorno! Wake up and start the day with some pasticciotto, the gorgeous breakfast pastry. Enjoy your free time in the morning by strolling through Lecce’s old town and admiring its unique architecture. The city’s Baroque style is so unique it got the name of its own, ‘Lecce Baroque’.

Next, contrast the splendour of Lecce with the laid-back seaside towns of the Salento Peninsula. You leave at noon and travel through the ochre-coloured fields and olive groves to Otranto. Enjoy your time here strolling around the fortifications or harbourside promenade and try some local dishes.

You continue your adventure to the “beautiful city” – that’s what Gallipoli means. And you won’t be disappointed by this gorgeous beachside town. Take a stroll around the old town, with crystal blue water surrounding you on all sides.

Cast your eyes for the last time at the magnificent vistas of the coast and journey inland to Lecce, where you arrive in the early evening. (B)

Accommodation: Hotel Eos or similar, Lecce

Day 11Lecce - Matera - Castelmezzano - Salerno

  • Step back in time as you explore the ancient cave dwellings in Matera
  • Travel off the beaten track to the remote village of Castelmezzano

You leave Lecce and head to the UNESCO World Heritage Site of Matera. This city is so perfectly adapted to the terrain that it blends in with its rocky surroundings on a cliff edge. It’s a higgledy-piggledy jumble of sassi, the ancient cave dwellings, houses and churches.

Spend your time uncovering the rich history of this place and visit ancient churches with paintings on stone cave walls. You can also check out what the 18th-century dwellings were like and stumble upon locations used in Mel Gibson’s Passion of the Christ.

Your adventure takes you off the beaten track again as you journey into the heart of the Lucanian Dolomites and the village of Castelmezzano. One of the highest villages in the Basilicata region, it’s located on a narrow ledge that drops away into a dramatic gorge. But Castelmezzano wasn’t built here just for the stunning vistas. Find out about its rich history as you explore the village or go for a hike to see the ruins of the castle which gave the village its name.

After a busy day, you travel through the hills and mountains of Basilicata towards the west coast of Italy, where you spend two nights in Salerno. (B)

Accommodation: Hotel Plaza or similar, Salerno

Day 12Salerno - Sorrento - Positano - Salerno

Fall madly in love with the colours and scents of the glamorous Amalfi Coast
Savour the local cuisine and a glass of cold limoncello

Today is all about the glamourous Amalfi Coast.

Pastel-coloured houses and villas, chic boutiques, gourmet restaurants; this is La Dolce Vita at its finest.

You start the day by exploring the gateway to the Amalfi Coast, Sorrento. This town of lemons and plunging cliffs allured literary geniuses from Byron and Goethe to Dickens and Tolstoy. Wander through the sun-drenched piazzas and savour a glass of cold limoncello before you continue your day.

You head to Positano, which looks like a colourful multi-tiered cake clinging to a sea-cliff. Find a restaurant to enjoy your lunch and drink in the magnificent views of the Tyrrhenian Sea. Then, peruse the local boutiques and take photos as you meander through the streets. Alternatively, walk down the steps to the beach for a swim and some sun.

Reinvigorated after your visit to Positano, its time to jump on the ferry and drift along the dazzling Amalfi Coast, visit another quaint town, and stop for photos on the way back.

Jumping back on the ferry, you arrive in Salerno late in the afternoon where you can watch the sunset with a drink in your hand.  (B)

Accommodation: Hotel Plaza or similar, Salerno

Day 13Salerno - Mount Vesuvius - Pompeii - Rome

  • Feel the thrill of walking along the crater of the infamous Mount Vesuvius
  • Explore the ruins of Pompeii, the ancient city frozen in time

Today it’s time for something more dramatic.

In the morning, you travel north to face Mount Vesuvius. In ancient times, this mountain was considered to be divine and had connections to Jupiter – god of sky and lightning. Legends say that the giants used to inhabit the volcano, which explained the loud noises and rumbling.

Scary as this sounds, the titan is dormant now. So, put on your sturdy boots and get ready for an unforgettable experience because you can hike up to its crater.

After the exciting start of the day, you go to Pompeii, which fell victim to the eruption of Vesuvius. There was no time to flee, so people and buildings were buried and preserved in volcanic ash. Get a glimpse of the world of the Ancient Romans as you take your time to explore this archaeological site.

Then you leave the past behind and take a road that leads to Rome. Enjoy your leisurely ramble north through Campania and Lazio before you arrive in the Eternal City early in the evening.

Included Activities: Entrance to Vesuvio Volcano Crater and Entrance to Pompeii Archaeological Site

Dates and Prices - Hotel accommodation
Departure Dates and Days Double/Twin (pp) Single Rate
2024: August 19, 26 $5,420 $6,750
2024: September 16, 23 $5,880 $7,380
2024: October 14, 21 $5,600 $6,910
2024: November 11 $5,600 $6,900
2025: April 7, 28 $7,430 $8,710
2025: May 5, 26 $7,430 $8,710
2025: June 2, 23, 30 $7,430 $8,710
2025: August 25 $7,430 $8,710
2025: September 15, 22 $7,430 $8,710
2025: October 13, 20 $7,430 $8,710
2025: November 10 $7,430 $8,710

All guaranteed departures.

Pricing

Pricing is per person (pp) based on twin/ double occupancy.
Rates are in $ CAD.

 


Contact DHTour at 1-888-597-3519 or 905-639-9954 or dhtour@dhtour.ca  to book.

Ask us for the best available pricing for your dates & choice of airline.

 

Notes
Mobility: All of our tours involve walking and require our guests to board and disembark our vehicles several times a day making this tour unsuitable for those with reduced mobility.

Luggage: You’re restricted to 20kg (44lbs) of luggage per person. This should be one piece of luggage similar to an airline carry-on bag (approximately 55cm x 45cm x 25cm / 22in x 17in x 10in) and a small bag for onboard personal items.

Want to extend your stay in Milan or Rome?  Ask us for a hotel package. 

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