Basilica di Santa Croce | Lecce | Italy
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FROM: CAD $6,047 pp
Milan to Rome, Puglia & Amalfi - 13 days map

SMALL GROUP TOUR: Journey from Milan on this 13-day group tour, taking in the dazzling villages of Cinque Terre, the Leaning Tower of Pisa and the Renaissance capital of Florence. Explore Siena and Tuscany, enjoy free time in Rome to visit the Colosseum and Forum, and discover the highlights of Puglia in Italy's south. Delve into the caves of Matera, visit the gorgeous Amalfi Coast and see the ruins of Pompeii. Hike to the crater of Mount Vesuvius before returning to Rome.

Prices & Dates

Trip Highlights

Cinque Terre - Spend an afternoon exploring these famous, picturesque seaside towns
Siena - Visit this famous UNESCO-listed town, known for its narrow streets and picturesque town square
Trani - Admire the whitewashed 12th-century cathedral and delve into the vibrant Jewish quarter in the city known as the 'Pearl of Puglia'
Lecce - Stroll through the old town and admire the city's unique 'Lecce Baroque' architecture
Mount Vesuvius - Hike up this infamous volcano, which buried Pompeii in 79 AD, reaching the rim of the volcano's crater
Florence - Enjoy a free day to see the sights of the 'Cradle of the Renaissance', including the beautiful Palazzo Vecchio
Rome - Stay for two nights in the Italian capital, with free time to explore, then end your tour back in the Eternal City
Alberobello - Marvel at the traditional conical-shaped Trullo houses made from local Italian limestone
Matera - Explore the historic centre of the city, Sassi di Matera, which is known for its cave dwellings carved into a river canyon
Pompeii - Discover the history and tragedy of the most famous eruption in history and learn about the lives of those who lived in Pompeii


12 breakfasts
Escorted by an English-speaking guide
Train to Cinque Terre as part of the Cinque Terre Card
Entrance to Montecassino Abbey
Entrance to Vesuvio Volcano Crater
20kg luggage - see Trip Notes for details
Note: This tour is operated in conjunction with our trusted partner and you will join travellers from different operators, not solely On The Go.
12 nights in 3-4 star hotels
Transportation in an air-conditioned luxury mini-coach with a local driver
Wine tasting and tour of the Solaria Winery
Amalfi Coast Ferry tickets
Entrance to Pompeii Archaeological Site
Tourist taxes

Not Included

International flights & visas
Meals not specified in itinerary
Entry fees unless specified
Airport transfers
Tipping - an entirely personal gesture!


Day 1

Exploring Cinque Terre

Milan - La Spezia - Cinque Terre - La Spezia. Our journey begins as we depart for La Spezia, hailed as the gateway to Cinque Terre. We take the train to this Italian highlight, a group of five colourful coastal villages, each boasting its own unique charm: Riomaggiore, Manarola, Corniglia, Vernazza, and Monterosso. Nestled along the rugged cliffs of the Italian Riviera, these villages offer a feast for the senses—vibrant houses, winding streets, breathtaking vistas, hiking trails, local delicacies, vineyards, and picturesque harbours await.

After exploring, we'll hop back on the train and return to La Spezia for the evening.

Please note: Check-in closes at 08:15 (tour departs at 08:30)- Milan Pick Up, Business Palace Milan, Milan.
Overnight: La Spezia

Day 2

Pisa & Lucca to Florence

La Spezia - Pietrasanta - Pisa - Lucca - Florence. As we bid farewell to La Spezia this morning, we embark on a journey back in time to the era of narrow medieval streets, charming piazzas, and majestic cathedrals. Along the northern Tuscan coast lies the picturesque town of Pietrasanta, affectionately known as the "City of Artists." Renowned for its rich tradition as a hub for sculptors and artists, we have time to explore this captivating destination.

Our next stop is Pisa, famed for its iconic Leaning Tower. There's free time for you to take in this famous building, stroll through the enchanting Piazza dei Miracoli (Square of Miracles), wander along the banks of the Arno River or explore the Camposanto Monumentale at leisure.

Next is the enchanting walled city of Lucca. Take a leisurely stroll along the ancient city walls, explore the picturesque Piazza dell'Anfiteatro, or immerse yourself in the beauty of Lucca's splendid churches, like the Cathedral of St. Martin. Then, we make our way to the vibrant city of Florence, where we stay for the next two nights.
Overnight: Florence  |  Breakfast

Day 3

Florence free time

Today is completely free for you to explore Italy's Renaissance capital. Discover the mighty Duomo and visit some of the city's famed galleries, such as the Uffizi or the Galleria dell’Accademia, home to Michelangelo's David. Perhaps end the day at the Boboli Gardens, home to a myriad of statues, fountains, ponds and hidden mazes. We strongly recommend booking in advance any attractions you wish to visit in Florence on this day, to avoid disappointment.
Overnight: Florence  |  Breakfast

Day 4

Florence to Siena & Montepulciano

Florence - San Gimignano - Siena - Montepulciano. Bid farewell to Florence as we embark on a journey to explore Tuscany's enchanting medieval hill-towns. Travelling through the lush hills of the renowned Chianti wine region, we will be captivated by the 14 soaring towers of San Gimignano. Learn about the noble families which raced to build the tallest tower houses and savour local delicacies during a leisurely lunch.

Continuing south, we arrive at the day's highlight: Siena, a breathtaking red-brick city renowned for its Gothic architecture. The heart of Siena lies within the unique shell-shaped Piazza del Campo, this iconic square featured in James Bond's 'Quantum of Solace' chase scene. Our journey then winds along scenic country roads, until we reach Montepulciano in the early evening. This charming hilltop town in rural Tuscany will be our home for the next two nights.
Overnight: Montepulciano  |  Breakfast

Day 5

Discovering Val d'Orcia

Montepulciano - Pienza - Montepulciano. Today, immerse yourself in the serene beauty of UNESCO-listed Val d'Orcia, where time seems to stand still. We begin our day with a self-guided exploration of Montepulciano, then journey to Pienza, a jewel of urban design and UNESCO World Heritage Site, often referred to as the 'Ideal City.' Next, we indulge in an included wine tasting at Montalcino's Solaria Winery, renowned for producing Brunello, a coveted red wine with protected status.

Concluding our Val d'Orcia exploration, we visit Bagno Vignoni, renowned for its therapeutic hot springs. Today, you can admire this ancient spa and trace the flow of spring waters through the archaeological park. After savouring the best of rural Tuscany, we return to Montepulciano in the early evening for your second night.
Overnight: Montepulciano  |  Breakfast

Day 6

To the Eternal City

Montepulciano - Sovana - Capodimonte - Rome. We say goodbye to the rolling Tuscan hills and begin our journey to the Italian capital, Rome. Along the way there's an optional visit to the Sovana Necropolis and the Vie Cave, an ancient road network carved way back in the Bronze Age. We stop in the small town of Sovana so you can grab some lunch, before continuing to Capodimonte. Soak up the views of this small town, located on the shore of Bolsena Lake. Then it's on to Rome, where the evening is at leisure.
Overnight: Rome  |  Breakfast

Day 7

Rome free time

Today is free for you to explore the country's capital. Obvious highlights include the Roman Colosseum, one of the New Seven Wonders of the World. There's also the historic Roman Forum, the Pantheon, the Trevi Fountain and the Spanish Steps to discover.

We suggest you book tickets to the city's main attractions in advance, to save time and avoid disappointment.

Please note: In Rome, some members of your group may be ending their tour, and others may join. You may also meet a new guide for the next part of your trip, and change vehicle.
Overnight: Rome  |  Breakfast

Day 8

Rome to Benevento & Ariano Irpino

Rome - Montecassino - Benevento - Ariano Irpino. Departing Rome this morning, we head south to serene Cassino. Perched atop a mountain, Montecassino Abbey, a working monastery and pilgrimage site, boasts a rich history of art, culture, and learning. It was also a pivotal World War II battle site. The entrance ticket is included, allowing us to explore the monastery and contemplate its war-torn past.

Next, we visit the overgrown ruins of San Pietro Infine before journeying through hilltop villages and mountains to Benevento. This ancient city is steeped in memories of Samnites, Romans, and Longobards. Legends even tell of witches gathering by an ancient walnut tree along the local river. After a day filled with history, legends, and stunning views, we continue southeast to Ariano Irpino where we stay overnight.
Overnight: Ariano Irpino  |  Breakfast

Day 9

The Pearl of Apulia, Alberobello & Lecce

Ariano Irpino - Trani - Alberobello - Lecce. Today we head south to Puglia, the 'heel' in Italy's boot. We begin our day with a journey south to Trani, known as the 'Pearl of Puglia.' This historic stone-built port and fishing town features a marina promenade, medieval churches, cathedral, and a historic Jewish quarter to explore. Next, we head to Polignano a Mare, an idyllic seaside town perched on cliffs. Enjoy lunch independently amidst sun-bleached stone buildings and watch brave cliff divers disappear into the Adriatic waters.

Our adventure continues in Alberobello, home to over 1,500 unique trulli houses, which are round and made of stone. They have been awarded UNESCO World Heritage status. Stroll through the charming streets and marvel at these photogenic dwellings. Finally, we head south to Lecce, which serves as our base for the next two nights.
Overnight: Lecce  |  Breakfast

Day 10

Exploring Lecce, Otranto & Gallipoli

Lecce - Otranto - Gallipoli - Lecce. This morning, there is free time after breakfast to explore Lecce's old town, admiring its unique Baroque architecture, often referred to as 'Lecce Baroque.' In the afternoon, we depart for the relaxed seaside towns of the Salento Peninsula. We travel through ochre-coloured fields and olive groves to Otranto, where we can stroll along the fortifications, harbour promenade, and sample local cuisine.

Continuing our journey, we head to the aptly named "beautiful city" of Gallipoli, a charming beachside town with crystal blue waters surrounding its old town. Here we take a leisurely walk before concluding our coastal exploration. Finally, we journey back to Lecce for the evening.
Overnight: Lecce  |  Breakfast

Day 11

Matera & The Lucanian Dolomites

Lecce - Matera - Castelmezzano - Salerno. We leave Lecce for the UNESCO World Heritage Site of Matera, a city seamlessly integrated into rocky cliffs with a maze of ancient cave dwellings, houses, and churches. Here we explore its rich history by visiting churches adorned with stone cave wall paintings and discovering locations featured in Mel Gibson's "Passion of the Christ."

Our adventure continues as we journey into the heart of the Lucanian Dolomites, arriving at Castelmezzano, one of the Basilicata region's highest villages perched dramatically on a narrow ledge overlooking a gorge. We can discover its rich history and hike to the castle ruins that inspired its name. After an eventful day, we traverse the hills and mountains of Basilicata, heading towards the west coast of Italy, where we spend two nights in Salerno.
Overnight: Salerno  |  Breakfast

Day 12

The Amalfi Coast

Salerno - Amalfi - Salerno. Today we indulge in the glamour of the Amalfi Coast, where pastel-hued houses, chic boutiques, and gourmet dining embody La Dolce Vita. We begin by exploring Sorrento, a town famous for its lemons and dramatic cliffs, which have inspired literary greats throughout history. We can wander sun-soaked piazzas and savour a glass of cold limoncello. Next we reach Positano, a vibrant and colourful, multi-tiered town clinging to the sea cliffs. Enjoy lunch at a scenic restaurant overlooking the Tyrrhenian Sea, and then peruse local boutiques, or descend to the beach for a swim and sunbathing.

After our Positano visit, we board a ferry for a leisurely cruise along the dazzling Amalfi Coast, with stops in charming towns and opportunities for photos. As the day winds down, we return to Salerno in the late afternoon. We recommend watching the sunset this evening with a drink in hand.
Overnight: Salerno  |  Breakfast

Day 13

Mount Vesuvius, Pompeii & Rome

Salerno - Vesuvius - Pompeii - Rome. This morning we head north to find Mount Vesuvius, once considered divine and associated with Jupiter, the god of sky and lightning. Legends even speak of giants inhabiting the volcano, explaining its rumblings. Now dormant, we enjoy an unforgettable hike to its crater - remember to pack suitable walking shoes!

Following this, we visit Pompeii, a city frozen in time by Vesuvius' 79 AD eruption. We explore this archaeological site which offers a glimpse into ancient Roman life. Then we begin our journey back to Rome, leisurely travelling through Campania and Lazio. Arriving back in Rome in the early evening, our tour comes to an end.

Please note: This tour finishes at 18:30 - Rome Pick Up, Hotel American Palace, Rome.

Prices & Dates

Departure dates are guaranteed with a minimum of 2 persons. 'Twin Share' prices are per person when there are 2 people sharing a room. 'Single Room' prices are applicable to those who don’t have anyone to share a room with or anyone wanting the privacy of a single room.

Twin Share
Single Room
22 Jul - 03 Aug 19% off
CAD $7,605
CAD $6,160
CAD $9,535
CAD $7,723
19 Aug - 31 Aug 19% off
CAD $7,465
CAD $6,047
CAD $9,305
CAD $7,537
23 Sep - 05 Oct 19% off
CAD $8,105
CAD $6,565
CAD $10,165
CAD $8,234
14 Oct - 26 Oct 19% off
CAD $7,715
CAD $6,249
CAD $9,525
CAD $7,715
21 Oct - 02 Nov 19% off
CAD $7,715
CAD $6,249
CAD $9,525
CAD $7,715
11 Nov - 23 Nov 19% off
CAD $7,715
CAD $6,249
CAD $9,505
CAD $7,699


The hotels listed below are ones which we frequently use on this tour. We reserve the right to substitute these hotels to ones of a similar standard.

CDH Hotel La Spezia, La Spezia

Our Category: Superior   |   Regional Category: 4 Star Hotel

Located in the enchanting town of La Spezia, Italy, CDH Hotel La Spezia offers a perfect blend of comfort and accessibility. Situated near the stunning Cinque Terre, guests can easily explore these iconic coastal villages. The hotel's rooms are tastefully designed, providing a cosy and modern retreat, while some offer captivating views of the Ligurian Sea. Amenities include a restaurant serving delectable Italian cuisine and a bar for unwinding with a drink. CDH Hotel La Spezia is an excellent choice for travellers seeking to immerse themselves in the beauty of Cinque Terre while enjoying a comfortable and convenient stay.

B&B Hotel Firenze Laurus Al Duomo, Florence

Our Category: Superior   |   Regional Category: 4 Star Hotel

B&B Hotel Firenze Laurus Al Duomo is a charming gem nestled in the heart of Florence, Italy. Its unbeatable location places guests just steps away from the iconic Florence Cathedral, offering a front-row seat to the city's artistic and historic wonders. The hotel's rooms are tastefully decorated, providing a comfortable and welcoming atmosphere for a restful stay. Amenities include free Wi-Fi, air conditioning, and a buffet breakfast, ensuring a convenient and enjoyable visit. B&B Hotel Firenze Laurus Al Duomo is the perfect choice for travellers eager to explore Florence's rich heritage while enjoying a cosy and central accommodation.

Albergo San Biagio, Montepulciano

Our Category: Standard   |   Regional Category: 3 Star Hotel

Albergo San Biagio is a charming retreat nestled in the heart of Italy's picturesque countryside. Located in a serene and scenic area, this hotel offers a tranquil escape from the hustle and bustle of city life. The rooms are cosy and comfortable, providing a peaceful atmosphere for a relaxing stay. Guests can savour delicious Italian cuisine at the on-site restaurant, featuring locally sourced ingredients, and swim in the indoor pool. With beautiful natural surroundings, Albergo San Biagio is an ideal destination for those seeking a peaceful getaway and a taste of authentic Italian hospitality in a serene countryside setting.

Hotel Incontro, Ariano Irpino

Our Category: Superior   |   Regional Category: 4 Star Hotel

Hotel Incontro is a luxurious haven nestled in the heart of Campania. Its perfect location offers easy access to Ariano Irpino's historic town centre, where guests can explore local culture and attractions. The hotel's rooms are elegantly designed, providing a comfortable and upscale atmosphere for a rejuvenating stay. Amenities include a world-class spa, fitness centre, indoor pool, and a gourmet restaurant serving delectable Italian cuisine. With its serene surroundings and top-notch facilities, Hotel Incontro is the perfect choice for travellers seeking both relaxation and convenience while immersing themselves in the cultural richness of Campania.

Eos Hotel, Lecce

Our Category: Standard   |   Regional Category: 3 Star Hotel

Eos Hotel Lecce is a charming oasis in the heart of Lecce, Italy. Its location allows guests to explore the enchanting Baroque architecture and rich history of the city, with the historic centre just a short stroll away. The hotel's rooms offer a comfortable and contemporary retreat, perfect for both business and leisure travellers. Amenities include a bar for relaxation and a rooftop terrace offering panoramic views of this picturesque city. Eos Hotel Lecce is an excellent choice for those seeking a delightful stay in Lecce while enjoying modern comforts and easy access to local attractions.

Hotel Plaza, Salerno

Our Category: Standard   |   Regional Category: 3 Star Hotel

Hotel Plaza enjoys an enviable location along the stunning Amalfi Coast. With its position overlooking the Tyrrhenian Sea, guests can relish breathtaking sea views and easy access to the vibrant Salerno city centre. The hotel's rooms are comfortable and inviting, perfect for a restful stay. Featuring a bar, Hotel Plaza is a superb choice for travellers seeking a delightful stay on the Amalfi Coast while enjoying modern comforts and the convenience of exploring both Salerno and the surrounding coastal treasures.

At a Glance

Trip Type
Group Size
Min 2 / Max 16
Hotel Rating
3-4 star hotels
Tour Guide
Yes - escorted by a tour guide
Breakfast: 12
Minimum Age
16 yrs, accompanied by an adult
Arr. Transfer
Dep. Transfer
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