Iconic Italy, 5 – 17 September 2022

September 5, 2022
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  • Twin or Double Room$3,895/Person
  • Own Room$5,145/Person

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13 Days
Lake Como
Max People : 12
Tour Details

Explore the absolute best of Tuscany and Umbria on foot; starting with the medieval and Renaissance hill-top towns of Siena and Pienza, on to historic Perugia and ending in iconic Florence. Nestled in the green heart of Italy. We’ll walk through landscapes of rolling hills, past soldier-straight lines of cypress trees, through vineyards and olives groves. 

From Siena, on to Montepulciano, Montefollonico/Pienza, Monticello. In Cortona we’ll stay in a 15th-century mansion, high up on a hill. Crossing into Umbria, stay at a quaint villa and country inn, with a wine tasting and optional cooking lesson. Immerse yourself in Perugia’s fascinating museums, markets and arcades before finally arriving in Florence, with time to discover some of the romantic stories behind this incredible city. 

From Florence, we head to Lake Como, the third largest of the Italian lakes and arguably the most stylish of them all. Located at the foot of the Alps, it offers a picture-perfect escape. 

Picture yourself following panoramic mountain trails gazing down onto the shimmering lake and wandering along lakeside paths between pastel-hued villages. Be dazzled by the world-famous neoclassical villas and immaculate gardens, not forgetting über-chic Bellagio with its flower-filled lakeside promenade and cafés, where you can pause for a chilled spritzer cocktail and watch the world go by.

ICONIC Italy Itinerary 2022

Start Location


End Location

Lake Como

Price Includes

  • Small Group - Fully Hosted
  • 12 Night's accommodation
  • 9 Breakfasts
  • 2 Dinners
  • Vineyard wine tasting
  • All group transfers from Siena to Lake Como
  • Luggage transfers whilst on hike
  • Historical tour - Florence
  • Assistance with flights/private transfers/

Price Excludes

  • International Flights
  • Travel insurance (compulsory)
  • Transport to Siena/from Lake Como
  • All meals not mention in itinerary
  • All expenses of a personal nature

Day 1Arrive Siena

Arrive in the medieval city of Siena (we can assist you with getting here), where you will feel as if you are stepping back in time. 

At Siena’s heart is Il Campo; the central piazza and where the Palio horse race takes place twice every summer. 

After checking in at your hotel, head here for a coffee or glass of chilled wine and let yourself soak up the Italian ambience and relax into ‘la vita bella’ (a beautiful life). 

There’s no better way to help you recover from jet-lag! 

Day 2 & 3Tuscany

Day 2 (B) 

After a good night’s sleep it’s time to discover more of Siena which is, after all, a UNESCO World Heritage Site and one of Italy’s must-see attractions. The city is well-known for its wine and cuisine, art, museums and Gothic architecture. Take time this morning to explore this charming historic town. 

This afternoon, we’ll take the train (approx.1hr duration) on a picturesque journey through classic Italian landscapes to Montepulciano, from where we will transfer to our hotel, for a welcome meeting.

Day 3 (B)

Today starts with a transfer to Pienza, a stunning hilltop gem that inspired poets, writers and artists of the Renaissance era. Enjoy roaming the cobblestone streets admiring the architecture favoured and influenced by Pope Pius II or take a pleasant stroll down the “Via Dell’Amore” (love street), for spectacular views of the Val d’Orcia. 

Sample some Pecorino cheeses, a local delicacy in Pienza, before journeying towards the hamlet of Monticello. In town, enjoy a light lunch of Ribolitta Italian bean and bread soup or a bruschetta snack at local cafés before continuing along the winding, cypress tree-lined path back to Montepulciano.

Day 4Tuscany

Depart Montepulciano with a short walk through the iconic Tuscan countryside of yellow fields, golden grasslands and hillside villages to Acquaviva. Take an afternoon transfer (approx. 2 hours, departing 1:00 PM) to Cortona. Famous as the setting for the book, “Under the Tuscan Sun” written by Frances Mayes, Cortona continues to be a Tuscan highlight. 

Upon arrival, wander the steep and narrow streets to the distinguished Etruscan Academy for its vast collection of bronze and ceramic relics portraying the town’s Etruscan past. 

Walk: 10km (3hrs approx.) 

Day 5 & 6Umbria

Day 5 (B)

Our day begins with a short (10 mins) transfer to Ossaia, where we start our walk to Tuoro. We’ll be walking with spectacular views over the Valdichiana Valley and Lake Trasimeno, scene of Hannibal’s ambush of the Roman Army in 217 BC. 

Today we cross into Umbria at the village of Tuoro, where there are several lovely shops and a café to quench your thirst. A transfer will take you onwards (20 mins) to the medieval village of Castel Rigone, with its late 15th century church. 

Walk: 16km (4h30-5hrs) 

Day 6 (B)

We’ll start the day with a 30 mins transfer to Castello di Mongiovino, from where we will walk to the charming hill-town of Panicale. 

It’s easy terrain to Panicale; a picturesque medieval village with a nice square and café where we can enjoy a light lunch and a glass of good local wine. After lunch we’ll take another transfer (30 mins) to our accommodation at la Corte del Poggio. 

Walk:12km (3hrs approx.) 

At La Corte del Poggio, not far from Perugia, we will stay in a charming old stone house. It is possible to book a cooking class (arranged and paid for locally). 

Day 7 & 8Umbria

Day 7 (B)

After breakfast a vehicle will transfer us (20 mins) where we will visit the vineyards of Castello Monte Vibiano. This is not any old winery, they stand out from the crowd as they have achieved ZERO CO2 Emissions. In 2009, the first farm in the world to achieve this without using carbon offsets, at a time when it was not trendy or cost-effective to be sustainable; leading as a true Pioneer. Also, only 40% of the total estate is for agriculture, 31% is dedicated “forestry fencing” to block the influences of man. 

After a little wine tasting, we shall return on foot to our accommodation (probably a good idea) at La Carte del Poggio. It’s a peaceful and relaxing walk along an almost-flat path that traces the Nestore River Park. Walk: 13km (5hrs approx.) 

Day 8 (B)

After a transfer to Monte Tezio (approx. 40 mins), we’ll start our walk to Perugia along a historic route that leads to the Tezio area—an important location in the Middle Ages as it was the source of drinking water for the city. It is still possible to see remnants of the ancient aqueducts. 

Perugia’s huge Etruscan arch gate welcomes you to the capital of Umbria. Crossed by the River Tiber, Perugia is home to the Palazzo dei Priori, which looms above the main piazza. Here you will find some of the best museums in Umbria, including the Galleria Nazionale dell’ Umbria. Wander the markets, shops and arcades of this enchanting city. Walk: 17km (6hrs) 

Day 9Florence

Today we catch the train direct to Florence’s Santa Maria Novella station (approx. 2h15), speeding through photogenic Italian landscapes. Upon arrival in Florence, known as ‘The Athens of the Middle Ages’, we’ll make our own way to our hotel, then enjoy time at leisure to explore this incredible historic city. 

This evening we will discover the magic of Florence under a different and beautiful light just after the sunset. Our guide has said, ‘I’ll take you on a lovable journey that is more than just facts and information, this is historical gossip and if you are a curious person like me, you will definitely love it!’ 

Love is in the air and in Florence, you can feel it even more at night. The city is surrounded by centuries of love stories, that in some cases ended in tragedy. We will be taken to the places where they took place. Fall in love with the city through a private storytelling tour, full of romance stories, gossip and local tales! 

Day 10 Lake Como

Lake Como, is the third largest of the Italian lakes, located at the foot of the Alps and arguably the most stylish of them all. It offers the picture-perfect escape. 

Picture yourself following panoramic mountain trails gazing down onto the shimmering lake and wandering along lakeside paths between pastel-hued villages. Be dazzled by the world-famous neoclassical villas and immaculate gardens, not forgetting über-chic Bellagio with its flower-filled lakeside promenade and cafés, where you can pause for a chilled spritzer cocktail and watch the world go by. 

Today we’ll take the train from Florence to the town of Como and take a leisurely ferry ride to Menaggio where we will check into our accommodation and chill!

Day 11 - 13Lake Como

Day 11 & 12

This is the time to be as active and adventurous as you like or stay put in one of the most beautiful locations in the world. There are no planned activities on these days, however, if you’d like help planning we’re here to help. People in the group will be going where ever they like, and if you want to tag along, please, just ask .

Day 13

All good things must come to an end, sadly. Depart any time after breakfast. Arrivederci! 

We can help you with the transfer to the airport/onward journey from the accommodation. 

Your Guides
Suzanne Holden



From her starting position as tea lady, a job she took way too seriously (trust us, tea is something of an obsession with her), she wins the gold star for giving everything a go.

As a former police office, Suzanne, joined the ICON team with not only a can-do attitude but also a bloody-well-will-do attitude too.  If she’s in charge of a tour or helping to organise independent travel for you, you can be rest-assured it will be like her tea, done to the highest and most meticulous standard.