Explore the absolute best of Italy starting in Rome and finishing at Lake Como.
Join us as we wander through the Tuscan countryside, hiking and cycling from village to village while our luggage goes ahead of us, giving us plenty of time to explore at leisure. We’ll finish our time in Tuscany in Florence before heading onto the relaxing shores of Lake Como – perfetta!
We’ll walk and cycle (e-bike or pedal power) through the very heart of Tuscany. We will stop in charming hilltop towns with spectacular panoramas, where you can climb feudal towers & see early Renaissance frescoes. Between the towns, we will walk through the rolling vineyard hills, where you can stop to taste some of the best wines in the world. We’ll cycle into the historic town of Siena, a UNESCO World Heritage Site & home to some of the most remarkable art & architecture from the 13-16th centuries. With its natural parks, centuries of culture, complex wine & perfectly simple cuisine, nothing beats the beauty of Tuscany. We’ll complete our time in Tuscany with a visit to its capital, Florence.
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.
Rome, Italy
Lake Como
Arrive today in Rome, if you’re arriving with the group airport transfers are included. There’s nothing planned, just take your time to get over your jetlag, if you’re up for it go for a wander, you don’t have to go far to get the feel for the city vibes.
After breakfast, we’ll meet a local guide for a quick and quirky history lesson on the people and architecture which make Rome the dynamic city it is today.
Learn about the lady with chemistry skills who helped many unhappily married women get out of their marriages long before divorce was a thing. Or stand under the protective eye of the saint who looked protected the women whose occupation is touted as the oldest profession in the world. It’s not all about women, the men have their stories too.
After this you are free to discover the city for yourself. If you would like assistance booking tours of the colosseum, Vatican City or somewhere off-beat, we can help you with this. It is advisable to do this well in advance. Or you may like to join your host for a lunch of prosciutto, prosecco and people-watching. The choice is yours.
This morning we will take the 2-hour train to Chiusi, Tuscany where we will be met with our local contact and taken by road to Montepulciano. He will give us a hiking and cycle briefing and answer any questions you may have.
The afternoon is perfect for discovering this little medieval hilltop town which is full of elegant Renaissance palaces, ancient buildings, charming squares, and hidden cobblestoned laneways. It’s also known for delicious Nobile Wines – just sayin’.
If you have never eaten in a Michelin Guide Restaurant you have the choice of not one, or two but three restaurants in and around Montepulciano – you’ve got a lot of exercise ahead of you, so it’s only right that you fuel your body well!
Day 4 (B) Montepulciano to Pienza Hike: 16km 5hrs
After breakfast in the little cafe on the corner, we’ll start our hike.
From our beautiful accommodation in the heart of Montepulciano, we walk out of town to San Biagio Church where the road leads us to Monticello, a quintessential little village to stop for a little snack or just a cappuccino. If you are not already in love with Tuscan villages by the time you leave Monticello, you will be by the time we reach Pienza, a jewel of Renaissance architecture.
Day 5 (B) Pienza to Bagno Vignoni 15km 5hrs
The Crete Senesi is a fascinating and unusual landscape that we walk through today. The ‘crete’ famous for its distinctive dry clay hills, and sparse lunar-like landscape, it’s a place unlike any other in Tuscany. Crete landscape is no doubt one of the most famous in the world: rolling hills in all shades of brown or green; sturdy brick farmhouses crowning the hilltops and cypress-lined alleys design a perfect scenery that inspired painters since the Middle ages. Often described as ‘lunar’, as much for the odd shapes formed from the clay, as for its grey and off-white in colour.
We really are going to be challenged with the hiking, but will be rewarded by some amazing scenery and furthermore be rewarded with our destination hotel’s wonderful spa facilities!
Here we rest our weary legs for two nights. For centuries, the beneficial springs of Bagno Vignoni have refreshed the body and spirit of visitors who stop over in this oasis of nature and tranquility.
The tubs, the Roman sauna, the green spaces of the garden, are combined with a rich choice of massages and treatments for unparalleled regeneration. You deserve this, you know it!
After our long haul flight, plus go, go, go of city hustle and bustle, followed by strenuous hikes you’ll be thankful for this day. If you don’t want to partake in a thermal bath, Roman sauna, massage, and a variety of wellness treatments you may be interested in taking an optional cooking class, or why not do it all – you are on holiday after all.
Eat well at the included dinner tonight, then sleep well as we are back on the tracks again tomorrow.
Day 7 (B) Bagno Vignoni to Montalcino Cycle: 45km 3hrs
This morning we get fitted for our bikes have a practice ride then we are off. Choose a pedal bike if you enjoy the challenge or take the gentler option of an e-bike. If you can balance on a two-wheeled bike you are going to love the e-bike.
We’ll make more ground on two wheels than we do on foot. It’s not a race with plenty of time to stop and enjoy the views, take photos and stop off for a cappuccino. We’ll take quiet country roads winding our way from village to village until we come to our own town of Montalcino, Our hotel is reputed to have given refuge to the Sienese from the Florentine Army in the Middle Ages – let’s hope it’s not haunted!
Day 8 (B & D) Montalcino to Buonconvento Piece Cycle: 40km 3hrs
After breakfast we cycle off to Buonconvento, normally the tour goes in the opposite direction and starts with a rather challenging up hill ride, but thanks to a quick itinerary spin around our ride instead ends with an easier down hill ride – you can thank us over our included dinner tonight.
We’ll have time to visit Monte Oliveto Monastery along the way to break up the journey. Tonight’s accommodation is self described as a beauty farm in a beautiful natural setting, rich in history, art and sacred traditions. Perfect!
Day 9 (B) Buonoconvento to Siena Cycle: 38km 2.5hrs
Our final day on the bikes is an easy one as we make our way into Tuscany’s loveliest medieval town, Siena.
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 ambiance and just embrace ‘la vita bella’ (a beautiful life).
The option is to join us for dinner at one of the laneway restaurants, with tables and chairs precariously balance on the hillside
Today we catch the train direct to Florence’s Santa Maria Novella station (approx. 1h15), speeding through photogenic Italian landscapes. Upon arrival in Florence, known as ‘The Athens of the Middle Ages’, we’ll make our way to our hotel, then enjoy time at leisure to explore this incredible historic city.
The day is yours to enjoy in Florence, tick off the shopping list of leather goods, take in the classical artworks, sculptures, and architecture or just sit back with an Aperol Spritz and watch Florence pass you by.
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 12 & 13 (B)
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 14 (B)
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.
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.
