Its beauty, reflecting the stunning setting in the middle of the Tuscan hills, draws gasps of admiration. The town's position, 1650ft atop one of those hills, involuntarily draws even more sharp intakes of breath as the realisation dawns that, in 35C heat, we are going to have to climb to reach it.
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Whoever said a walking holiday was a stroll in the park? They should consider the idiom you have to travel a mile in a man's shoes to realise what they are all about.
In this case, it is more than a mile. Today's walk, from our drop-off point at Badiaccia a Montemuro, where we parted company with our luggage for it to be taken to our hotel in Radda, has seen us cover 10 miles.
Well, 13, if you factor in the extra section after one slightly ambiguous direction in the route notes leads us up the wrong path, but we get back on course.
It is not as though there is anyone to ask. The only other living things we see in the morning are some cinghiale, the wild boar which scurry around the hillsides. They are the symbol of Tuscany, and pappardelle with wild boar ragu sauce is a staple in every restaurant in the region - and so much tastier than grilled goat, an error of choice never to be repeated. However, tasty as they are, wild boar are no use whatsoever at helping you find the correct route to our next watering hole. And how we need to refuel.
Eventually, by retracing our steps, we are back on the right road or, in sections, rocky path, and the midway point of today's walk to Radda comes into view.
The castle hamlet of Volpaia is tourist-brochure Tuscany; sleepy, garnished in bright flowers with an excellent enoteca where locally-produced wine is available to quench the thirst of weary travellers.
What Volpaia does not have is a bus service, nor a taxi service. So, even if we were considering cutting short our walk to Radda to escape the increasingly fierce sun, the option isn't open to us.
Stocked up with more water, we head out of Volpaia and our first glimpse of Radda on the other side of the vine-covered valley.
Initially, the tree-lined route takes us downhill, but we quickly realise that every step down will eventually require us to take a step up. Add in the zig-zag nature of the final climb to counter the fact the rise is so steep and a long, hot afternoon beckons.
Which may prompt the question: Why would anyone choose such a holiday? Well, the answer is all around you, the reward in every step. As we hurtle through life at break-neck speed, the opportunity to stop and smell the flowers along the way is seldom offered or available.
The frantic lifestyle forced upon most of us means that the senses have been dulled, almost to the point of becoming redundant.
What a pleasure it is, therefore, to slow everything down to walking pace, literally, and enjoy the sights, smells and tastes of a holiday meandering through the beautiful and captivating landscape of Tuscany.
Travelling on foot down poppy-pocked white gravel roads or along forest tracks, with just my wife and those wild boar for company, is the perfect release valve to the pressure of everyday life.
Admittedly, having a GPS system on my mobile phone to check that we are not completely lost is a concession to modern living which is gratefully embraced.
Likewise, travelling in the knowledge that a very comfortable hotel, often with a fabulous pool, awaits at the end of the journey is another comforting thought as we make our way from our starting point in the beautiful city of Florence to the equally memorable city of Sienna.
The stops between are far removed from the iconic Tuscan tourist magnets, but Greve in Chianti and Radda in Chianti prove to be well worth discovering.
Having flown into Pisa direct from Edinburgh, and completing our journey to Florence by the frequent and inexpensive train system (there is also a direct bus from Pisa Airport to the centre of Florence) the fear that the city is over-hyped by those who insist it is the most captivating of all in Italy is quickly removed.
The terracotta hues, the stunning architecture, the shimmering Doumo, the plethora of statues and cafe-edged piazzas all combine to make this city on the River Arno the complete package.
Add in world-class museums, including the Uffizi, and beautiful gardens such as the Boboli, and you could easily spend a week in Florence and only scratch the surface of things to do.
However, after two days using the classical Hotel Park Palace, high on a hill on the south side of the river as our base, we are on the move.
Macs Adventure, which organised our trip, has left nothing to chance. It specialises in walking and cycling holidays covering as diverse terrain as the West Highland Way and Mount Kilimanjaro.
The packages are graded according to how able and energetic you are so, not wishing to jump in at the deep end, we opted for an easy level walking tour, and are soon into our stride.
A short familiarisation walk on the outskirts of Florence gets us on our way, then it is time to move on to our next stop, Greve, a small town with a charming three-sided square, on which our hotel is situated.
A loop walk gives us the opportunity to see the olive and vine clad countryside surrounding Greve, and thoughtfully included a stop-off at the winery, Fattoria Terreno, where the Swedish owners are proud to offer samples of their produce from their bountiful 150 hectares.
The following day, a shorter hike up to the small town of Panzano helps develop an appetite for a wonderful lunch of pecorino cheese and pear salad, washed down with a chilled glass of Prosecco.
Moving on to Radda is a much more strenuous affair, but again the reward comes with every step as the opportunity to get up close and personal with the flora and fauna of Tuscany would pass you by if you were travelling by car or coach. Even for novices, reading the map and following the route notes provided is manageable, give or take the odd little interpretation-induced diversion.
What nobody could have predicted is the heatwave which, while making Tuscany's green hillsides even more picturesque under an azure sky, make walking up those hills pretty hard work.
Reaching Radda, the luxury and warm welcome offered at the Palazzo San Niccolo Hotel in the heart of the historic town is just what is required to put a spring back in our step.
The lofty position of the town offers stunning vistas all around and, as the sun sets over the hills, the smell of clematis and chamomile hangs in the air.
Another loop walk allows us to explore at close quarters some more of the vineyards which make the Chianti region world famous and set us up for the final leg of this journey of discovery.
However, the walking is over, and it's the mini-bus which has been ferrying our luggage from hotel to hotel which now transports us to Siena.
That allows us to recharge our batteries before we begin to meander through the narrow streets of this bustling city, all of which seem to lead to the Doumo or the vast Piazzo del Campo where the famous biannual Palio horse race is staged.
The barricades to separate spectators from the 10 horses which charge around the cobbled square in each three-lap race, seeking honour for the city area each represents, are being erected.
The festivities are also building, with the colours of each area being worn with pride by the people from that contrada.
It is also Notte Bianca, or White Night, when the summer solstice is celebrated, so thousands of people are streaming into the city. Rock bands and classical musicians are vying for the best make-shift stages from which they will perform until around 4am, while shopkeepers move their wares on to the street to attract passing trade.
The sweet smell of boar being roasted competes with savoury aroma of freshly-made pizza, and the clink of glasses filled with the aperitif-of-choice, spritz, confirms the party is in full swing.
It's a complete contrast to the sedate way of life which we have experienced in Greve and Radda and on the walks in between, but is also the perfect end to a holiday with a difference, in every sense.
Tuscany is the ideal venue for a break like this, and having a company like Macs Adventure take care of all the planning, booking and transporting removes any potential hard work.
All you have to do is put one foot in front of the other - and get up those hills.
Ronnie Cully was a guest of Glasgow-based walking and cycling tour specialists, Macs Adventure (macsadventure.com, 0141 530 1950).
The package, Tuscany: From Florence To Siena, includes 26 miles of walking and includes seven nights bed and breakfast in four towns and cities, luggage transfer between hotels, plus detailed information pack including maps and route notes. Availability is between May and October, and prices start at £755 per person.
Flights and transfers between airport and hotel at the start and end of the trip are not included. Ryanair flies direct from Glasgow Prestwick and Edinburgh to Pisa. There is a train service from the airport to Florence.