The drive up to Castellina in Chianti was quite astonishing. We climbed and climbed through square miles of vines. The town isn’t very impressive by the standards of the others but had a number of restaurants. I pondered if this was to cater for the very wealthy residents who lived in local villas. An estate agent displayed properties of around €2 million. They were lovely abodes with pools and land attached and no doubt cellars full of roubles.

Next came San Gimgnano. This little town with its famous pillars was very easy on the eye.

For reasons hard to fathom it was busy with a lot of Germans and Austrians. We saw the centre but then wandered down some twisty lanes and found a bench near a small park for our picnic lunch. What is clear that is if you’re an expat with a few quid and fancy living in Tuscany then deciding where to buy would be a headache. There are so many stunning options.

Lastly we stopped off at Volterra. This town was attractive but quiet with few tourists. In fact it was a place we might have liked to have stayed. It had plenty of restaurants and walks. It was here I got a call from the car rental company telling I was late returning the car! I wasn’t. However it made me concerned about getting to their office for 5pm and so we left and gunned our little car to Pisa.

Anna had fortuitously booked a B&B very close to the airport and the car rental office. This made for an easy transfer.

After settling in we waked into Pisa to find the Leaning Tower. This proved to be quite tricky to find and there was much wandering about before the magnificent Tower and adjacent Duomo came into view. I was glad we’d sought them out despite the fading light. Pisa is very tatty and a bit run down, I was walking along with little expectation but it was stunning. I say this as if it were the first time. I’d seen it twice before and once ascended the spiral stairway. We were jiggered after our day in the car and this route march. In fact I clocked up 22,000 steps for the day.

Next morning we flew home.

In summary the driving was demanding and I felt I should have researched the places we visited prior to getting there to extract the most out of the visit. But in some ways this tour was mainly about bolting a couple of days on to the end of the trip after staying with Tony and Karen. The scenery and little towns are sumptuous and the Italian food and wine fabulous. I would recommend that you pick your time of the year to visit as the summer seems to be uncomfortably busy to sightsee.

Assisi was very busy with Italians. It was the weekend and there are worst places to trip out to. The town is beautiful and folk wandered up it’s steep main drag. The proliferation of souvenir shops was wearisome, in fact it is a feature of all these beauty spots. However, the town is immaculately kept and no doubt the car parking fees extracted by all these hillside attractions helped the upkeep.

I was harassed by one young man twice. I never gave him the time of day and the second time loudly told him to “leave me alone”. Clearly a hazard in a tourist spot. An unhappy incident but it made me wonder out of his target market and the hundreds here why I seemed worth tapping up?

Back in the car my target was Siena. It was some way off and we settled down to my music (played via Bluetooth off my phone) and the entertainment that Italian motorways offer. In fact the day before we’d played BBC Radio 5 Live and were able to listen to match commentary of Watford versus Leeds United. I like to escape many things from home on a foreign trip but I’m wired into the football and there is no escape. Beside the motorway there were many factories. I’m always impressed and sadden when this is the vista. Pleased that manufacturing is still evident but sorry that in the U.K. we’ve lost so much. I accept and voted for the politics that led to a lack of subsidy for these industries and as a buyer at Ford or Moores I actively moved business abroad in pursuit of lower prices, better designs and more reliable quality: I can’t really complain.

Siena brought with it a whole new world of pain prior to entry. The hilltop city prohibited tourist traffic, what to do with the car? After dropping off the luggage on a short term pass I was faced with parking at the bottom of the hill, say, two miles away or subsidising Siena into the next millennia by paying €35 overnight. Being the last of the big spenders I opted for Option B. I had been to Siena before with Anna in 1987 and then in 2002 with Jim on our bicycles. In 1987 it was on honeymoon and I have happy memories. Probably much to Anna’s disappointment 2002 also offers happy memories. We watched England vs Argentina in a bar where Beckham’s penalty settled matters.

Again Siena was sensational. Unlike Perugia someone cared for the buildings and the central square (Piazza Del Campo) was dramatic and stunning. The cathedral in its black and white marble was similarly imposing. The many side streets and parks were full of Sunday night strollers eating ice cream, looking in the shops or hanging out. A very typical Italian scene. How the Italians communicate is worth a mention. It can often hover between walking together closely and indulging in what appears to be a conspiratorial whisper or something far more animated that could be mistaken, by the less demonstrative British, as a lively loud argument with wild hand gesticulations.

Anna had booked an apartment that included a small outside yard and galley kitchen. After all the dining out it was a break to eat a few simple things we’d bought at a supermarket in the afternoon. It would have been super to drop anchor here for a day or two but the plan was to leave the next day. Soon we were barreling down the hill looking for another beautiful hill top town, Castellina in Chianti.

The Italians have a tolerance or nay… even affection for potholes. The road surfaces can be terrible. For a modern European country many of their roads, including motorways, are simply a disgrace. We crunch along doing our best to protect the car but many road chunks are missing and vigilance is not always successful. On one country lane the surface was so deformed it resembled a ski mogul field: it was astonishing.

There are no three lane motorways, only two lane. A roads as dual carriageways don’t exist. Single lane roads with bad surfaces, undulations or adverse cambers are common. You also may recollect when a bridge collapsed in Genoa killing 43 people in 2018: the Italians have got ‘previous’ on this type of thing. In the U.K. we’re blessed with much better quality, design and engineering.

Oh yes, and speed limits are discretionary.

First stop was Gubbio in Umbria. Another ancient hilltop town with dramatic buildings and vistas.

We drove on to check in at our night’s accommodation. The remarkable Castello Di Ramazzano.

Anna found this amazing £130/night establishment on the internet. The original castle dated back to the 12th Century and swapped hands many times until it fell into a ruinous state. After much investment the castle has been partially refurbished and has a suite of rooms and facilities for hosting grand weddings. Alongside this they offer bed and breakfast when not booked out. The costs of restoration must be mind boggling. Certain legal restriction were applied to its rebirth including no lift. There are 62 steps to carry your luggage up to your room! We did rattle around in it as the owner lives off site but in the morning we discovered three other guests.

However, after checking in we went to Perugia. Whilst it meets the ‘grand city built on a hill top’ specification with some dramatic ancients buildings it just had a lot going for it than other cities we visited. It was dirty, busy and rather uncared for. There was a lot of graffiti. 

This seems even less acceptable on antique heavy wooden doors or ancient stone walls: a couple of local youth beheadings would end it immediately I suggest. We had a look round and then headed back to Ramazzano for a bite at a local restaurant. Maybe typically for Italians as we left at 9.10pm there were families turning up with dogs and young children! For us it was about returning to the castle to sleep like a king and queen.

(Anna fell over on the steps from the car park up to the castle. She wasn’t impaired by local vino but attempting to flee from a toad she saw on the steps. The countryside eh?)

There was happiness at breakfast as the Italians celebrated the victory of Ferrari in the Australian Formula One Grand Prix. The castle in bright sunlight still amazed yet it was time to go.

Down the narrow lane from the top we squeezed past cars and church goers attending worship. Many were clutching olive branches and Anna opined it was Palm Sunday. The church was nearly a mile up this steep hill and it had been there for a couple of centuries. I imagine getting to and from Sunday worship was a workout for the village before spontaneous combustion came to the rescue.

We were off to Assisi, a well known tourist spot and another place I’d reached by bicycle with the intrepid Jim.

In 2002 I cycled to Urbino all the way from Pisa, and back, with a work colleague, Jim. I recollect it was a windy and hilly ride but I can’t remember it being as demanding as it seemed in the car. With Anna urging caution I threw our little, under powered, French car up and down these precipitous hilly hairpin climbs. As always I had another car behind and it turned into a bit of a competition as I drove to drop him and he drove to hang on! Soon we’d left the Tuscany region and were in Marche.

Urbino doesn’t allow many cars in the city walls and we parked in an underground car park outside the city. (A great solution to the large number of cars and little space on these hilltops.) With some huffing and puffing we lugged our cases up to the hotel. Pleasingly, despite our early arrival, there’s no problem checking in. We unpacked and then strolled around the small city in the sunshine. The streets are narrow and seemingly untouched by modern redesign or construction over the centuries.

It must take a lot of money to maintain these buildings. The facades are so tall and their maintenance must be specialist. We look around the cathedral and also observe the many students who attend the university. Their smart dress is remarkable. Stylish and tasteful every one of them; such a contrast to York’s throngs. After a salad we take a siesta. This isn’t typical but after the walking and gardening of the previous days it was overdue!

Eventually grumbling stomachs lure us outside again. We’re out too early for dining and have 45 minutes to spare before our reservation. We find a bar and ask the barman for a glass of red and white. What does he recommend? He selects and they’re memorable. As is the way the drinks are served with snacks and forgetting our imminent meal we heartily get stuck in. We sat there like teenagers and perused our phones but soon it was time to dine.

Our small restaurant (Taverna degli Artisti), seemingly in a basement, is soon packed. As we take our seat a procession of American students file past to take their seats in an adjacent room; it’s surprising to hear English spoken. Like their Italian counterparts they’re smartly dressed and complement the neat, tidy and elegant walled city. We order our food, the waitress noting our earlier visit and booking has translated the menu into English, how thoughtful.

Our food is delicious and the portions are so appropriate that we have space for three courses.

In fact I thought I had ordered two courses but didn’t argue when it turned out to be three! Anna has a beer as she’s thirsty and I have a glass of red wine. There was no choice if you ordered a glass and my drink is a little sweet and cheap. On a close table there’s two smartly dressed businessmen.

The waitress approaches with menus but they have no interest in the detail and after much dialogue the waitress departs. A minute later the restaurant’s chef appears to greet both men warmly and no doubt resolve their demands. We look on and make a contribution to their evening – Anna passed across a city map for them to use. They solve a wobbling table by placing it beneath the offending leg and tell her “grazie mille”.

A short stroll back to the hotel helps the food settle and I take some more snaps of this beautiful place.

At breakfast we discover that Covid has meant self service is forbidden and we queue and wait to visit the buffet to then point (we don’t know the Italian for the food) and obtain our coffee, cereal etc. Close by at an adjacent table in Bill. He’s 72 and from Vancouver. He travels widely and has Italian heritage. He’s not religious but likes visiting churches. Italy is over endowed with sumptuous temples and he’s working his way around many of them. However there’s a hint of sadness about this solo traveller. He grumbles about the buses, trains and getting around. The vicissitudes of weekend timetables make his movement difficult and he complains of finding it physically hard going. He says he’s ‘a little down’ about it all and comments that talking to us is a lift. I think we can all agree that talking to Anna was the tonic and not me.

I pop out for some groceries and a couple of postcards to write and post. With this complete we pack and descend to the car park and steer our pocket rocket south. We pass Saturday lycra clad cyclists out for a spin; I know a man who would have liked to have joined them. Common throughout Italy is the national flag adorning many buildings; they’re very proud. In Britain many people, including the BBC, sneer if you fly the Union Jack or the Cross of St George: they need to get across here.

Anyway next we’re headed for Gubbio.

In daylight we surveyed the house in its setting. Gosh!

Our hosts had deemed that we were walkers; we were. The walks were their favourites. The Tuscan countryside was sublime. Small but steep hills with not another soul in sight. Often we’d crest a hill and another terrific vista would be before us in the Spring sunshine. Our layers peeled off as we ascended and the day warmed up. It was a true delight and we saw small villages often built on steep hillsides and many fields of olives. We chatted away merrily.

Back at the villa lunch was eaten outside after our first walk

One challenge of having a property abroad is the need to do gardening and/or DIY when you visit. Both Karen and Tony work full time back in Blighty and finding these chores to complete can be a burden. Tony’s ‘to do list’ included resolving a dodgy water pump that sounded very poorly, a dishwasher that wouldn’t switch on (that had worked perfectly until some local friend’s teenagers had used the property for a party) and wi-fi that had stopped working due to problems the provider had created. During the few days we were there he worked his way through these items and all were successfully resolved by ourselves, the plumber or a local handy man.

The latter was a German national called Markus who was fluent in several languages and whilst mainly a gardener had many practical talents that the various expats in the area relied on. When we met he had the new replacement internet router in his van and a plan to prune olive trees. This isn’t a job for a hacker like moi. The tree has to be shaped to enable better picking in the autumn as well as a reduction of too many branches. I’d like to think the Ives’ put their ‘backs to the wheel with a few tasks not least gathering up of branches from around the large garden and creating a bonfire. Such was the too’ing and fro’ing that I clocked up 11,000 steps in the process. Anna did this but also attempted to do some pruning.

As we worked through Tony’s repertoire of home made Italian staples we enjoyed homemade pizzas in the purpose built brick oven and delicious ravioli from homemade pasta. I took several photos as I have no talent and could only look on with envy and gratitude.

All this carbohydrate was vital as the second full day involved more walking. This jaunt took us past the plumber’s gaff. Tony was tempted to knock on the door and enquire as to his overdue scheduled visit? More exciting was the plumber’s private life. He was now partnered with an English project manager/estate agent, who had left her husband, and he his wife to live together. Maybe it could be the start of a racy boxset based on life in the Tuscan hills?

Karen kindly laundered our washing. EasyJet limit your luggage and due to the chilly but sunny weather we found ourselves repeatedly wearing the heavier items of our wardrobe and not the lighter ones we’d also brought. As time rolled by we were on our last night in their company and we went to Sansepolcro to a superb restaurant. Our waitress was nearly worth the visit as she practised her English on us with considerable volume and mirth. I shall never look at a dessert trolley in the same way again. Tony sadly for him, was driving and much of the mirth was left to the rest of us with Karen and myself doing irreparable harm to a very nice bottle of red he’d chosen.

Next morning as we rose and packed our bags there was a new voice downstairs as Tony and Karen greeted Markus. He was here to trim the olive trees and give advice on several matters. Happily and surprisingly he had a new broadband router. As Tony discussed olives I attempted to drag the internet into life. Eventually I got it close to working but was short of a code. Markus had it and the information was typed in.

We munched our toast, hugged and thanked our generous hosts and then pointed the Citroën toward Urbino.

Our Italian odyssey started in Stockport (obvs…) with a quick visit to the Favourite Eldest’s to drink a toast to her birthday. She’s starting to accumulate the kind of numbers where women request that disclosure is applied with discretion.) I don’t like driving in Manchester as it has been dangerous on occasion and I worry that the recklessness is created by drivers on drugs. Five minutes from Katrina and Matt’s abode we stopped at the front at some traffic lights. First an old BMW 3 Series pulled up in front of us and then a VW Golf. With the lights at red one turned right against the traffic and the other just kept going. I suspect they were peddling rather than taking drugs and either chasing each other or escaping. Lovely.

Sophie and Harry attended the celebration as well and Katrina’s milestone celebrated. We then proceeded to the Premier Inn at the airport for an overnight stay. We had a fairly early flight and bottlenecks in Security meant getting there well in advance. Even in the ‘Fast Path’ lane we idled for 40 minutes. Worse was to come as my bicycle multi tool was confiscated. I have several but I tearfully said goodbye to something that has traversed America, most of Europe and a long way up Australia with me. I took it because our host had threatened a bike ride. (This never came to pass!)

The flight was routine albeit we were back to wearing masks during the flight (thank you Italy). In fact it was a special kind of mask, more substantial and uncomfortable. After having mooched around the Terminal for so long before the flight, cheek by jowl, with other unmasked travellers then what this mask was going to prevent is anyone’s guess. Italy was also enforcing Covid vaccination status in restaurants and insisting on masks before you sat at a table. Bonkers as regards a preventative measure, but it was nice to use my App after never having used it since my last trip to Lanzarote.

Finding the car rental office near Pisa Airport wasn’t routine. It wasn’t located in the main area for the other rental companies. More by a hunch than knowledge we came across it on a side street near an underpass away from the Terminal. Oh how we laughed over the 40 minute hunt. The chap on Reception then badgered me about extra insurance due to high excesses on car damage. On my declination he took a long video around the car to capture it’s pristine state and waved us away. This small Citroën was so under powered that it couldn’t pull a sailor off your sister let alone comfortably cope with all the hairpins and climbing to come.

The drive to Anghiari is the type of excitement you usually have to pay for at a fun fair. Narrow dual carriageways with cars flashing you from behind if you strayed into the outside lane or massive articulated trucks straddling both lanes as they coped, at speed, with the winding carriageways. The central reservation is a solid concrete barrier. I thought hard at this point about the extra insurance I’d declined. We texted Tony, our host, close to Anghiari and was delighted after the meet up with his idea of a drink and stroll around this medieval hillside town along with Karen, his wife. Frazzled nerves were calmed. Tony is on my website and blogs as an accompanying cycle tourer. We met in 1985, on our MBA course at Bradford University.

The drive into the countryside, to their palazzo, was predictably windy and mainly up hill (welcome to most of Tuscany). This is their second home and much time, love and resources have been poured into creating an idyll over a decade. Such was the remoteness it wouldn’t have surprised me to learn that the locals were still finding German soldiers, in the 1970s, hiding in the woods unaware the war was over. As Tony commented there would be no noise or light pollution at night. The villa with its pool is stunning and the tranquility complete. A frustration is the proliferation of wild boars in the area. They dig up the ground in pursuit of things to eat and a lot of the ground has been ‘turned over’. A fence around the house garden is in place to stop this damage closer to the property. Anna was keen to see the said pigs during her stay but they failed to materialise but we knew they were there due to the ground condition. Apparently they are hunted in the autumn but a licence is needed and a gun!

We enjoyed a brief tour of the home and then especially catering for Mrs Ives a courgette pasta was rustled up and after some wine near a log fire we tumbled into bed ready for sleep. A great start with splendid hospitality and lovely surroundings.