Our holiday in Italy (part three) | final stop was a medieval village in the Tuscan region of Chianti

We departed Lucca and as our next check-in wasn't until late afternoon, we decided to explore the Tuscan countryside first and headed up the hill we had been admiring from our accommodation, the winding road really took us off the beaten track and through the vineyards and olive groves.  We'd seen many cyclists passing us during our stay and it would be some steep climb on a bike but the views were worth it and it gave ua a closer insight into real life in Tuscany.

We then started the main part of our journey towards the Chianti region, we'd chosen this area as our final stop so we could do some wine tasting, and explore a different area of Tuscany.  We also thought that by this point in our break, we'd want some down time for relaxation and the house we chose was in a very sleepy village.

Missed part one and two, read them here, Florence and Lucca.

Castelnuovo di Val Di Cecina in Chianti, Tuscany

Our arrival in Castelnuovo di Val Di Cecina was like stepping back in time. This tiny village boasts narrow, cobbled streets, medieval gates, and captivating views of the valley below. While we knew it was off the beaten track, we weren’t quite prepared for its utterly charming and unspoiled atmosphere. With no vehicular access through the ancient streets, carrying our bags was a bit of a challenge (especially with my husband still nursing a sore back!). But the effort was worth it when we arrived at our beautifully restored Tuscan home, brimming with character and tradition. It was built into the rock of the hill!  Bonus: the bed was wonderfully comfortable, just what we needed to help with the back pain!

The Chianti region became our base for four nights of relaxation and adventure, including a day out exploring on Vespas, a quintessentially Italian experience that we couldn’t wait to try.

Castelnuovo di Val Di Cecina - I loved seeing the washing drying in Tuscany!

San Gimignano

Our first truly rainy day coincided with our trip to San Gimignano, which was a bit of a shame as this stunning town is best appreciated under sunny skies. Located about an hour from where we were staying, parking fills up quickly, so be warned if you are visiting!
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San Gimignano is one of Tuscany’s most popular towns, famed for its beautifully preserved medieval architecture. As a UNESCO World Heritage Site, it boasts a rich history and was once a vital stop for pilgrims travelling to Rome. In fact, the Pilgrims’ Way passes through San Gimignano, which was a delightful connection for me, having grown up in Kent along the same historic route! Originally, the town boasted 72 towers, symbols of wealth and power, today only 14 remain, but they still make an impressive sight on the skyline.

Despite the weather, we made the most of our visit. We wandered through charming shops, took shelter in a pretty pavement café with a glass of wine, and enjoyed an early dinner while waiting out a dramatic storm and torrential rain.  The storm did make our drive back a little hairy though!
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Fortunately, we had another chance to experience San Gimignano on our Vespa day. Our guide took us beyond the crowds, revealing the hidden and authentic side of this enchanting town, and sharing snippets of history we missed by ourselves.

One of the stunning views our guide showed us! My phone camera doesn't do it justice.

Vespa tour of Tuscany and a visit to Volterra

There’s plenty of debate in the Tuscany Facebook groups about the safety of Vespa tours, and my advice is simple: if you’ve never ridden a motorbike before (or are inexperienced) don’t risk it!  Tuscany’s roads can be bumpy, and Italian drivers, can be a little unpredictable (no offence intended!).

We opted to hire one Vespa and booked a private tour with a guide (my husband is an experienced biker who’s ridden extensively in the UK and Europe so he drove while I rode pillion). Our guide, Dr. Bruno Squartini of Tours Under the Tuscan Sun, was exceptional. Born in San Gimignano (and now living in the house where he was brought up), Bruno has a deep knowledge of the region’s history and geology. He showed us breathtaking landscapes, quaint towns, and off-the-beaten-track spots that offered an authentic glimpse into Tuscan life.

Even if riding a Vespa isn’t for you, I highly recommend booking a private tour. Options include riding in a Vintage Fiat 500 or other guided excursions tailored to your preferences.  Avoid coach tours and large groups!

Bruno gave us a proper introduction to Volterra, including a visit to Rossi Alabaster, where we watched Franco give us a fascinating demonstration of this iconic Tuscan craft. We also saw the Roman ruins outside the town and learned more about Volterra’s rich history.

Volterra, Tuscany

Riding through the Tuscan countryside on a Vespa was magical. Bruno showed us hidden gems, stunning vistas, and even took us to the Pilgrims’ Way, a meaningful highlight for me. While the language barrier occasionally led to amusing moments, Bruno’s self-taught English was impressive, and his charm, intelligence and local expertise more than made up for any confusion (our Italian, sadly, is non-existent!).

Wine tasting at an organic winery in Tuscany

We ended the day at Palagetto, an organic winery in San Gimignano, where we enjoyed wine tasting and a light lunch. Obviously we couldn’t leave without buying some Chianti wine, local honey, and olive oil.
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It was a truly fantastic day, zipping around on a Vespa was so much fun, and having such a knowledgeable and personable guide made it even better. Touring this way was the perfect balance of adventure, learning, and appreciating the beauty of Tuscany which we totally fell in love with.

We hired our Vespa through Bellini Bruno in San Gimignano (we also hired a Vespa for our guide) - Bellini Bruno offer lots of different Tuscany Tours!  But all tour companies get booked up very early so organise as soon as you know your dates, preferably around six months in advance.

A vespa day in Tuscany is pefect, but only if you are an experienced rider!

Castelnuovo di Val Di Cecina

For our last day we decided to explore the village then relax at our Airbnb in Castelnuovo di Val Di Cecina, it had a stunning terrace, although the water in the outdoor jacuzzi was too cold (for us) this time of the year but I can imagine it would be a welcome treat in the hot summer months.  

Our only disappointment was on our last night, it was a Wednesday, and we wanted to stay in the village for dinner and had decided to go back to the local Trattoria but when we wandered up to La Vecchia Fonte, it was closed!  The only night of the week it doesn't open!  And there is literally nowhere else in the immediate vicinity, the closest main town is an hour away and we just didn't want to make that journey, the roads are pretty twisty, turny and bumpy!  So we went back to the house and managed to cobble together tuna on toast with peppers and finish off some delicious red wine!

Castelnuovo di Val Di Cecina

Travel tips and reflections 

Don’t overschedule your time - embrace the art of going with the flow. Some of our favorite moments in Italy were unplanned, like people-watching over a chilled glass of white wine as life unfolded around us. There’s something magical about soaking up the atmosphere without a rigid itinerary.

Although we wanted to make the most of our 11 days, we quickly realised we needed to ease back on our plans. Partly because of my husband’s backache and my own health hiccup (possibly kidney stones - bumpy roads didn’t help!), but also because slowing down allowed us to truly enjoy the experience.

We did end up with quite a view bites during our stay in Tuscany and this was September so go prepared  if you are travelling in high season.
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Always book a walking tour or a private guide. It’s worth the investment, you’ll learn so much more about the local history, culture, and hidden gems. Plus, guides often share great recommendations for restaurants and must-see spots.

Speaking of restaurants, finding good ones can be a challenge. I admit, I overthink it! For Florence, I pre-booked, and it didn’t go as planned. Next time, I’ll trust my instincts: stroll past a few, read menus, and decide on the day. Sometimes, spontaneity is best.

I hope my Italian blog posts inspire your own Tuscan adventure! Tuscany is a region I’d love to revisit, hopefully without health niggles. Siena is high on my list, and I’d love to pair it with a trip to Rome - a bucket-list destination for us both.  I was bought up as a Roman Catholic and I'd love to visit the Vatican one day.

If you’re planning your own trip, keep in mind that 2025 is a Jubilee Year in Italy. This Holy Year, celebrated every 25 years, holds deep significance for Roman Catholics and will draw even more visitors to the country. Be prepared for busier-than-usual crowds.

Love from 
Michelle xx
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​Read more ...
Our holiday in Italy (part one) | the top things to do in Florence
​Our holiday in Italy (part two) | all the best things to do in Lucca

We were treated to some beautiful sunsets during our time in Tuscany, this was our last night in Castelnuovo di Val Di Cecina

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