Tuscan Road Trip

Tuscany has sat on the travel list for a few years, alongside her companions of countries, cities and many other places we long to see. Much to our delight, our friends decided to get married in Tuscany this year so there was every excuse for a road trip! Our 12 day trip of 8 stops included Rome, the Italian coast and Tuscany.

Whenever you see a picture of Tuscany, be it in travel brochure, a magazine, in an advert or a film, it never looks real. And when you get there, it feels even more surreal. Your eyes can’t quite believe it and your photos resemble an hours’ worth of work on Photoshop. Our trip was peppered with wow moments and a running joke about the tallying panoramic shots. It is SO beautiful, more than I could have imagined it to be. Picturesque views, endless green carpets of vineyards, cobbled medieval streets, B&Bs you desire as your own home and wine tasting with home baked focaccia and balsamic vinegar that’s been aged for 10 years; Tuscany is a real romantic treat that unravels more and more surprises as you spend more time discovering her.

Tuscany is vast with many regions. We spent the majority of our time in one of Tuscany’s finest areas, Chianti, and gradually made our way south towards the wedding. Here’s a whistle stop tour of the few things we saw and highly recommend.

  1. First stop: Radda in Chianti

Our first stop was Radda and this was definitely our favourite out of the many places we visited.

There’s no such thing as a diet in Italy

Try a Pizza Pie in the charming town of Radda. Supersize, delicious thin crispy pizza, this place is much loved by tourists and locals alike. We got here just before sunset and was bowled over by the stunning view and surrounding cute little shops . As we stomached our way through this huge pizza, we watched the sun go down in the distance.


Get tipsy off good wine

We did two wine tasting courses in Radda but our favourite was Castello Monterinaldi. We were taken on a short tour of the cellars and the garden where a beautiful house stood. (Turns out it was once a chicken coop!) We then tasted 5 wines and some magnificent balsamic vinegar. The staff are lovely and super friendly. We’d highly recommend this place over the other place we visited (Castello di Radda) which felt more corporate and lacking a personal experience.


Stay in the Campomaggio

Rooms boasting high ceilings and a warm and cosy decor, breakfast that takes place outside in a sweet little courtyard and a pool overlooking the stunning Tuscan vineyards out front; Campomagggio is a stunning hotel. Tip: There’s a couple of deck chairs in the spa below where you can sunbathe over  a view of the Tuscan fields if you fancied a quieter spot away from the pool and a regular dip in and out the spa facilities.


  1. Second stop: Greve in Chianti

Medieval Montefiorialle

Our highlight in Greve was the charismatic medieval village of Montefiorialle. It is endearing and we promise it’s a must see. We loved walking through the cobbled streets, turning corners until we stumbled across one of the best views of our holiday. Alberto’s Home Restaurant has ridiculously cute gingham tables lined up for the perfect viewing experience. We had intended to spend the evening at the restaurant next to our farmhouse B&B but it was impossible to leave this spectacle.


Stay in a remote B&B

Our farmhouse B&B Il Cielo Bio, was a bit further out of town and tucked higher in the hills. For anyone looking for something a little more unique, definitely check out this one bedroom B&B hosted by a lovely lady called Michele – she was absolutely fantastic during our stay.  We enjoyed a quiet walk near the B&B and passed lots of idyllic Italian country homes.



Stop off at Piazza Matteotti for cheese and wine tasting

Definitely pay a visit to Piazza Matteotti, the main square in Greve; it’s packed with beautiful little shops, wine bars and restaurants. Michele actually recommended we go back there in the evening as the lit up square is a sight not to miss but we didn’t make it back there as we were too busy soaking up that glorious and mighty view in Montefiorialle.


  1. Third stop: Siena, central Tuscany

We had heard so many good things about the city of Siena so we were keen to stop by. Unfortunately our time in Siena was short lived, a couple hours at most but we are definitely going back one day to fully experience it. Walking through the centre of Siena we got the impression this was a much loved destination, like Rome, packed with history and architecture to die for.


  1. Fourth Stop: The Wedding, Foiano della Chiana

We didn’t explore the area or the sites in Foiano della Chiana but we did experience the most stunning wedding ever. Our friends’ wedding couldn’t have been any more perfect, they got hitched in style! We adored every minute of it and so happy to have shared this incredible moment with them.


  1. Fifth stop: Val d’Orcia

In the southern region of Tuscany, south of Siena, Val d’Orcia is another mesmerising, untouched region with landscapes of vineyards that stretches on for miles and miles. The notorious image of Val d’Orcia is where our Tuscany dream began. We ended our trip here but Tuscany is not over; I’ll be back here again one day!



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