A Self-Drive Through Tuscany

Jasmin Shaw on 08 June 2019
Tuscany. The very word conjures images of slender Cypress trees and rolling hills. Divine wines and pretty towns. We spent a week self-driving through this famously beautiful region picking up tips, must dos – and a few very decent bottles of plonk!

The rare example of a favoured holiday destination where the countryside wins out over the coast, we based ourselves just outside of Florence, giving us the option to dip into the city when we wanted, and discover the rest of the region easily too.

We’re pack-it-all-inners and so I’d already earmarked several places I wanted to visit during our trip. Early June, when we went, is prime time for exploring, with temperatures inching up into the late 20s and early 30s so expect long sunny days made for strolling through beautiful squares, dining al fresco and cooling off with Italy’s famous gelato.

Our first port of call was Florence. For me, I think we made a mistake by visiting over a weekend. Florence is so busy now. And it’s little wonder. With more than its fair share of beautiful architecture, great shopping and delicious food, holidaymakers are clamouring to get their fix of Firenze. I’d plan to stop here midweek, making time to admire the beautiful Duomo with less hordes, and the opportunity to wander a little more freely across the postcard perfect Ponte Vecchio – the city’s unique bridge complete with shops.

Laidback Lucca was next, and for us, we found it much more our cup of tea. Friends had recommended this sleepier spot after their own Tuscan honeymoon several years back. Ringed by thick medieval walls, the old city is a pretty delight with a clutch of lovely restaurants, shops and cafes, a huge rambling street market with literally hundreds of stalls (we visited on a Sunday), and a much more local feel. Without a doubt, the best thing to do here is hire bikes from one of the many rental shops – we paid around seven Euros each for two hours – and cycle the wide tree-lined promenade atop the walls. The views are spectacular.

It’s no visit to Tuscany without exploring Chianti. The famed wine region is beyond pretty with winding country lanes lacing through rolling hills. We found there to be quality vineyards dotted all across the landscape here, some demanding to be pre-booked, others with a more laid back approach. If you know your wines, and one is of a particular interest, I’d recommend getting booked in in advance. We dropped into a vineyard, met the owner and enjoyed a private tour and wine tasting. It was only around 15 Euros each, and a real highlight of our experience. Unfortunately our bill for taking wine home was a little higher!

We’d just missed the famous Paleo when we travelled to Siena. If you’ve not heard about it, it’s when Siena’s neighbourhoods are at their most rambunctious, rivalling one another in a centuries-old horse race in the city’s main square. The floor is trodden with sand, and the whole place is absolutely alive. A little more sedate when we went, but still packed with character and charm, we loved this place with its atmospheric streets and a bit more of a rough-around-the-edges appeal.

San Gimignano is the place that tops many an Italian wish list. Outlandishly attractive and perched above a hilltop, you’ll find cobbled lanes and grand squares loomed over by medieval towers. If I’m honest, I’d say this is likely a place that’s best enjoyed out of season. With spectacular settings like this come huge crowds, and as much as we liked it, we felt that it did dampen the atmosphere a bit. Spring or autumn would be just perfect here.

And finally, with many of Tuscany’s drawcards already under our belt, we clamoured for something a little different on our last day. And beyond the big-hitters, more undiscovered gems still lie. We visited Arezzo, and absolutely loved it. In the process of gearing up for its annual medieval jousting event, there was a buzz in the air, but still a distinctly authentic feel in the quality restaurants, shops and historic spots. It was the perfect way to wrap up a Tuscany tour of two halves: part touristy, part hidden and all absolutely blissful.

Planning your own Italy trip? I’ll fill it with tips and recommendations and wrap it up in a friendly expert service, tailored uniquely to you.