What to do in Tuscany: If Tuscany was a woman and you were dating her

It’s  a fact. Tuscany just keeps getting more popular. Unlike those popular girls in high school, however, who looked down on you because you were lame at sports, Tuscany welcomes you with plump open arms, an open bottle of Chianti Classico and tantalizing scents of basil and lavender.

(Take that, popular high school girls, because you will never age as well as the Leaning Tower of Pisa or a Super Tuscan wine like Ornellaia.)

And if you’re wondering what to do in Tuscany on vacation, read on.

If Tuscany was a woman she would welcome you

Welcome to Tuscany


First you need to forgive Tuscany for being more beautiful than you, and more eternally captivating, then you need to figure out how to spend your time here. So imagine you are a man (if you are already a man, that shouldn’t be a stretch) and that Tuscany is a woman. And here’s what you would do on a date.

What to do in Tuscany activity 1: Drink red wine

View of Tuscany near Terme di Saturnia

Tuscany will steal your heart


Doesn’t everyone drink on a first date? How better to get over those nervous jitters? You’ll find plenty of opportunity to drink delicious reds in the hill town of Montepulciano, but be forewarned, you may also be fighting the crowds of American tourists who come here in search of an authentic Tuscan experience.

This is what you should do in Montepulciano: Not only should you buy a bottle of Vino Nobile di Montepulciano, a red wine with layers of cherry and plum that’s been topping wine-tasting charts since at least the 15th century, you should wander into a few of the medieval-looking shops to eat all the free samples of salami, bread drenched in olive oil and pecorino cheese the shops so willingly give out.

Tuscany travel tip warning #1 – you will feel guilty about eating all those free samples and ending up spending huge amounts on artisanal sliced meat and cheese.


Watch where you park


Tuscany travel tip warning #2 – do NOT park by a sign outside the old walls of Montepulciano that says ’30 minute baggage unloading zone’, thinking that you can wander around Montepulciano happily for 30 minutes pretending you are taking your bags through the cobbled pedestrian lanes to your hotel. Tuscany is all-seeing. It knows you’re just after free samples of cured meat.

You will get a parking ticket, not know how to pay it and it will follow you back to Canada and cost you lots of money. Not that that happened to us. (Except it did.)

What to do in Tuscany activity 2: Drink some more red wine

Doesn’t everyone drink on a second date? How else do you get over those … oh, never mind. Luckily I’m married now and can give my liver a break. But here’s a confession. My boyfriend (now husband) and I both prefer the smaller town of Montalcino to eye-catching Montepulciano, mainly because there are fewer crowds, it’s easy to find a (legal) parking spot and because this is the home of Brunello di Montalcino, possibly the very best Italian wine in … um, Italy.

What to do in Montalcino: Along with the Museo Civico e Diocesano d’Arte Sacra and the 14th-century castle, I recommend going to a pharmacy, at least that’s what I did after being bitten on the bum by a bee on the drive there. (Seriously, who get’s bitten on the bum by a bee?)

Charming Italian pharmacy in Tuscany

What do you have for a bee bite?


Even though my posterior was throbbing painfully, I wasn’t too distracted to notice that the pharmacy was a time capsule with rich wooden cabinetry, the pharmacist was as charming as Tuscany itself, and the view of the Tuscan fields from the window a classic scene of rippling hills.

Overall it was a pharmaceutical experience that almost, but not quite, made it worth being stung in the bum by a black and white Tuscan bee.

Tuscan fields outside Montalcino

A pharmacy with a view


Tuscany travel warning #3 – If you go to Montalcino with your boyfriend or husband, you’re in terrible trouble because he will taste Brunello wine and from then on, will love it more than he loves you, and you will have lost him to Tuscany forever.

Brunello wine and wine tasting in Montalcino Italy

A bottle of Brunello please

What to do in Tuscany activity 3: Go to the hot springs

Nothing says romance like soaking in a pool of hot water. If you’re near Montalcino anyway, you should keep on going to the gorgeous spa at Terme de Saturnia, where hot springs fill a vast swimming pool built over a volcanic crater before dripping down the Tuscan hillside.

There are so many wonderful hot springs resorts in Tuscany, you can pretty much get yourself into hot water no matter what corner of the region you’re in. If you’re Penelope Cruz, I’d suggest Fonteverde Spa Resort. More down to earth is the former pilgrimage hot springs stop, Bagno Vignoni.

Hot springs of Bagno Vignoni in Tuscany

Breathtaking Bagno Vignoni


And if you’re a hip gorgeous Italian couple on a weekend break from your  job in advertising, you might think about Terme di Petriolo near Siena.

What to do in Tuscany activity 4: Rent a villa or better yet, move there

Renting a villa or even buying a house (if you really want to get Under the Tuscan Sun) is the stuff holiday dreams – and movies – are made of, because you can spend lazy days lying around the pool, shop for local produce in atmospheric hilltop villages and cook endless dishes of pasta al pomodoro and/or fall in love with the handsome local handyman who comes to clean your pool or unclog your 400-year old drains.

Need I say more?


Florence Florence Florence

What to do in Tuscany activity 5: Sightsee

Let’s just run through a few of the top sights of Tuscany, shall we, because once you’ve seen them you can go back to lying by the pool?

In Florence, you must visit the Uffizi Gallery to see Botticelli’s Birth of Venus – even though Venus is so exquisitely beautiful it will bring up all your deep-seated insecurities caused by those popular girls in high school. But then you won’t care, remembering that the handsome local handyman at your villa has declared undying amore.


Tuscany is the Venus of Italy


In Florence you must also see the famous Ponte Vecchio Bridge, a shop-encrusted medieval bridge that spans the River Arno. Walk back and forth looking at all the shops selling gold, but do not, under any circumstances, lock a padlock onto the Ponte Vecchio like all those other dumb couples who believe that this will unite them forever, because by now your boyfriend/husband is in love with: a) Tuscany b) a bottle of Brunello and c) Botticelli’s Venus, so you’re sort of wondering if your relationship will last.

And, because the handsome local handyman is still haunting your dreams, you’re  wondering if you even want it to.


Falling in love with Tuscany


But also don’t put a love lock on the Ponte Vecchio Bridge because the authorities have a terrible time getting them off and you don’t want to be that kind of tourist now, do you?

What to do in Pisa: In Pisa, of course you want to see the Leaning Tower (and if you’re taking me up on my hot springs recommendation, you can stay at Bagni di Pisa Spa Resort, which is only 5 km away)

What to do in Siena: Gaze happily at the Piazza del Campo, the stunning town square where a medieval horse race called the Palio de Siena is held twice every summer (July 2 and August 16). In this centuries-old tradition riders risk life and limb to careen around the piazza bareback while wearing the colours of their contrade (the neighbourhood they are representing).

Whosever horse gets around the Piazza del Campo 3 times first wins – whether the rider is still on it or not. (And, if you’re taking me up on my hot springs recommendation, you can stay at Terme di Petriolo, which is about 20 kilometres south.)

Near Siena is Terme di Petriolo a hot springs resort

Soaking near Siena

What to do in Tuscany activity 5: Cycle

If bucolic images of riding along quiet country roads past olive groves and cypress trees make you think more of getting clipped by a speeding car or chased by a snarling Tuscan dog (and let’s not even get started on bees) then I’d say you might just be a wee bit phobic. But don’t worry, many of us are.

Cycling in Tuscany beautiful fields

Are there dogs here?


The solution is to go to the lovely walled city of Lucca, where you can rent a bicycle and ride around on top of the city’s Renaissance walls. Cycling the walls of Lucca is so much fun, just thinking about it makes me fall in love with Tuscany all over again … you know, if I were a man and Tuscany was a woman and I was dating her.

So go to Tuscany and fall in love with it for yourself – it will be the start of a beautiful relationship (and possibly the end of your old one).


Read more about Top Destinations in Europe to Visit 

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  1. Michele Peterson says

    Cycling, fabulous wine, hot springs, handsome handymen and pharmacies with a view – Tuscany has everything I love in a destination ( minus the bee stings). It’s definitely on my list of places to go.

  2. says

    When in Tuscany, don’t do as the turist do! If you have time to visit Tuscany then your next step is the Tuscan “Maremma” off the beaten path and out of ordinary. Maremma is the southest area of Tuscany and still undiscovered but reach of natural beauty, old small medieval village, Etruscan eritage, organic wine, food and cheese, wellness with natural hot springs, beaches and natural reserve, golf………Tuscan Maremma (province of Grosseto) What else???

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