I decided to do the holidays a little differently this year. 

This morning, in the last days of December, I drove to the top of a dirt driveway for a yoga class led by my friend Elena, an incredible yoga instructor here in Pienza. Inside a white-beamed room with a hand painted mural on the ceiling and a view of cypresses beyond, a group of women of all ages began the hour smiling, and ended the hour smiling. Everyone said hello to one another, everyone said goodbye. There was such an easy friendliness in that room, it felt almost… what’s the right word? Affirming? Reassuring? Just… as it should be, I suppose :)

In a few days, I will officially be one year older, and it isn’t until this past year that I have come to really appreciate women's strength, generosity, and resilience. In that room of about 8 women practising, there were, coincidentally, two familiar faces. Because that’s the thing with community; if you give, it grows. If you return, if you’re consistent (which these days doesn’t require much), if you lead with kindness... they’ll be there.

I’ll never forget visiting Stefania’s property a few years ago and watching her collect, on a whim, a bouquet of flowers from the ridge overlooking Montepulciano. We had only just met, and she handed them to me before I got in my car. I put them in a case and included the scene in a book of photography. It’s imprinted on my heart, though, because of the moment, because of Stefania— not because I physically printed it. On my first morning here over a week ago, I walked into the bar (which opens at 6am, aces), and heard my name from someone already sitting with their cappuccino. “Come sit!” When I leave my apartment, I immediately cross paths with a familiar face. They greet me by name. These little things are the big things. Your world is what you build, your people are relationships you water, and so, when you decide you want to go to Pienza for Christmas, you know you won’t be alone. 

I read this, said by the immensely talented Rob Reiner, who we will collectively miss forevermore: “If you have tapped into something that is real for you, chances are you are going to tap into something that is real for someone else.”

There’s a reason you’re drawn to certain people, right? In my third book, my main character jumps ship and moves somewhere where she knows no one. Someone says to her, it’s the people that make a place. It’s not a novel concept, but it’s usually quite true, isn’t it? I do travel solo a lot, and when I go somewhere new, I suppose I am a bit of a chameleon and fall in love with it all quite easily, but the truth is… threading into a little familiarity— even if you make it from scratch within a few days, well, a little bit of warmth goes a long way. 

On Rob again, there’s a story he once told that feels like, boom, right to the chest. It’s this one: “The first time I felt real validation, I was 19. I had directed a play and my dad came backstage afterwards…and he never lied to me about any of this stuff…he looked me in the eye and he said, 'That was good. No bullshit.’ He said those words to me. It meant everything. The next day I came into the house and we sat in the backyard and he said, ‘I’m not worried about you. Whatever you choose to do, you’re going to do it great.’” 

Everyone I’ve met here in Pienza is an example of someone who followed their joy, and if their joy somehow led them astray and they found themselves on a path with some pot holes, they approach that path with the same smile. The same good humour. Because it’s all a hell of a lot easier and more fun when we just… choose to be happy.

Tis a roundabout way of saying, a few weeks ago, I listened to my gut, cancelled a plane ticket, booked another, et voila…. 

Here I am in Pienza, a place I’ve been visiting for almost a decade. I first came when I was between apartments one May, many Mays ago. I was moving from Florence to Milan, and I wrote to John, the owner of La Bandita. ‘Sure, come hang for as long as you like.’

It was a transition period for me— new job, new flat, same (tsk-tsk) male flame. I was high on anxiety and adrenaline, and that gorgeous Pienza weekend settled me almost as swiftly as the xanax my Milanese doctor used to prescribe with a simple whatsapp request (“Sure, how many do you want?”)

As I was to learn, May is my favourite time of year in Pienza. It is the greenest place you’ve ever seen— lush and bright as a highlighter. May is when I do my Pienza retreats (this year, both all-women and co-ed, because as it turns out, guys love adventures too :) ) By June, the fields are already turning gold.

However, December in the area is a joy; far fewer tourists and cars on those winding roads, gorgeous mild weather during the day, red wine that feels v justified at night. Driving from Montalcino to Pienza, all is copper and fir-hued. It feels like spring, smells like wood burning, and sounds like serenity. There are many discreet second-home (or third-home) owners in the area who you might see at the local bar or trattoria, rejoicing in the calm. Whether you’re George Clooney or Danny Meyer, the cast of Succession or the founder of a European clothing company, everyone’s got their opinion on how to Pienza off-Season. (Pienza as verb, obviously).

I admittedly did not come here this December to explore, as I’ve done that x infiniti on previous visits. I came to run (like, lots), see people I love dearly, and work on my fourth book, which has been stalled for too long. So, this isn’t a pitch for the abbazia or the thermal baths or the twelfth hilltop village you probably don’t need to visit. Put that pecorino down, man. 

Kidding, have it.

Actually I think December is the perfect time to simply check out from the world. Eat a million clementini, enjoy a morning doppio at Bar La Posta with a side of belly laughter courtesy of the hilarious guys picking up all our rubbish (renaissance men) and who will buy your drink before you arrive some mornings (Gregory Peck, is it you?) Illegally traverse mud tracked colline  (those rolling hills that used to be your screensaver back in 1998) without being mistaken for a pheasant (a high possibility). Take baths morning and night, try to convince John to go in on La Bandita 2 with you (no dice), watch David the marathon-running head chef do morning prep while distracting him with a million questions about suppliers and herbs and burger recipes and run routes. Run morning, afternoon, and evening in the valley until you’re so high on air you’re practically singing through mile 5.

Just don’t forget to pay for parking. (x2, x3, x20, x 100) (In Pienza, FYI, you have to pay for parking). (Every day.) (Also on xmas).

I have accumulated a nervous habit with the EasyPark app. I find myself jumping to re-up when I’m not even in town. My thumb goes more immediately to EasyPark than to WhatsApp, so capitalism is alive and well in the Val d’Orcia.

Some people dream of a charming, quiet holiday. Some dread the entirety of it and numb their way through. Some are without their kids, some go halfsies. Some switch houses with a total stranger and fall in love with Jack Black. There are so many ways to do this time of year. 

E niente, if you find yourself craving a few winter weeks in the Val d’Orcia, specifically here in Pienza or environs, here is how we do it, December style: 

Stay: 

La Bandita Townhouse, Pienza. Because no one is cooler or funnier or tells better stories than John Voigtmann, there is no better restaurant than the Townhouse Caffe for something ‘other’ than the typical menu— nor any better wine list—, and also because… these people are my family. To top it off, there is a jar of v badly made cookies in the restaurant, which you WILL eat. And you will have no one to blame but yourself. And John knows they’re bad, so don’t remind him. There is also a divine dessert menu, of course, but for those 4pm fingers… it’s a cookie jar situation. 

Casa Newton, Pienza, for a property that feels like the home you’ve always dreamed of and gardens to die for, by star landscape designer Luciano Giubbilei

Eat: 

- Townhouse Caffe (La Bandita). Like eating at home, only better and boozier. Hands down, the best place to be annoying with your dietary peculiarities.

- Trattoria il Pozzo, Montalcino (a favourite of Danny Meyer, and John, but reader should know that there is nothing on this list that John doesn’t like, unless explicitly mentioned, because I only go where John goes. And in fact the best way to do anything in this area is to preface your visit with “I am a friend of So&So”, and this requires a few things that costa poco in life: Likeability, Loyalty, Not Embarrassing Your Friends Who Send You Places.

- Il Rossellino (Pienza): John says ‘Go see the boys at Il Rossellino’, so …. go see the boys at Il Rossellino. 

- Dopolavoro (across from La Foce gardens) A big space, friendly service, very dependable, good food. Servings are generous.

- La Scottiglia (one of Elena’s favourites). Toward Monte Amiata. Traditional food, lovely atmosphere. 

- Da Silene (Elena recommends). A Michelin starred restaurant about 30 minutes from Pienza 

- Podere le Ripi (not for a meal but for a tasting) the coolest group of young vintners and farmers who are making incredible wine on a gorgeous property in Montalcino. 

Meat: 

There are a number of butchers here in Pienza and to be fair you cannot go wrong, and they’re all the loveliest people, but because I am a David prodigy (wishful thinking), and because I am very loyal, I go to Marco (Macelleria Scroccaro). This is where David, the chef at La Bandita, buys his meat. And if you’ve ever had the Bandita burger or the tartare, well……. you go to Marco. Also best ragu of my life from here. Every time I bought it, they asked what kind of pasta I’d make it with and then gave me a very confused look when I said no, I eat it on its own, with a side of vegetables. (mi dispiace tanto… I guess I am guilty of embarrassing my friends here…)

Christmas Market: 

Montepulciano (charming. don’t be put off by the disastrous parking here; you will find a spot) I admit I did not go to this but ….. John recommends. 

Run: 

At your own risk, wherever you fancy. David takes one of the main asphalt roads to San Quirico and back. I am gutsy but not that gutsy. I run in the valley, where trails turn into UNESCO drone shots and there is hardly a soul in sight. In winter, it’s especially enjoyable because the strada bianca’s are packed down; in spring and summer, it’s a tornado of white dust every time a car passes. You get: fresh air, quiet, views, elevation, and somewhat uneven terrain because of the rocks and pebbles. I actually ran in a sports bra a few afternoons. In December. Oh, the satisfaction and the joy.

I am partial to the strada bianca that goes toward what the map calls Casalino. You’ll pass Agriturismo Podere Spagliarda before you get to the Strada Provinciale 53, at which point, yes, you might as well join David and finish the run to San Quirico. Needless to say, my ex-dancer hips are not my biggest fans this week but the whites of my eyes are re-born. 1000 points, Tuscany, for rejuvenating fresh air.

There are trail markers everywhere, but truth be told I don’t think they are actual trails; I think some of them are just sick jokes, probably placed by my funny friends with whom I espresso every morning. 

The weird thing about this place is that there is so much nature, but the running is not obvious. I’ve been coming for about ten years, as I said, and I’m still trying to figure out the best routes. Keeps things interesting. John has been living here for 20 years and he just found wine from Montepulciano he likes, so, there is novelty, if you seek it out. 

If you like snow:

Monte Amiata is a beautiful place to explore in the winter. If there is enough snow, you can even ski. This is one of Elena’s favourites.

il mare:

I’m a water baby. I need the coast, as often as possible, so you can pop in the car and head out to Castiglione della Pescaia or Bolgheri or wherever you fancy. John says: Ristorante Il Garibaldi Innamorato

Yoga:

Write to Elena. She has the voice, the temperament, the experience, and the pacing. She should be the yoga empress of the Val d’Orcia. On Instagram @Elenantoni

*I will add to this list as more suggestions trickle in. Waiting on George (C) to share his faves.
To be noted, there is so much to do and see here, but this is just a few ideas for this time of year. If you like thermal baths, they’re still open in Bagno Vignoni. One day I will write about my personal favourites for a gorgeous May or summer-month. I have many. Many, many. Many. And even more photos than words, if that’s possible :)

now scroll please for a random smattering of photos and videos. choosing was, as always, sophie’s choice. and if youve read my articles for a while and still haven’t seen this meryl streep film, only watch if you’re ready to bawl your eyes out.