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Hello! I’m Anjali. I’m a board certified health coach, author, wife, mom and food lover from the SF Bay area (now living in Seattle, WA!); with a passion for delicious food and a desire to make healthy eating easy, tasty and fun! Learn more about me here and stay for a while!

Anjali Shah

A Week in Montepulciano: Under the Tuscan Sun

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1a - Montepluciano town2

Rolling hills, very few tourists, warming Tuscan food, breathtaking views and unique wines — these were some of the highlights of our stay in Montepulciano – a small town in the province of Siena, Italy. We had been to Tuscany before but hadn’t been to Montepulciano, so this time we were excited to see a new region and relax after the two weeks we spent in bustling Rome.

We drove from Rome to Montepulciano, which was pretty easy albeit some mishaps with a majorly busted rental car:

We found out our car had a slow leak in one of the tires about 2 hours into our journey and that the tire was almost flat.

Yes, an Italian on a scooter flagged us down and managed to communicate that to us in Italian (no English).

No, we had no idea what to do – we were in the middle of nowhere and the car didn’t have a spare.

Yes, we did end up going to a gas station every morning to fill up the tire with air praying that it would last us the week in Montepulciano and get us back to Rome safely (somehow it did!)

Meanwhile, while getting to our Montepulciano B&B….

Yes, we almost drove off a cliff on a tiny, unpaved Tuscan road.

No, the car didn’t fall off the cliff.

Yes, the back wheel of the car was hanging off the cliff.

No, somehow we didn’t think to look back before we reversed.

Yes, we found help and managed to push the car out (with the help of the owners of the B&B we were staying at and a local farmer with a tractor!)


After all that though, we were greeted with some amazing scenery and views upon entering the road to our hotel for the week:

1 - Entrance to hotel

1a - Montepluciano Countryside2

We stayed at the Relais San Bruno, one of the most beautiful B&B style hotels I’ve every stayed at. The grounds were huge, we got our own private “villa,” and the entire place just felt meant for relaxing.

It was also super close to the town (but far enough away that you felt secluded), so it was the best of both worlds. The owners were great, really helpful and gave awesome recommendations on restaurants and wineries to visit.

We also got to have the most amazing complimentary breakfast in this room every morning:

Relais Breakfast

Our first night in Montepulciano, we had dinner at La Grotta, one of the best restaurants in the region. The service was impeccable, and they have an outdoor garden that is wonderful for dining in the summer.

We started with their warm, house made garlic and walnut breads (to die for). Then I had the Tuscan tomato soup with garlic, bread and basil – a classic Tuscan dish where the bread is used to thicken the soup.

1b1 - First dinner Montepluciano

It reminded me of a deconstructed bruschetta — the flavors just exploded in your mouth.

The husband ordered the steamed soft egg topped with shaved pecorino cheese and shaved fresh truffles. 

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Need I say more? The egg is hiding under that pile of truffle shavings 🙂

Our entrees: “Irregular” home made pasta with tomato, garlic and swiss chard. 

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And the Aubergine alla parmigiana – grilled zucchini, and spinach with garlic. 

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This is not your typical eggplant parmesan. The eggplant was SUPER thinly sliced, layered with tomatoes and baked with mozzarella in the oven. It was served with the zucchini also shaved in thin slices and the spinach on the side. Filling but not heavy.

And finally, for dessert – Bitter chocolate terrine with English cream.

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The chocolate terrine was like a warm chocolate cake. But the cake – even though the texture was dense, was actually super light and fluffy somehow. It was served with a couple fruit slices which gave it some depth beyond the chocolate flavors. Overall, La Grotto was a wonderful, memorable, peaceful, beautiful first dinner in Montepulciano (especially after our adventures getting there!)

The next few days were spent exploring the town of Montepulciano, and the neighboring towns of Montalcino, Pienza, and Cortona. On the way to Cortona you’ll find the most gorgeous sunflower fields, where we stopped and took an inordinate amount of photos 🙂

1a - Monteplucianosunflowers

How happy do those sunflowers look? I still can’t get over how they turn and face the sun throughout the day – so cool!

1a - Montepluciano Sunflowers

We also saw some expansive wildflower fields and farmland.

1a - Montepluciano flowers

At times it felt like we were in a painting.

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1a - Sunflower sky fiew

In the town of Montepulciano, we found one tiny restaurant that happened to have really delicious food. It was called La Dolce Vita Enoteca: a wine bar/restaurant where we grabbed dinner one night.

I was surprised at how flavorful and fresh the food tasted – and they had some great wines too!

We had the Bruschetta – which in Italy is like nothing you’ve ever tasted.

1d - Dinner1

A soup with farro, spinach, potatoes, carrots, celery and white/bortolli beans…

1d - Dinner2

And bruschetta with pecorino, prunes, and honey.

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Simple but flavorful – a true Tuscan meal.

A couple fun and unique highlights in the town of Montepulciano were:

Our visit to the coppersmith.

1c - Coppersmith collage

Yes, that’s right, a real-life coppersmith.

He is the sweetest person we have ever met.

He speaks no English – he talks to you in Italian but somehow through gestures and broken understanding it’s very easy to communicate! He is just genuinely interested in meeting people and learning about them.

When he met me and the husband, he wanted to create a little bronze plate commemorating our anniversary – it’s something he and his wife had done for themselves over 50 years ago (yes, they’ve been married for 50 years and are the cutest couple ever). The shop is a little hole in the wall off the main piazza in Montepulciano. It’s not touristy at all – you would totally miss it if you didn’t look hard for it! Oh and the best part, for the plate he made us – he didn’t charge for it at all – we realized that it’s just his way of meeting new people and forming relationships – so cool.

1c - Coppersmith Montepluciano

He does have an actual shop, which his wife runs (he called her the “Finance Minister” – ha!) We ended up buying a beautiful bronze pot from them that is now displayed on one of our bookshelves. And we have our copper plate to match. Such an interesting and unique experience that we just happened to stumble across!

1c - us with coppersmith

Another highlight of our visit was an outdoor Symphony / concert that we were able to watch one night (due to a music festival that happened to be going on while we were staying in town).

3 - Night concert 2

It also ended up being an unusually cold/foggy night, which just made for even more great scenic photos of the town.

3 - Montepluciano night collage 3 - Montepluciano night

3 - Montepluciano night 3

3 - Montepluciano night concert 3 - Montepluciano night 4

The next day, we headed to Avignonesi winery for what turned out to be an almost all-day wine tour and 5 course lunch. Avignonesi is the only organic/biodynamic-certified winery in the region – and they showed us all of the measures they take to make sure their wine is free from all pesticides, contaminants, etc.

1f - Avignonesi

It really made me respect their winemaking process.

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Montepulciano is known for its Vino Nobiles, while Montalcino is famous for Brunellos. Avignonesi, of course, makes Vino Nobiles, among a selection of many other wines (Cabernets, Merlots, Malvasia, Chardonnay, and Vin Santo to name a few).

1f - Avignonesi3

We were impressed with their wines and the grounds – they took the time to show us how their wine is made, what factors they consider when recommending varietals, pairing with food, etc.

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After our wine tour, we headed to lunch in their outdoor dining room facing the vineyards.

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Best dining experience ever.

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This was like the meal that kept on giving.

Our First Course: A fresh salad with goat cheese, tomatoes, cucumbers, onions, yellow peppers, salt and pepper. The vegetables were so fresh and crispy it felt like they had been brought from the garden that morning.

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Second course: A cool summer soup with tomatoes and green peppers served with paprika grilled bread (gaspacho style).

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Third course: Homemade maltagliati pasta with vegetable sauce and saffron from Val d’Orcia (the sauce was made from pureed veggies, seasoned with saffron, and tossed with the pasta).

1f - Avignonesi8

Fourth course: A broad bean and red pepper flan served on a puree of pecorino and red pepper sauce.

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I’m not usually a fan of flan, and I had never had a savory flan before, but this was actually pretty good. It was somewhat one-note but still really well made.

Dessert #1 was the provociazone: A mini tasting plate with Vin Santo pairings: dark chocolate truffle with ginger, fresh raspberry sorbet served on a super thin biscuit, a walnut cookie, a caramelized slice of super thin orange, goat cheese cream with poppy seeds, a leaf of fried sage, and a salted fresh caramel.

1f - Avignonesi14

Dessert #2: Pineapple carpaccio marinated in a dry martini and served with homemade coconut ice cream.

1f - Avignonesi13

The Vin Santo was so cool – it’s such a heavily reduced wine that it takes 10 years to make, and it literally coats the outside of the glass.

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Needless to say, after that meal we were full for the rest of the day!

The next morning we headed to Montalcino, where we visited Casanova di Neri winery. The wines were excellent, but the winery itself had horrible service. It was like they didn’t even care that you were there. I’d recommend just going to a tasting shop and trying some of their wines – not worth visiting the actual winery.

Montalcino itself is a cute little town that’s worth exploring.

1a - Tuscany towns

1a - tuscany towns2

We came across a small shop that made honey — and decided to do a honey tasting (fun!)

2 - Honey

Um, yes please.

2 - Honey tasting

We also found an awesome bakery where the husband had to get a slice of cheesecake.

2 - Cheesecake

We had started our day off super healthy, as you can tell 🙂

On the way back from Montalcino we couldn’t get enough of the rolling Tuscan hills.

1a - Montepluciano hills 1a - Montepluciano hills2

We also went back into Montepulciano to watch the sunset. From blue…

1e - Sunset2

To purple…

1e - Sunset1

Totally worth the hike up the hill for the view.

1e - Sunset4

On our last day in Tuscany, we ventured over to Pienza: the most picturesque small town you will ever see.

They are famous for their Pecorino cheese.

4 - aPienza

We had dinner at this tiny restaurant run by an old couple: Ristorante Il Rossellino. If you ever are in Pienza, you HAVE to eat here.

4 - Il Rosellini 1a

It’s located in Piazza di Spagna, but it’s so tiny you really have to search for it to find it. The inside of the restaurant literally has 4 tables, and the kitchen. In the summer, they put some tables outside to accommodate more people, but in total I’d say about 10-12 people can dine here every night.

4 - Il Rosellini dinner

Our appetizers were an Asparagus souffle over a pecorino cheese sauce.

4 - Il Rosellini dinner1

And an eggplant and mozzarella layered dish over a tomato/olive oil puree.

4 - Il Rosellini dinner2

I know, the eggplant dish looks kind of gross, but I promise it tasted amazing. The souffle was good too, although it was a little too eggy for my tastes (the husband really liked it though).

Then came our star dish for the night: gnocchi made with fresh truffles, shaved right over the top.

4 - Il Rosellini dinner3

I have never had gnocchi that tasted this good in my life.

And can you just take a look at the truffles?

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Ahhhhh. Heaven.

We also had a homemade tagliatelle with a fresh tomato sauce. Still delicious but nothing compared to those truffles. The husband and I came home still thinking about those truffles.

4 - Il Rosellini dinner5

Dessert was out of control. First we had a warm, chocolate souffle with chocolate fudge inside.

4 - Il Rosellini dinner7

It was about the most perfect chocolate “lava” type cake I’ve had.

Then we had a warm, pastry-esque cake with strawberries. Filled with a fresh vanilla custard, served on top of an orange sauce.

4 - Il Rosellini dinner6

Might be one of the best desserts we have ever had in our lives.

It disappeared in approximately 5 seconds.

When we were done with dinner we had a chance to talk with the owner and cook, Enzo. He had come out between each course to check on us and to show us the food he was cooking before he cooked it. It was like eating at someone’s (gourmet, 5 star) house. After dinner we thanked him for the delicious meal and took a picture with him. He was the best.

4 - Il Rosellini dinner8

After that night we packed our bags and headed to Salina, one of the Aeolian Islands, and our last destination in our month-long Italy trip! But before that we did get a chance to drive through the Tuscan hills on our way to the airport, one last time.

Memorable, peaceful, and breathtaking.

1a - Montepluciano Countryside

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