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Road to Rome

Our last morning at Villa Cicolina and there was only one thing on the agenda.

That pool.

Infinity pool at Villa Cicolina with Tuscan valley views
No tours. No guides. No wine tastings. Just this.

We had spent two days running around Tuscany — olive oil tastings, dairy farms, wine, Montepulciano, photography tours — and hadn’t properly used the pool yet. Criminal.

Sumi Bear at the infinity pool edge with Tuscan valley panorama
Infinity pool. Olive trees. Tuscan valley. I could stay here forever.

Now, to be clear, I do not approve of pools. Pools are just organized water, and water is my enemy. Pokin has threatened me with baths enough times that I have a healthy distrust of any body of liquid larger than a cocoa mug. But I will admit — from a safe distance, on a dry lounger, under an olive tree — this pool looked very good.

Nicholas was in his SpaceX shirt, lounging under the olive trees, scrolling his phone. Pokin was somewhere being productive. I supervised from the lounger. Dry.

This is what the villa was for. Not racing to appointments. Not navigating bollards. Just sitting by a pool that drops off into a valley and pretending the rest of the world doesn’t exist. Preferably without getting wet.

We could have stayed all day.

We did not stay all day.


On the way out of Montepulciano, we stopped at a vineyard. Not for a tasting this time — just for the views. At this point we’d had enough wine education to last a lifetime. But the landscape around these estates is something else entirely.

Sumi at vineyard railing with hilltop town in background
Montepulciano on the ridge. The vines get a better view than most people.
View from vineyard window toward hilltop town
Through the window of the vineyard. Montepulciano framed like a painting.

The vineyard had a little garden, neat rows of vines running down toward the valley, and that view of Montepulciano up on its ridge that makes you understand why people have been making wine in this exact spot for centuries.


Before getting on the road to Rome, we stopped for lunch at a little deli in town. The kind of place with a glass counter full of cured meats and a guy behind it who just starts putting things on a board without asking too many questions.

Charcuterie board lunch at a Montepulciano deli
A tagliere, some bread, and four people who were not ready to leave Tuscany.

Salami, prosciutto, cheese, bread, pickled vegetables. Simple. Perfect. The kind of lunch that doesn’t need a menu or a reservation, just a counter and someone who knows what they’re doing.

Then we got in the car and pointed it south. Rome was waiting. But Tuscany had been good to us.