Come fall, the Italian region of Umbria is a rich, fertile oasis.

Here’s how to reap a bounty of culinary and cultural pleasures.

Me, friend to all dogs!

A pool on the grounds of an estate hotel in Umbria, Italy

The pool at Reschio.Credit:Federico Ciamei

It was late October, black truffle season and also peak rainy season.

Now off-leash, Artu, still spry at 12 years old, bounded ahead.

We passed it around, cupping it in our hands like gold.

A villa shrouded in mist, in Italy

Villa Castiglione Ugolino, set in a 13th-century church on the Tenuta di Murlo estate.Federico Ciamei

Calderini pocketed the mushroom while Artu sat patiently for photos.

I was finally able to pat his silky coat as he looked up at me with forbearance.

Then it was time for his reward: a game of fetch, initiated by Calderini.

Pair of photos from Italy, one showing a truffle dog, and one showing a plate of scrambled eggs with truffles

From left: Giovanni Calderini and his dog, Artù, after a successful truffle hunt at Tenuta di Murlo; scrambled eggs with white truffles at Il Caldaro, the restaurant at Tenuta di Murlo.Federico Ciamei

It sounded like a line from Shakespeare.

Isnt it strange that life has brought you to a place where you could write that sentence?

But judging from my admittedly brief time in Umbria, the comparison doesnt quite hold up.

Pair of photos from Tenuta du Murlo hotel in Italy, noe showing a guest room, and one showing the owner Carlotta

From left: A guest room at Tenuta di Murlo, an estate in Umbria; Carlotta Carabba Tettamanti, the estate’s owner.Federico Ciamei

Umbria is its own thing.

Maybe it was the cool autumn air, or the moody clouds that shadowed us throughout the week.

The land has been in Alessios family for more than 300 years.

Pair of photos from Italy, one showing a man eating pasta, and one showing a staff member lighting candles at a table

From left: Guide Rudston Steward digs into a plate of strangozzi at L’Alchimista, in Montefalco; setting the stage for in-villa dining at Tenuta di Murlo.Federico Ciamei

Eventually the old Tenuta di Murlo farmhouses fell to ruin.

Since 2006, Carlotta has been carefully restoring them and turning them into fully serviced luxury villas.

The sense of solitude and serenity was enveloping.

Pair of photos from Italy, one showing a guide walking on a path, and one showing bees at an apiary

From left: Rudston Steward leading a tour through an olive grove near the town of Montefalco; the apiary at Tenuta di Murlo.Federico Ciamei

(For better or worse, I didnt encounter any.)

The most romantic of Tenuta di Murlos villas, it wouldnt look out of place in a Monet painting.

The most recent renovation was also the most spectacular.

Pair of photos from Italy, one showing a view from inside a villa, and one showing pomegranates on a tree

From left: An entryway at the San Michele suites, housed in a former church vestry on the grounds of the Reschio resort; pomegranates in the village of Rustichino.Federico Ciamei

Every corner of Italy offers its own treasures.

you’re free to have a huge variety of experiences in one country, he told me.

A few weeks before my trip, we had spoken by phone.

Pair of photos from Italy, one showing a landscape with cypress trees and one showing the frescoed, domed interior of a church

From left: Cypresses along the drive to a restored farmhouse on the Reschio estate, as seen from the Castello; a fresco by the Renaissance artist Benozzo Gozzoli in Montefalco’s church of San Francesco.Federico Ciamei

Goats peered skeptically at us from behind fences; dogs barked at our approach.

Just outside Giano dellUmbria, we passed hunters darting in and out of the woods.

Do you want to walk with us?

Pair of photos from an estate hotel Italy, one showing a sitting room, and one showing a plate of filled pasta

From left: The Palm Court, the main reception hall at Reschio; cabbage ravioli in a verbena broth at the estate’s Ristorante al Castello.Federico Ciamei

Where are you going?

the man queried in Italian.

We told him our destination, pointing toward the hill town in the distance, still some miles away.

Pair of photos from an estate in Italy, one showing the property’s owners, and one showing a bathtub on a terrace with landscape views

From left: Benedikt and Donna Nencia Bolza, owners of Reschio, in the estate’s design studio; the terrace of Reschio’s Tower Suite.Federico Ciamei

Youd better have some food before you get there, he replied, laughing, or youll be hungry.

(Indeed, Steward had packed us a snack of fruit and trail mix.)

We finally reached Montefalco, a little tired but invigorated and hungry.

Pair of photos from a restaurant in Italy, one showing a bowl of soup, and one showing the smiling owner Chiara

From left: Ribollita soup at Locanda di Nonna Gelsa; Chiara de Chirico, the restaurant’s owner.Federico Ciamei

to eat a pasta dish at almost every meal.

It might be the most beautiful conference room in the world.

Like Tenuta di Murlo, Reschio was once a farm that operated under themezzadriasystem.

We watched a freshly shampooed horse dry off under an enormous heat lamp.

We sat on deck chairs by the pool and ordered pressed sandwiches from the adjacent bar.

We monkeyed around at the outdoor gym and watched other guests playing tennis on the Astroturf courts.

The latter is a tall, airy room with floor-to-ceiling windows that sits a short walk from the Castello.

Umbrias famous wild boars, we realized, and picked up the pace.

Reschio is fizzy and social and whimsical.

Tenuta di Murlo is a little more grown-up, a little more subdued.

Stay first at one, and then the other, in whichever order suits your emotional needs.

It was a Wednesday night and the main street was deserted.

The decor was simple and unfussy; the tables were covered with checkered cloths.

The jolly owner, Chiara de Chirico, brought a blackboard with the nights menu.

I ordered a heartyribollitasoup and then fagottini, star-shaped pockets of pasta, drizzled with arugula pesto.

(My entree, she pointed out, was Meryl Streeps favorite.)

But it was clear that no amount of celebrity had changed Nonna Gelsa, and no amount would.

If you are posh, said de Chirico, this is not the place for you.

I thought of something Count Benedikt had told me: The world has changed, but Umbria hasnt.

And you dont want it to change.

Its beautiful as it is.

Each house is handsomely decorated and comes with its own private pool.

The service is outstanding.

While Umbria isnt currently on his roster of planned itineraries, he can custom-design a private tour.