A scenic view of rolling green hills with winding roads lined by tall, slender cypress trees, and red flowers in the foreground.

Places To Visit

This is one of the most culturally rich places on earth.

We’ve been coming for more than 50 years and we’re still discovering, and rediscovering, fabulous places.

These are the closest, but only an hour away are Siena and Orvieto.

Use discount code TIPTOP for 20% off

Or if you have already booked elsewhere, we can help you cancel, and rebook with us.

Crowded street scene in Cortona with people walking and shopping near historic stone buildings with clock tower in the background.

Cortona

24 minutes away, Cortona is a beautiful and lively town to visit, especially at the weekend and in the evenings.

Restaurants range from great value to show stoppers.

Be sure to check out the view from outside the Duomo.

Historic Montepulciano town square at dusk with a stone fountain in the foreground, ancient brick buildings, and a church tower illuminated against a blue evening sky.

Montepulciano

30 minutes due West of us is the delightful town of Montepulciano.


Famous for the wine from the surrounding vineyards, it's a town we never get tired of visiting.


Be warned the streets are very steep, and filled with near irresistible leather shops.

Many a handbag has been purchased.

Tall, narrow buildings with colorful facades and shuttered windows on a hilly street in Montepulciano.
Aerial view of a historic Montepulciano with tightly packed stone buildings, surrounded by lush green trees and rolling hills in the background.
People walking along a narrow street in Arezzo with stone buildings, some with black window shutters, and flags hanging from the buildings.

Arezzo

Often overlooked, even by Italians, Arezzo is a lovely little city just 50 minutes away.

Unlike Assisi (below), it never gets too many tourists, and has a charm all of its own.


The main reason to come to Arezzo is for the Frescos in the Basilica di San Francesco, by Piero della Francesca.

One of the masterpieces of the Renaissance, and a joy for all ages with its graphic novel layout.

Fresco by Piero Della Francesca depicting a medieval battle scene with knights on horseback, soldiers, banners, and flags, in Arezzo.
A scenic pathway leading to a white cathedral in Assisi with a large rose window, surrounded by greenery and flowers, during sunset.

Assisi

Even as you approach it, it's difficult to not be impressed by Assisi.


An hour's drive from the house, it sits just the other side of Perugia airport.

When St Francis died he asked for there to be no fuss around his burial.


So they entombed him in a simple stone chamber, which they surrounded with a small church.


On top of which the built a larger church with a monastery, and of top of that they built a cathedral.


More gorgeous frescos this time by Giotto, painted much earlier than the ones in Arezzo.

Interior of a historic Assisi cathedral with ornate vaulted ceilings, stained glass windows, and religious murals on the walls, with people walking inside.
Aerial view of a historic Assisi with a church on top, surrounded by a town, above a thick layer of fog or clouds in a mountainous landscape at sunrise or sunset.

Use discount code TIPTOP for 20% off

Or if you have already booked elsewhere, we can help you cancel, and rebook with us.

View of a Mediterranean-style shopping plaza with a central courtyard, decorative sculptures, potted plants, and storefronts with arched windows and balconies.

Valdichiana Shopping Outlet

Let's face it not everyone has an insatiable appetite for Italian Hill towns.

23 minutes away, where the local motorway meets the main A1, is the Valdichiana Shopping Outlet.

Very American in feel, some great bargains can be found here, though much of it is similarly priced to elsewhere.