The Val d’Orcia in late spring, Tuscany

Tuscany

Base yourself in two places, drive the middle, and let the days go slow.

The Rolodex

City , The GUIDE

Photos & words by

Coco Tran

share FB PN X

Category

THE TRIP

Visited

Travelled in Italy, May 2025

Basis

Updated

27 Oct 2026

The short answer

Tuscany is the one place where I’ll ask you to take things out of the itinerary rather than add them, because the real pleasure is the long lunch and that amber light across the hills. I’d base you in two places, have you drive the middle and let the days go slow. Late April to early June is the best version, and May is the sweet spot.

At a glance

Setting
Rolling green hills, cypress lanes and honey-stone hilltowns, the Tuscany we all daydream about
Best for
Wine lovers, slow travelers and all you incurable romantics
Standout
A long lunch with a Chianti view, Florence and Siena within easy reach, and those cypress roads at sunset
Consider
A car unlocks the real magic, so base yourself in the countryside and day-trip to the cities
Stayed
Tuscany, May 2025

Hotels here can be booked through Coco Tran Travel. How we review.

The Val d’Orcia in late spring, Tuscany

The Val d’Orcia in late spring, when the poppies come up through the wheat.

Tuscany is the rare place where I’ll ask you to subtract from the itinerary rather than add to it. The pleasure here isn’t in covering ground; it’s in the long lunch, the hour when the light goes amber across the hills, and the drive you take twice because it was that good the first time.

I drove the Val d’Orcia with my mother on a second trip to Italy, and we had barely thirty-six hours. It’s still one of my favourite stretches of road anywhere. That’s the magic of this region: it rewards you almost immediately, and then it keeps on rewarding you for as long as you’re willing to stay.

So here’s my Rolodex, the whole thing: where I’d base you, what’s genuinely worth the drive, where to eat, and the handful of bookings you’ll want to make months ahead.

You’ve reached the quiet door.

FOR MEMBERS ONLY.

Behind it: the full reviews, the complete guides, every route story we’ve written. Subscribe today, and continue reading this article and more.

Choose your access →

Already a member?  Sign in

Curious about Membership?

→  Learn More

 Stay a while and read it all.