Romantic Val d'Orcia

There are trips you take to see places, and trips you take to feel alive together.

This is the second kind: a journey where every stop is designed to slow down, look into each other's eyes, breathe the same view, and take home something that goes beyond photos.

Val d'Orcia knows how to be romantic like few other places in the world: sunsets that light the hills in gold, centuries-old trees where you stop to embrace, steaming water squares that seem made for whispers.

Six stops. No rush. Just the two of you and Tuscany embracing you.

A route made to be experienced slowly

This itinerary follows the logic of "let's live every moment to the fullest."

The distances are short, the roads scenic, the pace relaxed. You can stop wherever you want, for as long as you want. You can skip a stop if you get lost watching the sunset. You can return twice to the same place if it stole your heart.

Val d'Orcia simply asks to be breathed in.

STOP 1: MONTICCHIELLO

Start from Monticchiello, a small village where silence is part of the experience. Walk hand in hand through flowered alleys and stone walls while the outside world disappears. From the ramparts, the valley opens before you like a gift: rolling hills, changing light, no one to disturb.

💑 The perfect moment
Look for the viewpoint near Teatro Povero. Early morning or late afternoon, the light is magical and you'll have the view all to yourselves.

🍽️ Where to have lunch
La Guardiola Wine & Food - In the village center. Quick but well-prepared homemade cuisine with valley views. Perfect for a break without losing too much time before continuing.

STOP 2: PIENZA

Pienza couldn't be missed: it has the streets of Love, Kiss, and Fortune that lead to terraces where you can kiss with Val d'Orcia as your backdrop. Get lost among the shops, breathe in the scent of aging pecorino, and let the village slow you down even more.

🧺 Romantic picnic with Montepulciano view
Make a detour to Caseificio Cugusi (10 min from Pienza) and have them prepare a platter of freshly made cheeses. Sit at the outdoor tables in their park: from here the view of Montepulciano is postcard-perfect. A simple, authentic, romantic lunch. Much better than a crowded restaurant.

🍽️ Where to have lunch

If you prefer dining indoors Terrazza della Val d'Orcia - Breathtaking panoramic view from the terrace. Refined cuisine, intimate atmosphere. Book in advance and ask for an outdoor table with a view.

STOP 3: THE CYPRESSES OF SAN QUIRICO D'ORCIA

Between Torrenieri and San Quirico d'Orcia, along the Via Cassia (SR2) at kilometer 189, you'll find a place that seems straight out of a fairy tale: an avenue of centuries-old cypresses winding through the fields.

This isn't the classic "cypress road" everyone photographs. This one is less known, more intimate, perfect for a walk hand in hand while light filters through the tall trunks.

Just a few minutes on foot, but the atmosphere is magical. Silence, scent of resin, and the feeling of being the only ones in the world.

🌲 Podere's advice

Set your GPS for "SR2 km 189, San Quirico d'Orcia". There's a small parking area to leave your car. Go in late afternoon when golden light crosses through the cypresses. It's one of Val d'Orcia's most photogenic spots, but almost no one knows about it.

STOP 4: LA QUERCIA DELLE CHECCHE

Between San Quirico and Torrenieri, in the middle of the fields, grows an oak tree that's 300 years old. It's called Quercia delle Checche and it's one of Tuscany's most photographed trees.

But it's more than just a photo: it's a symbol. This tree has withstood three centuries of seasons, storms, and changes. Stopping here, embracing under its branches, has a meaning that goes beyond the moment.

It's a brief stop, but it's one of those images you'll carry inside forever.

📸 The perfect shot

Position yourselves under the branches with Val d'Orcia in the background. If you arrive at sunset, the side light makes the leaves shine and creates a dreamlike atmosphere. This is the photo you'll end up printing.

STOP 5: VITALETA CHAPEL

Small, perfect, surrounded by cypresses and golden fields: the Vitaleta Chapel has become Val d'Orcia's symbol to the world.

But experiencing it at sunset, when the sun sets behind the hills and the light turns pink and gold, is an experience that changes your breath. The silence, pure beauty, just the two of you and no other sound.

Arrive 30 minutes before sunset, find your viewing spot, and let nature do the rest.

🌅 The magic moment

Sunset here is a daily show that never gets old. If you want to avoid too many photographers, go on weekdays. But even if there are other people, the moment remains yours.

AFTER VITALETA - Make these moments last forever

You've just walked through some of the most photogenic places on Earth: the Vitaleta Chapel, the Quercia delle Checche, timeless villages suspended in time.

Imagine reliving all of this with a professional photographer by your side. Not selfies in front of monuments. Not random snapshots. A real photoshoot capturing you two in these dreamlike settings: sunset light, embraces under centuries-old trees, kisses with Val d'Orcia behind you.

At Podere Grotta Antica, we organize professional photoshoots in Val d'Orcia's most iconic locations. Expert photographers who know every corner, every light, every perfect moment.

Perfect for:

• Marriage proposals (Vitaleta Chapel is one of the most requested locations)

• Important anniversaries

• Honeymoons

• Or simply to have memories that never fade

Moments pass. Photographs last forever.

👉 Discover the photoshoot service

STOP 6: MONTALCINO OR MONTEPULCIANO

After a day like this, you need a dinner that measures up. You have two options, both perfect.

MONTALCINO if you want elegance and wine: Elegant, quiet, perched on the hills: Montalcino is the kingdom of Brunello, one of Italy's noblest wines. From the Fortress walls, your gaze embraces all of Val d'Orcia and the Crete Senesi. The village is small but refined: historic wine shops, stone alleys, an intimate atmosphere that invites you to slow down. Here wine isn't just for drinking: it's culture, it's history, it's the way this land speaks.

MONTEPULCIANO if you want liveliness and romance: Renaissance, elegant, enveloping: Montepulciano is one of Tuscany's most beautiful villages. Its streets climb gently toward Piazza Grande, among historic palaces, artisan shops, and underground cellars carved into the tufa. Vino Nobile here isn't a product: it's an identity. At sunset, when the lights come on and tourists thin out, Montepulciano becomes magical. The alleys smell of warm stone, wine shops light up, and everything seems made to slow down and enjoy the moment.

🍷 Tasting you can't miss

Cantina Salvioni - Small family winery producing one of the area's finest Brunellos. Tasting by reservation in an intimate and authentic setting. It's not touristy, it's real. Book at least 2-3 days in advance. The experience is worth every minute.

🍽️ Where to dine with a view

Boccon DiVino - Panoramic terrace over Val d'Orcia, refined cuisine, intimate atmosphere. Tasting menu with paired Brunello. Book in advance and ask for an outdoor table at sunset.

🍷The experience you won't forget

Cantina Contucci - Historic palace in Montepulciano's heart with 1500s underground cellars. Guided Vino Nobile tasting with visit to tufa-carved cellars. Solemn yet welcoming atmosphere. It's like entering the heart of Tuscan nobility. Reservation recommended.

🍽️ The perfect dinner to close

Romantico - The name says it all. Panoramic terrace with candles, refined Tuscan cuisine, breathtaking view. Perfect for the dinner that closes the most beautiful day. Book in advance and specifically ask for a terrace table. At sunset it's spectacular.

INFO SECTION

📍 Distance from Podere

First stop (Monticchiello): 35 min Last stop (Montepulciano): 25 min.

Leave in the morning at your leisure, return in the evening with a full heart.

⏱️ Recommended duration

Full day, but slow
This isn't an itinerary to rush through. Dedicate at least 8-9 hours, breaks included. The goal isn't to see everything, but to feel everything.

🌅 The perfect time

April-May: flowering fields, soft light

September-October: harvest, warm colors

But every season has its magic. Just avoid August weekends if you're seeking intimacy.

Ready to experience Val d'Orcia as a love story?

Start from Podere Grotta Antica and return with memories that last forever.