Many couples tell us when they arrive: “We want to hike. Where should we go?”
We love this question. Because Tuscany seems made for “I like walking through pretty places”.
No technical gear needed. No super fitness required.
Here at ABBADIA WINE RELAIS, surrounded by vineyards, silence, and space, perfectly located between Val d’Orcia, Pienza, and Montepulciano —the hiking paths are gentle. They lead through oak forests, past cypress trees and wildflower meadows. Sometimes you lose yourself in thought. Sometimes in conversation. Sometimes you say nothing at all – and that feels exactly right.
We don’t offer overcrowded “Top 10 Trails.” Instead, we share walks that make you slow down. Walks where you drift side by side. Walks where you suddenly realize: you’ve arrived.
Here’s how to explore the Tuscan hills in Val d’Orcia — slowly, side by side, with someone you love.
What to expect
You’ll be walking through vineyards, olive groves, medieval villages, and country lanes. The kind of places where you occasionally stop just because the landscape looks like a painting.
You’ll want comfortable shoes, water (we’ll fill up your bottle), sunscreen, and a hat.
And yes — your phone. Because Italian trail markers are not always… let’s say consistent.
The Walks We Recommend (From Short to Long)
1. The Vineyard Circle
0.5 hour — gentle slope
This is the walk everyone ends up doing at least once. You leave from our wine cellar, enter the vineyard to wander down through our Merlot vines, pass wildflower meadows, then curve around our olive grove.
All the time the whole valley is spread out in front of you — vineyards, hills, the distant line of the Apennines. It’s the perfect “Yes, we’re really in Tuscany” moment.
You can do this before breakfast, or later afternoon to be back in time for aperitivo or a romantic picnic, which is honestly half the reason people choose this one.
2. Montefollonico Loop
1 hour — some uphill, then medieval village stop
This walk is a warm-up. You start from out estate, wander through a bit of forest, along fields, pass an ancient 15th-century well, then climb (just once, and not too steep) towards Montefollonico from the quiet side. As you emerge from the forest you will pass a vantage point offering far views towards Montepulciano, Pienza and even Montalcino. From there you continue to Montefollonico.
It is exactly what you want a Tuscan hilltop village to be — stone arches, narrow streets, older locals who observe you from windows with no judgment but plenty of curiosity.
Have an espresso at Bar dello Sport. Walk home downhill with a sense of accomplishment.
If you time it right, you can stop at 13 Gobbi for lunch. Or go for a Vin Santo wine tasting at the local Cantina Innocenti. Don’t worry, we won’t tell anyone that you actually went eating and drinking on your hike.
3. Sentiero del Vin Santo
2 hours — forest, meadows, rolling hills
The trail follows the ancient medieval road that connected the two castles of Torrita di Siena and Montefollonico, which were the last bulwarks of the Republic of Siena in wars against Montepulciano (allied with Florence).
You start from ABBADIA and follow its winds through quiet forest, soft meadows and gentle hills with glimpses of Montepulciano and Torrita di Siena in the distance.
You arrive at the edge of the town. You can either go in for an espresso, or turn around, and take it all in from the opposite direction.
It’s peaceful, soft, and perfect for those “just walk with me a while” conversations.
4. The Montepulciano Walk
3 hours — skyline in sight the whole way — iconic finish
This one is a favorite for couples who like a sense of direction — literally. You start walking toward Montepulciano… and you keep walking toward Montepulciano. The skyline stays with you like a quiet companion.
The path rolls past vineyards and open fields, through long views that feel like wine labels come to life.
You arrive at Tempio di San Biagio, glowing in white marble at the foot of the hill. One of the most iconic churches in Tuscany — and you get to walk right up to it like you discovered it yourself.
From there, it takes another 15 minutes to head up into the town for wine, lunch, or just a view that makes your camera panic.
5. Via Francigena (San Quirico to Bagno Vignoni)
3.5 hours — historic — postcard landscapes — thermal-water ending
This is the “we want the classic Tuscan walk”. Part of the medieval pilgrimage route from Canterbury to Rome, it winds through some of the most photographed landscapes on earth.
Note that you will need to drive 30 minutes to San Quirico d’Orcia, where the hike starts.
Visit the village and then leave San Quirico d’Orcia, walk through cypress-lined paths and rolling hills, and end in the thermal village of Bagno Vignoni — where you can dip your feet into one of the natural, thermal pools. Have lunch at the village and then head back, either on foot or catch the bus.
Beautiful, meaningful, and best done in spring or autumn.
Some practical Stuff
Italian Trail Markings
There are, but they may stop without reason. My advice: Use your phone’s GPS. Download the maps offline before you go (cell service in valleys is unreliable). If you want, I’ll give you coordinates for key points. Follow those, not the romantic idea that Italian trails are well-marked.
Best Season? All of them.
Tuscany changes with the seasons, each one is different, and beautiful:
Spring (March-May):
Perfect hiking weather. 15-22°C. Wildflowers everywhere. Green is the color. Some rain possible (bring a light jacket). Best season for walking.
Summer (June-August):
Hot. 28-35°C. Morning walks only. Rolling hills turn Mediterranean, lots of yellow, brown – contrasting with olive trees’ silver green. Best season to explore golden wheat fields in Val d’Orcia.
Fall (September-November):
Beautiful. 18-25°C. Golden light. Grape and olive harvest. The mood is orange and red. Most colorful season.
Winter (December-February):
Still beautiful, just different. 5-12°C. Quiet. Misty mornings. Shorter days. The time when you can have Tuscany almost to yourself. Professional photographers tell me it’s the best season.
Still wondering when to come to Val d’Orcia? Check out our month-by-month guide to visiting Tuscany.
What to Wear
You don’t need to bring fancy hiking gear to Tuscany. Here’s what makes sense:
- Comfortable walking shoes (no, not the sandals)
- Layers (mornings are cool, afternoons warm up)
- Long pants if you’re doing forest walks (brambles exist)
- Hat (I sound like your mother, but seriously)
Snakes, Boars, and other Dangers
Snakes: Yes, they exist. Rarely seen. Not aggressive. Mostly grass snakes, sometimes vipers. We’ve been here two years, seen a venomous snake once.
Wild boar: Nocturnal. You’ll see their tracks and digging, but not them. They avoid humans.
Dogs: Farm dogs bark behind fences. They’re not actually threatening, just loud and bored. If you were to meet Maremmanos, large white sheepdogs, avoid them. Pass by leaving a distance or simply return if not possible.
Getting lost: Unlikely. This area is small. Worst case? You end up in a different village, get espresso, get back on track. Not exactly a survival situation.
The Best Part of Hiking
Of course, the views – they’re mind-blowing. And the exercise – to earn that extra bowl of Tiramisu.
But there’s also something else to walking side by side — it’s pure couple time. No distractions. Just a common goal — and time. Time that unlocks conversations you didn’t know you needed.
Sometimes you can solve a problem that you had been arguing about for months. All it takes, is walking and talking and somehow finding clarity.
That’s what these Tuscan trails can also do. Couple magic
Ready to Explore?
When you arrive, we’ll give you our advice about which walk suits you on that particular day. Then it’s up to you.
Do one hike. Do all. Do none.
Each is perfect. Tuscany isn’t a checklist. It’s a mood. Waiting to be explored on foot, slowly, with someone you love.
Whenever you’re ready.
Welcome to ABBADIA.
Welcome to scenic trails in Val d’Orcia.
