The 5 Best Wineries in Val d'Orcia, Tuscany (2025 Guide)

Exploring Val d’Orcia One Glass at a Time
Few places on Earth capture the timeless romance of Tuscany quite like Val d’Orcia. A UNESCO World Heritage Site, this sweeping valley of golden hills, cypress-lined lanes, and storybook villages is also home to some of Italy’s most celebrated wineries.
Framed by medieval towns such as Montalcino, Pienza, and San Quirico d’Orcia, the region’s unique terroir and centuries-old winemaking traditions have produced wines that are not only rich in character but deeply connected to the landscape.
This stunning part of southern Tuscany is best known for its production of Brunello di Montalcino—one of Italy’s most prestigious red wines. But beyond Brunello, Val d’Orcia also offers exceptional Rosso di Montalcino, Orcia DOC wines, and a variety of Super Tuscans and lesser-known boutique vintages.
In this guide, we’ll explore five of the best wineries to visit in Val d’Orcia, each offering a unique expression of the region’s winemaking excellence. You’ll also find tips on how to get there, where to stay nearby, the best time to visit, and a suggested itinerary to help you make the most of your Tuscan wine adventure.
Let’s uncork the magic of Val d’Orcia.
Table of Contents

1. Castiglion del Bosco – Brunello Royalty in a Fairytale Setting
A visit to Castiglion del Bosco is not just about tasting wine—it’s an immersion into the high art of Tuscan living. Owned by the Ferragamo family, this historic estate is one of the original Brunello di Montalcino producers and offers a luxurious experience nestled within a UNESCO World Heritage landscape.
What makes Castiglion del Bosco so special is its seamless blend of viticulture, heritage, and hospitality. The winery tour in Brunello production—from the sun-drenched vineyards to the state-of-the-art cellars with vast French oak barrels. Tasting sessions include vertical samplings of Brunello vintages in an elegant stone-walled room that smells of leather and oak.
The estate also houses a Rosewood resort featuring a world-class spa, gourmet dining, and even a private golf course. You can sip your wine while overlooking cypress-lined ridges, or unwind with a massage after a long day of tasting. For wine lovers seeking luxury, Castiglion del Bosco is the pinnacle. It’s ideal for honeymooners, couples on a romantic getaway, or anyone wanting to elevate their wine experience to something unforgettable. It’s not just a visit—it’s a full-bodied escape into Tuscan splendo

How to Get There
By car: Best reached via scenic SR2 roads, reachable in under two hours from Florence or Rome; parking is on-site.
Without a car: Book taxi or private driver to rural location.
- Compare these *Car Rental* Rates
Visiting & Tasting
Excellent spot for a weekend stay. Tasting is often paired with olive oil sampling and a farm-to-table meal on-site. Advance booking recommended, especially in high season. Even if your visit to the area is limited to just hours, you can still explore Castiglion del Bosco and taste their exceptional wines.
The winery offers well-organized wine tastings and tours for visitors with varying schedules. To ensure a personalized and memorable experience, they require that each visit be booked in advance.
You can arrange your visit by contacting their dedicated team at wine@castigliondelbosco.com or via phone at +39 0577 1913750. Don’t miss this opportunity to immerse yourself in the captivating world of Tuscan wine-making, even if your time in Val d’Orcia is brief.

2. Poderi Boscarelli – Montepulciano’s Vino Nobile Icon
Tucked away in the rolling vineyards near Montepulciano, Poderi Boscarelli is a family-run winery with a legacy built on tradition and passion. It stands out as one of the most respected producers of Vino Nobile di Montepulciano—a noble wine that has quietly rivaled Brunello for centuries. Unlike flashier estates, Boscarelli offers an authentic, down-to-earth atmosphere where the focus is entirely on the wine.
What makes Boscarelli a must-visit is the deep-rooted story of a family who have worked the land for generations, crafting exceptional wines from local grapes like Prugnolo Gentile, Mammolo, and Canaiolo. Their flagship labels, including Il Nocio and Riserva Sotto Casa, are refined, age-worthy reds with elegance and structure. The wines here are nuanced, earthy, and profoundly tied to the terroir.
Tastings at Boscarelli are intimate and led by passionate staff or even family members. You’re not shuffled through a scripted tour; instead, you walk among the vines, learn about pruning techniques, and taste wines in a rustic yet refined setting. It’s an experience steeped in knowledge, care, and a bit of old-world magic.

How to Get There
By car: From Siena, drive ~50 minutes via SR2; from Florence, ~1 h 30 via A1 and SR2.
Via di Montenero, 24
53045 Montepulciano, Italy
Public transport: Train to Chiusi, bus to Montepulciano, or involve local taxis otherwise.
- You can book a *Car Rental* here.
Visiting & Tasting
Advance reservation is essential. Tastings cost between €10–50, with several wines tasted on-site, usually in a rustic yet refined setting.
Wine Tour Reservations
Wa: +39 391 7274070
Telephone: +39 0578 767608
E-mail: cantina@poderiboscarelli.com
Tip on which wine to buy there? Boscarelli Prugnolo! Flawless!

3. Poggio al Vento – Organic Vines with a View
Perched high above the Val d’Orcia hills, Poggio al Vento is the kind of place that embodies everything idyllic about rural Tuscany. ( We loved our stay here) As both a working vineyard and organic agriturismo, this small, family-run estate offers an immersive wine and countryside experience that is as enriching as it is relaxing. It’s the perfect choice for slow travelers, eco-conscious guests, and those seeking authenticity off the beaten path.
What sets Poggio al Vento apart is its natural approach to winemaking. Here, Sangiovese, Merlot, and Cabernet Sauvignon grapes are grown organically and fermented with minimal intervention. The wines are bold, pure, and expressive, offering a taste of Val d’Orcia’s wild heart. Their red blends are especially noteworthy for their depth and balance, paired beautifully with the estate’s homemade olive oil.
But the magic doesn’t stop at the wine. The estate offers accommodations in rustic-chic apartments, many with panoramic terraces overlooking the valley. Guests are invited to tour the vineyards, relax by the pool, take cooking classes, or simply sit under a fig tree with a glass in hand. Tastings are often paired with homemade bread, cheese, and family recipes handed down for generations.
If you’re looking to slow down, connect with nature, and enjoy wine as a way of life—not just a beverage—this is your place.

How to Get There
By car: Best reached via scenic SR2 roads, reachable in under two hours from Florence or Rome; parking is on-site.
HOW TO REACH US
Located in the countryside, 4 km away from San Quirico D’Orcia.
To reach Poggoi al Vento you must travel 4 km of dirt road.
Once in San Quirico d’Orcia you must enter the village follow the signs for “Castello di Ripa d’Orcia”, after about 2.5 km of dirt road you will find the signs for Agriturismo Poggio al Vento, follow these signs for about 2 , 5 km more.
If you use a navigator you have to enter the name of “San Quirico d’Orcia” and from there reprogram and put the name of Castello di Ripa d’Orcia. Once you reach the dirt road you will find the signs for Agriturismo Poggio al Vento.Without a car: Book a taxi or private driver to a rural location.
- Compare *Car Rental* prices here
Visiting & Tasting
Excellent spot for a weekend stay. Tasting is often paired with olive oil sampling and a farm-to-table meal on-site. Advance booking recommended, especially in high season.
Spend a weekend there, you won’t regret it!

4. La Rasina – Small-Scale Brunello with Heart
If you’re searching for an intimate Brunello experience away from the crowds, La Rasina is the place to go. This modest, family-owned estate near Montalcino has been producing handcrafted wines since the 1970s, and its dedication to quality over quantity has earned it a loyal following. Unlike some of the larger estates, La Rasina offers visitors a truly personal and unpretentious tasting experience.
At La Rasina, the focus is firmly on Sangiovese. Their Brunello di Montalcino is bold yet elegant, aged carefully in Slavonian oak casks to develop balance and complexity. The estate’s Brunello Riserva in particular has gained critical acclaim, offering a structured, long-finishing wine with notes of dried cherry, tobacco, and spice.
Visitors to La Rasina are often greeted by family members who share the story of the land, the vines, and the evolution of their winemaking. It’s the kind of place where you walk through the vineyards with the winemaker himself and learn how climate, soil, and tradition come together in every bottle.
Set among softly rolling hills and cypress-dotted ridges, the estate is peaceful and quietly beautiful. It doesn’t aim to dazzle with opulence—instead, it draws you in with authenticity and warmth.. It’s Tuscany in its purest form: honest, heartfelt, and unforgettable.

How to Visit
Reception by appointment—email ahead to reserve a tasting or tour. They’re open to showcasing local production in an unhurried, personal setting. To book a memorable experience at La Rasina, simply send an email to larasina@larasina.it and embark on a captivating journey through their exquisite offerings.
Travel Tips
Situated near Montalcino, you can easily combine a visit to La Rasina with stops in Pienza or even Castiglion del Bosco using a driver or local taxi service. If you need to rent a car compare these *Car Rental* prices.

5. Podere Albiano – Boutique Winery of the Orcia DOC
Tucked between San Quirico d’Orcia and Pienza, Podere Albiano may be small in size, but it delivers big on charm, quality, and the kind of hospitality that lingers long after your visit. It’s one of the standout producers in the Orcia DOC, a lesser-known wine designation that’s quietly gaining recognition for its bold, expressive reds and commitment to craft winemaking.
What makes Podere Albiano so worth visiting is the genuine warmth of the owners, who often host tastings themselves. Guests are welcomed like old friends and taken through a tour of the vineyards, cellars, and bottling room. Tastings are often accompanied by homemade snacks and local cheeses, including the famous pecorino from nearby Pienza.
The setting is breathtaking—rolling hills, golden fields, and vine-covered slopes stretch to the horizon. It’s the kind of place where you want to linger, whether sipping wine on the terrace or strolling between the vines at golden hour.
Podere Albiano is ideal for travelers seeking something special beyond the well-trodden paths of Chianti or Montalcino. It’s a hidden gem that embodies the future of Tuscan wine: small-scale, high-quality, and full of soul.

How to Get There
Podere Albiano lies between San Quirico d’Orcia and Pienza. Best accessed by car or via a local guide/tour operator. Some agriturismi nearby may offer transfers.
Visiting & Tasting
Ideal for a quieter, off-the-beaten-track experience. Tasting usually includes several single-vineyard wines; pair with homemade pecorino and olive oil.
Best to book your visit, especially in the high season.
Ph.+39.0577.66.53.86
info@poderealbiano.it and wine tasting

Getting There & Getting Around
Best Way: *Rent a Car*
Val d’Orcia is best explored by car—public transit is sparse between towns, and wine estates are scattered across the countryside From Rome or Florence the drive is scenic and relatively easy. Be cautious of ZTL zones (restricted traffic areas) in historic towns. Park outside and walk in to avoid fines. Compare *Car Rental* prices here.
Public Transport
Take a train to Chiusi‑Chianciano Terme, then bus lines to towns like Buonconvento, Pienza, Montalcino. Buses are infrequent and don’t reach remote wineries. From Buonconvento there’s a station with local buses into the valley
Guided Tours & Drivers
If you prefer not to drive, consider hiring a private driver or booking a guided wine tour out of Florence or Siena. Many wineries will help arrange transport or pick-up

Where to Stay
Luxury & Vineyard Hotels
Rosewood Castiglion del Bosco – on-site at Castiglion del Bosco, luxury spa, gourmet dining, elite wine experiences.
Castello Banfi – Il Borgo – over vineyards near Montalcino; elegant rooms, curated dining, wine-focused hospitality.
Boutique & Historic Properties
Relais Il Chiostro di Pienza – a converted 15th-century convent just steps from Pienza central piazza, with garden views and historic charm.
Castello di Spedaletto – a castle-B&B surrounded by beautiful gardens and far-reaching valley views, ideal for a peaceful base.
Agriturismi & Local Stays
Poggio al Vento agriturismo – ideal if you want rustic, peaceful lodging on-site with wine and olive oil included.
Smaller FARM STAY near La Rasina or Podere Albiano may offer B&B options with breakfast and easy access to local wineries.

Best Time to Visit Val d’Orcia
Late Spring (May – Early June)
One of the best windows: mild temperatures (around 20–25 °C), landscapes lush and green, wildflowers and golden wheat fields in bloom. Very comfortable for vineyard walks and sightseeing
Summer (July – August)
Summer can get hot (mid-30s °C), but the long sunny days highlight golden landscapes. Good for outdoor festivals and long hazy light—but beware smaller operations with midday closures and booked tours.
Harvest / Early Autumn (September – Early October)
This season brings grape harvest energy and stunning autumnal colors; a magical time for wine events like the Orcia Wine Festival in late April and the Fiera del Cacio in Pienza in September . Harvest timing varies, so book early if you want to witness vendemmia.
Winter (November – March)
Not ideal due to gray skies, chilly temperatures, and muddy roads. Some wineries operate with limited hours. On the upside, much quieter and potential for more intimate tastings

Sample Five-Day Itinerary
Day 1: Arrive & Settle In
Travel by car from Florence or Rome into Montalcino.
Check into Castiglion del Bosco or Castello Banfi.
Afternoon wine tour and tasting at Castiglion del Bosco.
Day 2: Montalcino & La Rasina
Visit La Rasina in the morning for a personal cellar tour.
Lunch in Montalcino, then explore the fortress and hill town.
Optional spa or olive oil tasting at the hotel.
Day 3: Montepulciano & Boscarelli
Drive to Montepulciano (~30 min).
Wine tasting at Poderi Boscarelli, followed by lunch in Montepulciano town.
Evening stroll and dinner in Piazza Grande.
Day 4: Orcia DOC & Pienza
Head toward Pienza, stopping at Podere Albiano for tasting.
Visit Pienza, stroll alleys, sample pecorino.
Stay in Pienza at Relais Il Chiostro di Pienza or a countryside agriturismo.
Day 5: Scenic Drive & Final Stop
Morning drive along the Strada del Vino Nobile photographing iconic cypress-lined roads.
Visit Poggio al Vento for wine and olive oil tasting; stay if you like.
Late afternoon return drive to Florence or onward journey.

Wine Styles & Food Pairings
Brunello di Montalcino (Castiglion del Bosco, La Rasina): robust, oak-aged Sangiovese; pairs well with grilled beef, wild boar, aged pecorino.
Vino Nobile di Montepulciano (Boscarelli): refined Sangiovese blend with fruit and spice; complements pasta al ragù, pici pasta, cured meats.
Orcia DOC wines (Podere Albiano): often lighter, fresher Sangiovese; excellent with lighter tomato dishes, local cheeses.
Organic table wines and olive oil (Poggio al Vento): ideal for pairing with bruschetta, cheeses, vegetables, and antipasti.
Travel Tips & Recommendations
Book tastings in advance—especially for Castiglion del Bosco and Boscarelli.
*Rent a car* for maximum flexibility; otherwise, arrange guided tours or local transport ahead.
Stay outside ZTL zones and walk into historic centers.
Allow 4–5 days for an unhurried experience—covering Montalcino, Montepulciano, Pienza, and local wineries
Events: plan for April festivals or early September for harvest-related activities.
Pace yourself: local cuisine, olive oils, pecorino and wines are rich—balance tasting with countryside hikes or thermal baths (e.g. Bagno Vignoni)

Final Thoughts
Val d’Orcia is not just a wine destination—it’s a landscape where art, food, and vinyards converge. From luxury estates like Castiglion del Bosco to small family-run wineries like La Rasina and Boscarelli, each stop offers its own flavor. Add to that the rolling hills, cypress-lined roads, Renaissance towns, and slow‑food culture—and you’ve got a trip that’s as enriching as it is delicious.
PLAN YOUR TUSCANY ADVENTURE
These are our favorite companies we use when planning a trip, they consistently have the best prices, great customer service, and overall, are better than their competitors.
BOOK YOUR FLIGHT – SKYSCANNER – we always start here and usually always finish here. They price check over 1,200 travel sites to help you find the best prices. You can also try GOING to search prices across a variety of sites.
TRAVEL OPTIONS
CAR RENTAL – We recommend using Discover Cars or Rental Cars when booking a car rental, they work with hundreds of companies worldwide to help you find the best car for your needs.
TRAINS – TRAINLINE – is our favorite, this site is very reliable and easy to use.
BUS – OMIO – this website allows you to book train or bus tickets to travel from city to city the best and cheapest way. FLIXBUS is another terrific website with routes between 20 European countries.
ACCOMMODATIONS
BOOKING.com – is our go to for hotel searches around the world, we find they always have the cheapest rates and offer different payment options. In addition, VRBO is another terrific website for all types of accommodations.
HOSTELWORLD – is great if you’re traveling on a budget, and if you need a cheap place to stay.
SIGHTSEEING TOURS
GET YOUR GUIDE – is our favorite; they have stacks of tours and excursions available in cities all over the world. VIATOR is another great website for all types of tours.
TAKE WALKS – This walking tour company provides inside access to attractions and places you can’t get elsewhere.
TRAVEL INSURANCE
SAFETY WING – is our go to travel medical insurance company, especially for longer trips. You can either purchase a monthly plan or a plan for specific trip dates (i.e. 1-2 week trips). They cover people from all over the world, while outside their home country.
ARC’TERYX – is a go to reliable brand for outdoor adventure and travel, their wide range includes light weight durable, easy to clean travel gear.
Check out our RESOURCE PAGE for more additional planning.
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