SIENA & THE VAL D'ORCIA
Siena & the Val d’Orcia is the heart of Tuscany, where medieval Gothic grandeur meets a landscape of unparalleled, rolling beauty. It is a region of both history and sublime, photogenic nature.
This corner of Italy is home to the stunning UNESCO World Heritage sites of Siena’s historic center and the iconic, perfectly sculpted hills and cypress groves of the Val d’Orcia.
Most Popular Attractions
Siena City Core:
Piazza del Campo: Siena’s central shell-shaped square, famous for the Palio horse race and considered one of Europe’s greatest medieval squares.
Duomo di Siena (Siena Cathedral): A magnificent masterpiece of Italian Gothic architecture with a striped bell tower and an ornate facade.
Torre del Mangia: The tall, slender bell tower of the Palazzo Pubblico, offering spectacular panoramic views of the city and surrounding Tuscan hills.
Palazzo Pubblico: Siena’s historic town hall, housing the Museo Civico with famous frescoes like the “Allegory of Good and Bad Government.”
Baptistery of San Giovanni: Located beneath the Duomo’s apse, known for its superb Renaissance baptismal font by artists like Donatello.
Complesso Museale Santa Maria della Scala: A former medieval hospital complex, now a vast museum housing art, archaeological exhibits, and stunning architecture.
Pinacoteca Nazionale: The national picture gallery, holding a core collection of Sienese paintings from the 13th to 16th centuries.
Museo dell’Opera del Duomo: A museum displaying original works of art from the Cathedral, including the famous Maestà by Duccio.
Val d’Orcia Towns & Hilltop Villages (Northern Section):
Monteriggioni: A perfectly preserved, tiny walled medieval fortress town with its recognizable crown of towers.
San Gimignano: A UNESCO town famous for its surviving medieval towers (often called the “Manhattan of the Middle Ages”).
Colle di Val d’Elsa: A town divided into a lower modern part and a spectacular, historically intact upper borgo (village).
Pienza: A beautiful Renaissance ‘ideal city,’ famous for its architecture and the production of pecorino cheese.
Montalcino: A walled hilltop town renowned worldwide for its production of the prestigious Brunello di Montalcino red wine.
Val d’Orcia Iconic Sites & Landscapes (Southern Section):
Capella della Madonna di Vitaleta: The iconic, solitary chapel set among rolling hills, one of the most photographed spots in Tuscany.
Bagno Vignoni: A unique thermal spa village featuring a large, ancient Renaissance pool in its main square.
Montepulciano: A graceful, high-perched Renaissance hill town, famous for its Vino Nobile di Montepulciano red wine.
Abbazia di Sant’Antimo: A striking, isolated Romanesque abbey set beautifully among olive groves and cypress trees.
Cipressi di San Quirico d’Orcia: The famous, distinctively clumped group of cypress trees often seen on Tuscan postcards.
Radicofani: A dramatic fortress on a volcanic rock outcrop offering incredible views over the southern Val d’Orcia and into Lazio.
Chiusure and the Crete Senesi: A small village on the Crete Senesi (Sienese Clays), a region known for its dramatic, barren, lunar-like landscape.
Cypress-Lined Roads: Several famous drives, particularly the road leading to Podere Belvedere, for quintessential Tuscan photo opportunities.
Activities & Experiences
Take a Tuscan Cooking Class: Learn to prepare local specialties like pici pasta, wild boar ragù, and ribollita soup from a local chef, often including a visit to a market or farm.
Wine Tasting in Montalcino: Visit one of the numerous cantine (wineries) around Montalcino to tour the cellar and taste the renowned full-bodied Brunello di Montalcino wine.
Explore Siena’s Piazza del Campo: Spend time in one of Europe’s greatest medieval squares, famous for its unique shell shape, and climb the Torre del Mangia for panoramic views.
Drive the Iconic Cypress Roads: Rent a car, e-bike, or Vespa and take a scenic drive through the famous rolling hills, capturing photos of the picturesque cypress-lined lanes.
Visit Pienza, the “Ideal Renaissance City”: Wander the romantic streets of this hilltop town, designed as a model Renaissance city, and sample the famous local Pecorino di Pienza cheese.
Hike the Via Francigena: Walk a section of the ancient pilgrimage route that passes through the Val d’Orcia, connecting you to the historic landscape and villages.
Relax in the Bagno Vignoni Thermal Baths: Visit this unique village, whose main piazza is a large, medieval thermal water pool. Enjoy a treatment at a local spa or visit the nearby free hot springs of Bagni San Filippo.
Go Truffle Hunting: Join a local tartufaio (truffle hunter) and their trained dog for an authentic experience hunting for the prized black or white truffles in the woods.
Explore Montepulciano’s Historic Cellars: Take a tour of an ancient, underground wine cellar beneath the palazzi of Montepulciano and taste the distinguished Vino Nobile di Montepulciano.
Stroll through the Horti Leonini: Discover this beautifully preserved 16th-century Italian Renaissance garden in San Quirico d’Orcia, a perfect place for a peaceful break.
Visit the Abbey of Sant’Antimo: Experience the mystical atmosphere of this stunning 12th-century Romanesque abbey, sometimes featuring Gregorian chants.
Discover Monticchiello’s Charm: Explore this tiny, fortified medieval village, which offers incredible views and is known for its summer amateur theatre tradition.
Local Tips & Transport
Car is Highly Recommended for Val d’Orcia: While Siena’s city center is pedestrianized, a rental car is the best way to explore the Val d’Orcia’s hilltop towns (Pienza, Montalcino, Montepulciano) and find the famous panoramic photo spots. Public transport links between the smaller towns are sparse, especially on weekends and in the low season.
Siena City Transportation (Walking & Escalators): Siena’s historic center is a UNESCO site and is best explored on foot. Since the city is built on steep hills, there are public escalators (e.g., from the train station up to the old town) to help you get around. Look for the signs to the scale mobili.
ZTL Zones: Be extremely careful of the Zona a Traffico Limitato (ZTL) in Siena and other historic towns. These are restricted driving zones for residents. Unintentional entry will result in a heavy fine. If staying inside the walls, your hotel can often register your license plate for temporary access to unload luggage.
Bus to Florence/Other Cities: The bus service (operated by Tiemme) is generally considered the fastest and most convenient way to travel between Siena and Florence, as the bus station in Siena is closer to the historic center than the train station.
Parking: In the Val d’Orcia towns, use the designated paid parking lots just outside the city walls. Parking inside the walls is almost always reserved for residents.
The Palio: If you visit Siena on July 2nd or August 16th, you will witness the legendary Palio, a fiercely competitive bareback horse race around the Piazza del Campo. This is a profound cultural event rooted in the city’s 17 historical districts (Contrade). Book accommodation and activities far in advance, and expect huge crowds.
The Language of Wine: Tuscany is the heart of Italian winemaking. When in Montalcino or Montepulciano, ask for DOCG (Denominazione di Origine Controllata e Garantita) wines, Italy’s highest classification. Don’t be shy about asking for a cellar tour or tasting (degustazione)—they are a cultural experience.
Dining and Cuisine: Tuscan cuisine is known as cucina povera (peasant cooking), characterized by simple, hearty ingredients. Be sure to try:
- Pici: A thick, hand-rolled spaghetti-like pasta.
- Cinta Senese: A prized local breed of pig, often served as cured meat or in a rich ragù.
- Pane Sciocco: Traditional Tuscan bread made without salt, meant to be eaten with salty meats and flavorful sauces.
The Pace of the Countryside: Life in the Val d’Orcia is significantly slower than in the cities. Embrace the quiet and plan to spend an afternoon relaxing at an agriturismo (farm-stay) or simply enjoying a long lunch overlooking the hills.
The Golden Hour: The light in the Val d’Orcia, particularly at sunrise and sunset, is famous worldwide for its golden hue. Plan your drives and photography stops around these times for the most spectacular views.
Hidden Gems:
- Crete Senesi: Just north-east of the Val d’Orcia, this area of rolling clay hills has a stark, almost lunar landscape that is dramatically different but equally beautiful. Drive the scenic route near Asciano for unique photos.
- Cappella di Vitaleta: The iconic small chapel, often seen in Tuscan postcards, is tucked between San Quirico d’Orcia and Pienza. Find a viewpoint nearby for a classic shot.
- Bagni San Filippo: A series of free, natural hot pools and waterfalls deep in the woods, with striking white mineral formations (known as the “White Whale”). Great for a natural thermal soak.
Top Restaurants
Osteria Le Logge [$30-$50] – Located near Piazza del Campo, this historic spot (since 1977) offers refined, authentic Sienese and Tuscan cuisine in a charming, nostalgic setting that was once a grocery store.
La Taverna di San Giuseppe [$30-$50] – Set in a medieval building with an Etruscan cellar, this is a beautiful and historic setting in the city center serving high-quality, traditional Tuscan dishes, including excellent pasta and Cinta Senese pork.
Osteria Boccon del Prete [$25-$40] – A traditional and welcoming osteria slightly off the main tourist track, known for local recipes, great service, and house specialties like pici pasta with sage and almonds.
Antica Osteria da Divo [$35-$55] – A sophisticated dining experience in a vaulted medieval hall with cavelike cellars, offering elegant, traditional Tuscan gastronomy near the Duomo.
Mugolone Ristorante [$30-$50] – A historic family-run restaurant since 1950, specializing in Tuscan tradition revised and renewed in a contemporary, refined key.
Osteria Il Grattacielo [$20-$30] – The oldest osteria in Siena, dating to 1840, offering simple, abundant, and authentic Sienese products in a tiny, classic atmosphere.
Trattoria La Torre [$20-$35] – A no-frills, authentic trattoria close to Piazza del Campo, popular with locals for its hearty portions of traditional Sienese food.
Osteria Castelvecchio [$25-$45] – Located slightly off the beaten path but near the historic center, this spot offers traditional Sienese flavors in an elegant and modern environment.
Trattoria Nonna Gina [$20-$35] – A rustic and popular trattoria in the city center known for classic Tuscan dishes, especially its homemade pasta and generous Florentine steak.
Osteria Permalico [$20-$35] – A quintessential, old-world osteria near the Pinacoteca Nazionale, serving delicious, traditional Sienese food at affordable prices.
Osteria Le Logge del Vignola [$35-$55] – A Michelin Bib Gourmand restaurant in Montepulciano offering refined Tuscan cuisine with a focus on local ingredients and Vino Nobile.
Osteria Acquacheta [$30-$60] – Located in Montepulciano, this informal, popular spot is renowned for its colossal, expertly-cooked Fiorentina T-bone steaks. Reservations are essential.
Dopolavoro La Foce [$25-$45] – Set in a beautifully restored historic building at the famous La Foce estate, offering traditional, genuine Tuscan cuisine in a bright, scenic setting.
Taverna dei Barbi [$25-$45] – The restaurant of the historic Fattoria dei Barbi winery in Montalcino, serving local specialties and old recovered recipes like beef cheek in Brunello wine.
Podere Il Casale [$30-$50] – The restaurant of an organic farm near Pienza, specializing in dishes made with their own organic products, including pecorino cheese, homemade pasta, and excellent views.
Il Giglio [$30-$50] – Located in Montalcino, this spot offers traditional Tuscan cuisine with a slightly contemporary style in a cozy, friendly environment.
Osteria Fra Paolino [$25-$40] – A simple but delightful osteria in the charming village of Monticchiello, known for traditional Italian and local dishes with fresh, genuine products.
Il Pozzo [$20-$35] – A characteristic and cozy place in the Montalcino area (Sant’Angelo in Colle) that serves local specialties, including hearty pasta dishes and Florentine steak.
Sette di Vino [$20-$35] – A small, typical, and popular restaurant in Pienza known for simple, traditional dishes, a friendly atmosphere, and trusting the waiter’s recommendations.
Osteria del Leone [$30-$50] – Located in the charming Bagno Vignoni, this historic osteria (a former stop for pilgrims) focuses on traditional, healthy Tuscan cuisine using local, seasonal products.
Trattoria Il Leccio [$30-$50] – In the village of San Quirico d’Orcia, this restaurant serves classic Tuscan fare like pici, homemade pasta, and grilled meats in an elegant country setting.
Osteria La Pieve [$25-$40] – Located in Pienza, this traditional spot is a favorite for local cuisine, particularly known for dishes featuring pecorino cheese.
Trattoria Caci e Pici [$20-$35] – A small, authentic trattoria in Pienza offering great value and quality, specializing in pasta dishes like pici al cacio e pepe and local cured meats.
Le Specialità di Annie [$20-$35] – Found in Montalcino, this small, simple place focuses on the quality of ingredients, offering traditional Montalcino cuisine.
Agriturismo Il Rigo [$35-$55] – Near San Quirico d’Orcia, this agriturismo offers a fixed 4-course menu (dinner) that changes daily, based on organic, local, and seasonal products, in a beautiful, sustainable setting.
Campo del Drago [$80-$120] – Located at the Rosewood Castiglion del Bosco Relais near Montalcino, this refined restaurant offers original, high-standard dishes by a chef with vast experience, focusing on local ingredients.
Boccon DiVino [$70-$110] – A well-regarded restaurant in Montalcino that masterfully blends traditional Tuscan substance with a touch of modernity to enhance the quality of the ingredients, accompanied by an excellent wine list.
Arnolfo [$150-$250] – Located just outside the region in Colle di Val d’Elsa (but close to Siena), this two-Michelin-starred restaurant is a temple of innovative, ultra-refined Tuscan cuisine and is worth the short journey.
Osteria La Canonica [$60-$90] – The other restaurant at Rosewood Castiglion del Bosco near Montalcino, offering a more rustic but equally high-quality take on Tuscan tradition in a beautiful setting.
Osteria I Terzi [$30-$50] – A wonderful enoteca (wine bar/restaurant) in Siena’s historic center with brick vaults and a focus on creative Tuscan cuisine paired with an extensive wine list.
Particolare di Siena [$40-$70] – A modern restaurant with a creative approach to traditional Sienese flavors, focusing on quality, local ingredients, and elegant presentation.
Osteria Piccolomini [$25-$45] – A highly-rated spot in Siena offering traditional Tuscan food with a contemporary flair and great wine pairings, slightly removed from the busiest streets.
Trattoria Fonte Giusta [$25-$45] – A centrally-located, yet authentic, trattoria known for reinventing classic Tuscan dishes with fresh ingredients and a modern touch.
Enoteca La Torre [$40-$60] – Located near Piazza del Campo in Siena, this spot combines a refined atmosphere with a menu that reinterprets Tuscan classics with creativity and a focus on great wines.
Drogheria Franci [$35-$55] – An elegant Montalcino inn, wine bar, and grocery store that offers skilfully revisited Tuscan specialties and innovative dishes made with excellent ingredients.
L’Olivo – Cucina Toscana Contemporanea [$40-$70] – Located in Torrita di Siena, this restaurant offers a sophisticated and contemporary take on Tuscan cuisine.
Ristorante Enzo [$25-$45] – Located near Porta Camollia in Siena, this restaurant offers delicious combinations and innovative presentations of traditional Tuscan recipes.
La Vecchia Posta [$35-$60] – Located in a relais near Bagno Vignoni, the restaurant offers seasonal menus with traditional regional flavors of Val d’Orcia with attention to high-quality, local produce.
Enoteca Italiana [$20-$40] – Housed in the Medici Fortress in Siena, this is a national wine cellar offering a curated selection of Italian wines by the glass, with a simple, high-quality menu to accompany them.
Casato Ristorante Wine Bar [$25-$45] – A few meters from Piazza del Campo in Siena, offering excellent cuisine and a wine list to match, in a refined yet comfortable setting.
Osteria Sotto le Logge del Papa [$20-$35] – A cozy osteria in the center of Siena, popular for its simple Tuscan food and a convenient location.
Vineria Le Potazzine [$20-$40] – Located in Montalcino, this wine bar offers simple, delicious local food like cured meats and cheeses, perfect for pairing with their excellent Brunello wine.
La Schiaccia dell’Opio [$10-$20] – A popular spot in Montepulciano for excellent, simple, and high-quality sandwiches (schiaccia)—a perfect non-touristy lunch option.
Drogheria e Vini Molesini [$15-$30] – A classic, simple wine bar and deli in Pienza, perfect for a quick, delicious platter of local pecorino cheese and cured meats.
All’Orto de’ Pecci [$20-$35] – A unique location in Siena, just outside the walls, set in a peaceful garden, offering simple, traditional cuisine in a relaxing atmosphere.
Trattoria Grotta del Gallo [$20-$35] – A simple trattoria in the city center of Siena, known for its friendly service and great value on traditional local dishes.
L’Orso in Tognazza [$20-$35] – An authentic, rustic osteria in the city center known for great portions, simple prices, and a strong local following.
Osteria Il Vicolo [$20-$35] – A traditional Sienese osteria near the center offering classic Tuscan meals in a cozy environment.
Trattoria Il Gigante [$20-$35] – Located in the center of Siena, this no-frills spot is highly regarded by locals for its authentic Sienese food and great portions.
Vineria del Fattore [$20-$35] – A small, cozy wine bar in the center of Siena, offering local wine and traditional Tuscan appetizers and light meals.
Il Cavaliere Errante [$15-$25] – Considered one of the best places in Siena for pizza and simple pasta dishes, offering excellent quality street food near Piazza Provenzano.
Pizzeria Ristorante La Finestra [$15-$25] – A popular spot near the walls of Siena known for quality pizza and a good view.
Ristorante Pizzeria La Veranda [$15-$25] – Located slightly outside the historic center of Siena, offering excellent pizza and traditional dishes with a good local following.
Top Cocktail Bars and Clubs
Charlie Mixology Bar di Aldinucci Riccardo: Found in the heart of Siena’s historic center, this spot is dedicated to the art of mixology, offering exquisite and creative cocktails in a chic atmosphere.
Un Tubo: Located in Siena, just a short walk from Piazza del Campo, this intimate venue is famous for its contemporary design in a medieval space, offering a refined selection of wines and classic cocktails, often accompanied by live jazz music.
Caffè del Corso: Situated on Via Banchi di Sopra, one of Siena’s main streets, this bar and restaurant is a magnet for the cocktail crowd, offering a lounge ambiance and often featuring a small dance area upstairs.
Il Barrino (Bagno Vignoni): Overlooking a small square in the thermal village of Bagno Vignoni in the Val d’Orcia, this institution is known for its refined and elegant atmosphere and its excellent, close-to-perfection cocktails. They often host jazz and blues concerts.
Idyllium (Pienza): This bar, with a unique location in the four-hundred-year-old stables of Palazzo Piccolomini in Pienza, is a destination for mixology fans. It offers a stunning terrace view of the Val d’Orcia, perfect for an aperitivo or after-dinner drink.
Alle Logge di Piazza (Montalcino): A young and dynamic bar in the heart of Montalcino, popular with local Brunello winemakers. It offers a rich list of local wines, excellent cocktails, and often features a DJ set for a lively happy hour.
Intralci (San Quirico d’Orcia): Located in one of the most typical towns in the Val d’Orcia, this small, charming wine bar offers an excellent selection of local and non-local wines, alongside great charcuterie boards.
The Tea Rooms: Near Porta Giustizia in Siena, this cozy, retro spot offers a selection of teas and coffee but transforms in the evening into a charming place for cocktails, alcoholic drinks, and occasional live jazz around a grand piano.
Garden Bar & Atrium Bar (San Quirico d’Orcia): Part of a luxury hotel in the Val d’Orcia, the Garden Bar is on a terrace overlooking a garden, offering a chic spot for a cool drink in the shade of olive trees, ideal for a refined aperitivo.
Bar Il Palio: Offering a coveted front-row seat overlooking the majestic Piazza del Campo in Siena, this is the quintessential spot for a classic cocktail or a glass of crisp white wine while people-watching at sunset.
Enoteca Italiana: Housed within the 16th-century Fortezza Medicea in Siena, this wine bar is primarily for serious wine tasting with an extensive selection of Italian wines, but its summery terrace offers a sophisticated setting for drinks.
Caffè Le Logge: Found in Siena, this bar offers a cozy atmosphere and is known for its exquisite cocktails.
BLANDIS – Wine & Cafè: A charming retreat in Siena’s historic center, this venue is a great spot for an afternoon coffee that seamlessly transitions into a wine bar offering local selections.
Trefilari Wine Bar: Experience the essence of Tuscany at this Siena spot, where exquisite wines and authentic Tuscan small bites can be enjoyed in a welcoming setting.
Barone Rosso: Centrally located in Siena, this is a lively favorite of young locals for draught beer, cocktails, and the occasional live rock concert or DJ set, open late.
SottoSopra Club: Considered one of the hearts of Siena’s active nightlife, this club offers a vibrant atmosphere with dance and music, often featuring a well-curated selection of music genres from the latest hits to timeless classics, and frequently hosts themed nights.
Al Cambio: Located on Via Pantaneto in Siena, this is a popular late-night spot, especially with university students. It often features evening DJ sets and live rock music, serving all kinds of drinks and staying open late.
Sette Noti in Sette Notti (Seasonal): A series of cultural evening events, occasionally hosted in Siena’s Civic Museum (Palazzo Pubblico), which can sometimes include wine tastings, concerts of classical music and jazz, and a unique, sophisticated late-night cultural atmosphere.
Casa del Boia: Located in Piazza del Mercato in Siena, this historic location has been transformed into a popular late-night venue, known for organizing special theme nights, particularly Cuban music nights.
Cacio & Pere: In Siena, this pub often hosts DJ sets and live music, creating a lively atmosphere that pairs well with aperitifs, cocktails, and their enogastronomical delights.
La Corte dei Miracoli: Near Porta Romana in Siena, this popular cultural, non-profit organization often organizes concerts, DJ sets, and theatrical shows, particularly on weekends, providing a vibrant alternative nightlife experience.
Bar Porrione: Located near Piazza del Campo in Siena, this bar is a hot spot for university students, popular for its lively atmosphere, cheap draught beer, music, and for staying open late.
Skilè MUSIC PUB: A vibrant pub in Siena where you can enjoy great music and a lively pub atmosphere, making it a good spot for a late-night drink and socializing.
Maudit Pub: Located in Siena, this spot is known for its vibrant atmosphere and is a go-to for craft beers, but its late hours and pub energy make it a destination for a fun night out.
L’Officina: A local hangout in Piazza del Sale in Siena, this venue is known for hosting live music and DJ sets, making it a reliable choice for a late-night vibe.