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Writer's pictureAmby Mathur

A Luxurious 3-Day Tuscany Itinerary in Val d'Orcia, Italy

Updated: May 8

Buongiorno, luxury aficionados! If you've been daydreaming about living your best life amidst Tuscany's rolling hills, vineyards straight out of a wine lover's fantasy, and medieval towns that make you feel like you've stepped into a time machine, then it's time to grab your sunnies and pack your bags for a trip to Val d'Orcia, in the province of Sienna. Join me on a whimsical journey through this enchanting landscape as we uncover the creme della creme in accommodations, dining, relaxation, and exploration.


Amby and Marco pose with a green vineyard in Val d'OrciaTuscany
Be sure to add a wine tasting in Val d'Orcia to your Tuscany weekend itinerary!

PLEASE NOTE: THIS POST CONTAINS AFFILIATE LINKS. I MAY RECEIVE A SMALL COMMISSION AT NO EXTRA COST TO YOU ON ANY PURCHASES MADE AFTER CLICKING/FOLLOWING A LINK. I ONLY PROMOTE PLACES/PRODUCTS/SERVICES THAT I VISIT, USE, & LOVE MYSELF. THANKS FOR SUPPORTING MY BLOG :)


Why should you include Val d'Orcia in your Tuscany itinerary?


Picture rows of cypress trees amongst a countryside that that looks like its been meticulously painted by Michelangelo, vineyards that produce wines so good they'll make you question if you've ever really tasted wine before, and villages straight out of a fairy tale - minus the evil witches, of course. Plus, it's a UNESCO World Heritage site, so you know it's legit. But what really sets Val d'Orcia apart is its vibe. It's like that friend who's always down for a good time but also knows when to kick back and relax. The pace of life here is slow, the locals are warm and welcoming, and there's an authenticity that is so refreshing. And let's not forget about the food and wine - because what's a trip to Tuscany without indulging in some culinary delights? Val d'Orcia is home to some of the finest wineries and farm-to-table restaurants in all of Italy, so get ready to indulge. Whether you're exploring medieval towns, soaking in natural hot springs, or simply sipping on a glass of Brunello di Montalcino with a view, Val d'Orcia promises an experience that's as unforgettable as it is delicious.



Montalcino, Val d'Orcia, Siena, Tuscany Italy itinerary, rolling green hills
Montalcino in Val d'Orcia is the first destination in our Tuscany itinerary


Day 1: Arrival and Relaxation in Montalcino: Val d'Orcia, Tuscany


We're starting our dreamy Tuscan weekend in the historical hilltop town of Montalcino. Arrive in style at one of Tuscany's most luxurious hotels, the Rosewood Castiglion del Bosco. Nestled amidst 5,000 acres of pristine countryside, this historic estate offers elegant suites, world-class amenities, and breathtaking views of the Val D'Orcia valley. After settling in, pamper yourself with a rejuvenating treatment at The Spa, which features a wide range of holistic Tuscan remedies, sauna, and turkish bath, amongst other services. Or, take a dip in the stunning estate swimming pool.


For a more affordable but still luxurious option, check out the Villa Le Prata Wine Resort. Housed in an 18th Century restored villa and surrounded by vineyards with a majestic Tuscan cypress avenue, this adults-only hotel offers lush gardens, an infinity pool, and a unique historical atmosphere.


You can enjoy a meal and wine tasting at your accommodation, or check out these experiences below:


In the afternoon, embark on a wine tasting adventure at Castello Tricerchi, one of the oldest and most prestigious wineries in Montalcino. Savor the complex flavors of their renowned Brunello di Montalcino as you tour the vineyards and cellars steeped in history. If you enjoy cooking, check out this Brunello Cooking Class offered at the castle, where you can cook your lunch, tour the winery, and enjoy a wine tasting at the same time!


For dinner (if you're still hungry, that is) indulge in Tuscan delicacies at Osteria La Porta, a charming restaurant in the heart of Montalcino. Feast on homemade pasta, succulent meats, and decadent desserts, all paired with exquisite local wines.


As the sun sets, take a leisurely stroll through Montalcino's winding streets and soak in the medieval ambiance. Don't miss the opportunity to visit the Fortezza di Montalcino, a medieval fortress overlooking the town.



view of Pienza in hills, Siena, Tuscany Italy itinerary
Pienza in Val d'Orcia is the second place in our Tuscany itinerary.


Day 2: Exploration and Culinary Delights in Pienza: Val d'Orcia, Tuscany


Today we're heading to the City of Light! No, not Paris, but Pienza!


Start the day off right with a delicious breakfast at your hotel. You can stay checked in, or for a change of scene move to La Bandita Townhouse, a 12 room luxury boutique hotel inside the historic center of Pienza, a romantic UNESCO Heritage site village set in the rolling hills of southern Tuscany.


For a more affordable option, check out Il Chiostro di Pienza, a charming boutique hotel set within a former 15th-century convent.


After breakfast, take a stroll in the cute little town. Soak in the atmosphere, and take a photo with the cute street signs: Via dell'Amore (love), Via del Bacio (kiss), etc. Visit the main square, Piazza Pio II and the old pope's home, Palazzo Piccolomini, which is renowned for its Renaissance architecture and stunning frescoes. There is also a labyrinth and crypt below the main cathedral, Cattedrale di Santa Maria Assunta, that is worth checking out.


For lunch, check out La Bandita Townhouse for a farm-to-table experience. La Buca di Enea is another option that is cozy and intimate.


In the afternoon, escape to the tranquil oasis of Terme di Montepulciano, a luxury spa retreat nestled in the rolling hills of Val D'Orcia. Treat yourself to a blissful massage or soak in the healing waters of the thermal baths, surrounded by panoramic views of the Tuscan countryside.


As evening falls, enjoy a romantic dinner at Il Rossellino, known for its innovative Tuscan cuisine and intimate ambiance. Toast to another day of indulgence with a glass of local Vino Nobile di Montepulciano.



chapel of the madonna di vitoleta, san quirico, val d'orcia, siena, tuscany italy itinerary
San Quirico in Val d'Orcia is the last spot in our Tuscany itinerary


Day 3: Culture and Countryside in San Quirico d'Orcia: Val D'Orcia, Tuscany


I've saved the best for last! San Quirico is a tiny town, but it really has a special place in my heart.


In the morning, savor a leisurely breakfast at your hotel. From there, stay checked in where you are, or move on to Palazzo del Capitano Wellness & Relais, a charming and elegant 4 star hotel in a historic 14th century building.


For a dreamy farmhouse stay, check out Agriturismo Podere Spagliarda.


After breakfast, visit Horti Leonini, a stunning Renaissance garden located in the heart of San Quirico d'Orcia.


Next, embark on a scenic drive through the idyllic countryside of Val d'Orcia, stopping at charming hilltop villages and hidden gems along the way. Don't miss the opportunity to explore the enchanting village of Bagno Vignoni, famous for its thermal baths and panoramic views.


For lunch, dine al fresco at Bistrot Languorino, a quaint trattoria located in Bagno Vignoni. Feast on traditional Tuscan dishes prepared with fresh, locally sourced ingredients.


In the afternoon, discover the artistic heritage of Val D'Orcia with a short drive and walk to the Chapel of the Madonna di Vitaleta, an iconic small chapel in the hills. After, make a quick stop at Cipressi di San Quirico d'Orcia, a famous circle of cypress trees. Head back to town, stroll through the little streets, take a peek at the boutiques, and also visit the Collegiata di San Quirico, the main church.


For dinner, enjoy a delicious and intimate meal at Antica Trattoria Toscana al Vecchio Forno, featured in the Michelin guide.



dreamy sunset landscape, siena, tuscan hills, val d'orcia, north italy itinerary
The region of Val d'Orcia in Siena, Tuscany, is not to be missed!

I hope you enjoy Val d'Orcia as much as I did! My fiance, Marco, had surprised me with the most romantic weekend here, and this beautiful region has a special place in my heart. I am so happy to be able to share this unique Tuscany weekend itinerary with you. Happy travels!


Un bacio,

Amby


P.S. Want my free 17pg 2 Week Southern Italy itinerary? Get the guide here.



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