If you’ve ever imagined yourself sipping wine on a sun-drenched terrace overlooking rolling hills and cypress trees, this list is for you. Tuscany is the heart of Italy’s timeless beauty—where Renaissance towns, vineyard-covered valleys, and slow living await.
Whether you’re planning a romantic honeymoon, a countryside retreat, or a luxury escape filled with food, wine, and history—these 9 boutique hotels are handpicked to offer something truly unforgettable.
When you book through Trudy Travels, you get exclusive perks at no additional cost: think $100 hotel credits, room upgrades, complimentary breakfast, and more.
⚠️ Some of the links below are affiliate links. That means I may earn a small commission if you book through them—at no extra cost to you. It helps support my travel content and recommendations!
1. COMO Castello Del Nero – Barberino Tavarnelle
A 12th-century castle turned five-star retreat, COMO Castello Del Nero sits on 740 acres in the Chianti countryside. Interiors fuse Renaissance details—frescoes, vaulted ceilings, antique fireplaces—with sleek, modern design by Paola Navone.
🧖♀️ Wellness
Home to the renowned COMO Shambhala Retreat, guests can enjoy holistic spa treatments, yoga, a thermal suite, and a hilltop vitality pool.
🍝 Dining
Savor Michelin-starred cuisine at La Torre, or try rustic Tuscan dishes at La Taverna, set in the castle’s ancient kitchen. The estate’s wine cellar highlights Chianti and Super Tuscan selections.
🌿 Experiences
Activities include truffle hunting, Vespa rides, cooking classes, and day trips to nearby Florence or Siena.
📍Check availability and price:
https://expedia.com/affiliates/barberino-tavarnelle-hotels-como-castello-del-nero.XriiChf
⭐️ Book with Trudy for perks: $100 hotel credit, airport transfers, breakfast, upgrade, early check-in/out.
2. Hotel Borgo San Felice – Castelnuovo Berardenga
Located in the heart of Chianti Classico, Hotel Borgo San Felice is a restored medieval hamlet turned wine estate. Surrounded by vineyards and olive groves, the property features cobblestone lanes, a chapel, curated gardens, and centuries-old stone buildings.
🍷 Food & Wine
Dine at Il Poggio Rosso, the hotel’s Michelin-starred restaurant, or enjoy seasonal Tuscan fare at Osteria del Grigio. The on-site San Felice winery offers private tastings of its award-winning Chianti and Brunello wines.
🌿 Experiences
Guests can join vineyard tours, cooking classes, olive oil tastings, or explore nearby Siena and the Chianti hills by bike or car.
📍Check availability and price:
https://expedia.com/affiliates/castelnuovo-berardenga-hotels-hotel-borgo-san-felice.AAGgOc2
⭐️ Book with Trudy for perks: $100 hotel credit, breakfast, upgrade, early check-in/out.
3. Borgo Pignano – Volterra
Set on a hilltop in the heart of Tuscany, Borgo Pignano is an elegant 18th-century villa surrounded by 750 acres of organic farmland, olive groves, and woodlands. The property blends luxury with sustainability and timeless rural charm.
🌿 Slow Living & Style
Rooms and suites feature reclaimed materials, antique furnishings, and panoramic countryside views. Guests can explore landscaped gardens, lounge by the infinity pool, or relax in the intimate spa.
🍽 Farm-to-Table Dining
The estate’s two restaurants focus on seasonal, biodynamic ingredients grown onsite, paired with regional wines and house-made olive oil.
🚲 Experiences
Activities include horseback riding, painting workshops, yoga, cooking classes, and guided hikes to nearby hill towns.
📍Check availability and price:
https://expedia.com/affiliates/volterra-hotels-borgo-pignano.W4gHMU9
⭐️ Book with Trudy for perks: $100 hotel credit, breakfast, upgrade, early check-in/out.
4. Rosewood Castiglion del Bosco – Montalcino
Nestled in the UNESCO-listed Val d’Orcia, Rosewood Castiglion del Bosco is a 5,000-acre private estate with a Brunello vineyard, private golf course, and restored 800-year-old village. It’s Tuscany at its most exclusive.
🍷 Wine & Dine
Tour the estate’s Brunello winery, enjoy tastings with expert sommeliers, and dine at two elegant restaurants offering seasonal Tuscan cuisine.
🧘♀️ Experiences & Wellness
Unwind at the serene spa, take a cooking class, hike through cypress-lined trails, or play a round of golf with panoramic views.
📍Check availability and price:
https://expedia.com/affiliates/montalcino-hotels-rosewood-castiglion-del-bosco.3fGVHDT
⭐️ Book with Trudy for perks: Welcome amenity, breakfast, upgrade, early check-in/out.
5. Lupaia – Torrita di Siena
Perched between Montepulciano and Pienza, Lupaia is a storybook farmhouse reborn as a romantic hideaway. Each room is uniquely decorated with rustic-chic charm, hand-painted tiles, and antique touches.
✨ Atmosphere & Style
Wander through flower-filled paths, sip wine by the infinity pool, and take in sweeping views of the Val d’Orcia. It’s intimate, whimsical, and perfect for couples.
🍽 Dining
Evenings begin with aperitivi in the garden and end with multi-course candlelit dinners made from local and garden-grown ingredients.
📍Check availability and price:
https://expedia.com/affiliates/torrita-di-siena-hotels-lupaia.yEKnx51
⭐️ Book with Trudy for perks: $50 hotel credit, breakfast, upgrade, early check-in/out.
6. La Bandita Townhouse – Pienza
Tucked inside the Renaissance town of Pienza, La Bandita Townhouse is a stylish 12-room boutique hotel set in a former 500-year-old convent. Think vaulted ceilings, stone walls, and sleek, modern furnishings—effortlessly cool yet steeped in history.
🏙 Urban Meets Rustic
The hotel blends minimalist design with original architecture, making it a cozy yet sophisticated base just steps from the town’s main piazza, artisan shops, and trattorias.
🍷 Insider Vibe
Owned by a former music executive, the vibe is unpretentious and welcoming, with a great in-house restaurant and curated local experiences.
📍Check availability and price:
https://expedia.com/affiliates/pienza-hotels-la-bandita-townhouse.kpME6UL
⭐️ Book with Trudy for perks: Welcome amenity, breakfast, upgrade, early check-in/out.
7. Reschio Hotel – Lisciano Niccone
Set on a 1,500-acre private estate near the Tuscan-Umbrian border, Reschio Hotel is a 10th-century castle transformed into a luxurious design-forward retreat. The interiors are a masterclass in craftsmanship, blending antique character with understated sophistication.
🌿 Nature & Design
Expect sweeping countryside views, custom-made furniture, and serene, airy suites. The estate includes a Roman-style spa, infinity pool, and curated nature experiences.
🐴 Experiences
Ride horses through forest trails, take art or cooking classes, or relax with a glass of wine in the former wine cellar turned bar.
📍Check availability and price: https://www.reschio.com/hotel
⭐️ Book with Trudy for perks: $100 hotel credit, nature experience (select suites), breakfast, upgrade, early check-in/out.
8. Borgo dei Conti Resort – Perugia
Located just over the Tuscany border in Umbria, Borgo dei Conti Resort is a serene 19th-century estate set amid rolling hills and centuries-old oak trees. It blends aristocratic charm with modern comforts for a peaceful countryside escape.
🪴 Atmosphere & Amenities
Wander landscaped gardens, swim in the panoramic pool, or unwind in the spa. The interiors balance heritage architecture with clean, updated design.
🍴 Dining & Leisure
Enjoy refined Umbrian cuisine at the on-site gourmet restaurant, or relax with wine on the terrace as the sun sets over the valley.
📍Check availability and price:
https://expedia.com/affiliates/perugia-hotels-borgo-dei-conti-resort-relais-chateaux.Ayeqck7
⭐️ Book with Trudy for perks: $100 food & beverage credit, breakfast, upgrade, early check-in/out.
9. Vocabolo Moscatelli Boutique Hotel – Umbria Border
Tucked into the peaceful hills near the Tuscany–Umbria border, Vocabolo Moscatelli is a former monastery reimagined as a bold, contemporary retreat. With just 12 rooms, it offers an intimate atmosphere where design and serenity meet.
🖤 Modern Meets Monastic
Polished concrete, warm woods, vintage Italian pieces, and hand-crafted details create a striking aesthetic that feels both minimalist and soulful.
🌿 Creative Escape
Perfect for couples, creatives, and design lovers, the hotel also features an on-site restaurant and garden courtyard ideal for slow mornings and sunset aperitivi.
📍Check availability and price: https://www.vocabolomoscatelli.com/
⭐️ Book with Trudy for perks: Welcome amenity, breakfast, upgrade, early check-in/out.
Why Book With Trudy Travels?
I partner with luxury hotel programs to unlock VIP perks for my clients—often for the same price (or better!) than booking direct. You get more value, more comfort, and more memories.
📌 DISCLAIMER
This post is not sponsored. Images and descriptions are for inspiration. For rights or credits, visit the About page to contact Trudy Travels. ⚠️ Some of the links below are affiliate links. That means I may earn a small commission if you book through them—at no extra cost to you. It helps support my travel content and recommendations!
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