Siena is one of the most rewarding Italian destinations to immerse in the splendours of Tuscany, from the region’s wine-producing culture and sumptuous cuisine to art, culture and architecture inspired by multiple eras, including medieval times and the Renaissance.
This wondrous Tuscan city charms travellers with its heady wines, captivating architectural gems, fascinating culture and world-famous festivals.
Some travellers like to explore boutique hotels in the city’s heart, while others prefer the serenity of historic estates in the Tuscan countryside. My roundup of the top 16 cool hotels in Siena, Italy, offers a glimpse into the local hospitality sector, including boutique hotels, B&Bs, medieval estates, and refurbished monasteries (in no particular order)…
1. Borgo La Torre alle Tolfe – a beautiful, lavish and tranquil hotel ideal for a couple’s romantic getaway
A sprawling 100-hectare estate comprising a historic villa, 5 farmhouse-style residences, olive groves, vineyards and an organic restaurant, the Bogo La Torre alle Tolfe is an oasis of serenity.
This estate is one of the finest destinations for Tuscan weddings, couple retreats, wine tastings and a heartwarming taste of the slow-paced countryside lifestyle.
Guests can opt for the villa’s luxurious guest rooms or explore a furnished apartment with a fully-equipped kitchen, lounging and dining spaces. Borgo La Torre offers 40 apartments in the Country Residence, 16 rooms in the historic villa and 3 independent apartments.
The onsite restaurant features its own vegetable garden, an organic farm and a winery to produce organic wines.
2. Hotel Certosa Di Maggiano – an upscale, unique and elegant boutique hotel housed in a stunning historic building and surrounded by picturesque olive groves and vineyards
The magical Hotel Certosa Di Maggiano beckons travellers to revel in the architectural splendour of a XIV Century Carthusian monastery, lovingly renovated to infuse the 14th-century antiquated interiors with modern amenities. This enchanting abode offers a scenic location in the heart of Tuscany without distancing travellers from Siena’s landmarks and attractions.
La Certosa is home to 19 guest rooms and luxury suites, featuring ornamental artworks, fine silks, and locally crafted furniture. Guests can explore multiple categories, including Classic, Deluxe, Prestige and Junior Suite, to find their ideal setting and amenities.
The onsite restaurant Il Canto is a popular dining spot, ideal to feast on traditional Tuscan cuisine.
3. Grand Hotel Continental Siena – Starhotels Collezione – one of the only 5-star hotels in the city providing guests with a lavish, elegant and Instagrammable stay
Grand Hotel Continental is the only 5-star hotel in Siena’s historical district, combining world-class luxury with a stellar location to experience the best this magical Italian city has to offer.
Originally constructed as a noble residence that Pope Alexander VII gifted to his niece Olimpia on her marriage to Palazzo Gori Pannilini, the Grand Hotel is revered as a site that celebrates the couple’s love.
The Grand Hotel features 51 rooms and suites curated with precious 17th-century frescoes, Tuscan cotto tiles and exquisite furniture. The hotel offers an onsite fine dining restaurant, Sapordivino, and a Renaissance-era event space, the Salone Delle Feste.
4. Casatorre dei Leoni Dimora Storica – a unique, upscale and rustic-chic hotel perfect for a romantic break
Casatorre dei Leoni Dimora Storica offers a dreamy setting for a romantic getaway, nestled in a convenient location between the Piazza del Campo and Porta Romana. This central location brings all the leading attractions within walking distance, including the Piazza del Mercato and the Basilica dei Servi.
This upscale venue is home to 3 luxury suites: Artemisia, Bartolo and Rutile, and three apartments: Design 4, Design 9 and Design 11. Each accommodation is uniquely adorned with a whimsical theme to play up the antiquated wooden ceilings, brick floors and vintage furniture.
Casatorre dei Leoni is also home to the Galo Nero restaurant, famous for its inventive spin on traditional recipes.
5. Ca’ Bianca – a historic, chic and traditional hotel where guests can hire bikes to explore around the area
Surrounded by green pastures and centuries-old olive trees, Ca’Bianca is a 17th-century historic manor featuring a charming stone façade and a farmhouse-like setting typical of ancient Tuscan architecture.
This historic manor exudes old-world charm and timeless elegance with its beautifully preserved interiors and antiquated soul.
Guests can explore decorated rooms and suites decked with comfortable bedding, modern appliances and fine linens. The Suite Spannocchi is Ca’Bianca’s finest offering, a splendid choice for couples and families seeking modern luxuries and sweeping views.
The onsite garden is a lovely spot for breakfast and outdoor dining with panoramic views of the rolling hills.
To book, check prices or availability for Ca’Bianca
6. Albergo Chiusarelli – a modern, vibrant and Neoclassical-style hotel where guests can enjoy the taste of traditional Tuscan cuisine
A neoclassical villa dating back to 1870, Albergo Chiusarelli commands a dominating presence in the heart of Siena’s action-packed city center. The hotel features 48 rooms and suites featuring magnificent frescoes from the 19th century, painstakingly restored to install modern amenities without disrupting the authenticity of the original architecture.
Staying at this historic residence is akin to turning back the hands of time, transporting oneself to an era defined by timeless sophistication and vibrant art. The accommodations are well-equipped with air conditioning and heating, in-room smart appliances, fine linens and ensuite bathrooms.
Guests prefer dining at the onsite restaurant, Gli Orti di San Domenico, offering ancient Tuscan delicacies with fresh ingredients.#
7. Villa Scacciapensieri Boutique Hotel – a charming, stunning and pet-friendly hotel in close proximity to local popular attractions
Elegantly perched on a hill overlooking the Tuscan countryside, the Scacciapensieri Boutique Hotel is housed in a 19th-century villa, the former residence of the Sienese bourgeoisie.
This location is fabulous for dividing one’s time between the rural landscape and Seina’s popular attractions. The Duomo di Siena and Gothic Pubblico Palace are nearby, and the Siena Train Station is only 4 km away.
Villa Scacciapensieri is home to 31 guest rooms, divided across the main villa and the two annexes: Villino and Limonaia. The rooms have earthy and muted colour palettes with traditional furniture, safes, flat-screen TVs and minibars. The premium rooms come with furnished living areas, balconies, and ensuite bathrooms with whirlpool tubs.
8. SUITE MONTAPERTI – a bright, modern and newly renovated hotel featuring a spa and wellness centre overlooking the Siena skyline
Nestled in the Tuscan countryside, Suite Montaperti delights serenity seekers with its tranquil rural setting, contemporary interiors and thoughtful amenities. Adventurers eager to divide their time between Siena and the countryside will find this location ideal for sightseeing and day trips.
Suite Montaperti features tasteful guest rooms and suites, a state-of-the-art wellness area, a swimming pool and an onsite restaurant. Travellers can browse through multiple categories, including Smart Rooms, Comfort Rooms, Deluxe Rooms, Family Apartments and Junior Suites with Balcony.
The onsite Restaurant 1260 offers a creative blend of traditional Tuscan dishes prepared with scented grapes and locally farmed produce.
9. Palazzetto Rosso – Art Hotel – a quirky, unique and contemporary accommodation offering guests a continental or buffet breakfast
Situated near the Rocca Salimbeni on Dei Rossi, the Palazzetto Rosso Art Hotel entices travelers with its medieval charm, contemporary décor and onsite art gallery.
A venue that celebrates art and culture, there’s never a dull moment at the Palazzetto Rosso. Guests divide their time between the urbane art gallery and the innumerable attractions located within walking distance.
This 13th-century brick building is home to 9 guest rooms, and each accommodation is an enthralling masterpiece of medieval art and modern design, featuring elaborate artwork and rich color tones.
Guests typically start their day with the hotel’s a la carte breakfast laden with fruit juices, cold cuts, cheeses, freshly baked bread and pastries.
10. Il Giardino di Pantaneto Residenza D’Epoca – a petite, charming and contemporary B&B just moments away from an array of art and architectural delights
An ancient residence 300 meters away from Piazza del Campo, Il Giardino di Pantaneto is surrounded by art, architecture, culture, and sumptuous gastronomic adventures.
The exterior and interiors are glorious specimens of neo-medieval architecture, and the building has retained its ancient architectural remnants despite undergoing extensive renovations.
Il Giardino di Pantaneto features 12 comfortable rooms, a private garden and a lovely sunbathing corner overlooking the lush Follonica valley.
This B&B serves one of the finest breakfast buffets in Siena, delighting its guests with an extensive spread of homemade cakes, savory delicacies and rare cheeses. Guests can enjoy breakfast in the ancient well room or opt for a garden setting brimming with marjoram, rosemary and thyme.
11. Villa Elda Boutique Hotel – a relaxing, newly renovated and romantic accommodation where guests have the luxury of enjoying a volcanic stone or bamboo cane massage
One of the most well-preserved specimens of Art Nouveau architecture in Siena, Villa Elda is positioned right at the entrance of the historical quarters, boasting a prestigious location surrounded by medieval and Rocco-style landmarks.
Villa Elda offers 10 guest rooms with panoramic views of the Torre del Mangia, the Church of San Domenico and the Duomo. One can spend hours sunbathing on the villa’s expansive terrace, overlooking the architectural gems of Siena, the slanted rooftops and the lush greenery of the Tuscan countryside.
Guests can reserve the expansive attic terrace for romantic and intimate dinners, tailor-made events and aperitifs.
12. Siena Vip B&B – a new, family-friendly and bright B&B neighbouring several interesting dining options
Perched opposite the medieval Fountain of Fontebranda, Siena Vip B&Bis a centrally located B&B featuring air-conditioned rooms, thoughtful hospitality and a sprawling terrace to soak up the Tuscan sunshine.
Guests can explore a wide selection of guest rooms designed with parquet floors, ensuite bathrooms and modern appliances. Vacationers seeking luxury will find the suites and apartments more suited to their taste.
The Suite Camollia, Suite Ovile and Suite Fontegaia are the most impressive accommodations in this B&B, while large groups will find the Noble Apartment ideally furnished for a home-away-from-home experience. The venue offers a private garden with elaborate seating areas and sun lounges to relax and feast one’s eyes on local architecture.
To book, check prices or availability for Siena Vip B&B
13. Villa del Sole Siena – a quiet, stylish boutique B&B located in the heart of the city
Villa del Sole positions travelers in the historic heart of Siena, in the Terzo di San Martino, within proximity to the vibrant Piazza del Campo, the Basilica of Sant’Agostino and the Torre del Mangia. Art and history enthusiasts couldn’t ask for a more fabulous location to explore the city on foot and enjoy magical views from comfortable rooms.
This intimate boutique hotel offers 9 colorful and well-lit guest rooms, beautifully embellished with vintage accents and traditional furniture.
The accommodations combine modern amenities and period-style details with impressive harmony, while the large windows offer delightful views of the Orti de’ Pecci and landmarks in old city quarters.
14. La Chicca B&B Siena – an intimate, cozy and themed B&B with each room being named after a famous Tuscan wine
La Chicca B&B is a homely and family-friendly residence welcoming travelers with its intimate setting and central location, a stone’s throw away from the historical landmarks and monuments. Guests can explore a liberty villa with six double rooms and a private garden, perfect for large groups, families and couples.
Each room is named after world-famous Tuscan wine blends that have allowed Tuscany to emerge as a prominent wine-producing region.
For instance, Room Chianti offers endearing views of Mangia’s Tower and other old buildings, and Room Brunello has an antiquated personality with delicate vintage furniture and period-style floors.
Room Moscadello is a double-bed accommodation overlooking the garden.
15. 1550 Residenza d’Epoca – a spacious, stylish and Medieval-urban accommodation in the perfect location to explore through the city
1550 Residenza d’Epoca allows transports travelers to medieval-era Siena with its majestic façade and interiors, high vaulted ceilings, terracotta floors, and abundance of rare antiques.
Nestled at a 4-minute stroll from the Piazza del Campo, this prestigious residence features 3 spacious rooms furnished with vintage furniture, air conditioning, smart appliances and ensuite bathrooms.
Equine enthusiasts flocking to Siena to attend the famous Palio will find this venue and location ideally suited to immerse in the spirit of the festival and watch the historical parade comfortably.
Residenza d’Epoca balances its palatial charm with a homely B&B-like environment, pampering guests with homemade breakfast and extensively personalized service.
16. Hotel Santa Caterina – a classic, Tuscan-style and cozy accommodation within walking distance of the Piazza del Campo
An 18th-century Patrician Villa situated a stone’s throw away from the Porta Romana, Hotel Santa Caterina offers a cosy, family-friendly setting to explore the medieval heart of Siena from a central location.
Santa Caterina features 22 bedrooms decorated with old Tuscan-style accents, featuring flat-screen TVs, high-speed wifi, air conditioning, minibars and ensuite bathrooms. Guests love having breakfast in the expansive garden and veranda, overlooking the unfiltered beauty of the Sienese hills.
The hotel has a cheerful and upbeat vibe, courtesy of the attentive and courteous staff who go overboard to personalize services and ensure a memorable stay. Guests can explore multiple hiking and walking trails nearby to explore the countryside.
Scott started his travelling life back in 1999, when he headed off on a solo jaunt to South Africa, Australia, New Zealand and South East Asia with just a backpack, a camera and a spirit for adventure. After that, the travel bug bit hard and now he is always seeking to head off somewhere new. Over the years he has lived in Italy, Qatar, Ireland, UK and the US but his spiritual home will always be Rome as this is the city which most satisfies his unrelenting craving for culture, good food and great football. Scott loves nothing better than to be behind the camera and also runs his own blog and Instagram page. He also counts Melbourne, Cape Town and Tel Aviv among his favourite places. Follow him on Twitter and Instagram at @scottbalaam
