Luxury Travel in Italy: The Best Hotels and Villas in Tuscany

Tuscany has long captured the imagination of travellers. Rolling vineyards, medieval towns, and villas framed by cypress trees make it one of Italy’s most enchanting destinations. When you plan Luxury Holidays to Tuscany, you combine timeless scenery with the highest levels of comfort and service. From grand estates to secluded villas, the region offers accommodation that turns a holiday into something unforgettable.

Why Choose Luxury Holidays to Tuscany

Choosing Tuscany for a luxury escape means blending art, history, and relaxation in one place. The countryside offers peaceful villas surrounded by olive groves, while cities like Florence and Siena bring centuries of culture to your doorstep. You wake to the sound of church bells, spend afternoons tasting Chianti wines, and end the day in hotels that feel more like private homes.

Luxury travel here is not just about elegant rooms. It’s about experiences that draw you into Tuscan life. Think private vineyard tours with local winemakers, cookery classes led by chefs, or truffle hunting in oak forests. Each stay can be personalised, and that’s what makes this region such a rewarding choice.

One of the reasons Tuscany stands apart is its pace. Life slows down, giving you time to enjoy simple pleasures. A glass of Brunello in the evening sun, a walk through a Renaissance garden, or the joy of finding a hidden trattoria in a tiny village.

When you book through Awake & Wander, you also get the reassurance of expert guidance. We know the properties that deliver real quality and can tailor an itinerary that matches your style. The focus is on you, your tastes, and how you want to spend your days.

Where to Stay in Tuscany: Hotels with Style and Soul

Rosewood Castiglion del Bosco

If you picture a Tuscan dream, it probably looks a lot like Rosewood Castiglion del Bosco. This estate, once owned by the Ferragamo family, covers more than 5,000 acres in the Val d’Orcia, a UNESCO World Heritage Site. Guests stay in suites or restored farmhouses, each one styled with rustic elegance. Terracotta tiles, wooden beams, and local stone set the tone, while modern comforts ensure absolute relaxation.

What makes the Rosewood special is the sense of immersion. You’re not just staying in a hotel; you’re part of a living wine estate. Brunello di Montalcino is produced here, and you can walk through the vineyards, tour the winery, and taste vintages that rarely leave Italy. For dining, the Michelin-starred restaurant, Osteria La Canonica, serves seasonal dishes created from local produce.

The estate also features a private golf course, a spa with views of the hills, and an infinity pool that seems to melt into the landscape. For families or groups, the private villas provide complete privacy, each with its own pool and kitchen.

Rosewood Castiglion del Bosco is more than a base. It’s an introduction to Tuscan life at its most refined. You leave with memories shaped by flavour, scenery, and a slower way of living.

Awake & Wander can help you secure the best offers available at this property. Whether you are looking for seasonal packages, family stays, or extended villa bookings, we have access to a wide range of options that can be tailored to your plans.

Belmond Castello di Casole

Staying at Belmond Castello di Casole feels like stepping into history. The estate dates back a thousand years and has been lovingly transformed into one of Tuscany’s most atmospheric hotels. Set on a hilltop, it offers sweeping views of olive groves and vineyards. The setting alone makes it unforgettable, but the experience goes far beyond the view.

Rooms and suites are decorated with exposed beams, stone walls, and rich fabrics that echo the character of the castle. At the same time, everything feels modern and indulgent. The spa, housed in an ancient wine cellar, provides treatments inspired by local botanicals. Guests can also join guided hikes across the estate, cycle through the countryside, or take part in cookery classes that celebrate Tuscan recipes.

Dining at Castello di Casole is a highlight. The hotel’s restaurant, Tosca, presents regional dishes with a refined touch, paired with wines from the estate and beyond. On warm evenings, dinner on the terrace becomes a memory in itself.

Belmond Castello di Casole is the sort of place where time seems to pause. Whether you’re enjoying a glass of Vernaccia by the fire or swimming in the infinity pool at sunset, the rhythm of life shifts into something more relaxed.

Awake & Wander works closely with Belmond properties and can arrange exclusive benefits for your stay. Speak to us about the current offers and packages that might make your time at the castle even more special.

Luxury Villas in Tuscany: Privacy and Elegance Combined

Villa La Massa

For those who prefer a riverside retreat, Villa La Massa offers something unique. Just outside Florence, the property sits along the Arno River, surrounded by rolling hills. Once a Medici estate, it now combines Renaissance grandeur with the intimacy of a country villa.

Each room is furnished with antique pieces and frescoed ceilings, while modern touches bring comfort without compromising character. Guests can relax by the outdoor pool, enjoy spa treatments, or take a shuttle into Florence to explore its art treasures. The hotel’s restaurant, Il Verrocchio, is perched above the river, offering fine dining with a view.

What makes Villa La Massa special is its balance. You have the peace of the countryside but are only minutes from Florence. It’s ideal for travellers who want cultural access alongside rest and seclusion.

Through Awake & Wander, you can explore seasonal offers at Villa La Massa, from romantic packages to longer stays that let you settle into Tuscan life at your own pace.

Borgo Santo Pietro

Borgo Santo Pietro is the kind of property that feels like a personal discovery. Tucked into the southern Tuscan countryside, it’s a boutique villa hotel surrounded by 300 acres of gardens, vineyards, and farmland. The philosophy here is about slowing down and reconnecting.

Rooms are individually styled with hand-painted details, fireplaces, and luxurious linens. The sense of intimacy is matched by service that feels both personal and discreet. Outside, guests can wander the rose gardens, visit the farm, or join cookery classes that celebrate ingredients grown on-site.

Dining is central to the Borgo experience. The Michelin-starred restaurant, Meo Modo, crafts seasonal menus straight from the estate’s gardens. For something more relaxed, the Trattoria Sull’Albero serves traditional dishes beneath the branches of an old oak tree.

This is a place for travellers who want to immerse themselves in Tuscan life without compromise. It works equally well for couples seeking romance or families looking for a memorable base.

Awake & Wander can advise on the best times to visit Borgo Santo Pietro and share the offers currently available. Whether you’re planning a short escape or a long stay, we’ll help design the perfect arrangement.

City Stays: Hotels in Florence and Siena

Four Seasons Hotel Firenze

Florence is often called an open-air museum, and staying at the Four Seasons Hotel Firenze allows you to live inside the city’s Renaissance beauty. The property is set in a former palace and convent, surrounded by 11 acres of private gardens. It feels both central and secluded, a rare balance in such a busy city.

The interiors are remarkable. Frescoes, marble floors, and grand staircases give a sense of history, yet the hotel delivers every modern comfort. Rooms are spacious, with high ceilings and views of either the gardens or the city. The spa, hidden within a small villa, provides a quiet retreat after a day of exploring Florence’s art and architecture.

The Michelin-starred restaurant, Il Palagio, serves refined Italian cuisine in a setting that feels both elegant and welcoming. Breakfast in the garden is a highlight, with sunlight filtering through centuries-old trees.

Four Seasons Firenze is ideal for travellers who want to be at the heart of Florence without sacrificing peace. It’s a hotel where culture and comfort truly meet.

Awake & Wander can help secure added benefits such as complimentary upgrades or spa credits when you book through us. Ask about the latest offers to make your stay even more rewarding.

Grand Hotel Continental Siena

In Siena, the Grand Hotel Continental stands as the city’s only five-star boutique hotel. Housed in a 17th-century palace, it sits right in the historic centre, close to Piazza del Campo and the Duomo. For those who love history and architecture, it’s an unbeatable location.

Inside, the hotel combines Renaissance and Baroque details with modern luxury. Rooms feature frescoed ceilings, elegant chandeliers, and antique furnishings, while bathrooms are sleek and contemporary. The Enoteca SaporDivino, located in the hotel’s medieval wine cellar, offers tastings that showcase the region’s celebrated wines.

Staying here allows you to experience Siena at its best. You can explore winding streets, admire medieval art, and return to a hotel that feels both intimate and grand. It’s especially appealing during the Palio, when the city comes alive with festivities and tradition.

Awake & Wander can assist with bookings at the Grand Hotel Continental and highlight seasonal packages that make a stay here even more appealing. Our team ensures your time in Siena is both comfortable and memorable.

The Benefits of Booking Through Awake & Wander Luxury Travel

When you plan your Luxury Holidays to Tuscany with Awake & Wander, you gain more than access to exceptional hotels. You also enjoy peace of mind knowing your booking is fully protected.

As a member of Protected Trust Services, your money is held securely in a trust account until your holiday has been completed. We also hold an ATOL licence, which protects you if your trip includes flights. Every tailor-made holiday we create includes both Supplier Failure Insurance and Scheduled Airline Failure Insurance, giving you extra reassurance.

Beyond protection, you benefit from a personal service. We listen to what matters most to you — whether it’s privacy, gastronomy, cultural access, or family-friendly facilities — and then design a holiday that reflects those priorities. With access to a wide range of suppliers and tour operators, we can match you with the experiences that truly fit.

When you book through Awake & Wander, you’re not just choosing a holiday. You’re choosing support, security, and expertise that ensure your trip runs smoothly from start to finish.

Our Take:

"Tuscany rewards those who slow down. The best holidays here aren’t rushed but lived at an unhurried pace. That’s why we recommend stays in properties where you can feel part of the landscape and not just a visitor passing through."

Making the Most of Your Luxury Holiday to Tuscany

A stay in Tuscany offers much more than beautiful hotels. The region is full of experiences that connect you with its culture and landscapes. Choosing the right activities can turn a trip into something unforgettable.

One of the most popular experiences is wine tasting. From Chianti Classico to Brunello di Montalcino, Tuscany is home to some of Italy’s best vintages. Many estates open their cellars for tours, where you can meet the winemakers and walk through the vineyards. Private tastings arranged through Awake & Wander can ensure you enjoy access to estates that are normally closed to the public.

Cooking classes are another highlight. Learning how to make pasta by hand or mastering a Tuscan ragù in a farmhouse kitchen gives you skills you’ll use long after the holiday ends. Truffle hunting is also a memorable option, especially in autumn when the forests are full of aroma and excitement.

For those who prefer relaxation, Tuscany’s natural hot springs are an appealing escape. Places like Bagno Vignoni and Saturnia offer warm, mineral-rich waters that soothe after days of exploring. If you’re interested in art and architecture, Florence, Siena, and Pisa are all within reach, offering galleries, cathedrals, and piazzas that tell the story of Italy’s past.

The best times to visit depend on your interests. Spring brings green hills and pleasant temperatures. Summer offers festivals and long evenings, though it can be busy. Autumn is perfect for food lovers, with harvest season and truffle festivals. Winter is quieter, ideal for those who prefer a slower pace. Many visitors are drawn by the UNESCO World Heritage sites in Tuscany—towns like San Gimignano, Florence and Siena play a starring role in Tuscany’s identity. For full details on Tuscany’s heritage list, see the official Tuscany tourism site.

A luxury holiday to Tuscany is about balance. You can mix cultural visits with days of pure rest, enjoying the privacy of your villa or the indulgence of your hotel spa. The key is to design a trip that reflects how you want to feel.

Final Thoughts: Planning Your Luxury Holidays to Tuscany with Awake & Wander

Tuscany is a destination that combines elegance, history, and natural beauty. Choosing the right hotel or villa is the foundation of your experience, and with Awake & Wander, you can be sure every detail is handled with care. From ATOL protection to tailored itineraries, your holiday is safe, personal, and designed around your wishes.

You can call us on 01495 400011 to begin planning your journey, or use the enquiry form on our website to share your ideas. You also now have the option to design and book your own bespoke holiday online with Jamie Wake Travel. Whether you prefer to take the lead or leave the planning to us, we are only ever a call or message away.

Luxury holidays are about more than comfort. They are about peace of mind, memorable experiences, and time spent in places that inspire you. Tuscany offers all of this in abundance. Awake & Wander is here to make sure you enjoy it to the full.

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