It could be said that no other province has had more impact on Italian—and European— culture than Tuscany. With its wine-soaked villages, art-rich cities, swathes of olive groves and truffle fields, and modern-fashion powerhouses (Gucci and Ferragamo, to name a few), Tuscany epitomizes la vera Italia. Travel to Tuscany to walk in the footsteps of history, and let Bespoke Travel Design show you the way.
top locations in italy
amalfi Coast | DOLOMITES | Italian Riviera | Milan & Lake como | Puglia | Rome
Tuscany & FLORENCE | Umbria | venice
hotels we love
Nothing but the best. Browse below to see the hotels that can feature in your bespoke Tuscany itinerary.
castiglion del bosco (top pick!)
One of the oldest and best-preserved estates in Tuscany, Rosewood Castiglion del Bosco is a 5,000 acres property located in Montalcino, Tuscany, in the heart of the UNESCO World Heritage Site of Val d’Orcia. Much like the wine produced in Tuscany, the scenery of this hotel is intoxicating, and demands to be savored. The heart of the estate is Il Borgo, made up of 23 suites and 3 of the 11 restored 17th and 18th century villas, plus La Canonica Cooking School, two restaurants, infinity Pool and Award-Winning Winery.
Overlooking the iconic Ponte Vecchio on the Arno River, Portrait Firenze provides a fashionable home away from home in this timeless city. The hotel is owned by the Ferragamo family, so you can expect haute couture touches around every corner; the 37 suites are warm and inviting with kitchenettes, handcrafted furnishings and lavish fabrics. Rooms are stocked with gourmet goodies, while private balconies reveal mesmerizing views of the river, city rooftops and Florentine countryside. Visit the hotel website.
Owned by the Ferragamo family, Hotel Lungarno is perched along the south bank of the River Arno, just a stone’s throw from the Duomo, the Ponte Vecchio and the Uffizi Gallery. After a recent refurbishment, the guestrooms are delightful, all of them with antique furnishings, original paintings from the hotel’s collection and soothing colors. Michelin-star restaurant Borgo San Jacopo, too, with the superb Italian cuisine.
The leafy boulevard that winds through the hillside just above the south bank of the Arno is packed with grand houses, but late 19th-century Villa Cora is one of the most sumptuous of them all. The hotel is set in a rose-scented garden with terraces, a large pool, and views over the city. There’s an excellent restaurant and in warm weather, lunch and evening cocktails are served by the pool.
The ethos at Borgo Pignano is a simple one: ‘Everything comes from the land’. That motto emanates from every organic corner of the 750-acre Tuscan estate. A resident beekeeper supplies fresh honey for your morning cornetto. Pignano’s soapmaker plucks aromatic plants to create guest bath products. Overseeing it all is an elegant 18th-century villa, its 16 rooms adorned with antique furnishings, original frescoes and artworks from the owner’s collection. Horse-riding excursions allow guests to experience Tuscany from the saddle. Visit the hotel website.
An 11th-century hamlet surrounded by vineyards and olive groves, Castel Monastero offers guests a romantic and luxurious oasis spectacularly located on the edge of a ravine in the gorgeous Chianti region, just 15 miles from Siena. Once a medieval monastery, this historic hotel offers 5star contemporary luxury. Taste the marvels of Tuscan cuisine in the hotel’s two fabulous restaurants (including one by Gordon Ramsay). Go bike riding, play golf or polo, join the kitchen team for an Italian cooking class or take a hot-air balloon ride over the Tuscan hills. Visit the hotel website.
borgo santo pietro
Out of the way and out of this world, Borgo Santo Pietro is the Tuscan retreat of your dreams. Follow a cypress-lined drive to this romantic 16-room boutique hotel and estate, where luxury meets seclusion with sumptuously private garden and pool suites. Amble amongst the 13 acres of fragrant gardens, lounge by the infinity pool with spectacular views over the Valle Serena or enjoy a spa treatment. Chef Andrea Mattei’s farm-to-plate approach uses the estate’s own organic harvest and has earned Meo Modo restaurant a Michelin star; learn kitchen secrets at the on-site cooking school. Visit the hotel website.
Enjoy glamor, luxury, and impeccable service at Il Pellicano, a long-time destination for celebrities and the elite, located in Porte Ercole on the Tuscan archipelago. Relax in classic rooms overlooking the limpid waters of the Tyrrhenian Sea and spend long days in the sun by the saltwater swimming pool or at the hotel’s beautiful private beach club. Also experience the tranquility of Il Pellicano’s lush gardens and delight in its restaurant’s refined, inventive cuisine. Visit the hotel website.
il falconiere (top pick!)
Silvia and Riccardo Baracchi welcome you to Relais Il Falconiere & Spa, their 17th-century family home just outside Cortona. Here, you are a cherished friend, as Riccardo shows you his wine cellar and Silvia shares cooking secrets in hands-on classes. The 23 rooms and suites exhibit a simple Tuscan elegance; local talents are on display in frescoed walls, antique furnishings and handwoven fabrics. The solar kitchen creates Michelin-star Etruscan fare sourced from the residence’s farm. Visit the hotel website.
corte dei papi (top pick!)
Tucked in the valley below the charming town of Cortona, Relais Le Corte dei Papi is an oasis of tranquillity in an enchanting setting. Housed in an 18th-century country residence, the property has been lovingly restored, maintaining its original rustic details, but enhancing them with sumptuous style. The resort features a wonderful wine cellar, and offers cooking classes, a wellness center, fine dining, as well as excursions to the local wineries, towns, and countryside. Visit the hotel website.
L'andana - tenuta la badiola
Escape into the mystical National Park of the Maremma in the heart of Tuscany at L’Andana Hotel and Spa Resort. Located in Castiglione della Pescaia, about ten miles from the charming town of Grosseto, the property is housed in a historic villa and a fattoria, which are connected by a lovely light-filled lobby and garden. Enjoy the exceptional cuisine at either of the two fabulous restaurants, helmed by Michelin-starred chef Enrico Bartolini. Visit the hotel website.
castello di casole
Taste dolce far niente, the ‘sweetness of doing nothing’ at Hotel Castello di Casole. Formerly home to the noble Bargagli family of Siena, the property features gorgeous fountains, courtyards and wide terraces where you can get lose yourself in the region’s beautiful rolling hills. Located just 45minutes from Florence or 20 from Siena, the Castello di Casole offers easy access to all the delights of Tucany. Visit the hotel website.
Occupying a storybook stone tower and medieval church built over ancient Roman baths, the Hotel Brunelleschi simply oozes history. Since its stylish refurbishment in 2012, it’s become one of the finest boutique hotels in the centre of Florence. For a city-centre pad, it’s perfectly placed: just two minutes’ walk to the Duomo complex and a four-minute amble to Piazza della Signoria and the Uffizi. Visit the hotel website.
castello del nero (top pick!)
When you can’t quite decide which of Italy’s glorious cities to visit, a stay at Castello del Nero Hotel & Spa will answer the question for you. This elegant retreat in the Chianti wine region is a short drive to Florence and Siena (with complimentary shuttle schedule). After you explore those cultural epicenters, take time to discover the hotel’s facilities and enjoy the Michelin-star restaurant La Torre and the Tuscan La Taverna. Within this 12th-century castle, each room boasts a unique layout, style and décor. The designer ESPA offers the latest in holistic treatments from around the world. Visit the hotel website.
castello di vicarello
Castello di Vicarello has had 900 years to cultivate its air of rustic majesty, so it’s little wonder that the honey-coloured buildings and gardens look like they’ve sprung from the canvas of an Italian master. Despite the romantic atmosphere, the hotel is still very much rooted to the rolling and fertile land on which it sits. Incredible home-style meals are prepared in the castle’s historic kitchen, which draws most of its produce from the grounds organic garden, vineyards and olive groves. There are two valley-facing infinity pools to choose from, an outdoor hot tub, and multiple levels of cyprus-studded gardens and manicured lawns to bask in the Tuscan sun. Visit the hotel website.