Hillside views in Tuscany

An insider’s guide to a luxury holiday to Tuscany

Bursting with romantic villages and picture-perfect countryside, Tuscany is one of the most beautiful regions in Italy. From world-class wine tours and Michelin-starred tasting menus to winding bicycle paths and hot air balloon rides; this is what a tailor-made holiday to Tuscany looks like. Though don’t worry, we’ve still got a few secrets up our sleeve when it comes to planning your Italy trip.

To really get the most out of the Tuscan region, the best time to visit Tuscany is April through to November. However, our favourite months for a Tuscany holiday is June, when the hills are scattered with wildflowers and the weather is warm, or October when truffle hunting season is in full swing and the Autumn leaves are glowing. Read on to discover our most-loved destinations and hand-picked experiences for a Tuscany holiday.

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View of Florence Cathedral
Making focaccia in Tuscany

Admire the architecture of Florence Cathedral

Kickstart your Tuscan holiday with a private tour of Florence, the region’s historic capital city. Accompanied by a private guide, you’ll explore the birthplace of the Italian Renaissance and unravel the enchanting Florentine history, from its establishment in 59BC to its urbanisation in the more recent years. After some time spent admiring the architecture of Brunelleschi’s Dome of the Cathedral, dine out at the three Michelin-starred restaurant Enoteca Pinchiorri on charcoal duck breast, salmice lobster and a glass of Chianti wine. Finish the evening with a romantic sunset cruise down the River Arno, watching the city come to life as you glide past the banks of Florence’s picturesque palazzos and historic churches.

Where to stay in Florence: Perched over the Arno River, take in the glistening water-side views whilst sipping on a freshly made margarita from the cocktail bar at Hotel Lungarno. Located at the heart of Florence, Lungarno is perfectly positioned to explore Italy’s capital city every hour of the day.

Try your hand at Tuscan focaccia-making in Chianti 

Today you’ll drive 45 minutes south past Tuscan villas, olive groves and lush vineyards to reach Greve in Chianti. From here you’ll be whisked away to meet Giulietta, your host and cooking instructor for the day. From the grounds of her hillside Tuscan villa, embark on a private cooking class in Chianti, hearing captivating tales of Tuscan cuisine, and being teased with much-loved family recipes. Learn to prepare focaccia, the technique of making the perfect risotto con zucca and the ingredients for Giuletta’s one-of-a-kind lasagne. After showing off your culinary talents, enjoy the delicious lunch you’ve prepared, accompanied with a glass – or three – of local Chianti Classico Riserva Badia a Passignano wine

Where to stay in Chianti: Nestled high in the Tuscan vineyards and twisting olive groves of Tavarnelle Val di Pesa, the 12th-century castle, COMO Castello del Nero boasts Renaissance frescoes and voguish design. Truffle hunt ahead of your afternoon cooking class, soar over the valley via hot air balloon and ride horseback through the hills; at this 740-acre estate, anything is possible.

Excited by Chianti wine and medieval towns?

Bicycle rides through verdant hills, sunset cruises down River Arno and gourmet offerings at Michelin-star restaurants; Tuscany serves up a heaving bowl of enticing activities. Get in touch with our Travel Experts today to start planning your Italian adventure.


Wine tasting in Tuscany
Instagrammable San Gimignano

Private wine tasting tour in a 12th-century Tuscan wine cellar

With wine production in Chianti dating back 2,500 years, this region is one of the most renowned wine regions in Italy. After a morning dip in Castello del Nero’s pool and a leisurely breakfast at La Torre Michelin-starred restaurant, you’ll spend the afternoon on a private tasting tour with the hotel’s very own sommelier, Roberto. From the castle’s 12th-century wine cellar, you’ll be guided through some of Tuscany’s finest wines like Brunello of Montalcino and Chianti Classico, as well as the estate’s own varieties. After some swirling of Tuscan wine, you’ll be treated to more sampling, but this time, fresh olive oils, pecorino cheese and Tuscan ham. 

Cycle through the Tuscan hills near San Gimignano

From the grounds of Castello de Nero, today travel to one of the most Instagrammable spots in Tuscany. With walls dating back to the 13th century, and the city’s historical centre boasting UNESCO World Heritage Site accreditation, San Gimignano is one of Tuscany’s best-kept secrets. Take some time to explore the medieval town and 14 of its perfectly preserved towers with an expert guide, as they teach you all about this beautiful city. Next, set out on a leisurely⁠—or challenging⁠—bike ride through the Tuscan vineyards to marvel at the breathtaking views and sunflower-scattered fields. Route for all ages and abilities, a bike ride is the perfect way to discover the remote areas of the region. Along the way, stop at a secluded opening for a picnic crammed with your favourite snacks and a bottle of bubbly, courtesy of your hotel.

Where to stay near San Gimignano: Set amongst 750 hectares of rolling Tuscan hills and a half an hour drive from San Gimignano, Borgo Pignano Hotel serves as the ultimate honeymoon hotel. Take a tour of the organic vegetable garden, learn to make honey with beekeepers and check out the hotel’s solar energy efforts – this rural villa is certainly doing its bit for the environment.

Palio horserace in Siena
Palio race, flags of the Districts

Sit front-row at Italy’s most famous horse race: Palio di Siena

The thunderous sound of hooves, the colour-clad jockeys and the roaring crowd; Palio horse race in Siena is one of Italy’s most exhillerating and historic events – and we’re here to bag you the best seats. Whilst buffalo and donkey-back races in Siena date back to the early 17th century, the first official Palio horserace in the city began in 1633, and now takes place twice a year: July 2nd & August 16th. The famous event sees 10 of Siena’s 17 districts compete in a three-lap race around Piazzo del Campo for the prize of the decorated Drappellone banner, but most of all, pride amongst its fellow districts. In the build-up prior to race day, Siena comes to life, with an array of horse and jockey selections, extravagant feasts and race-gossip circling the Piazza.

Where to stay near Siena: The beautifully restored Relais Borgo Santo Pietro is a 13th-century country villa set amongst a 200-acre estate. Boasting Michelin-starred cuisine, an extensive wine cellar, elegant tapestries and breathtaking valley views, this is one of our favourite hotels in Tuscany.

Tempted by Tuscany?

Whether it’s Florence and Siena in Tuscany, or Rome and the Amalfi Coast, our Italy Travel Expert is always on hand to plan a bespoke trip to Italy. Chat to us today to get your dream holiday booked.