Why Autumn Is Luxury Travel’s Best-Kept Secret

Wine Lovers, Take Note: The Douro Valley Harvest

At Six Senses Douro Valley

In September, the vineyards of the Douro Valley are flush with plump bunches of glistening grapes, allowing guests to join locals in plucking the grapes from the vines on those iconic terraced hillsides. And, if you’d like, you can participate in traditional foot-treading in granite lagares, too.

Of course, the experience wouldn’t be quite complete without enjoying exclusive wine tastings and pairings in these beautiful landscapes. But we can go a step further and introduce you to a little secret just a short walk from Six Senses Douro Valley, at neighbouring Mourão. The secret is Port Knox, a Port cellar set in the hills, filled with local Ports that you can taste directly from the cask.

Which Room to book at Six Senses Douro Valley?

Six Senses Douro Valley is a 19th-century manor house set on a verdant hill, with plenty of rooms overlooking the vineyards. But a favourite among 360’s Travel Designers is the Quinta River Room, with panoramic vistas of the Douro River winding through the vineyards.

If you need extra space, the Two Bedroom Pool Villa is ideal, with a full kitchen, sundeck and a heated pool set in your private garden, and you can add the 1-bedroom pool villa next door if you need an extra bed.

Live The Slow Life in Tuscany

At Castelfalfi

Oh, to live an authentic Tuscan life. Hear the church bells ringing much as they have since the 13th century. Take a stroll over the cobbles, centuries old and tipsy from age and so many glasses of spilt Chianti. Live as a neighbour to the undulating Tuscan hills, and their cypress, olive and grapevine punctuation.

Some hotels are just that: hotels. Castelfalfi is something more. It’s a restored medieval village with a castle, working vineyard, and olive groves, allowing guests to fully immerse themselves in the bucolic life of the Tuscan countryside.

The Castelfalfi Experience

October is a favourite time to visit Castelfalfi. Tuscany’s harsh summer sun has eased, temperatures are more comfortable, and woodland paths become layered with foliage, making for scenic autumn walks. But more than that, October is when seasonal activities like olive-harvesting and white truffle hunting are in full swing. The olive harvest is an immersive experience here, as you can pick olives directly from the trees and then witness their transformation into extra virgin olive oil at the Castelfalfi mill.

Add to this wellness experiences, dining on delicious regional fare, painting with the resident artist and shopping in the Borgo’s international shops, and Castelfalfi becomes a uniquely immersive travel experience — with all of Tuscan life on your doorstep.

Santorini’s Second Summer

At Grace Hotel, Auberge Collection

By autumn, Santorini’s summer crowds may have all but departed, but the island’s spectacular beauty remains. October in particular brings warm days without the intensity of high summer, making it an ideal season to explore these otherworldly volcanic landscapes. And for those who like to spend time on or in the sea, the Meltemi winds have typically faded, leaving calmer, glass-like waters ideal for kayaking and relaxed sailing. On land, the softer autumn light and crisper air make the whitewashed, blue-roofed buildings of Oia glow so much more vividly at sunset.

The Experience at Grace Hotel, Auberge Collection

The Grace Hotel’s setting in beguiling Imerovigli puts Santorini’s caldera and its iconic sunsets centre stage. This time of year is lovely to linger at the hotel, its facilities quieter than in the high season. Slip into the hotel’s heated infinity pool or indulge in a massage enhanced with Greek lavender oil, before taking a seat at Varoulko Santorini for mouthwatering Greek cuisine prepared with fresh local ingredients, with the Aegean glistening just beyond.

The experience is particularly seductive from the hotel’s cliffside suites, many of which open onto expansive terraces with uninterrupted caldera views, best enjoyed from the heated private plunge pools.

Browse more of our favourite autumn holidays in Greece here.

Autumnal Contrast on Sicily’s Eastern Coast

at Grand Hotel Timeo, A Belmond Hotel, Taormina

Sicily’s cypress, palm and lemon trees remain green year-round. But when autumn arrives, deciduous trees in the Taormina Public Gardens shift through soft amber tones, while fiery oranges and deep reds begin to colour the slopes of nearby Mount Etna. In October, the weather transitions from the warm, extended summer of September into a cooler harvest season, ideal for exploring the Teatro Antico, hiking Mount Etna and visiting nearby vineyards during the harvest.

Grand Hotel Timeo, A Belmond Hotel, Taormina

Exactly one hotel holds the distinction of being the first to be built in Taormina: Grand Hotel Timeo, A Belmond Hotel. And more than 150 years later, it remains the benchmark for a stay in this stunning Sicilian town. The hotel has 40 rooms and suites alongside the original Villa Timeo, as well as Michelin-starred cuisine at Otto Geleng, a swimming pool overlooking the coast, and six acres of landscaped gardens, all mere steps from the ruins of the Teatro Antico.

The rooms are individually styled, but the Signature Suites make particularly good use of the setting, with 180-degree panoramas showcasing the village of Castelmola, Mount Etna and the glorious sparkle of the Ionian Sea. For a stay connected to the hotel’s history, book a suite in the Villa Timeo, the classical residence carved into the hillside beside Taormina’s ancient Greek amphitheatre. This is where the story began: the villa was Taormina’s first hotel in 1873, and today its suites offer a more private way to experience the Grand Hotel Timeo.