Seasoning your winter with city breaks can make the dark months much more palatable. What’s more, as with all short breaks, you get much more bang for your buck because you feel like you’ve been away for longer than you have been, and with relatively little disruption to your day-to-day life.
A great way to explore a few cities in one short break is to take an escorted tour. Italian specialist Topflight, known for its winter ski holidays, also offers a range of escorted tours, some of which run through to October.
That includes its Taste of Tuscany and Umbria tour, a five-night programme which takes you to Perugia and Assisi, as well as the stunning Tuscan towns of Pienza and Bagno Vignoni. This last is on the Via Francigena, the historic medieval pilgrim route from Canterbury to Rome. The tour also includes a wine tasting stop in Montepulciano. Who needs city breaks when you’ve Tuscan hilltop towns to explore?
Topflight has recently expanded its escorted tour schedules to take in other countries too, including Portugal and Croatia. An October trip to Croatia sees you fly into Trieste before being transferred to the four-star Grand Hotel Adriatic in Opatija, known as the pearl of the Adriatic and a perfect base for exploring the coast. It has temperatures of 16 to 19 degrees in October, making it a lovely way to ease into winter.
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Where previously there was a perception that escorted tours attracted an older demographic only, that is no longer the case, says Liane Coleman from Topflight. She sees first hand how much people of all ages appreciate the value of experiencing all the highlights of a particular region, while having all the logistics – from transport to entry tickets – sorted for them.
It’s why the company has been extending its escorted short options in Austria and France too, and has a terrific two-centre programme in Sicily which takes in Syracuse, Taormina, Cefalu and Palermo.
The months ahead are also a great time to visit top-tier cities that traditionally get very packed in summer, such as Rome, Venice, Florence and Barcelona.
It’s a particularly wonderful time to visit the Andalucian cities of Seville, Granada and Cordoba, giving you an opportunity to explore its mighty palaces and cathedrals without the endless queues or the relentless sun.
But there are plenty of great smaller cities to explore too, many of which are often overlooked. “As Italian specialists we have a lot of experience in smaller cities. Some of my favourites are Lucca, which is a great place to see everything, including Florence, and is really under visited,” says Coleman.
Ditto Sienna which, in the shoulder season, is a lot less crowded and much more atmospheric as a result.
In Sicily, many holidaymakers head straight to popular spots such as Taormina, she says, but she recommends they consider staying in Catania instead. “It’s brilliant, fun and vibrant, but close to Taormina and a great base from which to explore,” she says.
While cities such as Venice and Florence are year-round attractions, heading further down to the boot of Italy to some of its lesser-visited spots is also rewarding, particularly in the shoulder seasons. Matera, in Basilicata – think of it as the instep – is not your typical city break, as the Unesco World Heritage Site is famous for its cave dwellings, including hotels.
If even that is too busy for you, Gravina, a town built along a deep ravine in Puglia next door, features cave homes of its own, and is a quieter, less crowded alternative.
Out of season is also a lovely time to visit Alberobello, recommends Coleman, with its famous and fairytale-like conical houses. And while Ryanair flies to Bari until the end of October, she suggests a stay in one of her personal favourites instead, the quiet whitewashed town of Locorotondo.
For her own next city break she’s keen to get back to Salzburg, a city she recently stopped at en route to a ski resort. “It was early December and the Christmas markets had just started up and it was just enchanting, like a fairy-tale town. I can’t wait to go back,” she says.
If a major city is your preferred city break option, autumn and winter can be a great time to go. “Off season has its own charms,” says Mary Masterson of luxury travel company Oroko. You’ll get a much nicer experience not just in terms of overcrowding but less queuing for museums and restaurants too, she points out.
If you have Paris or Venice in your sights, there is certainly no more charming way to arrive than via the Orient Express. Having just alighted from the iconic train herself, she can confirm it is everything we might dream, and more.
“It’s got amazing staff, beautiful food, and is just spectacular,” she says, still smarting at having had to get off. She travelled from Venice to Paris and reckons it was a great way to do it. “The timings of the train mean you get a lot of beautiful countryside scenery during daytime hours,” she explains.
Most of her clients choose to go the traditional route, from Paris to Venice, and to ensure they don’t have to cope with the shock of stepping off this palace on wheels and back into real life alone, she arranges for them to be met at the station and transferred by luxury water taxi along the Grand Canal to equally salubrious lodgings while they adjust. Her personal favourite is the famous Cipriani, on Giudecca, as frequented by George and Amal Clooney.
While in the city, she will prepare a bespoke itinerary for guests, taking in glassware sites, churches and museums, including the Guggenheim, as well as foodie tours. “Venice is a wonderful city in terms of there always being something new to discover,” says Masterson.
Those arriving in Paris are whisked to the George V, a hotel with a three-Michelin-star restaurant, or the Grand Hôtel du Palais Royal, a favourite of her own situated just opposite the Louvre in the heart of the first arrondissement.
If you’re not quite ready to push the button on a ticket for the Orient Express just yet, Italy’s popular summer resorts can be a great option in the off season, she suggests, including Sorrento and all the little towns along the Amalfi coast. These are stunning at any temperature, as well as being close to the archeological sites of Pompeii and Herculaneum, which can be overcrowded in summer.
“And the nice thing about these Italian places is that they are all functioning places, not resorts,” she points out. It means you won’t get that off-season sense of tumbleweed when you visit. “Or of being somewhere that was built for heat, in the wrong season,” she adds.
It’s why she also recommends Athens, Greece’s capital, which has so much to offer in terms of culture and style but can be suffocatingly hot in summer. “It’s an amazing city and one of that is, still, less homogenous than other cities – with loads of individual artisanal shops,” she says.
