The best places to travel in September

Chicago’s charming mix of big-city grit, culture and Midwestern friendliness are a winning combo. Head there in September to nab yourself a space in front of Anish Kapoor’s Cloud Gate (for the obligatory warped reflection selfies) and to beat the big crowds queuing for the lifts at the Willis Tower and gawping at the gold-topped art deco Carbide & Carbon Building. The weather’s still good enough for outdoor festivals then too: do as locals do and head to one of the city’s free jazz events, like the Chicago Jazz Festival, held in Millennium Park at the start of the month, or Hyde Park Jazz Festival in late September.

Discover the best things to do in Chicago

Japan’s most romantic city shines brightest in September. The weather is gorgeous, and the hotel prices plummet to make up for the out of season demand. How this is out of season, we don’t know, but there’s no need to complain. The autumn colours are staggeringly beautiful, while the end of summer is signified with several festivals and street events. Gardens and parties? Yes, please!

A relatively new international airport and an improved network of roads across the country make travelling to and around this underrated kingdom a lot easier – so get in there before everyone else does. This entirely landlocked country provides excellent mountain hikes, opportunities for rafting, zip-lining and mountain biking adventures, plus there’s plenty of wildlife – especially rhinos. Visit in September for springtime flowers and to get in there before the sticky summer rainy season begins in October.

Sure, Cartagena and Medellin have been filling up your Insta feed for years now, but the south of the country is still under the radar. And with its notorious local cartel bosses in jail, Cali is becoming Colombia’s next big thing. Known for its smoking-hot dancing, Cali has more than 200 registered salsa schools. In September, the annual Festival Mundial de Salsa is held here, so visit for free shows, live music and spontaneous dancing in its cobbled streets, as the best international salsa talent congregates in technicolour costumes to shake a collective tail feather.

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Sweden’s second city is ever-present in the upper echelons of the Global Destination Sustainability Index, thanks to its forests, parks, public transport system and the government’s push towards eco-innovation. Enjoy leafy walks in Slottsskogen or the harbour views from Keillers Park in between stops at the city’s wide choice of sustainable restaurants – try organic hotspot Taverna Averna, where they grow their own veg on the roof. And with the Swedish government pledging £4.3 million to work on overnight train routes into Europe, there could also be an opportunity for tagskryt (train-bragging) about your sustainable holiday. 

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The jaw-to-the-floor wilderness of British Columbia is best seen in burnt amber. Fly into the outdoorsy city Vancouver to acclimatise, with walking trails, parks and coastal hikes close to food trucks and buzzing neighbourhoods such as ex-warehouse district Yaletown and historic Gastown (Vancouver Island is also nearby, for some of the best autumn colours). Then to really feel a sense of escape, head out to the majestic forested mountains and glaciers in Northern British Columbia. Or if nature with wild swimming, local wine and a bit more proximity to civilisation is more your jam, try the Okanagan Valley.

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France has somehow managed to keep this sun-drenched, mountainous island, 174km off its south coast in the Mediterranean, a secret. And with around 200 beaches, there’s enough room for a quiet break. Stay entertained in the chic coastal towns, where you’ll find a mix of French, Italian and North African influence and barely any other English-speaking tourists. Bonifacio, perched on limestone cliffs at the southern tip of the island, offers cobblestone alleyways, a Game of Thrones-style fortress and coastal hikes to secluded beaches. Catch the end of the summer season when flights are a bit cheaper, but the sea’s still warm.

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The days of Montenegro being a little secret paradise are long gone, and Kotor is every bit as busy as Dubrovnik during summer. September, however, is a blissful time to visit, as the crowds thin out and the history and culture of this fascinating little country take centre stage. Perast (just down the road from Kotor) is the pick of the coast, while culture vultures should make a beeline for Cetinje (the royal capital) and the indomitable Mount Lovćen, the final resting place of 19th-century prince-poet Njegoš. 

There’s no such thing as a bad time to visit New Zealand. This place is a paradise, but the first days of spring make it jump off the page just that little more. The dying days of the ski season bring their own bargains, but it is the blossoms that demand the attention, as New Zealand gets ready for the warmer months in that inimitable Kiwi sort of way. It isn’t warm, so pack accordingly, but good golly is it beautiful. 

The grape harvest in the Golden State lasts from late August to early October when Wine Country is abuzz with events and tastings. For luxe sipping in chic surrounds, head to the Napa Valley, where you can catch the Wine Train or cycle between wineries. Or for the same calibre of world-class vintages in a more laidback setting, head to Sonoma: its leafy town of Healdsburg has plenty of tasting rooms offering diverse local selections from the big makers and smaller-scale artisan and family-run operations. They’re all walkable, too, which means grape times with no driving necessary.

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There are lots of reasons to love Boston: lobster rolls, the characterful charm that comes from being one of the oldest cities in the US, its major-league sports teams. The city’s home to NFL legends the New England Patriots and baseball bros the Red Sox – and the seasons for both sports coincide in September, so if stadiums are welcoming the public again, you’ll be able to catch (at least) one game of each while you’re in town. Sports not your thing? Boston is a total beaut in foliage season; for a tree-mendous leaf-peeping trail, wander through the Public Garden, then through the cobbled streets and brownstones of Beacon Hill and along the Charles River Esplanade.

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From beer halls to underground jazz clubs and museums, the Bavarian capital has a lot going for it at any time of year – but the real party starts in September. More than six million people visit Munich to drink about two million gallons of beer every year for Oktoberfest. Please, take a moment to consider just how much beer that actually is. Over the years, the start of the folk festival has crept forward, and now the mass enjoyment of traditional German cuisine, wiener dog races, lederhosen and polka music lasts from mid-September to early October. 

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This good-looking, underrated northern French city has a lot going for it. Beyond its cobbled streets, Flemish houses and art nouveau buildings, Lille also has some impressively sculpted modern architecture such as the Lille Métropole Museum of Modern, Contemporary and Outsider Art and the elliptical Stade Pierre-Mauroy. While design buffs might want to hold out for the WDC street festival in December, everyone else should visit in September for Europe’s biggest flea market, Braderie de Lille, which has developed into a massive street party. It’s been going since 1127, and you know what they say: practice makes perfect.

Discover the best things to do in France