Insider travel picks

If you like standing in lines, paying peak rates for accommodations and spending each day in an endless calculus of “Is this crowded activity worth the potential heat stroke?” summer travel is ideal.

- SARAH LAING

If you prefer more temperate weather, fewer crowds and easier-on-the-wallet prices, however, shoulder season is the sweet spot. Here, we tapped three travel experts for their insider picks on places to go this fall — and while you’re planning ahead, what to consider for the holiday season, too.

Kyoto, Japan

“Without any seasonality, the place we’ve seen the biggest demand for is Japan,” says Semia Bag, a travel designer at the Pelican Club, a travel club based in Toronto. “It used to be a popular destination for cherry blossom season in the spring, but for the past couple of years we’ve seen a huge demand in people wanting to go year-round. It’s booming.”

And while Tokyo is always popular, Bag recommends the city of Kyoto. Home to more than 2,000 shrines and temples, Japan’s former capital is a dreamscape of ancient architecture. “I’ve been several times, and I loved going to temples,” says Bag, “especially during fall. It’s my favourite season, with all the (changing) leaves.” When in Kyoto, she also recommends visiting a ryokan, a traditional Japanese inn, typically built around a hot spring.

Although prices for Japan don’t tend to fluctuate wildly by season, the current exchange rate means you’ll get more out of your travel dollars than usual: “People are going right now because the currency is so much lower,” says Bag of the yen, which hit its weakest level in decades earlier this year. “People feel like they’re saving money.”

The enchanting towns in Italy's Puglia include Alberobello, noted for these distinctive trulli limestone dwellings.

Puglia, Italy

“In Italy, they’re starting to call September and October the 45th or the 60th day of August because the weather is just as warm now,” says Jessica Avery, founder of the boutique travel company Ms. Guided Travel. “But the crowds are significantly thinned, and the prices are low.”