8 Cities That Might Be Better In The Fall

Now is the perfect time to book your trip

By Journy Admin

3 August 2018

There's nothing quite like a lazy afternoon lounging by the pool with a frosty drink in hand and relaxing book nearby. While the words summer vacation make us feel like an eager school kid all over again, the globetrotting adults in us know that sometimes the best trips are the ones that happen outside of the June-July-August trinity. In fact, there are some places that are done a disservice by going in summer. We've rounded up a list of our 8 favorite destinations that are better to visit outside of summer.

1. Havana, Cuba

Spencer Everett

When to go: December - May

Why: From locals spending their evening chatting in the city's crumbling squares to tourists dancing with daiquiri at hand, Havana pulsates year-round. But if you go in the summer, you'll face a daily afternoon downpour, along with humidity and heat to convince you the city really is a tropical destination. We recommend booking a tour for late winter or early spring (make sure your visa is in check before you do).

2. Cape Town, South Africa

Mountain Journey

When to go: Late January - late April

Why: Cape Town is full of fantastic outdoor adventures that you won't want to do in a sweater. Even nature skeptics will have a hard time keeping their mouth closed when they get their first glimpse of the city's striking Table Mountain. Take a day to hike up and enjoy the views, another to take a surfing lesson at the beach, and yet another to get out into the countryside for a wine tour in the lush Stellenbosch Valley. Going in the summer also means there's no excuse for not making a daily trip to Unframed Ice Cream, Cape Town's premier artisanal ice cream shop.

3. Copenhagen, Denmark

Visit Denmark

When to go: September - November

Why: While the weather will be warmer, sunnier and all around more pleasant in summer, it doesn't truly let you experience the hunker-down vibes that the Danish capital does so well. Hygge is by now a well known phenomenon, but to experience it for yourself, you'll need to go in fall or winter. Wake up in the dark, then spend your morning cozied up in a cute cafe with one of the city's famous cinnamon buns or a bowl of oatmeal. Bundle up for a walk around the harbor, then head over to famed Tivoli amusement park (if your feet can take, it that is).

4. Sydney, Australia


When to go: September - November

Why: The active life is essential to understanding what makes Sydney-siders tick and while it never gets super cold during the winter (i.e. our summer), we prefer to keep our vacations to the Australian summer and spring. A morning run around Bondi beach before the heat of the day is an essential Australia experience we wouldn't want to miss.

5. San Diego, USA


When to go: September - November

Why: There's no real time of year that's bad to visit San Diego—it stays a balmy 50 - 80 degrees year round. But for those of us who live elsewhere, there's nothing better than a warming mid-winter trip. Break out the bikini and go to the beach, flex those legs with a long bike ride and dig into al fresco tacos at Sandbar. You're not doing that in a Chicago winter.

6. Taiwan

Ningxia Night Market | Dave Krugman

When to go: September - November

Why: The fall season is when the weather in Taiwan is great everywhere. The southern areas will be warm, but the north begins to cool down. There’s almost no rainfall between central to southern Taiwan, where it’s sunny and clear in the fall. In the Northeast, however, you do have the monsoon season starting in October. Our team visited Taiwan during this month and still had a wonderful time, though it was a little wet and rainy while we explored the areas of Keelung, Hualien, Taroko Gorge and Yilan, which meant we had to wear rain parkas.

In September, you can visit anywhere in Taiwan without concern for rain, but in October and November you may want to consider spending your time outside of Taipei in central and southern Taiwan. It’s a perfect time to visit Sun Moon Lake in the Central Mountain Range, Taichung and Tainan.

READ MORE: Journy's Ultimate Taiwan Travel Guide

7. Madrid, Spain


When to go: September - October

Why: Madrileños concur; summer is unbearable in the land-locked capital. While artificial pools have been built in recent years to alleviate the triple digit heat, you'll still find the usually vibrant city a shadow of its normal self. Instead, go when the temperatures drop, which they never do too much. You'll avoid hour-long waits at the Museo del Prado, actually be able to see Guernica at the Museo de la Reina Sofia and can stroll through Buen Retiro park without suffering heat stroke. Plus, cooler weather means there's no excuse not to indulge in churros dipped in chocolate.

READ MORE: 7-10 Day Spain Itinerary: Where To Go, What To See, & Tips To Consider

8. New York, USA

Moostash Joe Tours

When to go: September - November

Why: There's a reason the song is called "Autumn in New York"—and for those who would point out "Summer In The City," we wouldn't exactly call it a trip-planning anthem. Come September and October, the city settles into a pleasant buzz with fewer tourists, plenty of locals and a jam-packed cultural calendar to keep them entertained. A stroll through Central Park is practically obligatory, as is a cup of hot apple cider from the Union Square Greenmarket. And if you'd like to get out the city, this is the best time of year for hiking, many of which are easily accessible by public transport.

READ MORE: The Best Pizza In New York City: A Complete Guide