Winter is here, the season known for chilly mornings and long nights, hot water bottles and curling up by the fireplace. Well, that’s what everyone else does, but not us Urban Explorers. Come rain or sunshine we’re on the road living our best lives, seeking only that which can be found when one explores. So how is a little cold going to deter us? Not now, not ever! 

We live for this.

As the title suggests in this edition of our Urban Explorer series, we cast our eye towards Winter festivals not to be missed. It only makes sense that we as Urban Explorers be part of the fun; after all, it is us that set the standard.

Wacky Wine Weekend

WACKY WINE WEEKEND (7 – 9 June 2019)

Our exploring kicks off in the Western Cape, town of Robertson, situated in the fertile Robertson Valley. Known to many as the valley of wine and roses, it then makes sense to call the festival hosted by this scenic town the Wacky Wine Weekend. 

Now going for its 16th anniversary the Wacky Wine Weekend is a wine institution in the social calendars of many across the country, attracting wine connoisseurs, novices and families & friends alike travelling far and wide. And of course, this is just the kind of setup that resonates with our Urban Explorer spirit. This year’s edition of the festival boasts produce from over thirty established wineries and tourism establishments in the Ashton, Bonnievale, McGregor and Robertson region. 

This jam-packed festival is definitely not one to be missed as it features an all-around good time whether you are there with your other half or travelling squad. From cellar tours, interactive tastings, live music, arts & crafts and of course the mouth-watering country cuisine the whole experience leaves one yearning for more.

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Kirkwood Wildsfees


Second, on our list is the festival that is dubbed as the “biggest festival to be produced by the smallest town”. The Kirkwood festival plays host to around 50 000 festival lovers and is a game festival like no other as it beautifully brings together the spirit of community building.

Established in 2002 to grow tourism in the Sundays River Valley and to support local socio-economic development, this community established festival is true to the Urban Explorer’s spirit of Ubuntu as it is for the community by the community.

What can we expect there? On the line-up for this year’s festival is the world-renowned songbird Lira. From Hilde-Alet Malan, a local painter of Patensie, who will be showcasing her creativity, to the local chefs who will be cooking up a storm. Missing this year's Kirkwood festival is just not an option.

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National Arts Festival


Founded in 1974, the National Arts Festival is amongst the most vibrant festivals the country has to offer, and this year’s festival promises to be nothing short of spectacular.

Hosted in Makhanda – formerly Grahamstown, the National Arts Festival is the gem of the Eastern Cape as it draws festival lovers from all over the globe. This 10-day spectacle features over 100 shows, from Children’s Festival to the Creative Digital Arts Festival, the 2019 Standard Bank Young Artists’ productions, world-class jazz, theatre, visual arts, dance and contemporary music productions and more. 

Just thinking about it excites one, as the festival’s heritage and pedigree are set to continue to deliver a solid and powerful programme, while each production will ensure that visitors are delighted and moved. It goes without a saying that this is an Urban Explorer kind of vibe.

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So, what are you waiting for? The festivals are calling, start packing and get ready to explore.

And like we always say, if it’s not living life to the fullest then it is not living at all.

Until next time Urban Explorers.