We're so over cookie cutter, one-size-fits-all Winelands tours. Luckily, so are the folks at Sideways — which is why they created a spectacular online platform (and app) that will help you decide on the right wine itinerary for you. Are you a connoisseur, a foodie, or a romantic? Would you like to combine wine tasting with whale watching or horseback riding? Or are you dying to visit some boutique wineries? Select the amount of time you'd like to dedicate to this wonderful wine cause and how many friends are jumping on the bandwagon, then discover which cleverly crafted and curated experience suits you (and your wine needs). All that's left is to go explore. Sideways, that is.


Bespoke, brilliantly curated Winelands tours.
Wine tastings should be an adventure, right?
Browse the options online.
This is your show: Choose the itinerary and venue that suits you best.