Let's be honest... Cape Town winters are confusing. You pack a rain jacket and end up sunburnt by noon. But... don't write off the Mother City just because it's June or July. If you know where to go (and when), you can still have a great weekend.

Friday night: Arrive hungry

If you're flying in late, don't waste time. Drop your bags and head straight to Kloof Street House, you'll get moody lighting, a decent fire going, and comfort food that’s not trying too hard.

Want something more laid-back?

Try The Dog's Bollocks in Gardens, as the name suggests, a rough-around-the-edges vibe, but legendary burgers, and no one cares if you show up in a beanie and boots.

Saturday morning: Cold air, hot coffee, Table mountain views

Wake up early and check the mountain... I mean, literally. If it's clear, get up there. The cable car still runs in winter if wind permits.

But if it's fogged in? Swap it for breakfast at JARRYDS Brunch & Bistro and a coastal walk to the lighthouse.

If they're packed, head to Oranjezicht City Farm Market for fresh bakes, coffee, and ocean views. It's covered, cozy, and full of locals dodging the wind.

Saturday afternoon: Penguins or wine (You choose)

If it's dry and sunny, go even more south. Drive the peninsula... Simons Town, Boulders Beach, maybe even Cape Point if you're up for it. Look at our top 8 secret beaches in Cape Town.

Less traffic during winter, and the penguins don't take winter off.

Rainy day? Do Constantia. Wine tasting indoors at Groot Constantia or Beau Constantia, warm fire, smooth reds. Keep the opening hours in mind... you're tasting wine, not coffee.

Tip: Book a Constantia wine tram (from R330) or grab an Uber in advance. Nothing worse than getting stuck out there, half-drunk in the rain.

Saturday evening: Fireside dinner or world-famous hidden bar

The Athletic Club & Social or Aubergine Restaurant are great winter picks - low light, warm dishes, no wind.

Feeling adventurous? Try a hidden speakeasy like The Art of Duplicity (Voted ~~88th~~ 86th Best Bar in the World by The World's 50 Best Bars), but... book ahead.

If you're still awake, the Crypt Jazz Club under St. George's Cathedral often has live gigs.

Sunday: Sleep in, then beach walk or brunch

Winter doesn't mean beach is off the table. Just swap your towel for a windbreaker.

Walk from Camps Bay to Clifton if the sun's out. Or head to Kalk Bay for brunch at Olympia Café and browse the small shops along the strip.

Olympia Cafe and Deli — Olympia Cafe and deli, source Google Photos

Bonus: Quick spa or rooibos soak

Cap off the weekend with something warm:

Steenberg Spa for a proper massage
Hot baths at Twelve Apostles Spa, if you're splashing out
Or a budget-friendly soak at Yemaya in Sea Point

What to pack

Layered jacket (weather changes fast)
Walking shoes that can take on both rain and brunch
Portable charger for all the photos you're going to take

Need a place to stay?

Check out the Cape Town stays that matches your energy with real-time availability.

Local-approved by StayHere, and winter-ready.