New month. New plans. New Property of the Week 👀

GM, Insiders ☀️

We’re a week into May and the Winelands has slipped into that golden between-seasons mood 🍂 The leaves are turning, the mornings are crisp, and somehow the calendar is already filling up with wine evenings, cosy dinners (Abrie Beeslaar + Bertus Basson, hallelujah!), live music and all the excuses to stay out a little longer before winter properly arrives.

From Thursday market strolls and sunset dinners to ABBA nights, wine walks, live music and harvest feasts under the lights - this issue is packed with the kind of plans that make you want to message the group chat immediately.

We’ve also got a few slower, feel-good moments in the mix too, like the beautiful new botanical art exhibition at the Stellenbosch Botanical Garden, kids’ creative sessions, and some proper cosy-season wellness ideas before the rain rolls in next week.

And… a little something new 👀

We’re officially launching our new Property of the Week feature - highlighting standout homes around the Winelands that genuinely catch our eye (starting with a very dreamy Paradyskloof spot this week).

As always, we’ve done the digging so you can skip the endless scrolling and get straight to the good stuff. Enjoy!

Here’s what we’ve got for you today👇

Before you get stuck in, check out today’s (7th May) events in case you needed an excuse to get out and about 👇

Market on the Plein - Special Thursday Edition
📅 Thu. 7 May | 08:00-16:00 📍 Rooiplein, Stellenbosch University
A Thursday pop-up with 50+ stalls, from fashion finds and vintage gems to local art and handcrafted pieces. Perfect for a midweek wander.
🎟 Free entry - No booking required

Take A Seat - An Evening for Women
📅 Thu. 7 May | Evening 📍 Mont Marie Wine Estate
A beautiful evening of connection, conversation and inspiration, with wine, canapés and a main meal included.
🎟 From R550 - Book here

Golden Hour Sunset Dinner at Uva Mira
📅 Thu. 7 May & Thu. 21 May | 18:00 for 18:30 📍 Uva Mira Mountain Vineyards
A refined four-course seasonal dinner paired with Uva Mira’s high-altitude wines and sunset views over False Bay.
🎟 Price on request - Book via email

First Thursday Blind Wine Tasting: Serious Whites
📅 Thu. 7 May | 18:00-19:00 📍 Bertha Wine Bar
Forget the label and trust your palate with a guided blind tasting of serious white wines.
🎟 From R200 - Details here

Droomsindroom Live @ Die Naguil
📅 Fri. 8 May | 18:00-02:00 📍 Die Naguil
A proper Paarl Friday night jol with live music, dancing and big local energy.
🎟 From R100 - Info here

ABBA Tribute Night at Paarl Golf Club
📅 Sat. 9 May | 18:00-21:00 📍 Paarl Golf Club
Calling all Dancing Queens - expect all the ABBA classics, big singalongs and a feel-good night out.
🎟 From R269 - Book here

Live Music with Dani Ville
📅 Sat. 9 May | 13:00 📍 Val de Vine Guest Farm
A laid-back afternoon of acoustic favourites, countryside views and relaxed Paarl charm.
🎟 Details here

Nic Stevens Live at Doran Vineyards
📅 Sat. 9 May | 17:00-21:00 📍 Doran Vineyards
Golden hour, live music, vineyard views and a complimentary glass of wine - a very easy Saturday yes.
🎟 From R300 - Book here

Koorfees met Joshua na die Reën
📅 Mon. 11 May | 18:00-21:00 📍 Toringkerk
A 150-year interschools choir celebration ending with a live performance by Joshua na die Reën.
🎟 From R50 - Book here

Chris Steyn Live at Kapstadt Brauhaus
📅 Thu. 14 May | Doors 18:00 | Show 20:00 📍 Kapstadt Brauhaus Stellenbosch
A lively night of local music, cold beers, great food and proper singalong energy.
🎟 Details here

’n Simfoniese Samekoms - Breytenbach Klassieke Konsertreeks
📅 Sun. 17 May | 15:00-17:00 📍 Paarl Gimnasium High School
A moving symphonic afternoon with local school choirs, soloists and the Winelands Philharmonic Orchestra.
🎟 From R100 - Book here

Dancing Lipizzaners in Groot Drakenstein
📅 Fri. 22 May | Gates 17:30 | Show 18:30 📍 Groot Drakenstein Games Club
A magical evening under the lights with the South African Lipizzaners, food, drinks and family-friendly Winelands atmosphere.
🎟 Details here

Red Bull Day at The Golf Village
📅 Sat. 9 May | 10:00-14:00 📍 The Golf Village, Somerset West
Golf, music, Red Bull activations, giveaways, free boerie rolls and good vibes.
🎟 Free entry - No booking required

Live Talk with Hannele Steyn + Ride Experience
📅 Fri. 15 May & Sat. 16 May 📍 Trail’s End Bike Hotel
An inspiring dinner talk with endurance legend Hannele Steyn, plus an optional guided ride the next morning.
🎟 R350 pp - Book via email

Wine Walk at Muratie
📅 Sat. 16 May | 09:00 for 09:30 📍 Muratie Wine Estate
A scenic ±3km vineyard walk with mimosas, mountain views and wine tastings along the way.
🎟 R245 pp | Kids U18 R100 - Book here

Titan Trail Run at Cavalli
📅 Sat. 23 May | 07:30 📍 Cavalli Estate
A scenic 5km or 10km trail run through one of Stellenbosch’s most beautiful estates.
🎟 Details here

Winter Warmer Outride - Paarl
📅 Sat. 30 May | 08:00 📍 Ford Paarl
A feel-good community outride for road, gravel and MTB riders - bring something warm to donate.
🎟 Free RSVP - More here

King of Grain Workshop & Mini Seminar
📅 Sat. 30 May | 09:00-14:00 📍 Vredenhof Organic Estate
A hands-on whole grain workshop where you’ll make pizza, pasta and oat-based treats while learning simple, feel-good food skills.
🎟 R700 pp | R650 pp bring-a-friend - Book here

Sip & Slide at Leopard’s Leap
📅 Tues.-Sat. during May 📍 Leopard’s Leap Family Vineyards
A fun mini-burger and wine pairing featuring gourmet sliders matched with Leopard’s Leap Culinaria wines. Kiddies’ options available too.
🎟 R210 pp - Book here

Winemaker’s Dinner at Jordan Restaurant
📅 Fri. 8 May | 18:30 📍 Jordan Restaurant
An intimate evening of Jordan wines, bold sharing-style dishes and storytelling with Gary Jordan and chef Marthinus Ferreira.
🎟 R1250 pp - Book via email

Somm Saturdays: Uva Mira
📅 Sat. 9 May | 11:00-15:00 📍 BX Wine Bar & Shop
A complimentary tasting of elegant Uva Mira wines - relaxed, informative and very easy to turn into a full afternoon.
🎟 Complimentary tasting - No booking required

Born 2 Fire at Stellenzicht
📅 Sat. 9 May | 12:00-15:00 📍 Stellenzicht Wine Estate
Open-fire cooking, live music and Stellenzicht wines in the vineyards - the ultimate long lunch energy.
🎟 Details here

Harvest Table Dining Experience
📅 Fri. 15 May | 18:00 📍 Pink Valley Restaurant
A three-course dining experience inspired by the award-winning Harvest Table cookbook, paired with standout wines.
🎟 R715 pp - Book via mail

Nantes Estate Harvest Dinner & Dance
📅 Sat. 16 May | 18:00-00:00 📍 Nantes Estate
Celebrate harvest season with good food, live music, gourmet burgers, dessert and dancing under the lights.
🎟 R550 pp - Book here

’n Aand met Abrie Beeslaar & Bertus Basson
📅 Wed. 20 May | 18:30-22:00 📍 Eike by Bertus Basson
An exclusive five-course dinner paired with wines from Abrie Beeslaar - premium, intimate and seriously special.
🎟 R1200 pp - Book here

🌿 Stellenbosch Botanical Garden Launches New Botanical Art Exhibition
The James & Shirley Sherwood Botanical Art Collection officially opens at the SUBG Garden Gallery this week - showcasing beautiful botanical artworks celebrating indigenous plant life, art and heritage. Running until September, it’s the perfect slow Winelands wander for garden lovers, art enthusiasts and anyone needing a peaceful cultural moment.
📅 9 May - 20 Sept 📍 SUBG Garden Gallery
🎟 Details here

🎓 Stellenbosch University Hosts AI & Research Session
As part of Library Research Week 2026, Stellenbosch University is hosting a free session exploring how AI tools can be used ethically and effectively in academic research. Ideal for students, researchers and anyone curious about the future of AI in learning.
📅 Tue. 12 May | 09:00-10:00 📍 Stellenbosch University Library
🎟 Free - More here

Kids Creative Sessions
📅 Sat. 23 May | 10:00-11:30 📍 PNA, Stellenbosch Square
A fun, hands-on art session for kids aged 5-12 filled with colour, creativity and guided play. Perfect while you grab a coffee or tick off a few errands ☕
🎟 R230 - Book here

Hot Yoga Stellenbosch - May Unlimited Special
📅 1-31 May | Various times 📍 Hot Yoga Stellenbosch
Unlimited May classes across Vinyasa, Yin, Power Yoga and more - perfect for a proper winter reset.
🎟 R990 Monthly Unlimited - Details here

A classic “make the most of it while you can” kind of week!
Thursday to Saturday are looking beautiful with sunny skies and temps climbing to 21°C - perfect for wine farms, markets and long lunches outdoors. Saturday is definitely the pick of the week.

From Sunday onwards, the weather turns properly autumnal with rain and cooler temperatures settling in through early next week 🌧️

Modern Estate Living in Paradyskloof

Set in sought-after King’s View Estate, this stylish 4-bedroom home blends easy family living with beautiful mountain views and fantastic entertaining spaces. Think open-plan living, fireplaces, indoor + outdoor braai areas, a swimming pool, and plenty of natural light throughout.

There’s also an inverter, battery system and solar panels already in place - a big win for modern Winelands living.

Available from July 2026.

👉🏼 View property here

A thoughtful conversation on why so many of us feel unheard - and how better communication starts with emotional regulation, clarity, and understanding how our words are actually received. Jay unpacks the gap between intention and impact, and why connection matters more than “winning” the conversation.

Prepable Protein Fillings - Spicy Chicken Feta Crunch 🌯

❤️ If you found something useful, please share it with others

👉🏼 Got a story or feedback to share? Email Us

👀 Want to see if your company is a good fit? Join our Partner Waitlist here.

NOTE: If anything is inaccurate, please contact us and we will rectify. Never want to hear from us again? Break our hearts and unsubscribe.