🤫 What Locals Are Booking Right Now

Good Morning, Insiders! ☕️

Hope you had a brilliant Youth Day and long weekend, and if you managed to sneak in a trail run, a slow lunch or an extra glass of something red, even better.

Now, back to it - because this week is properly chokka.

Winter Solstice lands on Friday, and the Winelands is leaning all the way in: Joshua na die Reën is doing a solo show at Drostdy Teater that will sell out before you remember to book. There's lavender picking at De Meye for anyone who's been promising themselves a slower afternoon. A Sinatra tribute in a wine cellar in Somerset West. And a Waterford + Remhoogte masterclass for anyone serious about understanding what makes Stellenbosch wine so special.

One more thing worth your attention: Ken Forrester Wines has just launched The Bookshelf - a monthly literary evening bringing together books, wine and good conversation on the last Thursday of every month. The kind of evening we could all use more of 📚

On Father's Day: last week's issue had the full guide - head back there if you still need a table for Sunday. A few spots remain.

Here’s what we’ve got for you today 👇

TOGETHER WITH MONKSCOWL ESTATE

THE HIDDEN GEM ON STELLENBOSCH'S MOST CELEBRATED ROAD

Thousands of wine lovers travel Annandale Road every year - and most of them drive straight past Monkscowl Estate without ever knowing it's there. Tucked quietly among the vines, just metres from Rust en Vrede, this intimate vineyard retreat is one of the Winelands' best-kept secrets.

The estate's star is the Owl Cottage - a private luxury haven with heated pool, hot tub and a fireplace, dressed in rich Moroccan-inspired interiors that feel utterly unexpected in Stellenbosch. Guests call it "a little slice of heaven." We'd have to agree.

With the Helderberg mountains as your backdrop and world-class wine estates on your doorstep, this is the Winelands winter escape you didn't know you needed.

Beyond accommodation, Monkscowl Estate is also available for intimate business events, strategy days, workshops and executive retreats in a peaceful vineyard setting.

Centre Stage - From Broadway to the West End
📅 Tonight (18 Jun) | 18:30-20:30 📍 Franschhoek Theatre, Franschhoek
Jannie Moolman and Riaan Hunter perform beloved songs from Broadway and the West End, including classics from Les Misérables, Phantom of the Opera and more.
🎟 From R280 - Info here

Open Call: Life is a Dream - La Motte Ateljee
📅 Submissions Close Fri. 20 Jun 📍 La Motte Ateljee, Franschhoek
Local artists are invited to submit original A3 works on paper exploring the theme Life is a Dream, with selected pieces featured in a future exhibition.
🎟 Full details here

Joshua na die Reën - Winterfees Solo Show
📅 Mon. 22 Jun | 17:00-21:00 📍 Drostdy Teater, Stellenbosch
An intimate winter evening with one of Afrikaans music's most loved singer-songwriters, featuring stories, songs and a fireside atmosphere.
🎟 Book here

Stellenbosch International Chamber Music Festival 2026
📅 3-12 Jul 📍 Endler Hall, Stellenbosch University
One of South Africa's premier classical music festivals returns with ten days of concerts, masterclasses, world premieres and exceptional local and international talent.
🎟 From R185 - Details here

Gallery of Hope at Doran Vineyards
📅 Sat. 4 Jul | 14:00-20:00 📍 Doran Vineyards
A winter afternoon of local art, wine tasting and vineyard views, all in support of a meaningful community initiative.
🎟 R130 pp - More info here

Swazi Made-Ins Exclusive Pop-Up
📅 Sat. 20 Jun | 09:00-12:00 📍 Avontuur Wine Estate Padel Courts, Somerset West
Browse 124 handcrafted pieces from Eswatini, including baskets, home décor and artisan treasures, while enjoying a complimentary glass of wine.
🎟 Free entry - More here

De Meye Lavender Picking
📅 Thu.-Sun. (ongoing) | 10:00-17:00 📍 De Meye Wine Estate, Stellenbosch
Pick fresh lavender, enjoy a glass of wine and spend a slow afternoon in the Winelands countryside. Bring your own basket and shears.
🎟 R120 pp - 📧 E-mail to book

Delheim Mushroom Forage 2026
📅 Fri. 3 & Sat. 4 Jul | 10:00-13:30 📍 Delheim Wine Estate, Stellenbosch
Join expert guide Gary Goldman for a hands-on mushroom foraging adventure through Delheim's mountain forests, home to more than 20 wild mushroom species.
🎟 R550 pp - Book here

The Elite Singles: Speed Dating Social
📅 Fri. 19 Jun | 18:00–22:00 📍 LEO Sky Farm, Paarl
A stylish evening for singles aged 25+ featuring structured speed-dating rounds, sunset drinks, great wine and the chance to make genuine connections in a relaxed setting.
🎟 From R200 - Info here

Silent Retreat Weekend - Winter Solstice
📅 Fri. 19-Sun. 21 Jun | 2 day retreat 📍 Mont Fleur Conference Venue, Stellenbosch
A restorative Winter Solstice retreat featuring yoga, meditation, sound healing, nature immersion and sacred ceremony, centred around the theme From Darkness to Light.
🎟 More info here

Norsemen Midwinter Night Run
📅 Wed. 24 Jun 📍 Casa Cerveza Courtyard, Dorp Street, Stellenbosch
Choose between a 8km social night run or a 5km night walk through Stellenbosch, finishing with food, drinks and a fire at Casa Cerveza.
🎟 Book here

Vitality Diamond Challenge 2026
📅 Sat. 27 Jun | 07:00-17:00 📍 FitLife Wellington
Five workouts, four divisions and a full day of competition for athletes looking to test their fitness.
🎟 R250 per athlete - Book here

Cellar Series: Mature Wines & Terroir Through Time
📅 Fri. 19 Jun | Arrival 18:00 for 18:30 📍 Vrymansfontein, Paarl
A guided tasting of five mature wines spanning four decades, hosted by South Africa's Best Sommelier, Armand Ridgard.
🎟 R950 pp - Info here

Scales: The Tipping Point & Fyre Dining
📅 Thu. 25 Jun | 18:45 Screening | 19:45 Dining 📍 Olijvenkraal Olive & Wine Farm, Paarl
An award-winning conservation documentary followed by an open-fire dining experience under the stars.
🎟 Limited seats - 📧 E-mail to book

Waterford Estate & Remhoogte Masterclass Experience
📅 Fri. 26 Jun | 18:00 📍 Waterford Estate, Stellenbosch
A three-course dinner and wine masterclass exploring two acclaimed Stellenbosch estates and their contrasting styles.
🎟 R1,600 pp - Book here

JC Fridays: Bubbles & Beats
📅 Fri. 26 Jun | 13:00-20:00 📍 The House of JC Le Roux, Stellenbosch
Sparkling wine, live DJs and a lively social atmosphere to ease into the weekend.
🎟 R295 pp - More here

Sinatra in the Cellar at Lourensford
📅 Sat. 27 Jun | 18:30 📍 Lourensford Wine Estate, Somerset West
An intimate acoustic tribute to Frank Sinatra in the estate's atmospheric wine cellar.
🎟 R250 pp - Book here

Babylonstoren Winter Harvest Table
📅 Sat. 27 Jun | 17:30-22:30 📍 Babylonstoren, Simondium
A seasonal long-table dinner celebrating the winter harvest, served in a secret farm setting with Babylonstoren's signature farm-to-table approach.
🎟 Details here

Brandy Festival 2026
📅 Sat. 4 Jul | 14:00-21:00 📍 The Salene, Stellenbosch
South Africa's leading brandy producers come together for tastings, cocktails, live music and food.
🎟 From R300 - Book here

🎶 Toyota Stellenbosch Woordfees Tickets on Sale Today. The 2026 programme is live and tickets open to the public this morning. Nine days of theatre, music, comedy, literature, visual arts and family entertainment in October. Get in before the headline shows disappear.

🧬 Innovator Spotlight: Prof Marinda Viljoen-Bloom. A Stellenbosch University microbiologist and co-founder of Urobo Biotech is using genetically modified yeast to tackle climate change, pollution and resource scarcity. In 2025, her team became the first South African entrants to reach the Hult Prize Global Accelerator finals - finishing among the top teams from 188,000+ entrants across 130 countries. Innovation isn't only happening in Silicon Valley.

🚜 Agri-Tech Practical Showcase at De Meye. Wed. 24 June | 08:30-13:00 📍 De Meye Wine Estate, Stellenbosch | 🎟 Free (Booking Essential). Live demonstrations from Adagin Technologies (precision farming) and WorkLight Solutions (farm admin and productivity). Aimed at farmers, farm managers, HR and financial decision-makers.

💬 WhatsApp for Business Mini Workshop. Tonight (18 June) 16:30 for 17:00-19:00 📍 SU LaunchLab, Stellenbosch | 🎟 Free. Brendan Pretorius of Green Pages runs a hands-on session on using WhatsApp to engage customers, automate communication and drive growth. 70 spots only. If you're a small business owner still using WhatsApp just for basic messaging - this could be game changing.

❤️ Safety Parent Information Session
📅 Tue. 23 Jun | 18:00 📍 ACVV Stellenbosch, 172 Merriman Avenue, Stellenbosch
Learn more about the Safety Parent volunteer programme and how you can help provide a safe, supportive space for children in the community. The session covers what's involved, the support available and how to get started.
🎟 Free to attend | 📧 E-mail here

🎨 Remembering Portchie (23 Nov 1963 - 12 June 2026). The Winelands, and South Africa, lost one of its most beloved artists this week. Portchie filled homes, galleries and hearts with colour and optimism for decades. His kindness was as recognisable as his canvases.

"Fietsry is soos die lewe - hoe harder jy trap hoe meer kry jy daar uit."

Rus in vrede, Portchie 🕊️🎨

Somerset Mall Ice Rink Experience
📅 24 Jun-19 Jul 📍 Somerset Mall, Entrance 4, Somerset West
The Helderberg's first-ever ice rink arrives just in time for the school holidays, with daily skating sessions suitable for all ages.
🎟 R100 per 50-minute session (including skate hire) - Book here

Kids Clay Sculpting Workshop
📅 Mon. 29 Jun | 09:30-11:30 📍 PNA Stellenbosch Square
A creative, screen-free morning of clay sculpting with Juffrou Kuns, with each child taking home their own handmade masterpiece.
🎟 R230 per child - More here

Junior Golf Holiday Programme
📅 29-30 Jun & 1 Jul | 09:00-11:00 📍 The Golf Village, Somerset West
Three mornings of golf coaching, skills challenges and games for junior golfers of all levels. Snacks and refreshments included.
🎟 R250 per day | R600 for all three days | 📧 Email

The Big Easy Burger at Ernie Els Wines
📍 Ernie Els Wines, Helderberg
A gourmet dry-aged beef burger served with triple-cooked chips and a glass of Big Easy wine. Available daily for lunch.
🎟 R285 - More here

Father's Day at BOA Beauty Bar
📍 BOA Beauty Bar, Winelands Square
Treat Dad to a King Mani & Pedi featuring exfoliation, massage and grooming treatment. Offer ends 21 June.
🎟 R330 - Info

Winter is taking a week off. Expect sunshine and mild temps right through the weekend, with highs climbing to a balmy 27°C on Saturday. Father's Day looks just as good, with sunny skies and 26°C. Conditions stay pleasant into Monday before cooler weather arrives from Tuesday, with showers currently forecast for Wednesday.

Completely Renovated Showstopper in Schonenberg | Somerset West

Set in the ever-popular Schonenberg Estate, this five-bedroom, five-bathroom home has been renovated from top to bottom - and the result is genuinely impressive. Think double-volume living spaces, engineered timber flooring, a kitchen built for serious entertaining and an indoor braai room that opens straight out to the pool. There's even a sauna. In winter. Just saying.

If you've been looking for a move-in-ready home in a secure Somerset West estate that ticks every box without compromise, this is the one worth a look.

🔗 Take a peak

Father's Day is a good excuse to check in - not just on Dad, but on the dads, brothers, mates and men in your life who might be quietly carrying more than they're letting on. Men are still significantly less likely to seek help for their mental health than women. Sometimes the most valuable thing you can do is just ask twice. Once gets a "I'm fine." Twice sometimes gets the truth. 💙

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