While the days get shorter and the weather gets cooler, Cape Town events are still on in full swing. Read on to find out everything happening in the month of May, from wine and beer events to ballet and theatre performances.
Winelands Autumn Expo
The second annual Winelands Autumn Expo will take center-stage in the Cape Winelands District town of Worcester. Visitors will once again have the opportunity to taste, experience, and celebrate everything the Winelands has to offer, all in one splendid location.
The Winelands Autumn Expo showcases the diverse tastes of the five distinct terroirs found in the district. The Winelands cover world the world-renowned areas of Breede Valley, Drakenstein, Langeberg, Stellenbosch, and Witzenberg.
All five of these unique areas will showcase their best in the industry, as well as various options for food, drink, music, hospitality, arts and crafts, and many more. All this while keeping your little ones equally entertained at the kids’ activity area. Entrance includes one branded wineglass and one tote bag.
Cost: R160pp (weekend pass, adult) | R60pp (weekend pass, teen) | R100p (day pass, adult) | R40pp (day pass, teen). Tickets available on Webtickets.
When: 30 – 31 May 2025 | Fri: from 3pm. Sat: from 2pm
Where: Montana High School, Worcester
Wynfees
Come and enjoy the golden season in the Cape with Netwerk24 and Die Burger, in collaboration with their partner Meerendal, and a total of 21 of the Cape Winelands’ leading wine estates.
Taste delicious wines from the Western Cape’s world-famous wine regions – all under one roof on the picturesque Meerendal wine estate. Tickets include a wine glass, as well as the opportunity to taste all the exhibitors’ wines. There will also be wine for sale to enjoy on the lawn or to take home.
Coffee and a few other snacks will also be sold on the day, and lucky draws will keep the excitement high. Celebrate the Cape Winelands at this exciting festival.
Cost: R350pp. Tickets available on Quicket.
When: 24 May 2025 | 11am – 5pm
Where: Meerendal Wine Estate, Vissershok Rd, Durbanville
University of Michigan Orchestra
A stellar line-up of soloists brings additional shine to the University of Michigan Symphony Orchestra (USO), when they visit South Africa.
Under the auspices of the School of Music, Theatre & Dance, The USO serves as a training ground for gifted young musicians, many of whom go on to significant careers in major orchestras, opera houses, and chamber music ensembles.
Under the baton of Kenneth Kiesler, who has been at the helm of USO as its music director and conductor since 1995, the USO is considered one of the world’s finest student orchestras. Soloists for the tour include renowned bass-baritone and tenured Professor of Music at the University of Michigan School of Music, Theatre & Dance, Daniel A. Washington, 2025 Grammy award-winner soprano, Karen Slack and South Africa’s own star soprano, Goitsemang Lehobye.
Cost: R100 – R200pp. Tickets available on Quicket.
When: 26 and 27 May 2025 | 7.30pm
Where: City Hall, Darling St, Cape Town (26 May) | Hugo Lambrechts Auditorium, 20 Picton St, Parow (27 May)
Joseph & the Amazing Technicolour Dreamcoat
Producers Pieter Toerien and the Luitingh Alexander Musical Theatre Academy (LAMTA) are set to dazzle Cape Town audiences with a thrilling new production of Joseph and the Amazing Technicolor Dreamcoat.
The much-loved musical, created by the legendary duo Tim Rice and Andrew Lloyd Webber, is bursting with vibrant energy, dazzling choreography, and unforgettable songs. This fresh staging promises to captivate audiences of all ages like never before. A global sensation, Joseph and the Amazing Technicolor Dreamcoat has enchanted audiences for decades, with countless performances on Broadway, in the West End, and across more than 80 countries.
Leading the cast is Dylan Janse van Rensburg, known for roles in Spring Awakening and My Fair Lady, alongside powerhouse vocalist Lelo Ramasimong as the Narrator and the charismatic Chris Jaftha as Pharaoh. With a stellar cast and a fresh creative vision, this production promises an unforgettable theatrical spectacle.
Cost: R275 – R475pp. Tickets available on Webtickets.
When: 9 May – 13 July 2025 | Weekdays: 8pm | Sat: 5pm & 8pm | Sun: 2.30pm
Where: Theatre on the Bay, Link Street, Camps Bay
BeerEx Africa
BeerEx Africa is a conference and expo dedicated to the world’s most popular alcoholic beverage: beer! The two-day expo and one-day conference showcases everything to do with beer, as well as hosting beer launches and food pairings at craft breweries around Cape Town.
The week finishes off with the awards party for the African Beer Cup – the continent’s biggest beer competition.
Cost: From R125 per event, tickets available on Quicket.
When: 22 – 24 May 2025 | Thu: 6pm – late. Fri: 11am – late. Sat: 9am – late
Where: Makers Landing, V&A Waterfront
Hedda Gabler
Hedda and her successful yet uncomplicated husband, Jurg, have just returned from their honeymoon. She’s already bored with marriage, so when her former flame Lovborg arrives, she sets her life alight. Why? Because she can. In this modern adaptation of “Ibsen’s Hamlet”, Hedda shows one fat middle finger to being nice. She is horrible, and proud of it. Do not miss this exciting production.
A talented cast includes Rolanda Marais, Albert Pretorius, Martelize Kolver, Ashley de Lange, Ludwig Binge and Stian Bam, with the production being directed and translated by Christiaan Olwagen.
Cost: R150 – R250pp. Tickets available on Webtickets.
When: 1 – 10 May 2025 (Afrikaans season) | 12 – 24 May 2025 (English season) | 7.30pm | Saturday matinee at 3.30pm
Where: Baxter Theatre, Main Rd, Rondebosch
A Journey Through Taste and Terroir
A SecretEATS evening isn’t just any ordinary dinner party – it’s a social soiree bringing together the very best in food, drink and fun with friends, new and old.
As always, the evening begins with a welcome drink on arrival and some canapes to kick things off. Prepare for a little mixing and mingling before settling in around a shared dining table to meet the Secret chef.
Enjoy course after course of gourmet goodness prepared by Secret Eats’ professional, classically trained Secret chef. All you need to do is sit back, relax and enjoy your evening.
Perfectly paired wines compliment each course and, of course, help the conversation flow as guests meet, mix and mingle to create an evening of magic.
Cost: R1800pp. Tickets available on the website.
When: 24 May 2025 | 7pm – 10pm
Where: The secret venue is revealed the morning of the dinner.
Intermezzo by Cape Ballet Africa
Cape Ballet Africa presents a new programme of short works at the delightful Drama Factory. The production is a gentle and cathartic artistic offering from this recently established company fresh from their exceptional debut at the Artscape Opera House in March.
Celebrating Tchaikovsky features the composer’s most loved works for ballet including The Sleeping Beauty, Swan Lake and The Nutcracker. A selection of iconic tunes form the basis for this suite profiling the beautiful artists of Cape Ballet Africa.
Desiderata, the much – loved prose poem by writer Max Ehrmann forms the inspiration for the collection of choreographic works by South African choreographers with Marcel Meyer, celebrated South African actor, narrating the evocative and stirring text.
Cost: R280pp | R260pp (group of 4). Tickets available on the website.
When: 16 – 25 May 2025 | 7.30pm | Sun: 4pm | Sat matinee at 3pm
Where: The Drama Factory, 10 Comprop Sq, Henry Vos Close, Asla Business Park, Strand
Tanqua Kuru Bicycle Race
The Tanqua Kuru Bicycle Race returns, inviting cyclists to a unique adventure through South Africa’s Tankwa Karoo. Celebrating its fifth year, the event reintroduces the iconic traverse across “The Pan,” a vast, flat expanse that offers riders a surreal and visually stunning experience.
Participants can choose between a challenging 113 km route or a medium 59 km route on the first day, followed by a 62 km ride on the second day.
In collaboration with Sling, a select few have the chance to take aerial flips, providing a bird’s-eye view of the breathtaking landscape. Beyond the cycling, the race features unique festivities, including themed water points, premium hospitality, and the “Bicycle Burn,” ensuring an adventure that extends beyond the race itself.
Cost: R3500pp (no meals) | R7900pp (incl meals and accomodation). Tickets available on the website.
When: 23 – 25 May 2025
Where: Tankwa Tented Camp, R355, Calvinia, Northern Cape
Mini Brandy Festival
Cause | Effect and SA Brandy present the Mini Brandy Festival, offering enthusiasts the opportunity to gather and to savour the finest selection of brandies.
Attendees enjoy three freshly made cocktails and four brandy tastings of their choice. Local DJs will have a music showcase in a cosy setting, with indoor and outdoor spaces, pyramid heaters, and a fireplace for comfort.
Cost: R300pp. Tickets available via Quicket.
When: 31 May 2025 | 1pm – 8pm
Where: The Salene, Devon Valley Rd, Stellenbosch
The Good Life Show
The Good Life Show, Africa’s premium food, drink and conscious living event, is back in Cape Town with even more exciting high-quality and innovative products, experiences and surprising content. The plant-based sector is growing worldwide, and The Good Life show is a must-visit for those interested in being part of the change.
The event focuses on health, wellness and sustainability, and includes innovative products, chef and mixology demos, expert wellness advice, and more. The event brings expert advice on everything from sustainable lifestyle choices to mental health strategies, and everything in between.
Make sure to get your tickets to learn all about the health and wellness industry, and the benefits it has for you.
Cost: Day Pass – R175pp. Weekend Pass – R265pp. Children under 15 free. Book via Quicket.
When: 30 May – 1 June 2025 | Fri & Sat 10am-6pm, Sun 10am-4pm
Where: Cape Town International Convention Centre (CTICC 2), Convention Square, 1 Lower Long Street, Cape Town
All About the Good Life Show
Cape Town Opera presents AIDA
Cape Town Opera presents Verdi’s Aida with an all-African cast in a bold, Africanfuturist reimagining of this iconic opera.
Set against a backdrop of war, forbidden love and cultural conflict, Aida follows the love story of an enslaved Ethiopian princess and an Egyptian commander. Under Minnaar’s direction, this production combines video, animation and Gregory Maqoma’s choreography to bring a vivid, futuristic world to life.
With a 56-member chorus and the Cape Town Philharmonic Orchestra under Kamal Khan, this production promises to be a cultural highlight of 2025.
Cost: R190 – R980pp. Tickets available on Webtickets.
When: 23 – 31 May 2025 | 23, 27 and 29 May: 7pm | 25 and 31 May: 3pm
Where: Artscape Opera House, D.F. Malan Street, Cape Town City Centre
Visit Norval Foundation
The Norval Foundation are hosting a variety of events in May, which include art-focused events, exhibitions launches, and wellness events. These events include:
- 14 May: Exhibition Opening: They Came and Left Footprints. The return of a significant exhibition, featuring the powerful and evocative works of South African artists Lucas Sithole and Cyprian Shilakoe.
- 17 May: Yoga in the Garden. Breathe and bloom at this upcoming yoga session in the Sculpture Garden at Norval Foundation, presented by Virgin Active Steenberg.
- 18 May: Museum Day. 50% off all tickets in celebration of Museum Day.
- 31 May: Art and Sip. Visit Norval Foundation for an intimate, guided drawing experience. Tickets are limited and includes beverages, a curator-led tour and a Museum Day Pass.
When: Wed to Sat 10am to 5pm, Sun 10am to 4pm | Closed on Mon & Tues
Where: Norval Foundation, 4 Steenberg Road, Tokai
All About the Norval Foundation
Paul Slabolepszy: Bitter Winter
After making its dazzling debut in Johannesburg in February, Paul Slobolepszy’s Bitter Winter is travelling to the Golden Arrow Stage at the Baxter Theatre.
Bitter Winter offers a heartfelt exploration of the artist’s life. It celebrates the legends of South African theatre while shining a light on the new generation of rising stars making their mark on the global stage. This tender tale takes audiences along the winding, sometimes rocky road that many artists feel compelled to travel in pursuit of their dreams.
With a stellar cast including André Odendaal, Oarabile Ditsele and Chantal Stanfield, and direction by Lesedi Job, this is a theatre experience not to be missed.
Cost: R160 – R220pp. Tickets available on Webtickets.
When: 21 May – 14 June 2025 | 8pm | Saturday matinee at 3pm
Where: Golden Arrow Theatre, Baxter Theatre, Main Rd, Rondebosch
Visit Minimalist Wines
Minimalist Wines is a new boutique working cellar in Gardens and home to some of the finest, world-class Syrahs produced in the Cape. The cellar practices minimal intervention wine-making techniques in their converted factory space in the upcoming Roodehek Precinct.
Make sure to book a tour of the premises, which includes state-of-the-art facilities, and a guided tasting with new generation winemakers Sam and Henry. Enjoy a charcuterie board from the neighbouring FlourMarket (a Truth Coffee venture) as the pair share their knowledge and infectious passion for their craft, as well as the stories behind Minimalist Wines’ three exceptional cool-climate Syrahs: Stars In The Dark, Connect The Dots and No Place Like Home.
Cost: Tours at R350p. Slots can be booked on Dineplan.
When: Monday – Saturday | 11am – 4pm
Where: Corner Roodehek Street and Hope Street, Gardens, Cape Town
A Seat at the Craft Table
A Seat at the Craft Table is all about celebrating makers — whether you’re a seasoned pro, making just for the fun of it, or dreaming of turning your passion project into something more.
Bring your current project and spend the day stitching, sketching or weaving, while listening to inspiring talks from some of Cape Town’s most creative minds and entrepreneurs. Between sessions, swap ideas with other crafters or get involved with one of the demonstrations, that include quilting and working with a knitting machine.
Some of the featured speakers include Danielle Clough aka Fiancé Knowles, Leila Badsha of Fabricate and Shalain Gregson of Turkey Dimple.
Cost: R220pp. Tickets available on Quicket.
When: 31 May 2025 | 10am – 2pm
Where: Vine and Dandy, Park Road, Gardens
Evil Comedy
After taking Cape Town by storm with a string of sold-out shows that left audiences roaring with laughter, Evil Comedy is back. This comedy showcase is set to deliver another unforgettable night of edgy, unfiltered humour and pure comic brilliance.
Headlining the night is Lazola Gola, and special guest Khanyisile Ngwenya, two of South Africa’s sharpest comedic voices known for their razor-sharp wit, fearless storytelling, and commanding stage presence.
They’re joined by an equally impressive lineup of rising stars and underground gems: Callum Hitchcock, Sarah Abraham, and Roland du Preez, all bringing their unique comedic flair to the stage.
Cost: R150pp, book via Quicket
When: Wednesday, 28 May 2025 | doors open 6.30pm | show starts 8pm
Where: District, 61c Harrington Street, Cape Town
