Don’t let the winter blues keep you inside this month! Check out our pics of the best events happening in the month of June in Cape Town, from music and comedy events to design and tech expos.

Jive Cape Town Funny Festival

The Jive Cape Town Funny Festival, South Africa’s oldest and most iconic comedy extravaganza, is back and bigger than ever. This celebrated festival brings together the finest local stand-up comedians and a dazzling lineup of international variety acts for an unforgettable month of non-stop entertainment.

Dalin Oliver and Alan Committee are acting as MCs for the event, and featured comedians include The Big Boys (SA), Charlie Caper (Sweden), Emo & Loukmaan Adams & Terry Fortune (SA), Kagiso Mokgadi (SA), Robby Collins (SA), and Baccala Clown (Italy).

Warm up with some laughs this winter and celebrate the local comedy scene.

Cost: R170 – R250 per show. Tickets available on Webtickets.

When: 2 – 29 June 2025
Where: Pam Golding Theatre, Baxter Theatre, Main Rd, Rondebosch

Rondomtalie / Marry-Go-Round

Fresh off its debut at Suidoosterfees earlier this year, Rondomtalie / Marry-Go-Round is lauded as one of the freshest most exciting comedies to hit the scene. Now, it’s back for a run of shows around Cape Town.

Relationship therapist, Mahesh Maharaj, is the best in the business. With his “alternative” methods, he is able to get any relationship back on track. Can Mahesh help Olivia and Alan save their 12-year marriage after Olivia caught Alan on the kitchen table with another woman? Here they are, in the third of six sessions, talking about their feelings with hilarious, yet very sincere consequences.

The couple is masterfully portrayed by Margit Meyer-Rödenbeck and Deon Lotz. Gary Naidoo is the relationship therapist, the glue that keeps this entire fragile, albeit hilarious affair together.

Cost: R160 – R280pp

When: 10 & 11 June (Die Boer, Durbanville) | 12 June (The Drama Factory, Strand) | 13 June (Die Koelkamers, Paternoster) | 8.30pm (10 & 11 June) | 7pm (12 & 13 June)
Where: Die Boer, Durbanville | The Drama Factory, Strand | Die Koelkamers, Paternoster

The Trophy Wine Show

The Trophy Wine Show once again welcomes wine-lovers to the single-night 2025 Public Tastings. Wine lovers can find no less than 150 wines of distinction – silver, gold and trophy winners, all on show for toasting, tasting and deliberating, as well as for purchase through specialist wine retailer, Port2Port.

Highlights are always the Best White and Best Red Wines of Show, the International Judges’ trophy winner, Discovery of the Show (best value wine) and Best Premium Wine with the medalists of the Most Successful Producer claiming the limelight.

In addition to the host of category winners, museum class vintages (at least four years old for white wines, eight years for red and sparkling) are also available for tasting. Patrons can enjoy the new releases from many favourites, but can also expect to meet some lesser-known cellars.

Cost: R220 – R275pp. Tickets available on Webtickets.

When: 10 June 2025 | 5pm – 9pm
Where: CTICC, cnr. Heerengracht & Rua Bartholomeu Dias, Foreshore, Cape Town

Comedy at Canvas

Get ready for a night of top-tier comedy at Comedy at Canvas! Some of South Africa’s best comedians are bringing you a killer lineup, with big laughs, sharp wit, and the kind of belly-aching comedy that makes you forget your problems—at least for the night!

Hosted by Mel Jones and featuring comedians Callum Hitchcock, Celine Tshika, Chuma Bentele and Nathan Levinrad, as well as headliner Ambrose Uren, enjoy a night of unique comedy and supporting local talents. Bring your own drinks and enjoy a fun night out!

Cost: R150 – R200pp. Tickets available on Quicket.

When: 12 June 2025 | 6.30pm – 9.30pm
Where: Brickfield Canvas, 35 Brickfield Road, Salt River, Cape Town

Philharmonia: Mozart and Haydn Masses

Fresh from their sold-out Messiah concerts and a showstopping performance with Andrea Bocelli on his international tour, the Philharmonia Choir of Cape Town returns with a spectacular new offering: two magnificent choral masses that promise to stir the soul.

This unmissable concert features Mozart’s jubilant Coronation Mass (Mass in C) and Haydn’s thrilling and emotionally charged Nelson Mass – a powerful pairing of classical brilliance.

Taking the podium is the acclaimed maestro Daniel Boico, leading the Philharmonia Choir alongside their renowned partners, the Cape Town Philharmonic Orchestra. Adding further excitement to the evening are four extraordinary soloists: soprano Brittany Smith, alto Jacobi de Villiers, tenor Lukhanyo Moyake, and bass Conroy Scott.

Cost: from R175pp. Tickets available on Quicket.

When: 21 June 2025 | 7.30pm – 10pm
Where: City Hall, 56 Darling Street, Cape Town

Franschhoek Mystery Weekend

The thrill of a mystery weekend in Franschhoek promises the ultimate escape – brimming with surprises and blissfully stress-free. A highlight of the winter Winelands calendar, these highly anticipated weekends provide guests with a seamless getaway, eliminating the stress of planning while showcasing the finest experiences Franschhoek has to offer.

Designed for those seeking an immersive and carefree retreat, the Franschhoek Mystery Weekends deliver a meticulously curated itinerary featuring luxurious accommodation, award-winning wines, gourmet dining, and bespoke activities – all kept a surprise until arrival.

Each weekend begins with a VIP check-in event, where participants are welcomed with a glass of wine before receiving a Mystery Weekend box, unveiling their unique itinerary. Set against the charming winter ambiance of Franschhoek, guests will enjoy the warmth of roaring fires and the warm, welcoming charm of the region.

Cost: R9500 per couple per weekend. Bookings can be made via email ([email protected])

When: 27 – 29 June 2025
Where: Various venues around Franschhoek

Sentech Africa Tech Week

Discover the future of innovation, network with industry leaders, and explore the latest trends shaping Africa’s tech landscape at Sentech Africa Tech Week. During this two-day expo, visitors can learn firsthand how to leverage technological change in order to gain a competitive edge and make a business relevant in an age of exponential disruption.

These tools and more are delivered by an unmissable line-up of top local and international speakers representing some of the world’s most influential companies including Microsoft, Google and TikTok. The expo features everything from a start-up pitching battle, to tech problem-solving workshops, exponential networking opportunities, and various eye-opening exhibitions.

Cost: R5 500pp (Delegate Pass) | R19 800 (VVIP Pass). Tickets available on the website.

When: 3 & 4 June 2025
Where: Century City Conference Centre, 4 Energy Ln, Century City, Cape Town

Encounters Documentary Festival

The Encounters South African International Documentary Festival is the country’s formative documentary event, screening both contemporary South African and International features and short documentaries.

The festival brings documentary-lovers a selection of over 50 diverse films available to watch at select cinemas in Johannesburg and Cape Town. The films fall under various categories, including feature documentaries and short documentaries from international and African filmmakers. Each film offers a unique look into a specific and unique pocket of the world.

There are a number of diverse films screening at the festival that are not to be missed, as well as live Q&As, Panel Discussions and Industry Events with acclaimed and emerging filmmakers discussing their latest films.

The full lineup of films on show can be seen on the website.

Cost: Varies depending on venue.

When: 19 – 29 June 2025
Where: Labia Theatre, 68 Orange St, Gardens, Cape Town | V&A Ster-Kinekor, V&A Waterfront, Dock Road, Cape Town

Tulbagh Christmas In Winter

Tulbagh turns into a magical winter wonderland for its annual Christmas in Winter festival – a weekend packed with festive fun, twinkling lights, and seasonal cheer.

The whole town comes alive with Christmas décor, live music, and family-friendly activities like pony rides, crafts, and tractor trips. Adventurers can explore Tulbagh’s scenic beauty on horseback or foot.

Savor the season with wine tastings, cellar tours, and hearty Christmas meals by a crackling fire. Don’t miss the dazzling Electric Light Parade on Friday night and the soulful sounds of the Winterland Blues Festival all weekend long.

Cost: R100 – R250 per day. Tickets available on the website.

When: 27 – 29 June 2025
Where: Church Street, Tulbagh

Crossed Wires Sensory Painting Workshop

Crossed Wires is a sensory painting workshop grounded in the concept of cross-modal perception — the natural, and often involuntary, way our senses blend and speak to each other.

Through a series of guided exercises – tasting wine, listening to music, feeling texture – attendees can explore the hidden links between sensation, memory, and emotion. There is then a chance to paint what you feel, perhaps what you remember, translating those inner responses into colour, form, and texture.

Cost: R350pp. Tickets available on Quicket.

When: 14 June 2025 | 2pm – 4pm
Where: LUMI Women’s Co-Working & Art Gallery, Shop 2, Village Gate, 7872 Main Rd, Hout Bay, Cape Town

Silver Mountain Music

The Silver Mountain Music festival is a yearly celebration of music and culture. ​The festival brings together some of South Africa’s most prominent musicians to this secretive valley, in the Overberg region in the Western Cape.

The tenth edition of the festival is a showcase of a dynamic fusion of music and culture inspired by the beauty and diversity of our planet Earth. Experience live performances from renowned artists, interactive workshops, and educational talks.

Some of the featured performers at this year’s festival include The Charl du Plessis Trio, percussionist Peter Auret, bass player Werner Spies, soloist Tim Moloi and the Zolani Youth Choir, among others.

Cost: R2000pp (full festival pass) | R50 – R380 per event. Tickets available on Quicket.

When: 13 – 16 June 2025
Where: Various venues in the Grootvadersbosch Valley

Willowbridge Father’s Day Markets

Celebrate Dad this Father’s Day with artisanal gifts and dad-approved treats, all available at the Willowbridge Market. Held over two weekends, this is the perfect place to catch up on some shopping and treat Dad.

The Willowbridge Slow Market are held on certain weekends throughout the year, and each market has a different exciting theme to celebrate. Bring the family together and spend a day browsing all that Willowbridge has to offer.

When: 7 – 8 and 14 – 15 June 2025
Where: Wilowbridge Shopping Centre, 39 Carl Cronje Dr, Tyger Valley

Decorex

Decorex showcases more than 230 of the most dynamic and creative companies on the African continent, and provides a unique opportunity for industry professionals and design enthusiasts to explore the latest trends and innovations in the world of interior design and decoration.

This much-anticipated annual exhibition showcases hundreds of dynamic brands alongside themed exhibitions, exciting collaborations, product launches, insightful talks and workshops led by industry experts. More than an event, Decorex is a celebration of innovation – and a move towards a better future, in which both the industry and consumers use the power of design to redefine the way we live, and create a better life for people and planet alike.

Cost: R150 per adult online | R160 per adult at the door | Children under 12 free | R50 per child age 12 – 16. Tickets available online.

When: 5 – 8 June 2025 | 10am – 6pm
Where: CTICC, Convention Square, 1 Lower Long Street, Cape Town

Vergelegen Crossover Music Concert

Vergelegen Wine Estate’s glass conservatory will be the elegant venue for an unforgettable evening of fine music, with a performance of the Charl du Plessis Trio’s latest production, Bach & Beatles.

The Charl du Plessis Trio comprises pianist Charl du Plessis, bassist Werner Spies and drummer Peter Auret. The Trio was formed in 2006 to promote crossover and jazz music, fuelled by musical chemistry and an understanding of each others’ musical personalities. Blending classical, jazz, and pop music, the Trio have earned international acclaim and multiple awards for their innovative performances.

Bach & Beatles will present interpretations of Beatles hits such as Yesterday, Hey Jude, and A Hard Day’s Night, alongside timeless works by Johann Sebastian Bach, including the Toccata in D minor, Air on the G String, and Jesu, Joy of Man’s Desiring.

Cost: R695 per person (includes a glass of Vergelegen wine, canapés on arrival and the show). Tickets can be booked online.

When: 12 June 2025 | 6pm – 8pm
Where: The Glass Conservatory at Vergelegen, Lourensford Road, Somerset West

Shakatak Live at Grandwest

Get ready for an unforgettable evening with Shakatak, as the legendary UK jazz-funk band takes the stage at the Grand Arena.

Known for their signature smooth melodies, Shakatak has captivated audiences worldwide with their fusion of jazz, funk, and pop. Expect live renditions of timeless classics such as ‘Night Birds’, ‘Down on the Street’, and ‘Easier Said Than Done’, alongside surprises from their extensive catalog. Make sure not to miss out on this evening of funky tunes and smooth rhythms.

Cost: R250 – R495pp. Tickets available on Ticketmaster.

When: 28 June 2025 | 8pm
Where: Grandwest Arena, 1 Jakes Gerwel Dr, Acacia Park, Cape Town

Hermanus Fynarts Festival

Celebrate the beauty and culture of Hermanus at the Fynarts Festival – an exuberant celebration of creativity in all its forms, from visual, musical and literary, to culinary and performance.

Enjoy a 10-day schedule packed full of delightful events, from theatre and live music in every genre to art exhibitions, talks, workshops, and food and wine experiences. See all that Hermanus has to offer in this cultural exploration.

Cost: R80 – R700 (event dependent). Tickets can be booked on Webtickets.

When: 6 – 16 June 2025
Where: Various venues around Hermanus

Open Book Festival: Workshop Week

Open Book Festival’s Workshop Week is an extensive lineup of workshops and master classes designed to help writers of all levels hone their craft and develop the skills needed to succeed in today’s competitive literary landscape.

Workshop Week offerings cover a wide range of genres and topics, providing unique opportunities for writers to learn from celebrated authors, editors, agents and industry professionals.

The workshops focus on key areas such as fiction writing, poetry, screenwriting, and marketing. In addition to workshops, the festival features invaluable master classes led by bestselling authors and literary stars. These intimate, in-depth sessions allow writers to receive constructive feedback on their works-in-progress.

Cost: R80 – R200 per event. Tickets available on the website.

When: 2 – 7 June 2025
Where: Bertha House, 67-69 Main Rd, Mowbray, Cape Town

Cape Town Philharmonic Winter Symphonies

The Cape Town Philharmonic Winter Symphonies concert series consists of three concerts: two of which are conducted by Thomas Sanderling, and the last one by Jeremy Silver.

The 12 June symphony, conducted by Sanderling, is of works by Brahms, with the stunning violinist Andrey Baranov as the soloist in the Violin Concerto. The main work is the Symphony No. 4. Baranov is the winner of the Queen Elisabeth Violin Competition of 2012, the Benjamin Britten and Henri Marteau International Violin Competitions, and a prizewinner of more than twenty other international competitions.

The 19 June symphony, conducted by Sanderling, features two of South Africa’s foremost pianists, Megan-Geoffrey Prins and Tinus Botha, in the Concerto for Two Pianos by Mozart. The concert opens with the overture to Der Entfuehrung aus dem Serail by Mozart and concludes with Beethoven Symphony No 7.

Finally, the 26 June symphony, conducted by Silver, is a concert version of Il Trovatore, Verdi’s masterpiece, with Opera UCT, the CPO Afri-Arts Choir and soloists Nontobeko Bhengu (Leonora) Mkhanyiseli Dyantyi (Manrico), Bongiwe Nakani Mcetywa (Azucena), Theo Magongoma (Conte di Luna) and Monde Masimini (Ferrando).

Cost: R175 – R400 per performance. Tickets available on Webtickets.

When: 12 June, 19 June and 26 June 2025 | 7.30pm
Where: Cape Town City Hall, Darling St, Cape Town

Artscape Youth Jazz Series

First launched in 2003, the Artscape Youth Jazz Series celebrates young jazz musicians and school ensembles by giving them a space to perform and learn the craft of jazz.

The project includes Masterclass programmes where the young musicians will learn from those experienced in the industry, and then they will take to the stage across two days. The first day spotlights the amazing young jazz soloists in the programme, while the second day gives school jazz bands a chance to perform.

Cost: R50 – R90. Tickets available on Webtickets.

When: 13 and 14 June 2025 | 13th: 7pm | 14th: 5pm
Where: Artscape Theatre, DF Malan Street, Foreshore, Cape Town

Sushiya Sushi Masterclass

Time Out Market will play host to a hands-on sushi collaboration, as head chef Ryan Reyes is joined by Sushiya founding partners Tempelhoff and Takagi for a sushi-making masterclass. The evening will include an opportunity to make sushi alongside the chefs and later enjoy a six-piece platter prepared by the trio, paired with Fukumitsuya Junmai Sake.

A sushi and Junmai sake special will be running for the day and will include an omakase platter prepared by Tempelhoff, Takagi and Reyes.

Cost: R450 including DIY sushi, 6-piece omakase platter and sake

When: 12 June 2025 | 6.30pm
Where: Time Out Market, V&A Waterfront, Cape Town