[category]
[title]
Goodbye May, hello winter! As we wrap up the final weekend of the month, it doesn’t mean the Mother City is slowing down one bit.
This weekend is a big one for Cape Town’s food, beverage, and wellness scene, with the Good Life Show taking place at the CTICC from Friday to Sunday. The Time Out team will be there too, so be sure to pop by and say hello – we’ve got all the details you need right here.
The CBD is also offering the perfect excuse to take some time out (wink, wink), step away from the screens, and enjoy some food, live music, and fresh air. And with sunny 20°C weather on the forecast, conditions are looking ideal.
There’s also something in store for makeup lovers, music fans, and fashion enthusiasts, making it a fittingly high-energy end to May.
We’ve rounded up some of the best winter activities in and around Cape Town, as well as budget-friendly getaway ideas if you’re planning a weekend road trip.
CBD
Inner City Street Feast
- Friday, 29 May | 11:30am – 2:30pm
- Location: Thibault Square, Cape Town City Centre
- Cost: Free
Arguably, it doesn’t get more Cape Town than this! Step away from the hustle and bustle of corporate life and enjoy a laid-back lunch with great food, live music, fresh air, and a moment of intentional connection. Expect burgers, wings, and pizzas, with vegan and vegetarian options available too.
Social Link-Up: DayTime Groove
- Sunday, 31 May | 1pm
- Location: Rooftop On Bree, 170 Bree St, Cape Town City Centre
- Cost: From R100 via Quicket
From day to night, this curated social space brings together music, connection, and atmosphere. Enjoy live DJ sets, great food, and a relaxed shisha lounge, all set against the iconic backdrop of Table Mountain.
The Good Life Show
- Friday, 29 – Sunday 31 May | 10am
- Location: Cape Town International Convention Centre 2, Corner of Heerengracht & Rua Bartholomeu Dias, Heerengracht St, Foreshore
- Cost: From R50 via Quicket
If your idea of a good weekend involves next-level food, wellness trends, free samples, and chef demos, this is a must-see event. Now in its sixth edition, visitors will have access to 90+ expert talks, interactive experiences, chef demos, health & wellness sessions, and more than 250 exhibitors, each of whom will showcase an array of products unique to Africa.
Cape Town's Original Sundaze Party
- Sunday, 31 May | 12pm
- Location: Hotel Sky, 9 Lower Long St, Foreshore
- Cost: From R200 via Quicket
Good Hope FM is saying goodbye to the Sunday scaries with its first-ever Cape Town’s Original Sundaze event. Expect a laid-back, no-pressure, feel-good evening soundtracked by some of Good Hope FM’s finest talent, including Kyeezi, DJ Dr Jules, DJ Eazy, and DJ Masoodah. For a behind-the-scenes look at the world of radio, Sunday hosts Irma G, Peadon Smith, The Humble LV, and Sonic6Teen will also be broadcasting their shows live from the venue.
ATLANTIC SEABOARD
Winter Wine Series
- Saturday, 30 May | 1pm – 5pm
- Location: Time Out Market Cape Town, The Old Power Station, Dock Rd, Victoria & Alfred Waterfront
- Cost: R250 via the Time Out Market Cape Town App
Hosted once a month at Time Out Market Cape Town, this series celebrates the very best of South Africa’s wine culture, paired with live music and a cosy atmosphere. Each ticket includes a glass and 10 tokens. If you’re planning to grab a bite afterwards, these are the best plates at the market.
Mojo XXL Music Nights Ft. Ross Learmonth
- Friday, 29 May | 7pm
- Location: Mojo Market, 30 Regent Rd, Sea Point
- Cost: Free entry
Former Ross Learmonth frontman Ross Learmonth returns to the Mojo stage for a live set, two years after his first performance at the market.
SOUTHERN SUBURBS
Me&B warehouse sale
- Thursday 28 – Saturday, 30 May | 9am
- Location: 2nd Floor, The Palms, 145 Sir Lowry Rd, Woodstock
- Cost: Free entry
If you’ve been wanting to get your hands on some Me&B items without your heart skipping a beat every time your bank balance updates, this is your chance.
Keanan Eksteen Duo Show
- Friday, 29 May | 6:30pm
- Location: The Commons, surfers corner, Beach Rd, Muizenberg
- Cost: From R150 via Fixr
Making his debut at the venue, Keanan Eksteen will take the stage at The Commons alongside ADV. Expect a mix of original music and a few familiar covers woven into the set.
The Jive Cape Town Funny Festival
- Thursday 28 – Saturday, 30 May | 4pm, 8pm
- Location: The Baxter Theatre, Main Rd, Rondebosch
- Cost: From R190 via Webtickets
If there’s one thing about South Africans, it’s our ability to turn even the most serious situations into something to laugh about. And if you’re in the mood for a good laugh, the country’s oldest and largest comedy festival is back, funnier than ever, as it celebrates its 27th year at the Baxter Theatre from 28 May to 21 June.
NORTHERN SUBURBS
Winter Night Market on Intaka Island
- Friday, 29 May | 4pm – 9pm
- Location: Intaka Island, Grand Central Precintp, 2 Park Ln, Century City
- Cost: Free
If your perfect Friday evening means soaking up nature, enjoying delicious street food, browsing locally made crafts, and listening to live music from talented local artists, then this northern suburbs market is the perfect outing for the whole family.
The Matte Affair NARS Masterclass
- Saturday, 30 May | 11am, 3pm
- Location: Woolworths Tyger Valley, Tygervalley Shopping Centre Carl Cronje Drive, Bill Bezuidenhout Ave, Bellville Park
- Cost: From R350 via Quicket
Calling all beauty lovers and enthusiasts! Join expert makeup artists for an immersive masterclass on creating a soft, natural matte complexion that lasts, featuring the new NARS Natural Matte Longwear Foundation. Best of all, your ticket is fully redeemable toward any NARS purchase on the day. Small bites and refreshments will be served.
CAPE FLATS
Mr Gold Coast Continental and Miss South Africa Continental 2026 Preliminary Pageant
- Saturday, 30 May | 6pm
- Location: Joseph Stone Auditorium, Protea St & Klipfontein Rd, Athlone
- Cost: From R200 via Quicket
The search is on for the King who will represent the Gold Coast family and the Queen who will represent South Africa at Miss Continental 2026 in Chicago, Illinois.
WINELANDS
South African Lipizzaners Extravaganza
- Saturday, 30 May | 11:30am
- Location: Stellenbosch District Riding Club, Stellenbosch NU, Stellenbosch
- Cost: From R50 via Quicket
Elegance and precision are critical to the world-renowned Lipizzaner stallions, which ‘dance’ to music through beautifully trained routines and remarkable movements once used on the battlefield. From graceful formations to breathtaking displays of skill, they offer a unique outing unlike anything else.
LGBT Social Networking
- Sunday, 31 May | 2pm
- Location: Thirsty Scarecrow, Mooiberge Farm, R44, Annandale Rd, Stellenbosch
- Cost: From R75 via Quicket
"Run by LGBT for LGBT", and in commemoration of the International Day Against Homophobia, Biphobia and Transphobia (IDAHOBIT) on 17 May, the event offers a welcoming, safe space for attendees to relax with friends or meet new people. The ticket includes a complimentary glass of wine, entry into a raffle, and a name tag.
WEST COAST
Blouberg Friday Night Market
- Friday, 29 May | 4pm – 9pm
- Location: Sunningdale Sports Complex, Waterville St, Milnerton Rural
Kick off the weekend at the Blouberg Friday Night Market with an evening full of food, crafts, games, and entertainment. Enjoy live music, a lively sports bar, unique thrift finds, and delicious baked goods – there’s something for everyone to enjoy.
Elandré
- Thursday, 28 May | 8pm
- Location: Kapstadt Brauhaus Langebaan, 1 Mykonos Access Rd, Mykonos, Langebaan
- Cost: From R185 via Quicket
Whether you’re a fan of Afrikaans music or simply enjoy great live performances, this evening with Elandré is set to be the perfect way to kick off your weekend.
RECOMMENDED:
🏨 The best hotels in Cape Town
🍷 The best wine farms in and around Cape Town
🍕 The best pizza in Cape Town
📍 The best things to do in Cape Town
Sign up to Time Out Cape Town's free newsletter for expert recommendations on new things to do, see, eat and drink in the Mother City. You can also follow Time Out Cape Town on Facebook, Instagram and TikTok!