Date Ideas – From First Date To 50th Anniversary

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Date Ideas – From First Date To 50th Anniversary

Something for everyone: Food, adventure, relaxed activities, and adrenaline-pumping experiences

Last update: 1 February 2019

Splendid natural beauty, a friendly atmosphere and glorious weather make Cape Town a prime place to fall in love. With trendy eateries, cosy bars and scenic wine estates on every corner and a plethora of fun activities at every turn, the city is chock-a-block with great options for a memorable romantic rendezvous, whether it’s a first date or a 50th anniversary.

Walk off any tension along the city’s iconic beachside path. The broad, paved promenade path that stretches along the curves of the Atlantic Seaboard offers spectacular views of the ocean and sunsets. There are beaches, a lighthouse and plenty of art installations along the way that serve as great talking points. Test your skills, patience or sense of humour with a game of putt-putt at the seaside mini golf course and stroll to the Mojo Market off Regent Road for a bite to eat in a casual setting. Read more about things to do in Sea Point

Stoney Point in Betty’s Bay and Boulder’s Beach in Simon’s Town are two of the only large endangered African Penguin colonies accessible from the mainland on our coast. And a visit can make a pretty cool date. Especially at Boulder’s, where there’s a boardwalk along the nesting site that’s free, but there’s also the option of paid entry (about R70pp, phone:+27 (0)21 786 2329) to the private beach, where you can also picnic and swim in the ocean.

Picnics are a winner because you can control the budget. Make this one meaningful by picnicking in the exquisite Harold Porter National Botanical Garden in Betty’s Bay. Some parts of the garden got burnt in the recent fires, but most of it survived, and did you know that fire enables fynbos to regenerate. What a lovely metaphor for love. You can find more awesome picnic spots.

The most famous landmark in the city is a mountain, and there are plenty more to explore. Peace, quiet, fresh air, beautiful scenery and hiking and walking trails that raise your heart levels to varying heights are waiting to be discovered. Heading out on picturesque hikes is a sure-fire way to connect with your date while at the same time connecting with nature. The spectacular scenery is a great excuse to take lots of photos and the endorphins rushing between you could reach new highs. From the Pipe Track to Tranquility Cracks, we have a selection of hikes for all levels.  

Sipping interesting drinks while toasting the sun dipping down into the horizon is part of a tried-and-tested formula for dating success. Choose from a diverse range of bars and lounges offering an assortment of city, mountain or sea views. Trendy Cause & Effect in Park Road in Gardens or Bascule Bar at the V&A Waterfront offer some prime spirit concoctions or head out to the colourful Caribbean-inspired Cape to Cuba restaurant and bar, which rests on the water’s edge at Kalk Bay (their mojitos are world-renowned). Alternatively, you could make your own and taxi to Signal Hill and watch the sunset. Sample the likes of crushed coconut mojitos or candyfloss gin cocktails and say cheers to a good evening. Check out the spectacular location of Tobagos or choose from our epic selection of cocktail spots.

Salt, sand and sun is a good look in Cape Town. Bronze your skin, splash in the waves, play bat ‘n ball and do some people-watching with your date. A picnic at Llandudno is the perfect scenic setting for indulgence. Don’t forget your sunglasses and sunblock! Visit some hidden gems with our overview of beaches in Cape Town.

Watching a movie is almost counter-intuitive when going on a date with someone you want to get to know, but this is a little different. Not only do you get to watch a film of your choice on a big screen, but also in a beautiful outdoor location, sitting on the ground leaning against a comfy backrest, under a blanket, beneath the stars. Arrive early to play games like giant Jenga or croquet, or do some hula-hooping before picking up some pizza or tacos from one of the food stalls. Get the schedule and read more about The Galileo Open Air Cinema.

Various venues | +27 (0)71 471 8728,

It doesn’t get more romantic than boarding a catamaran at the V&A Waterfront, sipping drinks and cruising out the harbour on tranquil waters. Behold the mountains from a different perspective and marvel at how the shape of Lion’s Head changes from different angles. Toast the day while watching the glowing sun dip down into the ocean and enjoy the live DJ and dinner on a luxurious cruise that the two of you will never forget. Read more about the weekly sunset cruise.  

Pier Head, T Jetty (next to clock tower), V&A Waterfront | +27 (0)21 418 0241

While not exactly suitable for a first date, a weekend away together is the mother of all dates. Leave your work and worries at home and be in the present at your new home away from home for a couple of days. Enjoy the fresh scenery and exciting activities on offer and you may even return with a fresh perspective on life. From a winelands stay in Franschhoek to a cave campsite where intrepid explorers stay in a natural cave, there’s plenty to choose from our budget getaways and romantic weekends.

Markets are not what they used to be. Does your date agree? Oranjezicht City Farm Market at the V&A Waterfront is very sexy for a first date, and now it’s open Sundays too. Or visit The Fort Food Truck Market at Fort Wynard for some interesting scenery and a little history lesson for the curious. You could even opt to make a day of it at the Art Deco and Art Nouveau-inspired Elgin Railway market. Do you know of any other markets that belong in the top ten?

Make the most of summer and head to the waters while temperatures are still soaring. Whether a public pool like the Sea Point Pavillion or an open-to-the-public pool like the Cloud 9 rooftop bar and pool, your partner really can’t judge you by the amount of flesh you show on a date at the pool. See what’s open from Cape Town’s selection of public pools and other pools that are open to the public. Alternatively, make an adventure out of it at Miller’s Point or Soetwater or by exploring some natural tidal pools.

Show off your prowess by hunting down a secret spot that will blow your date’s mind. It could be what the locals call Sunset Rocks, located right at the end of Ocean View Drive. This is a natural collection of flat granite boulders that overlook Clifton and Camps Bay. Here, you can relax and watch the sunset from a phenomenal outdoor vantage point. See what else is on our bucket list of Cape Town activities.

Situated in the heart of the Mother City, on iconic Heritage Square just off bustling Bree Street, Headquarters (HQ) is renowned for its no-fuss, full-flavoured food offering. It’s sleek, soulful and well-established with a reputation built over the past decade on the Cape Town restaurant scene. Tap into their awesome specials and discover why HQ regulars return week after week for cocktails, mouthwatering steaks and more. Read more about Headquarters Restaurant.

Heritage Square, 100 Shortmarket Street | +27 (0)21 424 6373,

There are few better ways to set first date nerves at ease than with some hearty giggles and guffaws brought on by top-notch stand-up comedy. Bond and laugh together while engaging with some of the country’s finest comedians as they perform. Nobody leaves without a good, gut-busting ab workout so why not indulge in some tipple from the bar and the Jou Ma Se Gatsby, their very own version of the Cape Town gatsby: a half-sized baguette filled with lamb, fries, lettuce, tomato, and homemade mint sauce. Read more about the Cape Town Comedy Club.

Just because it’s cold out doesn’t mean you need to hibernate. Leave your hot-water bottle at home and seek a restaurant with a fireplace to cosy up with your date. Head to Piano Bar or the eponymous Kloof Street House for a warm atmosphere. There are plenty to choose from in our selection of bars and restaurants with fireplaces.  

Jazz is hands-down one of the most romantic and relaxing genres of music; guaranteed to make you feel lazy like a Sunday morning. To truly transport you to another era, there are live jazz performances at The Art Of Duplicity speakeasy in the East City Precinct. After you make the required reservation, you'll be added to the mailing list and receive the monthly jazz line-up. Read more about the Art Of Duplicity or choose from our round-up of places to watch live jazz.

Red, pink and white and bursting with flavour. Impress your date with your taste in wine and enjoy a classy time out together. Our local wineries offer all sorts of entertainment including beautiful locations, wine tastings, art, live music and food. Head out to a winery of your choice for wine tastings or learn what’s on the list of South Africa’s best wine.

It’s awkward being a teen, full stop, but there are more opportunities for activities than ever before. Films, games, arcades, activities, the outdoors, and the list goes on with few limitations for teens. Battery Park at the V&A Waterfront offers a free skate park and basketball court. There are beaches, gardens, cafes, pools, putt putt and fun activities galore. Check out our suggestions for activities for teens.

You, me, the open water and a kayak. Get the adrenaline pumping with an exciting excursion on the ocean. View the city from a different perspective and you also have the chance of seeing penguins, dolphins, seals and whales. Read more about kayaking in Cape Town.

Put on your neon running shorts and hit the park, the road or the trails for an endorphin rush that will leave you both with a glow. Head to Silvermine for beautiful trails and fresh air and a spot of exploring in our beautiful great Cape outdoors. Fitness and friendships of all sorts pair well, so have a look at our selection of running routes.

Trying a new activity has the potential to bring you closer together. Learning to kitesurf is exhilarating and quite addictive based on all the colourful kites you can see in the kitesurfing hotspot of Blouberg with Table Mountain in the yonder. Read more about kitesurf lessons and free yoga.


Everything you need to know about a plant-based lifestyle at the Vegan Lifestyle Festival.

It’s the month of love, so check out our events for (music, beer and sport) lovers in our February events.

Romantics, here are all the coupley things you can celebrate with on Valentine‘s Day and other ideas for V-day.

Awkward first dates be gone! Choose from our selection of first date ideas.

Night owls, there’s plenty to keep you occupied in our list of things to do at night.

For the risque, check out some interesting Cape Town places to get it on.

Health nuts, you’ll love our collection of vegetarian restaurants and healthy eateries.


Use our events section for an up-to-date overview of what’s happening in the city, ‘burbs and dorpies. Join our newsletter and get quick access on the go by adding us to your mobile home screen for the ultimate guide to discoveries in Cape Town.

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Cape Town Events Calendar
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Polkadraai_and_popcorn_popcorn_and_wine1Polkadraai & Popcorn Wine Pairing Back ...

Check out the anti-serious wine pairing in the Western Cape with Polkadraai & Popcorn

Sound workshopLet Your Kids Scratch, Mix and Mashup ...

Expert DJ lessons and a guaranteed first SoundCloud mix for your budding EDM superstar

capegate-summer-splashWater Slides, Surf Simulators and ...

Plus sand building, kite making and water wars on Saturdays

aroundaboutnew3Season Specials And More With ...

From R200 vouchers and free upgrades, drive away with more value adds

robin_hoodTwo For One Tuesdays at Robin Hood ...

Where meat lovers and vegans can come together to enjoy good grill

Xmas Gift Fair11-Days Of Christmas Gifts at a Fab ...

Bring the kids for a show and games and get some good eats too

William_Kentridge_2A Monumental Exhibition At The Norval ...

The iconic South African artist’s largest exhibition in Africa in over a decade

tjing_pancakesTuesdays Are Pancake Days At Tjing Tjing

A fluffy soufflé pancake (or two) at Torii at Tjing Tjing House

Land_RewovenSee This Fascinating Interpretation of ...

Artist MJ Lourens pairs his modern landscapes with Pierneef’s, plus there’s cheese ...

dales_16Check Out the Everyday Lunch Menu at ...

The Milnerton family eatery also serves tapas

Kinky BootsSmash-Hit Kinky Boots Extended To 2020 ...

With music by Cyndi Lauper, several Tonys and a Laurence Olivier Award

fpl_5Get Moving in Functional Training Class

Improve your fitness, strength and overall functionality with the Functional Performance ...

royalteaA Tuesday Treat to Share with a Friend

Royaltea at the V&A Food Market is offering a second one of their special teas at half ...

devonvale15Free With Your Food: Specials at ...

From a free glass to a free bottle of estate wine, get something extra with your lunch or ...

Barrs14Your Pharmacy Medicine Delivered For ...

Just Whatsapp or email your request, from basics to travel medications and emergency ...

Comedyclub_new11End Hump Day With a Laugh At The ...

Share the experience at Cape Town Comedy Club in the Waterfront’s Pumphouse every ...

Comedyclub_new12Half-Price Sunday Special at Cape Town ...

Experience Cape Town’s funniest comedians (for less on Sundays) at the Waterfront’s ...

Om Revolution vinyasa poseHave an Outdoor Yoga Experience with ...

Embrace your inner yogi outdoors

asamisLove Sushi? Asami's Has The Best ...

Get two sushi plates, pay for one, plus women also get 50% off on all cocktails on ...

haskell_wine_1Save On A Gourmet Food and Syrah Wine ...

Sip the renowned wines and taste delicious gourmet food from Haskell Vineyards

date night hqTuesday Date Night Special To Wine and ...

This Parisian-inspired steakhouse is top class

WSDC Shark 5Bucket-List Special: Swim (Safely) With ...

Is it your dream to see a great white?

Masala dosaCook Traditional Indian Food on Long ...

Learn a few tips and tricks to make authentic Indian dishes

GrubandVine_food4Free Wine Tasting Every Wednesday at ...

Grub & Vine’s #VineNight hosts a different wine farm

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