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Dating Ideas

A selection of fun, romantic things to do for clueless couples Though it’s a well-known fact that Cape Town swoons visitors from around the world, the Mother City, with her splendid natural beauty, also happens to be a prime place to fall in love. With trendy eateries, intimate bars and scenic wine estates on every corner and a plethora of fun, innovative activities at every turn, Cape Town is chock-a-block with great options for a memorable romantic rendezvous, whether it’s a first date or a 50th anniversary

Nevertheless, despite the breadth of alternatives available, when it come to arranging a top-notch date with a prospective sweetheart (or even a long-term partner), it can be a challenge to come up with an original fail-proof plan. So, what follows is our carefully considered pick of timeless romantic (and at times unconventional) date ideas in Cape Town to help you hit the right note in your blossoming relationship. From dinner theatre and stand-up comedy to sunset cruises and open-air cinema, this overview includes a little something for all tastes and types, pockets and penchants.


Whether you pack your own hamper of tasty treats or have picnic basket professionals The Picnic Company (they create a variety of gourmet spreads and deliver to the chosen location) do it for you, dining under clear open skies in the Mother City's breathtaking outdoors is a sure way to win over a prospective lover. And fortunately, there are plenty of stunning natural spots in Cape Town to stretch out that blanket and tuck into a delicious alfresco feast. Fine examples include expansive botanical garden Kirstenbosch, one of the Mother City's many pristine beaches (the idyllic Clifton Fourth at sunset is a favourite choice) or one of the several viewing sites along Chapman's Peak Drive, a spectacular stretch of rocky coastline near Hout Bay. Should you decide to go the simpler route and recruit The Picnic Company to prepare your meal for you, consider opting for their Mezze Picnic (think Mediterranean finger foods like dolmades, pitas and nougat bites) or Afternoon Tea Picnic (it includes cucumber and smoked trout sandwiches, freshly baked scones and more), both of which are specifically designed for two. The Picnic Company: Unit C18 | Prime Park | Mocke Road | Diep River | Cape Town | +27 (0) 21 706 8470


Complete with expansive greens, colourful citrus orchards and a central Mediterranean-style stone villa, Waterford Estate in Stellenbosch's Blaauwklippen Valley is a particularly enchanting, dreamy spot. And their signature, widely-acclaimed wine and chocolate tasting experience – which pairs three of the estate's finest vintages (two reds and a dessert wine) with three complementary handcrafted chocolate squares – is bound to only enhance the romantic connection. This heavenly, flavour-rich sampling session can either be enjoyed inside in the tasting room (it features a roaring fire during winter) or outside in the stone courtyard, and is available from Monday to Saturday. Those with an adventurous spirit (and a little extra cash in their pocket) can opt to follow the tasting with Waterford's two-hour Wine Drive Safari, which takes guests in an open Land Rover on a breathtaking educational journey through the 120-hectare property, showing off the estate's vineyards, rich flora and fauna (small buck and birds are sometimes spotted) and spectacular mountain views (wine tasting is also included). Drives go off daily from Monday to Saturday at 10:30am and 2pm, and booking at least 24 hours in advance is essential (phone +27 (0) 21 880 5316). The Picnic Company: Unit C18 | Prime Park | Mocke Road | Diep River | Cape Town | +27 (0) 21 706 8470


Spruce up the traditional Ster-Kinekor movie date and take in a film together at this charming open-air cinema atop Long Street's innovative Grand Daddy Hotel. Nestled between vintage Airstream trailers – it's the world's only rooftop trailer park – and boasting views of the twinkling CBD skyline, the alfresco theatre screens cult classics and old favourites (think flicks like Dirty Dancing, Amélie and Pretty Woman) every Monday evening under the starry night's sky. The ticket price includes a welcome drink, popcorn and a mixed bag of sweets, and in winter, guests are given hot chocolate and warm blankets to cuddle under. Pre-ordered gourmet food baskets – which contain an array of delicious snacks – are also available for those keen to add a little something extra to their sky-high romantic rendezvous. All in all, there are few more magical and unusual city centre spaces to spend some quality time with that special someone.


There are few more sultry matches than oysters and bubbly, and this stylish city centre hotel's in-house bar claims the sort of opulent surrounds that are perfectly befitting for this luxurious combination. Decked out in royal purples and boasting rich velvet curtains and ornate furnishings, the circular watering hole – it's named for the 20000 crystal links from Murano that dangle from the ceiling – treats starry-eyed couples to freshly shucked West Coast molluscs (either chilled or tempura fried) alongside an assortment of authentic French Champagnes (Veuve Clicquot, Moët & Chandon and Tribaut). What's more, sweethearts can book the elevated private pod that rests right above the bar area for a more intimate evening experience. Should duos want to supplement their bubbly date with an elegant dinner, they can take a seat at the chic Savour Restaurant just next door and indulge in a diverse selection of delicious intercontinental cuisine. Do note, Murano Bar only opens at 4pm, and booking is recommended. Corner of Grey's Pass and Orange Street | City Centre | Cape Town | +27 (0) 21 469 8000


If fine music is a common passion, a fool-proof date idea is to spend an evening soaking up the soulful sounds of live jazz in an intimate Mother City setting. Being a proudly cultural city and base to its very own style of this musical genre, Cape Town claims a large number of spots where it's possible to catch a sensual performance or two. Prime options include Alexander Upstairs, an inviting 40-seater theatre space that rests above Alexander Bar and Café and hosts jazz evenings every Tuesday, and small, authentic New York-style jazz club The Mahogany Room (booking is essential); there are also a host of other top live jazz venues in and around the city centre too. Regardless of where you pick though, you can rest assured that the cool, complex harmonies of this particular musical variety are bound to lull your partner into a state of bliss. Alexander Upstairs: 76 Strand Street | City Centre | Cape Town | +27 (0) 21 300 1652 The Mahogany Room: 79 Buitenkant Street | City Centre | Cape Town | +27 (0) 76 679 2697


Though perhaps not a conventional date, heading out on of the Mother City's many picturesque hikes is one sure-fire way to get to know each other a little better while at the same time connecting with nature. From casual strolls along coastlines to strenuous climbs up mountain sides, Cape Town claims a plethora of pretty hiking trails and routes ideal for anyone, from amateur ramblers to committed adrenaline junkies. For instance, you could consider scrambling up Lion's Head or Devil's Peak (they both flaunt majestic views from the top), ambling along theOlifantsbos Shipwreck Trail in the Cape Point Nature Reserve or trekking through the fynbos- rich Spes Bona Forest in the mountains above Kalk Bay. With spectacular scenery and a good mix of challenging and easier stretches, they're all bound to get the blood pumping and the amorous energy flowing.


Whether you're celebrating an anniversary, Valentine's Day or just the simple pleasure of enjoying the company of someone special, CinCin Restaurant in Century City provides the kind of intimate, elegant atmosphere that makes for a magical evening. Instead of taking your love to the regular haunts in Cape Town's city centre or trekking to the Winelands, opt for a quiet sit-down in the Colosseum Hotel's restaurant, which boasts a sparkling Swarovski crystal chandelier at its centre and heart-melting views of the city skyline to set the scene for wooing and coy eye-gazing. CinCin – it's pronounced like the celebratory cheers – is a fine dining eatery that dishes up a selection of tempting and satisfying starters and mains: think mussels smothered in a creamy white wine sauce served in a potjie pot, followed by a hearty, deconstructed lamb shank pie, for example. The decadent desserts are a must-do, as they are more than ideal for sharing: the white chocolate, cookie cheesecake with whipped cream has basically been invented for flirty feeding. Add to that the friendly staff – they'll treat you like a royal Romeo and Juliet – and you have the makings for a truly unforgettable dinner. Cnr Century Way and Century Boulevard | Century City | +27 (0) 21 526 4000


For a slightly more refined romantic rendezvous, consider spending an evening at delightful Sea Point-based dinner theatre Richard's Supper Stage taking in their lauded long-running show "Kaapse Stories from the Mother City" (it plays on Tuesdays, Thursdays and Saturdays). Produced by co-owner and renowned showbiz heavyweight Richard Loring, the interactive musical – which is put on in an elegant, locally-themed dining area – sheds light on Cape Town's colourful history and vibrant people through theatrical, often humorous storytelling and captivating song. The entertainment is accompanied by a tasty four-course meal infused with traditional Cape flavours (expect a Bo-Kaap platter for starters; Chicken and Prawn Curry, Cape Malay Vegetable Breyani and more for mains; and melktert, koeksisters and malva pudding for dessert), and in between performance times, audiences are wooed by the sounds of live piano, guitar and banjo. As the combination of theatre and food allows for some time to chat while also filling up the silent moments with catchy rhythms and dance, this option makes for great date material. 229 Main Road (corner of Glengariff Road) | Sea Point | Cape Town | +27 (0) 21 434 4497


Hands down, one of the most romantic things to do in Cape Town is to take a cruise out on tranquil open waters at dusk and watch the glowing sun dip down into the ocean. Based at the V&A Waterfront, the Waterfront Boat Company runs a range of daily scheduled boat trips all year round, the most popular of which – especially amongst swooning couples – is their Sunset Champagne Cruise. This 1.5-hour trip takes guests out to sea in the early evening on either a large sailboat or a motor vessel that, depending on which is chosen, travel out either across Table Bay or along the Atlantic Seaboard towards the breathtaking Clifton Beach. Before returning to the harbour, the crafts generally come to rest in the shelter of Granger Bay, from where passengers can watch the sunset while sipping on a complimentary glass of sparkling wine (each guest is given two glasses gratis during the cruise). Those with some extra cash can also opt for the more costly Cruise and Dine package, which includes a three-course supper at one of three select V&A Waterfront restaurants on top of the standard sunset sail. Booking is essential. Waterfront Boat Company: Shop 5 | Quay 5 | V&A Waterfront | Cape Town | +27 (0) 21 418 580


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. On the first Wednesday of every month, the Bay Harbour Market in charming fishing village Hout Bay hosts their intimate monthly comedy supper club, bringing a side-splitting line-up of some of the country's wittiest funnymen – think Rob van Vuuren, Nik Rabinowitz, Siv Ngesi and many more – to the stage. The comedians performing change regularly, but, regardless of who's in the spotlight, the show, which costs R90 seated and R70 standing, promises a consistently good laugh – material for a truly memorable date. Couples can also combine top Mzansi humour with a tipple or two from the bar and with any of a wide range of delicious dishes – including wood-fired pizzas, Chinese dumplings and spring rolls – sold by the market food stalls. Bay Harbour Market | 31 Harbour Road | Hout Bay | Cape Town | +27 (0) 82 570 5997


It may be somewhat cliché and commonplace, but heading out for a dop together (particularly at sunset) is part of a tried-and-tested formula for dating success. And fortunately, Cape Town is jam-packed with a diverse range of city centre, suburban and seaside spots that are ideal for a relaxed couple's drink. For instance, for oceanfront sundowners, there's the Grand Café & Beach in Granger Bay (it boasts its own private beach; though, prices are quite high) or for poolside cocktails, there's the Hilton Hotel's Signal Hill Terrace, an oasis in the heart of the city. Alternatively, for a more laidback and affordable drink, pop in to Oblivion Wine Bar in Claremont and enjoy a glass of red or white on their rooftop deck or trek out to the colourful Caribbean-inspired Cape to Cuba restaurant and Che bar, which rests right on the waters of Kalk Bay (their mojitos are world renowned). Otherwise, a selection of additional fine drinks venues can be found on our overview of Cape Town sundowner spots


Though a particularly pricy date option, a scenic hot air balloon flight over some of the Cape's most breathtaking landscapes is guaranteed to impress any partner and make for a memorable experience. Paarl-based initiative Wineland Ballooning offers daily one-hour rides from November to April (weather-permitting of course) that take couples on a magical sky-high journey over the vineyards, farms, wheat fields and orchards of the Berg River Valley. The brightly coloured balloons take off at sunrise – arguably the most majestic and romantic time of the day – and go wherever the wind blows before landing softly on safe ground. Red-cheeked passengers are then transported back to Paarl, where they'll enjoy an indulgent champagne breakfast at opulent luxury resort the Grande Roche Hotel – an added extra that makes the hefty cost (R2750p/p) even more worth it. All bookings for this enthralling experience must be made beforehand by phone, and couples should bear in mind that the flights only run under safe weather conditions (a plan B therefore might be required). Wineland Ballooning: 64 Main Street | Paarl | Cape Winelands | +27 (0) 21 863 3192