Where to stay

Airstream Trailer Park at The Grand Daddy

It may not be to everybody's taste, but if you're up for trying out the unusual, then bed down in this world-first: a vintage collection of Airstream trailers parked on the inner-city rooftop of Cape Town's oldest hotel. Each shiny caravan was given an artist's makeover and designed according to quirky themes, such as retro-sweet "Pleasantville", polka-dotted Wizard of Oz-themed "Dorothy" or "The Ballad of John and Yoko" – an all-white love-nest, stocked with musical instruments. Besides the limitations on space (they're not for the claustrophobic; bathrooms are truly tiny), light sleepers might have a problem with noise drifting up from the streets below, and in summer you're forced to have the A/C flicked on full blast. Still, if you stay here, you're almost certainly in town to party, and you're a doorstep from the hotel's rooftop bar; below is the ultra-bling Daddy Cool bar, and the delights of Long Street. Nothing in Cape Town (except perhaps sister hotel, Daddy Long-Legs) comes close in conceptual outrageousness, and this really is nothing like any caravan experience you might have had before.

• 38 Long Street, City Centre, +27 21 424 7247, granddaddy.co.za. From £155

Best for breakfast

The Foodbarn Deli

It's firstly a bakery – the bakers arrive at 3am and set about preparing 18 different types of breads, as well as croissants and pastries using stone-ground flour from the nearby Eureka Mills. By the time you arrive, as early as 8am, the place will be full of pleasantly intoxicating aromas, making it almost impossible to walk out empty-handed. In fact, do yourself a favour and sit down – the traditional European country deli atmosphere is quite unique for Cape Town, and there's quite a bit more to take in here than at the slightly refined (even sterile) places that you'll find in the city. This takes as its cue a real, no-nonsense farm stall, only with the advantage of having The Foodbarn's chef Franck Dangereux at the helm. Breakfasts, light lunches, cold cuts, biscuits and cakes – the selection is dizzying but select one of the incredible 200g pies which are delicious.

• Noordhoek Farm Village, Village Lane, Noordhoek. +27 21 789 1390, thefoodbarn.co.za. Open: 8am-5pm daily

Best snack

Biesmiellah

A Cape Town institution, this authentic and downhome preserve of the Bo-Kaap community is where you can sample true-to-its-roots Cape Malay cooking, served up in a bare-bones environment by members of the multi-generational Osman family. Don't come here expecting a view, much by way of service, or anything resembling décor – it's a pretty empty shell filled with aromatic fragrances wafting up from the kitchen, and perhaps a chance to listen in on the kind of garrulous chat between members of this community. On the menu are chilli bites (or daltjies) and samosas, both snack-style finger treats that you must try, but the tamarind-spiked lamb stew known as denningvleis is what will make the adventure into this dishevelled cobblestone corner of Cape Town truly unforgettable. Another treat, while you're here – and since this Muslim establishment doesn't serve alcohol – is the Indian-style rosewater milkshake known as falooda. For a similar experience, coupled with extraordinary views (and a more tourist-centred atmosphere), try the Noon Gun Tea Room and Restaurant.

• 2 Wale Street, Bo-Kaap, City Bowl. +27 21 423 0850. Open 11am-10pm (11pm Fri/Sat), biesmiellah.co.za. Closed Sundays

Best for lunch/dinner

Cafe Roux

After the exhilarating views of Chapman's Peak Drive, this is a hugely rewarding stop as you gently ease your way around the Southern Peninsula. A major draw for surfers (who come to break their hunger with the famed Earl's All-Day Breakfast; also salvation from a serious hangover), Café Roux has a decidedly cosmopolitan atmosphere, and you'll be surrounded by a cross-section of Capetonians mellowed out beneath the oaks. There's also a fenced-off, supervised play area for children, which means the dining area stays tranquil and parents stress-free. Huge emphasis is put on fresh ingredients, so the menu – on chalkboards – changes daily, and even the simplest-sounding dishes (such as beef fillet with bone marrow, or crispy butternut and goat's cheese salad) tend to look – and taste – extraordinary. On Sunday afternoons, there's usually a live band and lunchtime spills over into the early evening, while on Thursday, there's a braai (barbeque) where you're expected to kick back and chill the South African way. And, if you find you just don't want to leave, it's good to know that the bar stays open into the night.

• Noordhoek Farm Village, Village Lane, Noordhoek, Southern Peninsula. +27 21 789 2538, caferoux.co.za. Open 8.30am-5pm daily

Best for dinner

Aubergine

Many consider Harald Bresselschmidt the best chef in Cape Town. His impeccably classy yet unstuffy bistro and lounge-bar arrangement occupies the 19th-century home of the first Chief Justice of the Cape, which was once an extensive estate. Today, the enclosed courtyard is where you can dine beneath the stars, while the modern interiors work reasonably well within the historic framework. Certainly the venue serves as an elegant backdrop to some avant-garde culinary creations; Harald (a German import from the Luxembourg border region) likes to play, and – when it comes to sauces – reduce, reduce, reduce, until he's uncovered a taste that's worth showing off. Yet, while he experiments with combining medallions of springbok with foie gras, or pork and pancetta pralines, he's equally adept at creating uncomplicated dishes, such as his rare fried ostrich medallions. Whatever you do, don't miss his exceptional signature aubergine soufflé with marinated goat's milk cheese. Aubergine is tucked away in a residential neighbourhood that tends to get very quiet after dark, but don't let that put you off – there's good reason it's such a consistent draw for well-travelled gourmands.

• 39 Barnet Street, Gardens, City Bowl. +27 21 465 4909, aubergine.co.za. Open: noon–2pm Wed–Fri

Best for drinks

The Waiting Room

A narrow near-vertical stairway behind an ancient doorway leads to this cosy bar, with its warm, home-away-from-home ambience. Having gained approval from the buff doorman (who'll sell tickets if there's a performance), head up as determinedly as your legs will allow – the old wooden steps are just wide enough for a single person, and their use is on a first-come, first-serve basis. High heels are not recommended. Once up there, though, you'll be happy to have made the trip. There's a warren of spaces, including a terrace overlooking the heaving part of Long Street from which you've just ascended, and myriad lounges, some of them tucked away (don't miss the back terrace). Mondays and Tuesdays see a line-up of small, excellent solo artists and bands; Saturdays, there's a DJ session known as The Boogie, and various other DJs take the decks on alternate nights. The atmosphere might remind you a bit of an arty bohemian hangout from your student days – there's a hint of grunge – but it's been cultivated with real warmth (and someone's grandmother's hand-me-down furniture and lampshades).

• Above Royale Eatery, 273 Long Street, City Centre .+27 21 422 4536. Open: 6pm–2am Mon–Sat

Best for music

Balkanology & Fiddle East Parties

Somewhere between a gargantuan theatrical happening and a full-on concert, Balkanology – together with the smaller, but no less energetic, Fiddle East parties (sometimes at the Albert Hall) – is the most sensational one-night party to hit Cape Town since the fabulous annual MCQP events started in the 1990s. Taking as its cue Europe's vibrant underground Balkan party scene, Balkanology is a local collective from the imagination of Israeli-born Ma'or Harris (a self-styled, self-taught DJ who grew up on a farm and ended up in Cape Town studying sound engineering). Determined to stoke Cape Town's cultural scene, Ma'or gave it wings with his love of Balkan music – not inherently "cool", but the type of unhinged fun-inducing sound that stimulates uninhibited dancing à la Black Cat, White Cat – and brought DJs, artists, designers, musicians and actors together to create a kind of ritualised party happening. Wild extravaganzas brimming with atmosphere – not to mention farmyard animals, mountains of hay bales, re-enacted weddings and revolutions, belly dancers, tarot readers, performance artists, kick-ass bands, and unabashedly alternative tunes (think Serbian rave, traditional Hebrew party anthems, mad remixes of Gypsy electronica, and even Mediterranean melodies, jazzed-up folk rhythms and oompah bands).

• Various venues around the City Bowl. + 072 211 5563 , balkanology.co.za . Parties happen every three months, more or less; join them on Facebook for regular updates

Culture

Coffeebeans Routes

The are around 400 tour operators in Cape Town, so no shortage of experts and pseudos eager to show you around the city. But if you prefer to dig deeper, Coffeebeans is the way to go. What started as a slightly clandestine operation taking visitors into unknown territory, this small, savvy organisation has quickly evolved into one that's earned accolades from visitors from around the world for its unique and inventive tours that explore diverse and exciting aspects of our local culture. Like other tour companies, they do versions of the highly recommended Township Tour, but have elevated this to the Township Futures tour which reveals how people living in some of the city's poorest areas are working to carve out a positive future for themselves and their communities. Their journeys aim to take you into untouristy places where you'll meet the locals – they work on the premise that while it's easy to get into a restaurant, it's another story altogether visiting a family, meeting them in their home and literally breaking bread with them. Most popular are the Cape Town Jazz Safari and the storytelling Route, both of which are interactive, as is the Soccer Route (where you get to play football with some locals) and the Rootz Reggae Route in which you discover the broad spectrum of reggae-related musical influences; not only that, but you get to bop for a while alongside members of the Marcus Garvey Rastafarian community at the Friday night reggae Dance Hall in Philippi, just outside Cape Town.

• 70 Wale Street, City Centre, +27 21 424 3572, coffeebeansroutes.com. Tours happen according to varying schedules

Nature

Penguin colony at Boulders

Among the quirkiest of Cape Town's "cultural" experiences, you'll hear these little fellows before you see them, their delightful donkey-like braying having spawned their alternative moniker – jackass penguins. Authorities have built boardwalks amid the dunes at the edge of Foxy Beach, so visitors can walk among the knee-high birds without disturbing them. The penguins have been expanding their numbers here since 1985, having grown from just two breeding pairs to more than 3,000 birds, and while human intervention has helped preserve the integrity of the environment, this remains a natural habitat for these creatures. It's possible to swim at nearby Boulders or Seaforth beaches, with the good chance of the penguins joining you in the False Bay waters, mercifully a little warmer than the sea at Clifton or Camps Bay.

• Kleintuin Road, off the M4, Simons Town, Southern Peninsula. +27 21 786 2329, tmnp.co.za. Open: 7am–7.30pm daily (Dec–Jan), 8am–6.30pm daily (Feb–Mar), 8am–5pm daily (Apr–Sept), 8am–6.30pm daily (Oct–Nov)

Kirstenbosch National Botanical Garden

Considered one of the most magnificent gardens on earth, Kirstenbosch is draped against more than 500 hectares of Table Mountain's eastern slopes – a green wonderland designed to blend with the fynbos-clad mountain. With the noted exception of the almond hedge (planted by Jan van Riebeeck in 1660 to indicate the "border" of his colony and protect his animal stock from the indigenous Khoi people), some magnificent oaks, and the Moreton Bay fig and camphor trees planted by Cecil John Rhodes, everything you encounter is indigenous. It'd be impossible to get to grips with even a fraction of the 9,000 or so species that grow here (many of them growing nowhere else on earth), but there are guided tours and audio guides that will at least give you an introduction to the Cape Floral Kingdom, the world's smallest and richest. You can seek out the fragrance garden, elevated for easier access to the scents; a pelargonium kopje (hill); a protea garden; a sculpture garden; and a section with plants used for muti (medicine) by sangomas (traditional African healers). Or you can join in with the locals who come to laze on the lawns, their children exploring the burbling brooks, and simply luxuriate in the setting – the perfect antidote to a night on the town. There are a couple of restaurants, and weekly Summer Sunset Concerts that draw massive audiences to the green lawns every Sunday evening.

• Rhodes Drive, Newlands, 13km from the city centre, Southern Suburbs. + 021 799 8899, sanbi.org. Open: daily, 8am–7pm (6pm Apr–Aug)

• Hedonist's guide to Cape Town costs £12. For details of other Hedonist's guides, go to hg2.com