Simba Road tour - Garden route, South Africa

Touch down in one of the most iconic cities on Earth — where the ancient, flat-topped Table Mountain, forged over 500 million years ago, watches over the Atlantic and Indian Oceans as they meet at the Cape. Cape Town was founded in 1652 as a refreshment station for Dutch East India Company ships, and its layered history of trade, struggle, and beauty sets the stage for the epic journey ahead. Rest, explore the vibrant V&A Waterfront, and let the city's energy fuel your spirit — because tomorrow, the adventure begins.

Ride out from the Waterfront and onto Chapman's Peak Drive — 114 hand-carved curves blasted into sheer cliff face between 1915 and 1922, where the Atlantic drops away beneath you into nothing. Push south to the Cape of Good Hope, where the cold Benguela and warm Agulhas Currents have been clashing for millennia, creating the storms that terrorised sailors for centuries — stop for an early lunch at the edge of the world. Carve back through False Bay and finish the day back at the City Lodge V&A Waterfront. 128km. 2 hours riding.

Ride through Stellenbosch, South Africa's second-oldest town and the beating heart of its wine culture, before crossing the Franschhoek Pass into the valley where French Huguenot refugees planted their first vines in 1688, then drop down Sir Lowry's Pass toward the coast and the road that changes riders forever — the R44, Clarence Drive. This is widely regarded as the finest motorcycle road in the world: high-grip tarmac hugging the granite flanks of the Kogelberg Biosphere Reserve, a UNESCO hotspot richer in plant species per square kilometre than the Amazon. Arrive in Hermanus, the world's whale-watching capital, where between June and November, Southern Right Whales nurse their calves just metres from the cliff paths. 240km. 3 hours riding.

Roll south through the vast wheat and canola plains of the Overberg — open, ancient farmland sculpted by tectonic forces over 300 million years ago — until the land runs out at Cape Agulhas, the true geographic southern tip of Africa. Stand at the 20° East meridian where the Atlantic and Indian Oceans officially meet, marked by a lighthouse built in 1848 and modelled on the ancient Pharos of Alexandria. Finish the day in Arniston, a tiny whitewashed fishing village so perfectly preserved it was declared a national monument — where fishermen still haul their boats up the same beach their great-grandfathers did. 172km. 2.5 hours riding.

Leave the open Overberg plains behind and ride east through Swellendam — founded in 1745 and one of South Africa's oldest towns — as the dry fynbos gradually gives way to something greener and far more ancient. Pass through Mossel Bay, where Portuguese explorer Bartolomeu Dias first set foot on Southern African soil in 1488, then drop through the Kaaimans River Pass — a gorge of primordial forest where yellowwood giants that pre-date any human settlement crowd the road above a crashing sea. Arrive in Wilderness, where lakes, lagoons, and rivers dissolve into the Indian Ocean, and let the magic of the Garden Route settle in. 365km. 3.75 hours riding.

Climb the Outeniqua Mountains and cross one of South Africa's great landscape divides — as you crest the pass, the lush coastal greens vanish and the red dust of the Little Karoo begins. Drop into Oudtshoorn, the Ostrich Capital of the World, where Victorian farmers built "feather palaces" from the fortunes made supplying plumes to Parisian fashion houses, then duck underground into the Cango Caves — a 20-million-year-old limestone labyrinth of cathedral chambers still growing at barely a centimetre per century. Push on to Barrydale, a fiercely independent Karoo village that marks the gateway to tomorrow's legendary road. 298km. 3.33 hours riding.

Ride Route 62 — the longest wine route on Earth, stretching over 850 kilometres through mountain valleys, orchards, and sun-baked Karoo plains — with a mandatory stop at the legendary Ronnie's Sex Shop, a roadside bar renamed as a prank in the 1980s that never changed back. Thread through the Tradouw Pass, a Khoikhoi word meaning "path of women," where narrow tarmac carves through fluted sandstone cliffs with surprising elegance, before the spectacular rock gateway of Cogmanskloof Pass leads you into Montagu. The day ends at Aquila Private Game Reserve, where Africa's Big Five roam under a sky that city lights have never reached. 192km. 2.5 hours riding.

Save the best for last — Bainskloof Pass, built between 1848 and 1853 by the father of South African road-building, Andrew Geddes Bain, is a masterwork of tight hairpins and steep gradients with the Winelands sprawling in every direction from the summit. Wind down through Wellington and Somerset West as the road grows familiar, and then — there it is — the flat-topped profile of Table Mountain rising on the horizon, the same mountain that welcomed you on Day 1, now your finishing line. Roll back into Cape Town for a celebratory farewell dinner, with over 1,500 kilometres of extraordinary road behind you and a story worth telling for the rest of your life. 196km. 2.5 hours riding.

Gather one last time for breakfast as Cape Town puts on its final show — because it always does. Swap stories, relive the highlights, and take a moment to absorb what the past nine days have been: from the edge of the continent to the winelands and back, across terrain most people only ever see on a map. Transfers depart for Cape Town International Airport — and wherever the road takes you next.

Cape Town (Nights 1, 2 & 8)

Sitting at the entrance to the iconic V&A Waterfront precinct — itself built on the historic working docks that have served Cape Town since the 1860s — this 207-room hotel places you steps from the harbour, restaurants, and the mountain that has defined this city for centuries. Recently completed a full two-year renovation, it offers a fresh, comfortable base with an on-site art gallery, making it both a practical and surprisingly characterful start and finish to the journey.

Hermanus (Night 3)

Originally built in 1896 as a sanatorium — designed to draw patients seeking the restorative sea air of Walker Bay — the Windsor Hotel has evolved into one of the Western Cape's most beloved heritage landmarks, its grand Victorian façade still commanding the cliff edge above the ocean. Perched directly above Hermanus's famous cliff paths, it offers perhaps the best seats in the world for whale watching, with Southern Right Whales frequently surfacing in the bay just below the hotel terrace.

Arniston (Night 4)

Built in 1933, the Arniston Spa Hotel is the oldest hotel on the southernmost coastline of Africa and remains the focal point of village life in this tiny, monument-listed fishing community — named after the British troopship HMS Arniston that wrecked on these treacherous shores in 1815. Flanked by two nature reserves and sitting directly on pristine Atlantic beaches, it has since won both Best Country Hotel and Best Beach Hotel in South Africa, and its spa makes it one of the most restorative stops on the entire route.

Knysna (Night 5)

Built in 1998 as a tribute to Knysna's identity as the historic hub of South Africa's indigenous timber industry, the Log Inn Hotel is constructed using the very yellowwood and ironwood that once made this forest famous — its grand lobby a cathedral of locally sourced timber that tells the story of the region without a single word. Centrally located in the heart of Knysna and recently merged with the neighbouring Graywood Hotel to offer 106 rooms, it puts you within walking distance of the lagoon, the famous Heads, and the best restaurants the Garden Route has to offer.

Barrydale (Night 6)

The Karoo Art Hotel began life in 1881 as Prynnsberg, a grand homestead built by a flamboyant Kimberley diamond era figure, and after years of faded glory was rescued and reimagined by owners Rick and Sue Melvill as South Africa's leading art hotel — a quirky, colourful, creatively charged property that has become the cultural heartbeat of Barrydale. Expect original artworks in every room, live music events, and a fiercely independent spirit that perfectly mirrors the character of Route 62 itself.

Karoo (Night 7)

Named after the black eagle that soars above its 10,000-hectare conservancy, Aquila holds a special place in conservation history as the reserve that reintroduced the first white rhino to the Western Cape after a 250-year regional extinction. Malaria-free and less than two hours from Cape Town, it offers the full Big Five safari experience — lion, leopard, elephant, rhino, and buffalo — under an uninterrupted Karoo sky, with a spa and lodge accommodation that make it feel like a world entirely apart.