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Last updated: 4 August 2022

A 9-day itinerary from Cape Town to Plettenberg Bay

Work your way along the Western Cape and you’ll come across some of South Africa’s most sought after spots, from the penguin-dotted beach in Cape Town, to the floral forest trails of the Garden Route, the dramatic cliff paths and hidden coves of the Whale Route, and the winelands of the Bubbly Route. If you’re on the hunt for luxury with a wild side, look no further than our handpicked hotel guide to the wildlife-filled, wine-fuelled Western Cape – with plenty of scenic stop-offs along the way.

South Africa


  • 9-day independent itinerary journeying along the south-eastern coastline of South Africa, based on flying in and out of Cape Town.
  • Enjoy the natural beauty of ‘Cape Town’s Vineyard’ in Constantia Valley, before taking in some spectacular sea views from the comfort of specially selected SLH hotels.
  • Highlights include playing with the penguins on Boulders Beach, water safari and whale-watching in Walker Bay, and catching some waves at popular surfing spot, Keurboomstrand.


Cape Town

This is an urban jungle like no other. From the soul-stirring views at the top of Table Mountain to the rich, diverse history spread out below, Cape Town isn’t short of natural and cultural wonders. Take a stroll along the V&A waterfront where centuries-old and cutting-edge modern buildings sit side by side, or hop into one of the slowly rotating cable cars and arrive at Table Mountain’s peak in minutes for views across the ocean and beaches one side, glinting tops of skyscrapers on the other.

Cape Town

For a brush with nature, you could also spend a day lost in the wild beauty of the famous Kirstenbosch National Botanical Garden, where you can wander across wild savanna, karoo, fields of fynbos and South Africa’s national flower, the protea. And as curious sights go, African penguins waddling between giant granite boulders in the heart of a residential area takes some beating. This protected colony settled on this sheltered beach in the Cape Peninsula nearly 40 years ago and are happy to let you observe their antics at a respectful distance.


The Cellars-Hohenort

Those that hear about The Cellars-Hohenort on the grapevine come for its fine wine collection, beautifully kept grounds, and homegrown produce. Wake up to Table Mountain views surrounded by nine-acres of fragrant gardens blooming with roses and Camphor trees at this historic wine estate, where you can have the best of both worlds with the Constantia Valley Wine Route and the South African capital’s city centre on your doorstep. Suggested stay 3 nights.


South Africa

The one-and-a-half hour drive from Cape Town to Hermanus is peppered with picturesque places to stop, from the Morgenster Wine and Olive Estate where you can sample Bordeaux-style wines and extra virgin olive oil in a tutored tasting, to The Imibala Gallery in Somerset West which showcases local Karoo arts and crafts alongside contemporary artworks from both South African and international artists and donates its profits to support of the work of the Imibala Trust. If you’re feeling peckish, Peregrine Farm Stall is a good mid-way point to pick up some local country goods, freshly pressed apple juice, and some delicious drinks from the pop-up craft cider bar.


Once you reach the historic fishing town of Hermanus, let the waterfront wonders wash over you from the Old Harbour or the wide and welcoming Grotto Beach. As one of the world’s top whale-watching destinations, you can tick off the big marine five while soaking up some sea air – from June to December every year, Southern Right Whales come to the warm waters of Walker Bay and along the Overberg shore, and you can also spy them from Hermanus’ spectacular clifftop path.


From water to wine, the cool Atlantic Ocean breeze here turns out some of the world’s best Sauvignon Blanc, Pinot Noir and Chardonnay – as well as the uniquely South African “Pinotage”. Drink in the region’s healing ‘Champagne air’ along 11km of crisp, cliff walks, or sample some of the bubbly itself at one of the local wineries in Hemel-en-Aarde (‘Heaven and Earth’) set in rolling farmland.


The Marine

Perched on a clifftop along the rugged Hermanus coast overlooking the breath-taking Walker Bay, The Marine more than lives up to its nautical name with two refreshing saltwater swimming pools, and by offering some of the world’s finest land-based whale watching – often directly from the comfort of its sea view bedrooms. Foodies can get a taste for the impressive bounty of the Overberg at the soulful Origins Restaurant, which divides its main courses into specialities from the land and sea. Suggested stay 3 nights.


South Africa

The five-hour drive from Hermanus to Plettenberg Bay is worth every mile, as it spans some of the country’s iconic Garden Route. Break your journey in Mossel Bay, an adventure capital with year-round sunshine, pristine blue flag beaches, and plenty of adrenaline-pumping activities from sandboarding to shark cage diving if you’re feeling brave. Pack a picnic for the Wilderness section of the Garden Route National Park, an oasis of rivers, lagoons, lakes, beaches, forests and mountains where you can truly immerse yourself in nature. If you’re tight on time, squeeze in a stop at Dolphin Point Lookout just west of Wilderness on the N2 towards George, where you’ll be best placed to get a glimpse of these majestic creatures.

Plettenberg Bay

Tucked neatly into the Garden Route, Plettenberg Bay is the kind of place where you can walk through ancient forests in the morning and be on the beach in the afternoon. If you’re arriving at sunset, head to Lookout Beach as the waters turn a dusky pink and the Tsitsikamma Mountains cast a spell-binding shadow. Or wake up early and grab your surfboard to catch some waves at Robberg. If you fancy somewhere a little more off-the-beaten track, make your way to the Keurboom river and its nearby lagoon.


The Plettenberg

As one of the few hotels in the area with direct beach access, The Plettenberg is serenely situated above one of South Africa’s finest bays. Soft blues and soothing tones mirror its waterfront setting, where private villas come with their own heated pools. Continuing the marine theme in the elegant Sandbar, widely known for its tipples and high tea, the hotel restaurant’s inventive seafood dishes and farm-fresh produce also come with views to match. Indulge in a marine-infused skin and body treatment at the Fresh Wellness Spa, or drift off in the infinity pool as seagulls and dolphins dart by. Suggested stay 3 nights.


The best time to visit South Africa is often less about the weather and more about the wildlife. That said, the dry seasons are ideal for going on safari and whales can be spotted from June all the way through to November, while summertime runs all the way through to March – this is prime time when it comes to the views from Table Mountain and Lion’s Head, when the skies are clearest. Remember to keep some cash on you to cover conservation fees when visiting some national parks and wildlife spots.

Seeing the most of South Africa is best done driving, which makes a car (with good working air-conditioning) the essential method of transport. If you’re in need of a rental or transport between hotels, our preferred partner is SIXT – or, as always, ask our Voice Reservation Team for further details.

South Africa


To book the hotels on this independent itinerary, get in touch with our Voice Reservation Team on 0800 0482 314 (UK) 1-877-234-7033 (US). You can find a full list of our dedicated toll-free numbers here. We’re ready and waiting to plan luxury adventures 24 hours a day, seven days a week. So whenever inspiration strikes, just get in touch.

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