Our journey begins in Cape Town, fondly known as the Mother City, where a private transfer brings you to The Winchester, your Atlantic-side hideaway in Sea Point. Fresh sea air sets the tone, with the promenade and open sea just across the road.

Take time to settle into the hotel’s black-and-white interiors and tranquil courtyard. Those arriving early may join an optional storytelling walk from mountain ridge to sea, tracing Cape Town’s layered histories with an award-winning travel writer (available on request).

As evening draws in, we gather for a welcome reception and dinner at Aubergine restaurant, set within the former home of Sir John Wylde, the first Chief Justice of the Cape of Good Hope. In this historic property, built in 1830, we enjoy seasonal dishes, South African wines, and moments to connect with each other – a taste of things to come.

Overnight at The Winchester Boutique Hotel

Follow the curve of the Cape Peninsula along Chapman’s Peak Drive – widely regarded among the world’s most scenic coastal roads – to the Cape of Good Hope. A guided walk on the Lighthouse Keeper’s Trail traces cliff-edge paths shaped by wind, sea, and stories of shipwrecks and beacons.

Signature Experience: Explore the coastline through its wild flavours alongside expert foragers, stepping into the intricate world of intertidal rock pools. Learn to identify native seaweeds and coastal plants, gaining insight into their nutritional value, medicinal properties, and nuanced culinary uses. Afterwards, settle in for an ocean-inspired lunch, where the day’s foraged finds are thoughtfully prepared and shared together.

Return to your hotel for time to unwind, then gather for dinner, watching the light fade along the promenade.

Second night at The Winchester Boutique Hotel

Leaving Cape Town, we journey into the Cape Winelands, where open valleys and distant peaks signal a slower rhythm.

Signature Experience: Step inside a botanical cellar to experience the distinctive flavours of South Africa’s indigenous herbs from the Cape Floristic Region. Guided by a culinary Fynbos specialist, explore rare botanicals and their refined culinary expression, then walk the surrounding renosterveld before sharing an experimental tapas lunch that honours these ancient plants and their enduring vitality.

Continue to Franschhoek for an evening among vineyards and mountain backdrops. We dine at Miko Restaurant, where thoughtfully prepared dishes celebrate contemporary Cape produce and cuisine.

Overnight at Le Franschhoek Hotel and Spa

Travel into the semi-arid landscapes of the Klein Karoo, pausing at Sheilam Cactus Nursery for a private tour of the garden and greenhouses with the third-generation owner.

Lunch follows at The Barn on 62 in Montagu, a characterful restaurant set in a small Breede River Valley town. Continue to Oudtshoorn to settle into Rosenhof Country House, our Signature Stay, a historic restored Karoo homestead framed by fragrant rose gardens and furnished with elegant antiques.

Signature Experience: After dinner at the hotel, enjoy a private stargazing session with expert astronomers, using specialised telescopes to observe Southern Hemisphere constellations and deep-sky highlights. Surrounded by the stillness of the semi-desert, the Klein Karoo is a place where the night sky comes alive.

Overnight at Rosenhof Country House

Today reveals the Klein Karoo through those who shape it. Begin on a fifth-generation mixed farm near De Rust, where the owner shares how resilient farming has evolved to sustain land, livelihoods, and community.

Continue through Meiringspoort’s dramatic gorge for a short walk to its waterfall, then pause in Klaarstroom for coffee and conversation with local hosts.

Lunch unfolds in Prince Albert, accompanied by traditional Riel dancers, before crossing the UNESCO-recognised Swartberg Pass, its winding gravel road opening onto vast mountain horizons and fynbos-rich slopes. The day closes with a Karoo-led dinner, celebrating regional flavours and hospitality.

Second night at Rosenhof Country House

Leave the Karoo and travel toward the coast, arriving at Cape Agulhas, the southernmost point of Africa and the meeting point of the Atlantic and Indian oceans.

After a seafood lunch near the lighthouse, a guided walk along the Rasperpunt Trail reveals the highlights of Agulhas National Park: shoreline fynbos, sweeping coastal views, and the Meisho Maru Shipwreck.

Continuing through historic coastal villages, we reach Hermanus and check into Harbour House Hotel, set just moments from the old harbour.

This evening, enjoy a private dinner in the Cypress Room at Burgundy Restaurant, paired with stories that trace the fishing heritage of Hermanus.

Overnight at Harbour House Hotel

Today is your Signature Day, where you can select an authentic, curated experience to connect deeply with South African culture. You could:

• Join a specialist guide in Zwelihle township, meeting local entrepreneurs and artists, with tastings of home-style dishes and traditional brews.
• Trace the Hermanus coastline on a private guided tour, combining seasonal whale viewing, penguins at Stony Point, and walks through botanical gardens.
• Follow the Hemel-en-Aarde Valley with a local wine guide, tasting cool-climate pinot noir and chardonnay before a leisurely lunch among the vines.
• Take a whale-watching boat trip, led by a whale specialist, with close-up marine encounters and expert interpretation (a private boat operates for our group).

Dinner this evening is enjoyed back at the hotel.

Second night at Harbour House Hotel

Signature Experience: Join marine specialists on an award-winning cruise around Dyer Island – nicknamed the Serengeti of the Sea for its rich marine biodiversity and breathtaking wildlife spectacles. With our expert guides, we have the chance to encounter the Marine Big Five – whales, dolphins, penguins, seals, and sharks – while also learning from a penguinologist how research and rescue efforts protect African penguins, now critically endangered, within this complex marine ecosystem.

Return to Hermanus with time to rest or browse local galleries, before we gather at Fisherman’s Cottage for a farewell dinner this evening. Here, Chef Michael Broughton leads an interactive and elevated potjiekos session before sharing the meal together, with dishes inspired by the Overberg coast.

Third night at Harbour House Hotel

After a last breakfast overlooking Walker Bay, the morning is yours to linger. Watch for whales from the terrace in season, stroll the cliff path one final time or enjoy a slow coffee in town as you reflect on coastlines, farms, and cellar doors now stitched into memory.

When you are ready, your private transfer returns you to Cape Town International Airport for onward flights. This chapter may close, but South Africa’s shores and winelands remain ready to welcome you back.

Alternatively, open a new chapter of discovery by speaking to your Signature Collection travel expert about extending your stay.