This is South Africa at its most sensory: ocean air, wild coasts, and regional flavours. Led by your handpicked Signature Guide, begin in Cape Town, then follow the southern edge where wind-shaped shorelines give way to vineyard-clad slopes and the vast stillness of the Karoo interior. Along the way, reconnect with wild flavours alongside coastal foragers, join marine specialists on a sea safari, and shape your own story in Hermanus on our distinctive Signature Day. This is South Africa revealed through those who know it best — shared slowly, thoughtfully, and with purpose.
Venture to the very heart of each destination on our Signature Collection, where every journey is shaped by our unrivalled local connections and insider expertise. Step beyond the ordinary with private invitations, rare encounters, and experiences few will ever share. So when someone says, “I’ve been there,” you’ll simply smile, knowing you’ve experienced it differently.
Signature Day: Experience our distinctive Signature Day, choosing between immersive optional activities such as a township-led cultural encounter, coastal wildlife exploration to see whales, or a guided wine journey through Hemel-en-Aarde
Signature Stay: Stay at Rosenhof Country House, a restored Victorian homestead in the Klein Karoo, part of this trip’s refined accommodation portfolio
Signature Guide: Let your handpicked Signature Guide lead you to the country’s soul — sharing their home, heritage, and heart
Activity Areas
Culture
Region & Country & City
Africa: Cape Town, South Africa
Included in the Price
Elegant, hand-picked accommodation (7 Premium nights). Signature Stay in Rosenhof Country House, a restored 1852 Karoo homestead - All breakfasts, five lunches and five dinners, featuring restaurants that capture the authentic cuisine of South Africa - Named Signature Guide with outstanding knowledge and guest satisfaction - Complimentary transfers on arrival and departure, plus comfortable transport throughout (private vehicles) - Gratuities for local support staff so every detail of your journey feels effortless
Not Included In The Price
Request a single room if required, purchase travel insurance and arrange any visas and vaccinations.
Map
Itinerary
Day 1 Settle into Cape Town’s rhythm | Welcome reception at Aubergine
Our journey begins in Cape Town, fondly known as the Mother City, where a private transfer brings you to Canopy by Hilton Longkloof, in the Longkloof neighbourhood beneath Table Mountain.
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 to prebook 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.
Day 2 Trace the Cape Peninsula | Join expert foragers to discover the flavours of the coast
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, with dinner at leisure.
Day 3 Travel into the Winelands | Explore the distinct flavours of the Fynbos with a botanical expert
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 Stellenbosch, where we check into our accommodation, before heading out for an evening at Webersburg Wine Estate, where a private cellar tour reveals the story behind the wines before a traditional braai served alongside expertly matched vintages. Surrounded by the beauty of the Cape Winelands, this is an authentic celebration of South African food, wine and hospitality.
Day 4 Journey into the Klein Karoo | An evening gazing at southern skies
After a relaxed start, we travel into the semi-arid landscapes of the Klein Karoo, where we settle into Rosenhof Country House, our Signature Stay, a historic Karoo homestead transformed into a five-star boutique hotel.
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.
Day 5 Discover the heart of the Klein Karoo | Meet farming families and cross the Swartberg
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 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.
Day 6 Stand where oceans meet | Arrive in harbour-side Hermanus
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.
Tracing the coastline through a series of historic villages, we reach Hermanus and check into Whale Rock Luxury Lodge, our home for the final few nights of the journey.
Day 7 Signature Day | Choose township encounters, whales, or wine
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 (9am-12.30pm)
Trace the Hermanus coastline on a private guided tour, combining seasonal whale watching, penguins at Stony Point, and walks through botanical gardens. (9am-5pm)
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 (9am-4pm)
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) (3pm-5.30pm)
Dinner this evening is at leisure.
Day 8 Encounter the Marine Big Five | Share an interactive dinner at Fisherman’s Cottage
Signature Experience: Join marine specialists to 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.
Day 9 Say a fond farewell to South Africa
After a last breakfast, the morning is yours to linger. Stroll the cliff path one final time or enjoy a slow coffee as you reflect on coastlines, farms, and cellar doors now stitched into memory.
When you are ready, your airport 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.
