Discover South Africa's finest wine regions with exclusive cellar access, owner-led tastings, gourmet dining and luxury stays in the Cape Winelands.
This is a journey curated for the gourmet seeker who understands that a true epicurean adventure is not merely about the meal, but the provenance and the people behind it. It is a multi-sensory immersion into the Cape’s culinary vanguard, where the soil, the cellar, and the chef’s table tell a single, seamless story.
Rare Access, Refined Perspectives
From the cool-climate, Burgundy-inflected precision of Walker Bay and Elgin to the sun-drenched, heritage-rich estates of Stellenbosch, you are granted entry into the region’s private cellars.
South Africa stands today as one of the world’s most electrifying wine destinations—not because it adheres to tradition, but because it thrives in the space where heritage meets fearless experimentation. It is a landscape that feels both familiar and surprising, offering wines that are deeply structured yet pulsing with a modern, vibrant energy. Under the guidance of Rex, founder of Wine to Share, this curated sojourn invites you to go beyond the label and discover the rebel spirit and artisanal heart of the Rainbow Nation’s finest boutique winemakers.
"For years, I’ve been importing South African wines directly from these very wineries. I know the people behind the labels. I’ve walked their vineyards, shared meals at their tables, tasted from barrels with the winemakers themselves. This trip exists because of those relationships and it’s something no tour company can offer." Rex Macaskill
We will start the tour in Walker Bay, including Hemel-en-Aarde and Bot River, discovering wines with Burgundy-like finesse shaped by ocean air and slow ripening vines. From there, we move into Elgin, one of South Africa’s most exciting cool-climate regions, celebrated for precision, purity, and vibrant natural acidity. The journey then shifts into the warmer, sun-kissed beauty of Franschhoek and Stellenbosch, where Bordeaux-style blends and Rhône-inspired wines bring depth, structure, and spice.
Wine To Share is a boutique wine specialist and distributor based in Singapore that focuses exclusively on championing South African winemakers. Founded by Rex, a South African native, the company operates on the philosophy that "all wines should be shared, enjoyed, and understood," rather than being reserved only for rare occasions. They specialize in connecting the craftsmanship of South Africa's independent, artisan winemakers with drinkers in Asia, emphasizing high quality and great value.
✨ A Seamless, All-Inclusive Escape: From the moment you arrive, everything is taken care of. Enjoy VIP airport assistance, private luxury transport, and the expertise of a wine-certified professional guide throughout. All food and beverages are included, with dining experiences that are intentionally unforced and unhurried, and can be customised to your preference. For those who wish to delve deeper into the Cape's delights, bespoke add-ons* can be arranged.
🍷 Unfiltered Access: Gain access to a world most visitors never see. Many of your tastings are hosted by the winemaker or vineyard owner.
🍇 Craft Your Own Blend: Become a winemaker for a day. In a signature, hands-on blending session, you will be guided by an expert to create your very own personal cuvée. Taste, experiment, and craft a blend that is uniquely yours—a tangible, personal souvenir of your journey.
*Optional Add-Ons: Challenge yourself on a world-class golf course nestled in the winelands, extend your trip with a thrilling safari escape, or immerse yourself in the region's creative energy with curated art experiences in Cape Town, from exclusive gallery visits to private studio appointments with local artists.
US $7,950 based on twin sharing. Min 8 to travel.
Specific tour dates are confirmed based on the seasonal availability of our partner vineyard owners. We recommend booking well in advance so we can secure a time that aligns with their production calendars.
VIP Arrival Assist upon arrival, fast track through customs.
Transfer to Hermanus, enjoy a Wine Tasting and lunch in the Hemel-en-Aarde Wine region at Creation Wines.
Situated just 140 kilometres from Cape Town and built between the beautiful shores of Walker Bay, Hermanus has grown from a small seaside resort town to become arguably the best-known place for whale watching in the world. This town is also famed for its natural scenic beauty, featuring long stretches of pristine beaches.
This afternoon, explore Hermanus at leisure. We will enjoy dinner at Perlemoen Restaurant.
Creation Wines
Nestled on the scenic Hemel-en-Aarde Ridge in the Western Cape, South Africa, is a haven for wine enthusiasts and nature lovers alike. This award-winning estate is celebrated for its innovative approach to winemaking, producing terroir-reflective wines that embody balance, elegance, and finesse.
Here, you can indulge in expertly curated wine tastings, explore the breathtaking vineyards, and enjoy gourmet food pairings crafted from locally sourced ingredients.
Perlemoen Restaurant
Situated at the water’s edge in the historic Old Harbour of Hermanus, Perlemoen Restaurant offers a selection of seafood dishes, with a focus on locally sourced abalone. The menu includes a variety of starters, mains, and desserts, blending traditional and contemporary flavours. The setting provides views over Walker Bay, and the interior reflects a relaxed, coastal atmosphere.
Accommodation
Harbour House Hotel, Hermanus OR SIMILAR (2 nights)
Located in the heart of the Old Harbour of Hermanus, the exceptional location of the hotel is perfect for exploring this stunning seaside town.
We will explore the Hermel-en-Aarde Wine region with visits to Genevieve MCC and Gabrielskloof Wine Estate.
Tucked between the mountains and the sea near Hermanus in South Africa’s Western Cape, the Hemel-en-Aarde Wine Valley offers a breathtaking fusion of natural beauty and world-class winemaking.
This cool-climate region is renowned for its exceptional Pinot Noir and Chardonnay, crafted by passionate, family-run wineries committed to sustainability.
Gabrielskloof Wine Estate
Gabriëlskloof is a family-owned and run wine estate just off the N2 outside Botrivier. With sweeping views of the Babilonstoren mountains and the surrounding wheat fields, understated architecture and stylish, comfortable interiors. In a relaxing atmosphere, taste their wines and olive oil.
The farm and vineyards were established in 2000, with their first vintage made in the cellar in 2009.
Fisherman's Cottage
Dinner this evening will be at The Fisherman's Cottage, originally a historic building that was built in the late 1800's which was then converted into a small restaurant in 1991. Meet owners Anton and Nicole, kown for their dishes that reflect the coastlines rich variety of seafood.
Accommodation
Harbour House Hotel, Hermanus OR SIMILAR
In the high-altitude Elgin Valley, the maritime breeze and shale soils produce Chardonnay and Pinot Noir of breathtaking, Burgundy-like precision. This is the Cape at its most ethereal—a region where the "cool-climate" isn't just a label, but a perceptible crispness in every glass.
Stellenbosch
Just 45 minutes from Cape Town, Stellenbosch is an enticing Western Cape destination with an exciting culinary scene, photogenic historic buildings, and a youthful atmosphere. The town is surrounded by mountains, vineyards, and nature reserves (Jonkershoek and Simonsberg), making it a charming base for wine tours, day trips, and outdoor adventure.
We will visit La Brune Wines, before continuing on to Beaumont Family Wines for wine tasting and lunch.
La Brune Wines
Winemaker Nico Groblier is known for making world-class Chardonnay and Pinot Noir from the Elgin Valley in the Western Cape. Primarily known for growing apples, Elgin has a cooler climate and produces some of the country’s best Burgundian-style wines. This Chardonnay comes from La Brune’s high density estate vineyard planted on Table Mountain sandstone soils.
Beaumont Family Wines
Beaumont Family Wines, located in Bot River in South Africa’s Overberg region, is a historic family-run wine estate. The farm features the region’s oldest wine cellar, a charming deli, a shop, and one of the country’s oldest working watermills. Visitors can enjoy wine tastings, explore the vineyards, and savour local produce.
This afternoon, we will visit Luddite Wine Farm , time permitting stop at Pergerine Farm Stall.
Luddite Wines
Luddite Wines is a small family winery situated on the Eastern slopes of the Houw Hoek Mountains. Niels and Penny Verburg started in 1999 with the sole aim of making world class Shiraz with a focus on traditional winemaking techniques. The farm spans 8.5 hectares of vineyards and is adorned with 480 olive trees, reflecting the Verburgs’ passion for agriculture and quality produce.
Peregrine Farm Stall
Established in the sixties, Peregrine Farm Stall in Grabouw offers an abundance of locally sourced artisanal goods and wholesome, responsibly farmed, fresh produce. Enjoy artisanal treats and a menu of locally inspired dishes in a scenic orchard setting
Accommodation
Ouwe Werf, Stellenbosch OR SIMILAR (3 nights)
Located in the heart of Stellenbosch on Church Street, Ouwe Werf is the perfect starting point for exploring the town’s world-class restaurants, trendy cafe’s, boutique shops and famous vineyards.
Spend the day in South Africa's Culinary Capital - Franschhoek.
The famed Franschhoek Valley is framed by the majestic mountains of the Cape Winelands, creating a stunning backdrop for its world-renowned vineyards. Founded by French Huguenots in the 17th century, the valley boasts a rich history that is reflected in its architecture and culture.
Visitors can explore charming boutiques, art galleries, and exceptional restaurants, many of which focus on local produce and fine wines. Wine tasting tours provide a chance to sample the region's acclaimed vintages, while outdoor activities such as hiking and cycling allow guests to fully appreciate the valley's breathtaking landscapes and peaceful atmosphere.
Today, we will visit Boschendal Wine Estate, Bellingham Wines and Old Road Wine Company.
Boschendal Wine Tasting
The iconic Boschendal Farm Estate was founded in 1685 and is one of the oldest farms in South Africa. A popular product is their chocolate wine.
Several multi-award winning and limited release vintages are offered by the experienced hosts as visitors are guided through various tastings, seasonal platters and expertly curated food-wine pairings.
Old Road Wine Co.
Both a winery and restaurant, this remarkable establishment is a colourful visual tribute to the artisans of the past, providing its' visitors with unconventional wines and tastings in the stylish tasting room, as well as mouth-watering meals at the restaurant.
Accomodation
Ouwe Werf OR SIMILAR
We will explore Franschhoek, a heritage town and a world-renowned food and wine destination. The estates here attract wine experts from around the globe with their Shiraz, Cabernet Sauvignon, and Cap Classique sparkling wine (among others).
Five-star restaurants alongside the cellars are surrounded by the same jaw-dropping valley scenes that have brought artists and writers to the area for centuries.
Mullineux & Leeu Family Wines
Mullineux & Leeu Family Wines is a highly focused family winery based near the village of Riebeek Kasteel, in the Swartland Region of South Africa. The estate produces a range of hand-crafted wines from the granite and shale-based soils of the area.
Mullineux Family Wines was established in 2007, and was owned and managed by Chris and Andrea Mullineux, with business partners, Keith Prothero and Peter Dart. Within a very short time period the winery established itself as one of South Africa’s most celebrated wine brands, both locally and on the international front. By 2014 they had received twelve 5 star ratings from Platter’s South African Wine Guide, as well as being awarded Red Wine of the Year in 2013 with their 2010 Syrah and Winery of the Year in 2014.
La Petite Colombe
La Petite Colombe is a fine dining restaurant located on the beautiful Leeu Estates in Franschhoek, South Africa. The atmosphere is bright and inspired by nature, using raw materials and transforming them into beautiful objects. There are subtle nods to the La Colombe Dove throughout the space.
Accommodation
Ouwe Werf OR SIMILAR
Included
Today, we will introduce you to our favourite pairing - Brandy and chocolate tasting at Van Ryn Brandy Distillery. We will also visit Uva Mira Mountain Vineyards and enjoy lunch at Spier Wine Estate.
Van Ryn Brandy Cellar
Situated in the heart of the Stellenbosch Valley alongside the Eerste River, Van Ryn’s Brandy Distillery boasts a storied history dating back to 1845. Founded by Jan van Ryn, the distillery upholds a proud tradition of brandy excellence in South Africa. With a focus on maturation, their diverse copper pot stills, including one over 200 years old, symbolize the art of fine brandy crafting. Explore this heritage by joining a Distillery tour, where visitors can sample their acclaimed products.
Uva Mira Mountain Vineyards
Uva Mira translates as "The Wonderful Grape". Uva is the Latin word for grape, Mira means wonderful, miraculous and full of charm. Uva Mira Mountain Vineyards, as high as 620 metres above sea level on the slopes of the Helderberg Mountain Range, nestle against the Helderberg Nature Reserve.
With breathtaking views of False Bay and Table Bay, often wrapped in clouds, a cool climate, sea breezes, a granite foundation and strong minerality of the soil, enhanced by acres of fynbos.... nature does her work.
The Estate is 127 hectares in size - 23 hectares of which are under vine. Six varietals are grown, namely Sauvignon Blanc, Chardonnay, Merlot, Shiraz, Cabernet Franc and Cabernet Sauvignon. The vineyards are positioned between 260 and 620 metres above sea level and only nine kilometres from False Bay.
Spier Wine Tasting
Set within the historic Spier Wine Farm in Stellenbosch, it offers a delightful and immersive experience framed by picturesque farm dam views. Guests may select from a range of thoughtfully curated wines, each designed to showcase the estate’s craftsmanship and connection to the land. With its stunning setting, rich heritage and sustainable practices, Spier Wine Tasting offers a refined yet authentic celebration of South African wine.
Accommodation
Ouwe Werf OR SIMILAR
Set at the confluence of the Indian and Atlantic oceans and backed by the iconic Table Mountain, the bustling city of Cape Town presents an alluring combination of drawcards. Incredible powdery white beaches, highly acclaimed wine routes, and astonishingly beautiful mountain trails surround a cosmopolitan hub. This diverse metropolis is filled with superb shops and restaurants, extraordinary heritage monuments, a multitude of entertainment venues, and a spectacular, chic waterfront harbour.
Table Mountain Cableway
High above Cape Town, the ascent through rocky cliffs reveals sweeping views of the city, coastline, and distant Robben Island. Opened in 1929, this iconic cableway whisks visitors to the summit of Table Mountain, where hiking trails wind through unique fynbos vegetation and scenic viewpoints. Photographic opportunities abound, with panoramic vistas and sunsets, and a diverse ecosystem.
Enjoy lunch at De Grendel Wine Estate
Set high up on Tygerberg Hill, this 300-year-old farm offers breathtaking views of Table Mountain and the Atlantic Ocean and produces premium wines. The tasting room combines modern elegance with historical charm. Vineyards stretch across rolling hills, complemented by fine dining options and guided cellar tours.
For dinner, we have organised an evening of African entertainment at GOLD Restaurant. Participate in interactive Djembe drumming followed by a 14 Dish African Feast with African Dancing and Singing entertainment.
Enjoy an award-winning,14-dish tasting menu inspired by ingredients and textures from all over the African continent. Be seduced by live dancing and singing to the rhythmic beating of African djembe drums.
Accommodation
The Commodore Hotel OR SIMILAR (2 nights)
With panoramic views of Table Bay and Table Mountain, the hotel is a well-known landmark in the Victoria & Alfred Waterfront precinct. Guests will appreciate its design featuring a nautical-themed experience that reflects the city's rich maritime history.
Discover the beauty of the Cape Peninsula - A trip to the southwestern tip of the Cape Peninsula offers some of the most spectacular views in the world! The drive itself is an inspiration and passes steep mountains, secluded coves and sweeping beaches, as well as villages and fishing communities.
Extending into the Atlantic, the rugged Cape Peninsula marks the southwesternmost tip of the African continent. Here, pristine white-sand beaches meet craggy mountains, dotted with charming coastal towns. The southern end features the iconic Cape Point and Cape of Good Hope, while the northern tip is crowned by the world-famous Table Mountain, towering above Cape Town.
Lunch at Two Oceans Restaurant
Renowned for its panoramic ocean views, Two Oceans Restaurant combines fine dining with a relaxed atmosphere. Guests can choose between indoor seating or an extensive outdoor deck, both designed to maximise the stunning scenery. The menu features fresh seafood, including the iconic Two Oceans seafood platter.
We will drive along the coastal route to Hout Bay (optional Seal Island trip out to Duiker Island), continue via the scenic Chapmans Peak onto Cape Point whee you will enjoy lunch with spectacular views.
Leaving Cape Point, stop off in Simons Town at Boulders Penguin Colony.
Boulders Penguin Colony
Boulders Penguin Colony is located near Cape Town, South Africa. This popular tourist attraction offers visitors the chance to observe African penguins at close range and learn more about them. The section also includes three boardwalks that provide easy access to the beach area, and sheltered areas for viewing the birds.
For dinner, enjoy Orpheus and the Raven wine tastings with light pairings of food, specially curated dishes like grilled meat, aged cheeses, stews or fish.
Brenden, owner of Bravo Design in Cape Town, and Etienne, a seasoned winemaker conceived of Orpheus and the Raven as alter-ego’s to ignite philosophical discussions and vinous storytelling.
The mythical character Orpheus, a master of poetry and song, could bend any living being to his will. Reciprocally, the Schwartz family name is celebrated as the Raven. Orpheus, symbolising forward vision, and the Raven, representing encouragement, mirror the core of their collaboration.
Inspired by Renaissance master Albrecht Durer, Schwartz’s ink drawings set the mood and expectation of wines with great depth and complexity. In addition, Louw’s background in engineering and insatiable love for music underscores precision and harmony in his winemaking style.
Accommodation
The Commodore Hotel OR SIMILAR
Included
Today, we say farewell to one of the most culturally and geographically diverse places on earth, South Africa
We hope you've enjoyed its gourmet restaurants, impressive art scene, vibrant nightlife, and beautiful beaches of Cape Town.
Check out after breakfast and transfer to Cape Town Airport.
