Stellenbosch Tours in Winter
Planning for a trip to Stellenbosch during Winter? We offer 20+ tour packages to Stellenbosch departing in Winter that have 130+ customer reviews. Operated by our hand-picked, qualified travel experts, you will experience the best of Stellenbosch on your Winter holiday.
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10 Best Winter Tours in Stellenbosch
Join one of these handpicked Stellenbosch Winter tour packages, tailored to the season.
3% Off Today
Cycling enthusiasts will find their dream getaway on the "Cycling the Cape & Winelands" tour—a 12-day bicycle adventure that circles out from Cape Town into the heart of South Africa’s most stunning regions. This moderate-activity trip is tailored for experienced travelers eager to immerse themselves in the area’s vibrant scenery, rich heritage, and unique wildlife, all from the saddle.
Pedal along peaceful, low-traffic roads that wind through the iconic Cape Peninsula, where Table Mountain looms over the city and the wild coastline unfurls in dramatic fashion. The route takes you through celebrated wine regions like Stellenbosch and Franschhoek, offering plenty of opportunities to sample local vintages and learn about the region’s deep-rooted viticultural traditions.
Beyond the vineyards, the journey ventures to Cape Agulhas—the continent’s southernmost tip—and traverses the rugged interior, where you’ll encounter distinctive flora and fauna found nowhere else on earth. The ever-changing landscapes, from rolling hills to rocky outcrops and tranquil bays, guarantee every day brings a fresh sense of adventure.
The unique selling point? This tour package combines classic rides, world-famous sights, and off-the-beaten-path discoveries, making it the ultimate way to experience the Cape’s diversity. With expert guides, comfortable accommodations, and small group camaraderie, you’ll enjoy the perfect balance of challenge, exploration, and relaxation in one unforgettable cycling trip.
12 days
USD 4,050fromUSD 3,929
5% Off Today
Tick the Garden Route off your bucket list on South Africa's most famous road trip. Get a view of Table Mountain from vibrant Cape Town, taste world-renowned wines in the Stellenbosch region and spot herds of elephants (as well as penguin colonies), as we travel via cities, beaches, deserts, and forests.
Stellenbosch - Taste world-famous wines as we explore the rolling vineyards of the Cape Winelands.
National Parks - Stay overnight at the coastal Tsitsikamma National Park and spot herds of Elephants on a safari in Addo Elephant National Park.
Hermanus - Visit the whale-watching capital of the world to catch a glimpse of the migrating mammals during the season.
12 days
USD 2,760fromUSD 2,620
11% Off Today
Experience the wonders of South Africa’s southern coast on the Cape Town and the Garden Route - Premium Adventure, a 12-day journey crafted for seniors who appreciate both comfort and discovery. Starting in Port Elizabeth and winding to Cape Town, this easy-activity tour showcases the region’s dramatic cliffs, pristine beaches, and lush forests.
You’ll begin with a luxurious stay at Amakhala Safari Lodge, where private plunge pools and unforgettable game drives await. Along the famed Garden Route, sample wines in Stellenbosch, scan the horizon for southern right whales, and wander through the botanical marvels of Kirstenbosch Gardens. The trip concludes in Cape Town, where the stylish Blackheath Lodge offers a perfect retreat with sweeping city views.
The highlight? This tour uniquely combines wildlife safaris, culinary delights, and coastal scenery, all wrapped in premium accommodation and seamless logistics. For those who wish to savor South Africa’s natural and cultural gems in comfort, this tour package is a top choice.
12 days
USD 7,198fromUSD 6,402
From the wilds of Kruger to the cosmopolitan buzz of Cape Town, "South Africa Highlights" is a 14-day trip that covers the country’s best in one sweeping adventure. This moderate-paced tour brings you face-to-face with elephants and lions on game drives, then whisks you down the iconic Garden Route to the marine wonders of Tsitsikamma National Park and the winelands of Stellenbosch. Whale watching in Hermanus and scenic mountain vistas round out the journey. For the experienced traveler, the USP is clear: a rich diversity of wildlife, landscapes, and local culture—woven together in an unforgettable South African tour package.
14 days
fromUSD 4,370
Step into the vibrant soul of southern Africa on the "Super South Africa" tour, a thoughtfully curated 8-day journey from Johannesburg to Cape Town crafted for travelers who appreciate immersive experiences with a relaxed pace. Begin in Johannesburg, delving into the dynamic culture and poignant history of Soweto, where heritage sites and modern city life blend seamlessly. Your adventure continues with a classic wildlife safari in the renowned Kruger National Park, offering exhilarating game drives and the unforgettable chance to spot Africa’s Big Five in their natural habitat.
The trip then shifts gears to the picturesque Cape Winelands, stopping in Stellenbosch, famous for its Cape Dutch architecture and world-class wines—a true delight for those who savor both culture and cuisine. Your South African escapade culminates in Cape Town, celebrated for its breathtaking scenery and rich historical tapestry. Whether you choose to ascend Table Mountain, meander along the vibrant waterfront, or indulge in some last-minute shopping, Cape Town’s charms are the perfect finale to an enriching exploration.
Combining wildlife encounters, cultural discovery, and scenic wonders, this tour package stands out for its seamless blend of iconic destinations and local flavor, all delivered with the comfort and insight ideal for seasoned explorers. Accommodation, transport, and meals are included, ensuring a worry-free and deeply rewarding South African adventure.
8 days
fromUSD 2,152
From Cape Town’s iconic Table Mountain to the rolling vineyards of Stellenbosch, the Garden Route & Wine Adventure 7D/6N weaves together South Africa’s most celebrated sights in a relaxed, small-group setting. This seven-day explorer tour is designed for young adults and experienced travelers who appreciate both nature and culture.
Explore the dramatic Cango Caves, spot wildlife on guided safaris, and drive along scenic coastal roads to the surfers’ haven of Jeffreys Bay. Savor local flavors in bustling markets and acclaimed wineries, all while enjoying seamless logistics and comfortable accommodations.
The unique selling point of this trip is its perfect balance of adventure, wildlife, and gastronomy—delivering a diverse South African experience with minimal hassle. For those seeking a tour package that’s as delicious as it is scenic, this journey offers something new each day.
7 days
fromUSD 1,126
From Johannesburg’s urban energy to Cape Town’s coastal majesty, this 8-day solo group tour of South Africa weaves history, wildlife, and wine into a wonderfully relaxed itinerary. Discover Soweto’s rich cultural fabric, then seek out Africa’s Big Five in the world-renowned Kruger National Park. Savor the Cape Dutch charm of Stellenbosch and sample local wines before arriving in Cape Town—regularly hailed as one of the world’s most beautiful cities. Stroll along the iconic waterfront, ascend Table Mountain, or simply soak in the scenery before your journey concludes. The real highlight of this tour package is the solo-friendly approach: no single supplement and your own private room, making it easy to enjoy South Africa’s treasures with peace of mind.
8 days
fromUSD 3,254
The "Cape Town & Garden Route Experience in 13 Days" puts the keys to South Africa’s most scenic highlights in your hands. This self-drive trip is ideal for both young adventurers and seniors who value flexibility and discovery. Start with Cape Town’s iconic Table Mountain sunrise, then choose between Robben Island or a full Cape Peninsula tour—each offering unique wildlife and coastal vistas.
Wine tasting in the Western Cape, whale watching in Hermanus, and ostrich encounters in Oudtshoorn add layers of excitement. Explore Knysna’s natural beauty, marvel at the Cango Caves, and paddle through the Featherbed and Tsitsikamma reserves. The journey ends in Port Elizabeth, leaving you with a treasure trove of memories.
The USP: This tour package combines independence with curated experiences, allowing you to set your own pace while still enjoying South Africa’s top attractions—perfect for travelers who want both structure and freedom.
13 days
fromUSD 2,800
15% Off Today
Cape Town’s dramatic coastline, rich heritage, and renowned food scene come alive on the 'Cape Town's Culture And Cuisine, Private Tour.' Tailored for senior travelers seeking relaxation and indulgence, this five-day self-guided trip weaves together the city’s vibrant culture, neighboring Stellenbosch’s wine legacy, and the natural wonders of Boulders Beach.
Discover Cape Town’s unique setting between sea and mountain, stroll through Stellenbosch’s oak-lined streets, and sample the region’s best wines and culinary creations. A highlight is the chance to see African penguins at Boulders Beach, adding a touch of wildlife to this culture-focused tour.
The trip’s unique selling point is its gourmet and cultural emphasis, offering a refined yet relaxed exploration of South Africa’s southern coast. With comfortable accommodations, thoughtfully arranged transport, and included meals, this tour package is perfect for anyone eager to experience the best of Cape Town’s sights and tastes.
5 days
USD 3,284fromUSD 2,792
Experience breathtaking views of South Africa's wine region, Stellenbosch, from a hot air balloon during this ten-hour, guided tour and taste locally produced Methode Cap Classique (MCC) wines, South Africa's equivalent of French Champagne. This tour starts with a pickup at your hotel in Cape Town form where we will drive you to the balloon launch site in Stellenbosch.
See hills swathed with neat rows of vines and quaint buildings from above as you fly over the area. Toast the landing where ever that may be with a traditional glass of sparkling wine and/or orange juice. Our retrieval vehicle will take you back to the venue for breakfast/brunch. Receive a commemorative certificate which proves that you defied the laws of gravity.
Time to sample some locally produced sizzling bubbles after your feet are safely back on the ground during a visit to the wine estates that you flew over. Without any delay, we head off to the house of JC Le Roux, a leading wine estate dedicated exclusively to creating sparkling wine. It was also the first wine estate in South Africa to undertake this endeavour. Using traditional French technique, this wine estate created South Africa's finest, vintage Methode Cap Classiques.
Our next stop Lanzerac Wine Estate. This wine estate came to existence in 1962 when Isaac Schrijver was granted a piece of land by the then Governor of the Cape, Simon Van Der Stel, and it has since grown into an iconic South African wine estate it is today. Sample their Methode Cap Classique (MCC) before it is time to head home. We will drop you off at your hotel in Cape Town after the tour is over.
10 hours
fromUSD 426
See all Stellenbosch Winter Tours
Top Stellenbosch Tour Activities for Winter
From overland journeys tours to explorer and others, here are some popular tour activities in Stellenbosch with departures in Winter.
Stellenbosch Winter Tours for all Age Groups
Stellenbosch tours in Winter designed for all ages—families, young adventurers, seniors, and everyone in between.
Stellenbosch Winter Tour Types
Discover Stellenbosch Winter tours in your way! Choose from group tours, private experiences, solo adventures, or guided and escorted tours.
Stellenbosch Travel Styles
Explore Stellenbosch with our diverse travel styles! Choose from luxurious tours that pamper you with comfort and elegance, or budget-friendly options that let you experience the beauty of Stellenbosch without breaking the bank. Whether you're indulging in fine dining or discovering hidden gems, there's a perfect adventure waiting for you.
Get a customized trip to Stellenbosch in Winter
Plan a multi-country or regional adventure across Stellenbosch in Winter, with help from a local expert.
Carla FerreiraTravel Expert in Mauritius & South Africa
Stephanie LouwTravel Expert in Namibia & South Africa
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