Outside the Square travel adventures for the "almost independent" Gay traveller and their friends.
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South Africa Cape to karoo

14-day adventure exploring the best of the Cape Town region, winlands and the Karoo all with delightful accomodation.

Small group adventure: Min 6, Max 12
Question? email us
Western Cape Wonders: A 14-Day Cape & Karoo Culinary Adventure

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Embark on an extraordinary 14-day journey that promises a feast for your senses across South Africa's magnificent Western Cape. This itinerary offers a deep dive into the region's diverse landscapes, vibrant culture, and truly exquisite food and wine. From the bustling energy of Cape Town to the serene beauty of the Cederberg, the charming towns of the Little Karoo, and the world-renowned Winelands, this adventure is full of unforgettable experiences with a particular emphasis on local flavours gastronomic delights, and the diverse plants of the region.
This tour is ideal for discerning travelers who appreciate stunning scenery, cultural immersion, exceptional food and wine experiences, and a perfect balance of guided exploration and cherished independent moments.

Day 1-4: Cape Town - The Mother City's Culinary Soul
(4 Nights)

Our South African odyssey begins in Cape Town, a city cradled by mountains and embraced by the ocean. These four full days allow for a comprehensive and immersive exploration of this iconic city and its stunning surrounds, with a special emphasis on its incredibly diverse and burgeoning culinary scene, and guided by our local OTS horticulturist Walter C.
A Taste of Welcome: Our journey begins with a sophisticated welcome dinner at a renowned Cape Town restaurant, designed to awaken your palate with modern South African cuisine, showcasing the nation's vibrant flavours.
We will  delve into the city's heart with a captivating Culture Walking Tour, leading us through the colorful and historic streets of Bo-Kaap, where vibrant houses and cobbled streets tell tales of heritage.
Table Mountain Majesty: Ascend this iconic landmark via the aerial cableway for breathtaking, panoramic views that stretch across the city, coastline, and beyond. Enjoy a leisurely hike around its unique summit, feeling the fresh mountain air.
Coastal Grandeur: Embark on a full-day Cape Peninsula Tour, a scenic masterpiece. Experience the drama of Chapman's Peak Drive, the charming penguin colony at Boulders Beach, and soak in the bohemian atmosphere of Kalk Bay.
Botanical Bliss: Find tranquility amidst the exquisite beauty of Kirstenbosch National Botanical Garden, a perfect setting for a leisurely stroll through diverse fynbos and indigenous flora.

Day 5-6: Clanwilliam & Cederberg - Rooibos & Rugged Beauty (2 Nights)
Leaving the urban buzz behind, we journey north (approx. 2.5 hours) to Clanwilliam, nestled at the foot of the magnificent Cederberg Mountains. This region offers a stark contrast to Cape Town, embracing you with its dramatic landscapes, unique indigenous flora, and distinctive flavours.
Rooibos Revelations: Gain fascinating insights into South Africa's national brew with a visit to a working Rooibos tea farm. Learning about its cultivation from field to cup, culminating in a delightful tasting of various Rooibos infusions and products.
Flavours of the Karoo: Experience a truly authentic dinner showcasing local ingredients, perhaps a traditional Karoo lamb dish or fresh, seasonal produce harvested from the region.
Ancient Art & Landscapes: Explore the Cederberg Wilderness Area, a realm of unique rock formations, stunning vistas, and ancient San rock art on the captivating Sevilla Rock Art Trail.

Day 7: Matjiesfontein - Victorian Charm & Karoo Starry Nights (1 Night)
Today, we journey deeper into the semi-arid Karoo (approx. 3.5-4 hours from Clanwilliam) to the extraordinary Matjiesfontein, a perfectly preserved historic Victorian railway village. This tiny village is a living museum, offering a enchanting step back in time with its own unique and warm hospitality.
Living History: We'll stay at the iconic Lord Milner Hotel, the heart of the village and a central part of this immersive experience. You'll have time to wander the village on foot, soaking in the perfectly preserved Victorian architecture and discovering fascinating historical vehicles and railway artifacts in the local museum.
Celestial Spectacle: As night falls, prepare to be mesmerized. The incredibly clear night skies of the Karoo offer an unparalleled opportunity for stargazing, revealing a universe of wonder above.

Day 8-9: Prince Albert - Olive Oil, Figs & Mountain Delights (2 Nights)
Departing Matjiesfontein, a scenic two-hour drive brings us to Prince Albert, a truly charming Karoo town celebrated for its beautifully preserved Cape Dutch and Victorian architecture, and its burgeoning gourmet scene.
Gourmet Tastings: Delight your palate with an Olive & Fig Farm Visit & Tasting to learn about the cultivation of Prince Albert's renowned olives, olive oil, and figs.
Artisanal Dairy: Indulge your taste buds further at Gay's Guernsey Dairy, where you can sample delicious artisanal cheeses and other dairy products made right on-site.
Farm-to-Table Feasts: Enjoy dinners at thoughtfully selected local restaurants that passionately highlight regional ingredients and authentic Karoo specialties, offering true farm-to-table experiences.
Quaint Discoveries: Explore the quaint streets at your leisure, Browse charming art galleries and artisan shops, soaking in the town's creative spirit.

Day 10: Cango Caves & Klein Karoo Flavors En Route to Montagu (Drive Day with Culinary Stops)
Today is a scenic drive through the heart of the Klein Karoo, punctuated by iconic natural wonders and delectable local flavours.
Panoramic Heights: (Weather permitting) Experience the awe-inspiring Swartberg Pass, one of South Africa's most iconic mountain passes and a UNESCO World Heritage Site, offering truly breathtaking views as we traverse its dramatic slopes.
Underground Majesty: Our main activity today is a visit to the renowned Cango Caves, where we'll explore magnificent limestone caverns, stunning stalactite and stalagmite formations – a truly humbling natural spectacle.
Local Delicacies: Near Oudtshoorn, we'll stop for an ostrich-themed lunch, offering a taste of this local delicacy (with delicious alternative options available for non-meat eaters).
Our day culminates with arrival at our magnificent Art Deco boutique hotel in Montagu, a stylish haven for the next two nights.

Day 11-12: Montagu - Hot Springs, Local Produce & Brandy Heritage (2 Nights)
Montagu
welcomes us with its picturesque charm, famed for its natural hot springs, stunning mountain scenery, and beautifully preserved historical architecture, all intertwined with an emerging focus on local produce and the nearby Brandy Route.
Brandy Route Immersion: Discover South Africa's unique brandy production with a visit to a local brandy distillery for a fascinating tour and tasting experience.
Relax & Rejuvenate: Indulge in the therapeutic mineral waters of the Montagu Hot Springs, a perfect opportunity to relax and rejuvenate amidst serene surroundings.
Historic Stroll: Take a delightful stroll along Long Street, home to beautifully restored Cape Dutch and Victorian buildings, soaking in the town's rich history.

Day 13: Stellenbosch - Historic Winelands Immersion (2 Nights)
Today, we drive from Montagu (approx. 2 hours) to Stellenbosch, the undisputed heart of the Cape Winelands. This charming town is globally renowned for its oak-lined streets, historic Cape Dutch architecture, and world-class wine estates. This day is dedicated to its rich viticultural heritage and vibrant culinary scene.
Town & Tastings: Embark on a fascinating Historic Town Walk through Stellenbosch's charming centre, discovering its numerous wine bars and tasting rooms for impromptu sips.
Vineyard Excellence: Enjoy a curated wine tasting at one of Stellenbosch's prestigious estates, learning about its history, unique terroir, and acclaimed flagship wines.
Culinary Delights: Experience the town's vibrant culinary scene with goodbye dinner at one of its many acclaimed restaurants, perfectly complemented by an excellent wine list.

Day 14: Stellenbosch & Departure - Winelands Grand Finale (Final Day)
Savour a final, delicious breakfast amidst the beauty of the Winelands. After reflecting on your incredible journey, you'll be transferred to Cape Town International Airport (CPT) for your onward flight (approx. 40-50 minutes drive from Stellenbosch), carrying with you unforgettable memories of South Africa's Western Cape.

Notes:
Transportation: This itinerary includes comfortable airconditioned private vehicle transportation with a knowledgeable driver and your dedicated OTS tour leader throughout the tour, ensuring seamless travel and local insights.


Accommodation Level: Enjoy stays in carefully selected 4-star boutique hotels and luxury lodges, offering comfort, character, and exceptional service.
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Pace: This itinerary is designed to offer a balanced pace, combining immersive driving days through stunning scenery with ample dedicated time for in-depth exploration, cultural engagement, and culinary enjoyment at each destination.
Andrew created this lovely video of Cape town on our trip there in 2019 and has kindly agreed for me to share it.
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An Epic South African Adventure.
Cape Town (CPT) to Cape Town
Dates are 11th April - 24th April 2027​


This years trip will be hosted by OTS South African Horticulturist and guide Walter
Open to all Gay and Gay friendly allies.


Highlights Include :-
  • 13 nights lovely accommodation; twin share
  • 13 Breakfasts 
  • 1 Lunches
  • 3 Dinners
  • Wine tastings at our favorite winery.
  • Ground in private aircon vehicle with driver.
  • Visit to Cape-point, and the Penguins of boulders beach.
  • Stellenbosch and exploring the wine region. 
  • 13 nights at our wonderful boutique hotels hand picked by OTS.
  • Table Mountain Cable car ticket.
  • Kirstenbosch gardens entry.
  • Castle of Good Hope entry.
  • Our special welcome and goodbye dinners.
​
Not Included :-
  • Visa, if required.
  • Airfare to and from your home country to (CPT) Cape town 
  • Drinks and meals other than above inclusions.
  • Personal spending money.
  • Local tips​
  • Optional extras on free day eg, Robin island, paragliding, etc

Expressions of interest in this trip are being accepted now. Please express interest ASAP as places are limited Max 12. 

Cost guideline USD (Being finalized)
U$ pp Sharing.
U$ Private room.


This trip requires a $1000 deposit you can secure your place for $500 with the remainder due 12 months out.


Due to the nature of Adventure travel and the prices of the resources on which it depends, the published price of any trip is subject to change at any time, before or after booking confirmation, up to 60 days before the departure.
​Options and methods of payment.
We need 8 people to express interest in joining this trip before we can push the GO button and activate "live" booking . So please  fill in the form below to be kept  up-to-date and ask any questions at any time.

    South Africa Cape & Karoo
    ​​Please add [email protected] to your contacts and check your SPAM folder as I will always reply.

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Picture of gay friendly venue - South African tourism destination
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  • Home
  • 2026 Adventures
    • India "The Ganges" Jan 2026
    • India "The Ganges" Feb 2026
    • Moroccan "Riads" Mixed trip April 2026
    • Moroccan "Riads" Boys trip April 26th 2026
    • Portugal "Vibe" May 2026
    • Sri Lanka "Bawa" Sept 2026
    • India Forts and Palaces Oct 2026
    • Bhutan and Nepal Nov 2026
    • Laos and Northern Thailand Nov 2026
    • Laos 2026 Xmas Mekong Cruise
  • 2027 Adventures
    • Bali for "Nyepi" March 2027
    • Moroccan "Riads" April 2027
    • South Africa Luxury April 2027
    • South Africa Cape to Karoo April 2027
    • South Africa Luxury May 2027
    • Botswana Luxury May /June 2027
    • Portugal "Vibe" May 2027
    • Namibia June 2027
    • Peru and the Inca heartland Sept 2027
    • Argentina and the Andean North Oct 2027
    • New Zealand, "Out" and about. Nov 2027
  • Coming up
    • Cambodia. Our "No single supplement" trip.
    • New Zealand "Epic Vistas"
    • New Zealand South Island "Walks"
    • North Thailand, Bangkok and the wonders of Angkor
    • Argentina Tango 8 day trip
    • Nepal Annapurna Trek
    • Japan explored
  • About us
    • Profiles
    • Philosophy
    • Q&A
    • Booking & Payment Options
    • Arrival and e-sim options
    • Travel Insurance
    • Terms and Conditions
    • Testimonials
    • Contact us
    • Opportunity to join us
    • Botswana extension
    • Victoria falls add-on
    • Cape town add-on
    • Amazon Extension
    • Japan with Alan
    • Moroccan "Mountains & Desert"
    • Links
  • Newsletters