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Ascot Private Travel

(L) Cape Cycle & Safari

Cape Cycle & Safari - Map
November 2025 - April 2026
8 Days
3 Location/s
From
USD 12474 
per person
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Full Itinerary

All package tours are fully customizable, allowing you to adjust accommodations and activities to match your preferences.

Talk To Us: seyms@ascottours.co.za

Captivate the most discerning clients with an extraordinary 8-day luxury cycling journey through South Africa’s most stunning landscapes. This exclusive tour combines adventure with sophistication, taking travelers from Cape Town’s cosmopolitan charm to the rolling vineyards of Stellenbosch and the breathtaking coastal routes of Hermanus and Gordon’s Bay.

Along the way, there are world-class dining, intimate wine tastings at renowned estates and unparalleled hospitality in boutique accommodations. With private transfers and expert guides ensuring a flawless experience, this is the perfect offering for those who seek elegance, exhilaration and exclusivity.

Tour Highlights
  • Full Day Guided Cycling Route: Hout Bay, Chapman’s Peak, Kalk Bay
  • Full Day Guided Cycling Route: Cape Town, Bottelary Road & Simonsig Route
  • Full Day Guided Cycling Route: Helshoogte Pass, Kylemore & Boschendal
  • Full Day Guided Cycling Route: Franschhoek to Hermanus
  • Full Day Guided Cycling Route: Hermanus to Gordons Bay 
Included
  • Accommodation
  • Sightseeing
  • Bicycle Rental with a professional cyclist for the cycle day tours
  • All airport transfers
  • Airport meet & greet on arrival
  • 24/7 On-call local support
  • All local tourism taxes and levies
Excluded
  • Flights
  • Visa processing fees
  • Insurance
  • All items of a personal nature
  • All items not explicitly stated

Trip Itinerary

South Africa
Dock House Boutique Hotel

Day 1

Cape Town

Dock House Boutique Hotel

Arrive in Cape Town

Touch down in Cape Town and step into luxury as your personal chauffeur meets you at the airport, ready to transfer you to the elegant Dock House Hotel.

Check in for a rejuvenating two-night retreat, where you’ll have time to relax and refresh. Later, savor a memorable dining experience at the celebrated Terrarium Restaurant.

Day 2

Cape Town

Dock House Boutique Hotel

Hout Bay, Chapmans Peak & Kalk Bay Route

Enjoy a fulfilling breakfast before setting out on a guided cycling journey along the breathtaking coastline. Ride through Hout Bay, traverse the iconic Chapman’s Peak Drive, and explore the charm of Kalk Bay. After a scenic lunch stop, complete your 50-60 km adventure and return to your hotel. Cap off the day with a gourmet seafood dinner at Harbour House, overlooking the harbor, before a relaxing evening stroll.

Cape Cycle & Safari
Lanzerac Hotel & Spa

Day 3

Cape Winelands

Lanzerac Hotel & Spa

Cape Town, Bottelary Road & Simonsig Route 

Check out as your luggage is transferred to the luxurious Lanzerac Hotel & Spa. Meet your cycling guide and begin a scenic 45-50 km ride along Bottelary Road and the Simonsig Route, passing rolling vineyards and stunning landscapes. Pause for a relaxing lunch at a charming wine estate before continuing to Stellenbosch. Arrive at Lanzerac Hotel, settle in for a two-night stay, then enjoy a refined dinner at the Manor Kitchen.

Day 4

Cape Winelands

Lanzerac Hotel & Spa

Helshoogte Pass, Kylemore & Boschendal 

Your day begins with an eager cycling guide and a thrilling ascent up Helshoogte Pass, where panoramic views reward your effort. A smooth descent leads to the quiet village of Kylemore, followed by a scenic ride to Boschendal, one of the Cape’s most historic wine estates.

Pedaling toward Stellenbosch, you weave through lush vineyards before stopping for a well-earned, wine-paired lunch. The relaxed return journey brings you back to Lanzerac, where a guided wine tasting awaits. As the day winds down, a refined dinner at Taphuis caps off your adventure, leaving you with lasting memories of the Cape Winelands.

Cape Cycle & Safari
The Marine Hotel - Hermanus

Day 5

Hermanus

The Marine

Franschhoek to Hermanus via Van der Stel Pass and Karwyderskraal

Transfer to Franschhoek, where bicycles await for today’s adventure. As the sun rises over the vineyards, cyclists embark on a challenging 90 km ride to Hermanus, tackling the demanding Van der Stel Pass and rolling hills of Karwyderskraal.

The ascent to 700 meters rewards with breathtaking valley views before an exhilarating descent. The ride transitions to peaceful farmlands before the final coastal stretch, where the scent of the sea signals the nearing finish.

Arriving in Hermanus, cyclists unwind with ocean views and a two-night stay at The Marine, concluding the day with dinner at The Pavilion Restaurant.

Day 6

Hermanus

The Marine

Hermanus - Day at leisure / Scenic ride

After a demanding ride, take the morning to relax with a slow breakfast and a moment to soak in your surroundings.

If you’re up for more adventure, pedal along the breathtaking Hermanus coastline, where cliffs meet the sea, and whales might make an appearance. Prefer a cultural dive? Wander through the vibrant market, sampling local treats and browsing handcrafted goods.

No rush - spend the day your way, whether exploring, cycling, or just enjoying the laid-back coastal vibe.

Cape Cycle & Safari
Cape Cycle & Safari

Day 7

Gordon's Bay

Chocolate Box Guest Houze

Hermanus to Gordon’s Bay via Clarence Drive

Your journey continues with a scenic cycling tour to Gordon’s Bay. Follow the iconic Clarence Drive, where the ocean meets rugged cliffs, and charming villages dot the coastline.

After an invigorating ride, savor a well-earned sundowner and a seaside dinner. Your chauffeur awaits to whisk you away to the tranquil Chocolate Box Guest House for a peaceful evening.

Day 8

Gordon's Bay

Chocolate Box Guest House

Day of Departure

Enjoy your final breakfast at a leisurely pace, savoring the last moments of your stay. Afterward, you'll check out of your accommodation, and a transfer will be arranged to take you to Cape Town International Airport.

Chocolate Box Guesthouse
Additional Info
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Meals

  • Breakfast daily
  • All lunches on cycle route
  • Welcome Dinner at Terrarium Restaurant
  • Dinner at Harbour House, V&A Waterfront
  • Dinner at Manor Kitchen
  • Dinner at Taphuis
  • Dinner at Pavilion Restaurant
  • Dinner at a local restaurant in Hermanus
  • Dinner at a local restaurant in Gordons Bay