Cape Town 3-Week Itinerary

WEEK 1: CAPE TOWN - CITY & COAST
Day 1-3: Arrival & City Immersion
Stay: Ellerman House – Clifton
Highlights:

• Private airport pickup with champagne welcome.
• Afternoon massage at Ellerman House spa.
• Sunset at Signal Hill with a picnic curated by the hotel.
• Dinner at FYN (Cape Town’s fine dining gem with a Japanese-African fusion menu).
• Visit Bo-Kaap – colorful historic quarter. Book a walking tour with a local historian. Photo stop: Chiappini Street for vibrant house backdrops. (our friends place is the red house on the corner)
• Shop local design at Watershed at V&A Waterfront (great for handcrafted home decor and fashion).

Day 4-5: Peninsula Adventure
Stay:
Ellerman House Highlights:

• Private Peninsula Tour:
  • Chapman’s Peak Drive (photo op!)
  • Hout Bay boat ride to Seal Island
  • Boulders Beach (swim with penguins)
  • Cape Point hike and funicular
  • Sweat1000 for a class with Andrew
• Picnic lunch by Cape Point Vineyards overlooking Noordhoek Beach.
• Dinner at The Pot Luck Club – lively tapas-style dishes with a view.

Day 6-7: Urban & Nature Contrast
Stay: Move to The Silo Hotel – V&A Waterfront
Highlights:

• Sunrise hike up Lion’s Head (for those Insta-worthy shots).
• Afternoon shopping at Kat van Duinen, Ruff Tung (Bridget), Merchants on Long (local designers).
• Visit Zeitz MOCAA museum (contemporary African art).
• Sunset drinks at The Silo Rooftop Bar.
• Dinner at Chef’s Warehouse Tintswalo – oceanside fine dining in Hout Bay.

WEEK 2: WINE COUNTRY – STELLENBOSCH & FRANSCHHOEK
Day 8-10: Stellenbosch Serenity
Stay:
Delaire Graff Estate Highlights:

• Wine tasting & art tour at Delaire Graff.
• Romantic dinner at Indochine – Asian fusion with vineyard views.
• Explore Old Town Stellenbosch: Boutique shopping, Schoon Café for brunch, and Oom Samie se Winkel for old-school charm.
• Visit Tokara for olive oil tasting and exceptional views.
• Bike ride through Spier Wine Farm, picnic on the lawn.

Day 11-14: Franschhoek Escape
Stay: La Residence – opulent vineyard retreat
Highlights:

• Take the Franschhoek Wine Tram – hop-on-hop-off through iconic estates like Babylonstoren, Grande Provence, and Rickety Bridge.
• Dinner at Le Coin Français – modern French dining.
• Visit Babylonstoren Gardens – spend the afternoon exploring, lunch at the Greenhouse.
• Afternoon spa & pool time at La Residence.
• Explore Franschhoek Village Market (weekend) for artisanal shopping and food.
• Take a hot air balloon ride for panoramic sunrise views over the valley.

WEEK 3: COASTAL LUXURY + HIDDEN GEMS
Day 15-17: Hermanus – Ocean Meets Wine
Stay: Birkenhead House
Highlights:

• Cliff Path walk – dramatic coastal views, whale-watching (June–Nov).
• Beach picnic curated by hotel.
• Wine tasting at Creation Wines and Hamilton Russell Vineyards – scenic Hemel-en-Aarde Valley.
• Dinner at The Restaurant at Newton Johnson.

Day 18-21: Hidden Coastal Retreat – Paternoster
Stay:
The Strandloper Ocean Boutique Hotel Highlights:

• End the trip in a quiet, romantic fishing village.
• Explore the whitewashed cottages and dine at Wolfgat – one of the world’s best restaurants using foraged ingredients.
• Beach walks, art galleries, and serene sunsets.
• Book a couple’s photography session on the beach during golden hour.

Bonus Tips:

• Photographic Views Not to Miss:
  • Table Mountain from Bloubergstrand
  • Sunrise from Signal Hill
  • Sunset at Clifton 4th Beach
  • Bo-Kaap’s vibrant facades
  • Wine country vineyards at dusk
  • Hermanus cliffs with crashing waves
  • Paternoster’s untouched beaches
• Private Driver: Hire a local guide with a luxury vehicle for day trips.
• Local Markets & Finds:
  • Oranjezicht City Farm Market (Saturdays)
  • Neighbourgoods Market at the Old Biscuit Mill
  • Artisan goods at Woodstock Exchange

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