Cape Town’s story arcs from indigenous San and Khoi histories through Dutch and British eras to a modern, creative capital. Dramatic Table Mountain frames neighborhoods of Victorian ornament, Art Deco, and edgy street art. It’s a city of two oceans, fynbos-covered peaks, penguin-studded beaches, and vineyards that built a global reputation in only a few decades.

Expect a rich mix of cultures on the plate—Cape Malay spices, braai (barbecue), modern South African fine dining, and winelands picnics. Top sites like the Cape of Good Hope, Boulders Beach, Robben Island, and Kirstenbosch Botanical Garden are world-class, while local markets keep things delicious and down-to-earth.

Practical notes: Uber and Bolt are ubiquitous, and the MyCiTi bus covers key corridors. Weather changes fast; book cableway tickets for early mornings and keep a flexible day or two for wind. Street-smart habits (use e-hailing after dark, keep valuables out of sight) go a long way, and sunscreen is essential—the Cape sun is no joke.

Cape Town

Settle into the City Bowl, Sea Point, or De Waterkant to be close to coffee, markets, and the V&A Waterfront. Sunrise lights Lion’s Head; sunset paints Camps Bay gold. Between, you’ll find design-forward museums, heritage neighborhoods, and ocean horizons that make even short walks feel cinematic.

Getting there & getting around

• Flights: Most international travelers fly into CPT. Typical nonstop times: ~14–16 hours from the US East Coast, ~11 hours from Western Europe (usually via Johannesburg), ~2 hours from Johannesburg. Compare fares on Trip.com flights or Kiwi.com. Expect economy roundtrips from $700–$1,300 outside peak holidays.
• Local transport: Uber/Bolt are the simplest. The MyCiTi bus connects the airport to the Civic Centre and key routes. For the peninsula and winelands, consider a rental car (left-hand driving; highways are excellent).

Where to stay (neighborhood picks)

• V&A Waterfront/De Waterkant: Walkable, great for first-timers, near boats, shops, and the Zeitz MOCAA.
• Sea Point: Oceanfront promenade, fantastic for morning jogs and sunset strolls; quick hop to Clifton/Camps Bay.
• Gardens/City Bowl: Central, leafy streets, tons of restaurants and cafés near Kloof/Long Street.

Browse stays on Hotels.com (Cape Town) or apartment-style options on VRBO (Cape Town).

Days 1–4: Waterfront, City Bowl, and First Mountain Moments

Start gently with the V&A Waterfront: watch working harbor scenes, browse the Watershed design market, and step into Zeitz MOCAA for contemporary African art. A spin along the Sea Point Promenade—rent a bike from local outfitters—sets the coastal tone.

Explore Bo-Kaap (go mid-morning for color-drenched photos and to learn about Cape Malay heritage), the Company’s Garden and the Iziko Slave Lodge for crucial context. If winds cooperate, take the Table Mountain Aerial Cableway near opening time to beat queues; otherwise hike short trails on Lion’s Head or Signal Hill for sunset.

• Coffee & breakfast: Truth Coffee Roasting (steampunk roastery; try the Flat White), Origin Coffee Roasting (single-origin tastings), Kleinsky’s (NY-style bagels; order the salmon latke benedict), Jarryds (brunch and great coffee, Sea Point).
• Lunch: The Granary Café at The Silo (smart casual; views), V&A Food Market (local vendors—get biltong and bunny chow tasters), Meloncino (Italian with harbor views).
• Dinner: FYN (Japanese–South African tasting menu), Kloof Street House (Victorian setting; bobotie spring rolls), Beluga (modern seafood and sushi), Cause Effect Cocktail Kitchen (inventive, Cape botany-led drinks).
• Evening ideas: Tjing Tjing Rooftop (cocktails over heritage rooftops), The Athletic Club & Social (multi-level speakeasy vibe).

Days 5–7: Cape Peninsula Grand Circuit (Table Mountain, Penguins, Cape of Good Hope)

This is the iconic loop: Camps Bay to Chapman’s Peak Drive, Noordhoek, Kommetjie, Simon’s Town (for African penguins), and Cape Point. Go early for empty roads and dramatic light; keep an eye out for ostriches and baboons near the reserve.

Prefer to let a guide handle logistics, entry tickets, and timing? Book a small-group highlights day covering the mountain, penguins, and the Cape.

• Featured tour: Table Mountain, Penguins & Cape Point Small Group Tour Cape Town

  

  Maximize time while hitting the big three; ideal if winds threaten the cableway—guides optimize the order.

• Self-drive tips: Buy a Chapman’s Peak toll e-ticket, bring a windbreaker, and plan 30–60 minutes for penguin boardwalks at Boulders.
• Food en route: Aegir Project (Noordhoek; wood-fired pizzas and craft beer), Olympia Café (Kalk Bay; seafood pastas), Harbour House (sea views over the breakers), The Lighthouse Café (Simon’s Town; Mediterranean-leaning, relaxed).

Days 8–10: Robben Island, Woodstock Creativity, Markets, and Gardens

Robben Island is essential for understanding South Africa’s journey—former political prisoners often co-lead tours. Back on the mainland, spend an afternoon in Woodstock around the Old Biscuit Mill: design stores, Espresso Lab microroastery, and weekend Neighbourgoods Market buzz.

Amble Kirstenbosch Botanical Garden, perhaps timing a summer sunset picnic or an open-air concert. Add District Six Museum to connect landscapes with lived histories.

• Featured tour: Robben Island Half Day Tour with Pre-Booked Entry Tickets.

  

  Pre-booking is wise—sailings sell out, and Cape winds can reshuffle schedules. Combine with city highlights if time allows.

• Eat & drink: The Pot Luck Club (share plates; book sunset), Hemelhuijs (elegant daytime plates; rooibos panna cotta), The Gin Bar (hidden behind Honest Chocolate; order a “Courage”).
• Market highlights: Oranjezicht City Farm Market (fresh, seasonal; Saturdays and Sundays, plus select evening sessions), Neighbourgoods Market (Saturdays; artisanal everything).

Days 11–14: Winelands—Constantia, Stellenbosch, Franschhoek

Shift to vines and valleys. Constantia is close to the city for easy tastings (Groot Constantia heritage, Beau Constantia views). Further afield, Stellenbosch blends Cape Dutch architecture and oak-lined streets, while Franschhoek offers mountain-framed estates and farm-to-table dining.

If you’d rather not drive, ride the famed regional tram and linger at two or three estates instead of rushing six—quality over quantity is the winelands secret.

• Featured tour: Full-Day Franschhoek Hop On Hop Off Wine Tram Tour from Cape Town

  

  Glide past vineyards, hop off for tastings and garden walks, and hop on again—no designated driver needed.

• Estate stops: Boschendal (picnic lawns; farm shop), Babylonstoren (vegetable gardens; seasonal menus), Spier (artisan market; raptor rehabilitation), Tokara (olive oil tastings; sculpture).
• Dining: Chefs Warehouse at Beau Constantia (tapas-for-two with killer views), La Colombe (Constantia; special-occasion tasting), Reuben’s (Franschhoek classic, modern SA plates), Post & Pepper (Stellenbosch; creative small plates).

Days 15–17: Ocean Adventures—Clifton, Camps Bay, Muizenberg, and the Sky

Hit the Atlantic beaches: Clifton’s wind-sheltered coves and Camps Bay’s sunset strip. For gentle surf and colorful beach huts, go to Muizenberg; rent a board and wetsuit right on the sand. Between swims, snack on koesisters (spiced doughnuts) or fresh fish and chips.

Ready for a big memory? Tandem paraglide from Signal Hill or Lion’s Head, soaring over Sea Point and the stadium toward the Atlantic—nothing captures Cape Town’s layout better.

• Featured experience: Cape Town: Tandem Paragliding with the Experts

  

  Weather-dependent; mornings are often smoothest. Photos/video packages are usually available.

  
  
• Eat & sip: Willoughby & Co (V&A; sushi staple—expect a line), The Codfather (Camps Bay; pick your fresh catch and cut), Paranga (Mediterranean plates at sunset), The Bungalow (Clifton; beach-chic).
• Coffee breaks: Deluxe Coffeeworks (old-school espresso focus), Shift (Sea Point; specialty beans), Bootlegger (reliable neighborhood roaster).

Days 18–21: Safaris, West Coast, and Slow Days to Savor

Round out the trip with a one-day Big Five safari near the city (Aquila or Inverdoorn offer guided game drives with transfers). Alternatively, head up the West Coast National Park for azure lagoons and, in August–September, wildflower displays that transform the landscape.

Keep one day open to revisit favorites: a second crack at the Table Mountain cableway if winds foiled it, another linger at Kirstenbosch, or a lazy City Bowl brunch before last-minute shopping at the Watershed and a sunset toast on the promenade.

• Optional featured cruise (for a relaxed final evening): consider a short coastal boat trip from the V&A Waterfront for skyline views and photo moments.
• Breakfast & brunch: Between Us (sourdough toasts, shakshuka), Our Local (plant-filled antique store–café; eggs and pastries), Swan Café (Parisian-style crêpes).
• Final-night dinner ideas: Pier (V&A; seafood-forward fine dining), Belly of the Beast (nose-to-tail tasting menu; intimate), GOLD Restaurant (pan-African set menu with drumming—fun and festive).

Optional add-on tours you can slot anywhere in the 3 weeks

• Table Mountain, Cape Point & Penguins—Private or Shared: Combines the city’s marquee sights in one expertly paced day.
  Book the Small Group Highlights Tour
• Robben Island: Pre-booked tickets and transfers simplify a weather-sensitive excursion.
  Reserve Robben Island with Entry Tickets
• Franschhoek Wine Tram: A carefree way to explore estates without driving.
  Secure Seats on the Wine Tram
• Tandem Paragliding: The most exhilarating city overview you’ll find.
  Fly with Expert Instructors

Booking checklist: Book Robben Island and Table Mountain early in the trip (to allow weather backups), reserve top restaurants weeks ahead (FYN, La Colombe, Chefs Warehouse), and keep one “flex day” per week. For flights, compare on Trip.com or Kiwi.com; for stays, keep an eye on seasonal specials via Hotels.com and VRBO.

Three weeks in Cape Town lets you breathe with the city: hikes when skies clear, winelands when the sun ripens vines, and museums or markets when the winds whip up. You’ll leave with sea salt on your skin, spice on your palate, and a head full of mountain silhouettes—and plans to return.