GREENWOOD GUIDES

EXPLORE CAPE TOWN & THE PENINSULA

CAPE TOWN & THE PENINSULA

Route 1

Hike Table Mountain with a FairTrade guide, then dive into Cape Town’s creative pulse by shopping its uber-chic independent boutiques like Afraid of Mice on Bree Street and sipping Fair Trade coffee at Bean There on Strand Street. Uncover the San people’s history at the Castle of Good Hope and reflect at the globally significant Robben Island Museum before dining in style at ethical restaurants such as Aubergine and Fyn, or enjoying sustainable bistros like Miller’s Thumb. Swig wine with Black female winemakers at Wine Shaq, reculture at What If The World—an urban art gallery in Woodstock—and dance pantsula, drink umqombothi, and eat shisanyama at Mzoli’s. Round it all off by snorkeling with fur seals in Hout Bay, savoring organic wine from Africa’s oldest wine region at Silvermist in Constantia, and getting goosebumps with a Xhosa Gospel choir on a Sunday morning.

Greenwood Guides - Explore Cape Town & The Peninsula - Map of Route 1

Cape Town – Day 1

Thrilling, laid back, chaotic, refined – Cape Town is all of these and the contradictions don’t end there.  The layers of history in Cape Town stretching right back to the San people and coming right up to date with the winter sun residences of the jet-set make this a city where nothing is what it seems and innumerable visits uncover surprising contrasts every time.  Small wonder then that it’s the continent’s most visited city.

Cape Town hike with mountain view
Experience Cape Town’s creative pulse with Kate Crane-Briggs of Culture Connect. Her expertly researched tours cover art, heritage, architecture, gardens, and private collections. Blending detail with storytelling, they offer insider access to the city’s cultural gems. Join a group tour or book a private experience for deeper discovery.

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Beyond their exteriors—colorful (Bo-Kaap), desolate (District Six), and imposing (The Castle)—lie stories of resilience and culture. A guided tour reveals The Castle’s surprising links to the San people, the deeper history of District Six beyond forced removals, and Bo-Kaap’s unique traditions.

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A UNESCO World Heritage Site and “University of the ANC,” Robben Island shaped leaders like Nelson Mandela. Travel by ferry, then explore privately with Five Star Guides. Guided by a former political prisoner, you’ll gain unforgettable, personal insight into South Africa’s struggle.

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Skip the cable car queues and hike with Dominic Chadbon of The Fynbos Guy. His guided walks reveal the mountain’s history, diverse flora and fauna, and hidden trails. With routes tailored to your fitness, Dominic brings the mountain’s many moods—from the Valley of the Red Gods to Skeleton Gorge—vividly to life.

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On Long Street, Nkula redefines the speakeasy as a space of cultural pride and quiet rebellion. Owned by Simbi Nkula, this 100% Black-owned bar serves only Black-owned wines and handcrafted cocktails. With handmade décor, local sourcing, and inclusive energy, Nkula honours South Africa’s heritage while reclaiming the city’s creative spirit.

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Cape Town image
Cape Town hike with mountain view
FYN $$$
Lion's Head offers breathtaking Atlantic panoramas via a spiraling trail, perfect for magical sunrises or full-moon ascents. For a gentler alternative, the Pipe Track shadows the iconic Twelve Apostles. Access Lion's Head via Signal Hill or Kloof Road. Reach the Pipe Track from Kloof Nek, conveniently located near a MyCiTi bus stop. VIEW LISTING
At VUE on Shortmarket Street, Absie Pantshwa and Chef Vusi Ndlovu redefine African cuisine with bold creativity and cultural pride. Their dishes honour nostalgic flavours—like ujeqe and mussels with Zamalek—while elevating them with refined flair. Locally sourced, Black-owned, and proudly rooted in heritage, VUE celebrates Africa’s evolving culinary identity. VIEW LISTING
A Cape Town classic, Miller’s Thumb blends homestyle charm with outstanding seafood. Run by the warm and lively duo Jane and Solly (“Sane and Jolly”), it’s famous for fresh, inventive fish dishes and a relaxed, joyful atmosphere. After 20 years, it remains a beloved local favourite for good reason. VIEW LISTING
For great value and authentic warmth, stay at the Black female-owned Ikhaya Lodge in Cape Town’s lively City Bowl. Since 2006, it’s been a welcoming hub for locals and travellers alike, offering terrace dining, a private function room, and delicious South and East African dishes served throughout the day. VIEW LISTING
A restored 1771 landmark saved from demolition, Cape Heritage Hotel blends history, art, and sustainability in Cape Town’s Heritage Square. Each uniquely designed room showcases preserved architecture and local artistry. Dine under a centuries-old vine, explore the courtyard’s diverse restaurants, and experience authentic local culture with ethical, community-driven flair. VIEW LISTING
Built in 1895 by Cape Town’s first mayor, Parker Cottage blends heritage charm with modern comfort in Tamboerskloof. This Black-owned, Fair Trade–accredited guesthouse runs entirely off-grid and offers exceptional service, character-filled rooms, and gourmet breakfasts. A tranquil, sustainable stay just steps from Kloof Street’s lively cafes and culture. VIEW LISTING
Cape Town hike with mountain view

Camps Bay – Day 2

Just over Signal Hill and not even ten minutes away from Cape Town’s City Centre lies the Atlantic Seaboard and Camps Bay: this wonderful stretch of coastline was for many years considered to be a hinterland but now plays host to the most popular city beaches and has the vertiginous backdrop of the 12 Apostles, the side buttresses of Table Mountain. This area is all about the beach, glamorous lifestyles and glorious views.

Cape Town hike with mountain view
Lion's Head offers breathtaking Atlantic panoramas via a spiraling trail, perfect for magical sunrises or full-moon ascents. For a gentler alternative, the Pipe Track shadows the iconic Twelve Apostles. Access Lion's Head via Signal Hill or Kloof Road. Reach the Pipe Track from Kloof Nek, conveniently located near a MyCiTi bus stop. VIEW LISTING
In 1988, Pieter Toerien transformed a disused cinema into Theatre on the Bay, building a South African institution. Here, you’ll find year-round, professional entertainment from comedy to musicals. Performers haven't truly made it until they’ve played this iconic venue. Arrive early to enjoy a meal or drink at the bar and restaurant before the show starts. VIEW LISTING
Endorsed by WildChoices.org, the Aquarium is a top Cape Town attraction. Its diverse exhibits highlight South Africa’s incredible coastline. The centerpiece is the entrancing kelp forest, the biome featured in My Octopus Teacher. We highly recommend diving in the tanks—a truly unique experience offered at a very reasonable rate. VIEW LISTING
Soar silently from Signal Hill over coastal mansions to a gentle landing at Winchester Mansions. Parapax Tandem Paragliding offers a sedate yet exhilarating adventure with breathtaking views of Table Mountain and the Atlantic. Whether a beginner or experienced flyer, this is a must-do for an unforgettable perspective on Cape Town. VIEW LISTING
The Atlantic Seaboard is lined with kelp forest, creating a diverse marine environment for wildlife great and small. If the wind is light, head to Kaskazi Kayaks. This unique perspective offers an unforgettable way to experience Cape Town’s coastal beauty and thriving marine life from the water. VIEW LISTING
Cape Town image
Cape Town image
La Parada Kloof Street is a vibrant tapas restaurant in Cape Town, offering a lively atmosphere and delicious small plates. With its trendy decor, excellent cocktails, and social vibe, it’s a perfect spot for a relaxed meal with friends or a fun night out in the heart of the city. VIEW LISTING
The Duchess of Wisbeach is a quirky and eclectic restaurant in Sea Point, offering a whimsical dining experience with delicious food. Known for its lively atmosphere and vintage decor, it serves a range of hearty dishes with a focus on comfort food. It’s a great spot for a fun, casual night out. VIEW LISTING
Codfather Seafood & Sushi is a renowned restaurant in Camps Bay, known for its fresh seafood and sushi. With a unique concept where guests choose their seafood from the display, the restaurant offers a personalized dining experience. The relaxed atmosphere and ocean views make it a favorite for seafood lovers. VIEW LISTING
Ocean View House offers sensational Atlantic views rivalling luxury hotels. This mid-century gem features lush gardens, koi ponds, and three pools. Choose Superior rooms for marginal extra cost to gain private braais or balconies. Located in quiet Bakoven, it’s a short, safe MyCiti bus ride from vibrant Camps Bay. VIEW LISTING
3 on Camps Bay offers surprisingly affordable rooms with stunning mountain and ocean views, just 600m from the beach. Choose Superior Rooms for sea vistas or the private two-bedroom cottage. While the minimalist décor is slightly dated, the value is exceptional. Enjoy buffet breakfasts before exploring nearby Bali Beach or the Kasteelspoort trail. VIEW LISTING
Boutique@10 feels like a welcoming Mediterranean villa, replacing minimalism with a soulful "home" vibe and 70s music. All four suites face the ocean, offering some of Camps Bay's best views. Enjoy breakfast on the pool deck or relax in the art-filled atrium. It’s a peaceful, adult-only retreat conveniently located near a MyCiti bus stop. VIEW LISTING
Cape Town hike with mountain view

UNLOCK THE FULL ROUTE

Sorry but full routes are only available to Greenwood Guide customers. We hope you’ve enjoyed a taste of what’s in included. Buy one of the routes today, now 50% off

UNLOCK THE FULL ROUTE

Sorry but full routes are only available to Greenwood Guide customers. We hope you’ve enjoyed a taste of what’s in included. Buy one of the routes today, now 50% off

UNLOCK THE FULL ROUTE

Sorry but full routes are only available to Greenwood Guide customers. We hope you’ve enjoyed a taste of what’s in included. Buy one of the routes today, now 50% off

UNLOCK THE FULL ROUTE

Sorry but full routes are only available to Greenwood Guide customers. We hope you’ve enjoyed a taste of what’s in included. Buy one of the routes today, now 50% off

UNLOCK THE FULL ROUTE

Sorry but full routes are only available to Greenwood Guide customers. We hope you’ve enjoyed a taste of what’s in included. Buy one of the routes today, now 50% off

Cape Town & Peninsula

Explore Cape Town by hiking Table Mountain, shopping, savoring ethical cuisine, diving into history and culture, and sipping organic wines with unique experiences.

$9.99
$ 4.99