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8 Day Southern Cape Trail Family Vacation

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Summary

This eight-day family journey links Cape Town, Hermanus, and De Hoop, blending city icons with coastal nature. Ride the cableway on Table Mountain, meet the African penguin at Boulders Beach, and scan Walker Bay for Southern right whale from June to November, with peak sightings in August and September along this dramatic Southern Cape coastline.

Price Per Person Sharing From:

From: POA

The price can be reduced by substituting accommodations

What influences prices?
Vacation Ref. Code
FV05
Starting Date
Any Date
Starting Point
Cape Town
Ending Point
Cape Town
Customizable
The itinerary can be tailored to your needs
Type
Family Vacation
Accommodation Level
Personal
Countries Visited

Detailed Family Vacation Itinerary: 8 Day Southern Cape Trail

Day 1

Arrival / Cape Town

Overnight: The Commodore
Meals: None

Arrival / Cape Town

Guests are met and welcomed at a location of their choice in Cape Town by their private African Sky guide. Thereafter, you’ll have the opportunity of experiencing a few attractions at the direction of your experienced African Sky guide. The looming Table Mountain was first summited by António de Saldanha in 1503 when he named it “Taboa do Cabo,” or “Table of the Cape.” Send a postcard from the upper cable station post office, take a mountaintop walk along one of the established walkways, or simply enjoy the fantastic panoramic views across the Cape Peninsula. During the cooler part of the day, enjoy a leisurely stroll through Kirstenbosch Botanical Gardens under Skeleton Gorge. Established in 1913, these gardens provide a comprehensive display of the region’s indigenous flora and include an impressive baobab tree in the greenhouse. The “Boomslang” treetop canopy walkway in the Enchanted Forest opened in 2014 and offers a memorable treetop perspective.

Day 2

Cape Town

Overnight: The Commodore
Meals: Breakfast

Cape Town

Prior to European arrival, the Khoikhoi people farmed the Cape Peninsula and surrounds and later traded with early European seafarers navigating the southern tip of Africa. Our morning departure traces a circular route around the Cape Peninsula. The African penguin at Boulders Beach is world-famous and even featured on Animal Planet in a regular documentary. Here it goes about its daily affairs, unruffled by many human eyes. Similarly, the Chacma baboon keeps a close eye on visitors in the Cape of Good Hope Nature Reserve before you head to the lighthouse for panoramic ocean views. Chapman’s Peak Drive hugs the west-coast mountainside toward the city. Watch for the bronze leopard statue that surveys Hout Bay, a memorial to wildlife that once dominated the Peninsula.

Day 3

Cape Town

Overnight: The Commodore
Meals: Breakfast

Cape Town

Today is dedicated to cultural pursuits. We’ll start with a visit to Robben Island, synonymous with Cape Town’s history.

A short ferry ride, departing from the V&A Waterfront, carries passengers across Table Bay. On arrival, guests join a guided tour of the prison buildings, including Nelson Mandela’s cell, where he was incarcerated for eighteen years. The excursion lasts about four hours, after which you’ll return to Cape Town by ferry. First on the afternoon agenda is a visit to the Castle of Good Hope, an early colonial fort that houses a period museum. Nearby, District Six—established in 1867—was a mixed community of freed slaves, merchants, artisans, laborers, and immigrants. Your museum tour offers insight into its history before returning to your overnight accommodations in the late afternoon.

Day 4

Overberg

Meals: Breakfast

Overberg

Saying goodbye to Cape Town, your tour traces the coast from Gordon’s Bay, traveling east via Rooi-Els and Betty’s Bay with the Hottentots-Holland Mountains to your left. Several stops are made at vantage points where the Southern right whale may be spotted. These whale frequent South Africa’s coastline from June to November, traveling roughly 2,000 km from the Southern Ocean to calve in secluded bays. Visit the penguin nature reserve at Betty’s Bay before stopping at Harold Porter Botanical Garden for lunch. Later, pass the Arabella estate en route to Hermanus. Since 1992, Hermanus has hosted the world’s only whale crier, who sounds a kelp horn when whale are sighted. Spend the afternoon exploring the village at leisure, watching whale (in season), or relaxing on a local beach.

Day 5-7

Overberg

Overnight: Opstal Manor House
Meals: Breakfast & Dinner Daily

Overberg

After breakfast, rejoin the N2 highway and continue along the scenic Overberg region of the Western Cape. Stretch your legs in charming Swellendam at the foot of the Langeberg Mountains, the third-oldest town in South Africa. Established in 1746, the town boasts over fifty provincial heritage sites, most in Cape Dutch style. Swellendam was once the eastern extremity of the colony, beyond which lay a largely unknown interior, and many famous travelers—including François Le Vaillant, Lady Anne Barnard, and William John Burchell—passed through. Opt to visit the Drostdy Museum before heading south to De Hoop Nature Reserve, a 34,000-hectare World Heritage Site with a protected marine reserve extending three nautical miles (about 5 km) out to sea. In late afternoon or early evening, consider an eco-boat trip on the De Hoop Vlei, a Ramsar wetland of international importance with around 260 bird species recorded. A variety of activities is available at De Hoop, from a guided interpretive marine walk during low tide to a morning birdwatching hike with a qualified field guide. A guided mountain-biking trail offers spectacular views and potential encounters with the reserve’s wildlife like eland, baboon, and ostrich, and rare species like the Cape mountain zebra and bontebok. Alternatively, head out to the tiny Elim Wine Route and visit the Shipwreck Museum in Bredasdorp.

Note: Activities mentioned are optional and at your own expense.

Day 8

Departure

Overnight: None
Meals: Breakfast

Departure

After breakfast, return to Cape Town along the scenic N2 route and transfer to Cape Town International Airport after a comprehensive tour of South Africa’s Western Cape region.

Included

Guides:
  • Private African Sky Guide: From Day 1–5
Vehicles:
  • Private Air Conditioned Vehicle: From Day 1–5
Accommodation:
  • 3 Nights Commodore
  • 1 Night Harbour House Hermanus
  • 3 Nights Opstal Manor House (De Hoop Collection)
Meals:
  • Only Meals Specified
Flights:
  • None
Transfers:
  • De Hoop Nature Reserve to Cape Town Airport
Activities & Entrance:
  • All Activities Included in the Itinerary, Unless Stated as Optional
  • All Entrance Fees to Places Mentioned in the Itinerary, Unless Stated as Optional
Additional Inclusions:
  • Tourism Levy
  • All Applicable Taxes
  • Park Fees, where Applicable
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Excluded

Excluded:
  • International Airfare (To and From South Africa)
  • Personal and Medical Insurance
  • Drinks
  • Gratuities

8 Day Southern Cape Trail

Plan
Last Updated: November 21, 2025 Curated By: Riaan Viljoen