
moderate
6 days
Suitable for travelers in average fitness; most activities are accessible with optional short hikes and cable car transport to Table Mountain.
A six-day private circuit from Table Mountain to Cape Point and the Winelands—this trip pairs iconic views, Robben Island history and boutique wine farms with private transport and luxury stays. Expect cable-car climbs, coastal drives and penguin encounters.
You step off the vehicle and the harbor air hits you—salt, diesel and a bright Atlantic cool that seems to polish the city’s colors. Overhead, Table Mountain lays out like a flat-topped ruler, its 1,086-meter summit cut sharply against the sky. This six-day private tour is built around those cinematic moments: the cable car lift to the plateau, the roar of waves below Chapman’s Peak Drive, the compact, waddling penguins at Boulders Beach, and the quiet rows of oak trees shading Cape Winelands estates.

Ferry tickets and tours to Robben Island sell out weeks ahead—reserve this day early to secure your preferred time slot.
Even summer evenings can be cold and blustery along the Peninsula—pack a windproof layer and a warm midlayer.
Boulders Beach and the Atlantic seaboard offer little shade; bring sunscreen, a hat and sunglasses for penguin viewing.
Many small farms, market stalls and parking attendants accept cash more readily than cards—keep some rand on hand.
Cape Town’s landscape is layered with maritime trade history and colonial settlements; Robben Island is a key site of the anti-apartheid struggle where Nelson Mandela was imprisoned.
The region faces invasive plant species and coastal development pressures; support local reserves, follow boardwalk restrictions, and avoid disturbing penguin colonies.
Protects against sudden coastal gusts on Chapman’s Peak and Cape Point.
Support for short hikes, cobbled streets in Stellenbosch and boardwalks at Boulders Beach.
Keeps water, snacks and layers handy during full-day Peninsula and Winelands outings.
Helps capture sweeping mountain-to-sea panoramas and vineyard vistas.