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5 days in Cape Town and the Winelands: a sample itinerary

Five days, one base, no packing up: a day-by-day plan for Cape Town, the Cape Peninsula, the Winelands and the coast.

Five days is enough to see the highlights of the Cape without rushing. This Cape Town itinerary uses Somerset West as a base, so you unpack once and still reach the city, the peninsula, the vineyards and the sea. Each day includes realistic driving times, and you can easily swap days around to follow the weather.

The Cape of Good Hope on the Cape Peninsula

Day 1: arrive and settle in Somerset West

Cape Town International Airport is 33 km from Somerset West, about 25 minutes by car. After check-in (from 14:00), take it slowly: a swim in the pool, a drink at the lapa and an early dinner in town. Our restaurant guide lists our favourite places nearby.

If you land early, you could also visit a Helderberg wine estate on the way. However, a long flight is usually reason enough for a quiet first evening.

Day 2: Table Mountain and the Cape Town waterfront

Leave early and drive into the city, about 40 minutes to Table Mountain. Because the cableway depends on the weather, check whether it is running before you set off. On a clear day, the views from the top stretch far across the Cape Peninsula.

In the afternoon, head to the V&A Waterfront for lunch, shops and harbour views. Alternatively, visit Kirstenbosch National Botanical Garden on the slopes of the mountain. For more ideas, see our city top 10.

Local tip

Keep this day flexible. If the mountain is covered in cloud, simply swap it with day 3 or day 4 and try again later in the week.

Day 3: Cape Point and the peninsula

Today is a full day on the road, and one of the most beautiful. Drive to Cape Point, about 1 hour 15 from Somerset West, and walk up to the old lighthouse. Next, stop at Boulders Beach near Simon’s Town to see the African penguin colony.

On the way back, you can return along the False Bay coast for a shorter drive. Alternatively, take Chapman’s Peak Drive along the Atlantic cliffs, if it is open, and come home via the city. Either way, you will be back in time for the hot tub.

Day 4: a day in the Winelands

Stellenbosch is only 15 minutes from Somerset West, and Franschhoek about 45 minutes. Choose two or three estates, book a long lunch and let a driver handle the roads. As a result, everyone can enjoy the tastings.

Prefer to stay closer to home? The Helderberg estates around Somerset West are excellent as well. Our wine estate guide and our comparison of Winelands towns will help you choose.

Day 5: coast, whales or a last hike

On your last day, stay close to the villa. Walk on Strand Beach, eight minutes away, or take a morning hike in the Helderberg. Between June and November, you could also drive the coastal road to Hermanus, about 1 hour 10 away, to look for southern right whales.

Check-out is at 11:00, but the airport is only 25 minutes away. Therefore, an evening flight still leaves time for a final lunch in the Winelands.

Planning tips for this Cape Town itinerary

A hire car gives you the most freedom on this route. In addition, it pays to book popular restaurants and wine estate lunches a few days ahead, especially in summer. If you would rather not drive, we arrange private day trips to the peninsula and the Winelands.

Finally, the order of the days is flexible. The Cape weather changes quickly, so keep a clear day for Table Mountain and Cape Point, and save the Winelands for a grey one.

Questions about this Cape Town itinerary

Is five days enough for Cape Town?

Five days covers the main highlights: the city, the peninsula and the Winelands. With a week, you can add the whale coast or a safari; see our seven-day plan.

When is the best time for this trip?

The Cape has a Mediterranean climate, with dry, warm summers from November to March and cooler, greener winters. Spring, in September and October, combines mild weather with the whale season.

Do I need a car for this itinerary?

A car is the easiest option. However, we also offer an airport shuttle and private day trips, so you can follow most of this plan without driving yourself.

Why stay in Somerset West instead of the city?

Because you unpack once and reach everything. The airport is 25 minutes away, Stellenbosch 15 minutes and the beach eight minutes, while the city is about 40 minutes. Read more in our guide on choosing a base.

Written by Sonny, Marije and Oliver, owners of Villa Helderberg Guesthouse in Somerset West. Meet the family.

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