Cycling the Cape & Winelands

Renowned as one of the most beautiful places on Earth, Cape Town and its surroundings provide a stunning backdrop for this tour. Our unique circular route allows us to take in the fantastic sights the Cape Peninsula has to offer. In addition to Table Mountain and the chance to sample the famous wine from the estates of Stellenbosch, the wild coastline and rugged interior provide classic riding on peaceful roads with little traffic. The stunning scenery, a rich cultural history, unique flora, and unusual wildlife encounters make this a fantastic destination to discover on two wheels.

We have selected a combination of three- and four-star hotels and lodges for this cycling adventure across the Western Cape. Each property is well located for our cycling or for nearby attractions. Many of the hotels and lodges have lovely views and most have pools. The normal accommodations used on this trip can be found on the day-to-day itinerary; however, below are a few of the notable places we stay.



Montague: Montague Hotel (night 3)







Between the Cape Winelands and the Garden Route is the Montague Hotel, an architectural gem that opened in 1875. It was refurbished with original art deco and Victorian furniture and has two swimming pools, two restaurants, a spa and a flower-filled garden. An idyllic stop while travelling through the Langeberg mountains.



Hermanus: Windsor Hotel (nights 7-8)







The 120-year-old Windsor Hotel sits opposite Walker Bay, one of the best whale-watching destinations in the world when southern right whales migrate to the bay to breed (July to November). Whale-watching is even possible from the comfort of the hotel restaurant. However, the location of the property is also ideal out of season with a central setting within town and quick access to the 7.5mi (12km) Hermanus Cliff Path.



Simonstown: Quayside Hotel (nights 9-10)







This bright and breezy boutique hotel is centrally located in Simonstown on the water’s edge. Rooms are outfitted with an elegant nautical design and have views of either the Simonskloof mountains or False Bay.