Ernest Hemingway

What we offer

Carefree, luxury cycling tours South Africa- Cape Town, Cape Winelands, Whale Coast, West Coast and the Southernmost tip of Africa. Cycling for wine- and nature lovers, beautiful beaches, top tourist attractions.

How it works

We arrange for the transportation of your luggage, route notes and arrange accommodation that offer the best service to our cyclists. It allows you to ride in your own way, at your own pace to relax, explore and remember. If you prefer more independence and are prepared to carry your belongings on your bike, we can offer Bikepacking. To find out more about us and what you can expect on one of our carefree, luxury cycling tours in South Africa, go to How our cycling holidays work.  

Self-guided cycling holidays near Cape Town.

Two of the most popular attractions in Cape Town

Cape Peninsula Cycling

Cape Peninsula Cycling is a 4 day self-guided cycling holiday offered by Trails and Travel. It is an opportunity to discover the most popular tourist destination in South Africa. Cape Town has been named as number one on the prestigious New York Times’ 52 Places to go in 2014 list. In Nov 2019 Cape Town was voted The Best City in the World by readers of the Daily Telegraph in London. This was the seventh consecutive victory for Cape Town.

Cycling tours South Africa

Cape Winelands Cycling

This is an opportunity to experience the Cape's finest wines while discovering the natural beauty of the Cape Winelands, its countryside, esteemed wine estates and historic towns. The tour offers an opportunity to experience the splendour of distinctive and spectacular countryside in and around Franschhoek, Stellenbosch and Somerset West first-hand, and in depth - covering a distance of some 160 km over 5 days.You will be able to sample renowned wines straight from the cellar and dine in some world class restaurants. Together with excellent accommodation, it will make this a trip to remember.

Hermanus cycling holiday includes visits to wine estates

Hermanus Cycling

Hermanus is famous for its champagne air, long stretches of beach, mild climate, rich floral kingdom and the best shore-based whale -watching destination in the world. It is also described as the Riviera of the South. You will have stunning views of Hermanus, the Fernkloof Mountains and Walker Bay, explore the beautiful coastline and cycle through the Hemel-en-Aarde Valley, with wine tasting opportunities at six estates. The cycling holiday is over 4 days (3 nights).

Shipwreck at Southernmost Africa

Shipwreck Cycling

Shipwreck Cycling is a 4- day self guided cycling tour exploring the the southern tip of Africa's rich natural and cultural heritage. More than 250 shipwrecks, interesting villages, history and unspoilt nature

Cycling in West Coast National Park

West Coast Cycling

West Coast Cycling is a 7 day/6 night cycling tour includes two nights’ accommodation in Langebaan and two nights in the quaint village of Paternoster, situated in a beautiful Klein Paternoster Bay, as well as two nights at the unique !Khwa ttu San (Bushman) cultural center. You will also experience the West Coast National Park and and the West Coast Fossil Park and can enjoy local cuisine and hospitality. Up to about 200 km cycling trails in safe environment.

Cyclist and antelope- Whale Coast

Whale Coast Cycling

Whale Coast Cycling offers you a relaxing 5 day, self-guided cycling holiday with an abundance of activities, mostly in a protected environment. It is an outdoor experience with river, sea, sand dunes, the vlei, a floral sensation of rare fynbos plants, diverse antelope and whale watching. Eco boat trip, interpretive marine walk and nature drive included.

Our bikepacking holidays in the Western Cape.

Mount Ceder

Cederberg Wilderness Cycling

Cederberg Wilderness Cycling is a 9 day Bikepacking tour exploring the Cederberg Wilderness area. It is a World heritage area renowned for its spectacular landscapes, rock formations, botanical diversity and ancient rock art.

struisbaai harbour e1596438674695

Southernmost Cycling

The Southernmost cycling is a 7 day bikepacking tour exploring the Agulhas Plain at the southern tip of Africa where the Atlantic and Indian Oceans meet. The route covers interesting villages with friendly, unassuming people, unspoilt nature, unique fynbos and birds, stunning views and an interesting history.

Walking and cycling holidays South Africa

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