Self-Launched: Cycling the Cape & Winelands (12 Days)

Land at Cape Town International and take the MyCiTi bus or an Uber (~£12-15) to your hostel in Observatory or the City Bowl (£16-22/night dorm or private budget room). Afternoon: ride the cable car up Table Mountain (book a timed slot on the Cableway website, ~£20 return) or hike Platteklip Gorge free if the weather cooperates. Evening: pick up your bike from a Cape Town rental shop (Cape Town Bicycle Company or similar, ~£150-180 for 11 days including helmet, lock and spare tubes, booked ahead) and grab a cheap dinner in the Waterfront or Long Street (~£10).

🚌MyCiTi bus or Uber from airport (~£13); walking around the city

🛏Hostel/budget guesthouse, City Bowl or Observatory (~£18)

• →Table Mountain cable car or free Platteklip Gorge hike
• →Collect rental bike
• →V&A Waterfront wander

Ride out along the Atlantic seaboard to Bloubergstrand for the classic Table Mountain postcard view (about 25 km), then north to Melkbosstrand and inland over the Hellshoogte Pass through vineyards. Aim for roughly 50 km. Rather than the tour's private transfer, take the Intercape or Greyhound bus from Cape Town to Stellenbosch (~£8-10) with your bike, or ride the full route if you're feeling fit. Check into a Stellenbosch backpackers (£18-25) and do a self-guided tasting at Boschendal or a town-centre wine bar (~£8).

🚌Bike ~50 km; backup Intercape bus Cape Town–Stellenbosch (~£9)

🛏Stellenbosch backpackers or guesthouse (~£22)

• →Bloubergstrand photo stop
• →Hellshoogte Pass climb
• →Boschendal wine tasting (~£8)

Ride through Franschhoek, up the Franschhoek Pass (a proper 8 km climb with huge views) and down towards Villiersdorp and the Nuy Valley (about 60-70 km if you do the full loop). To reach Montagu without a private van, take the early Intercape/Greyhound from Stellenbosch or Worcester towards Montagu (~£12-15, bike goes in the hold for a small fee) or arrange a shared shuttle via your Montagu guesthouse. Montagu is a compact Karoo town — budget guesthouse ~£25. Dinner at a local bistro ~£10.

🚌Bike ~50-65 km; intercity bus Worcester/Stellenbosch–Montagu (~£13)

🛏Montagu guesthouse or backpackers (~£25)

• →Franschhoek Pass climb
• →Nuy Valley valley views
• →Montagu hot springs (optional, ~£5)

The big Karoo day: from Montagu climb over the Tradouws Pass and ride the sweeping semi-desert plateau towards Barrydale (about 65 km, mostly paved, with a hard-pack section). Stop at the Barrydale or Tradouw co-op cellar for a cheap tasting of local chardonnay and brandy (~£5). Barrydale is tiny — book a guesthouse or the backpackers in advance (~£22). If you'd rather skip the transfer logistics, many travellers arrange a one-way local shuttle from Montagu to Barrydale for ~£20 and ride a shorter loop.

🚌Bike ~65 km; optional local shuttle Montagu–Barrydale (~£20)

🛏Barrydale guesthouse/backpackers (~£22)

• →Tradouws Pass
• →Little Karoo plateau riding
• →Co-op wine cellar tasting (~£5)

Ride back over the Tradouws Pass and down through the Langeberg Mountains to Suurbrak, then on to Bontebok National Park (about 45 km). Park entry is ~£10 and the short self-guided nature trails are free once inside — look for bontebok, Cape mountain zebra and blue cranes. Continue to Swellendam (~£20 dorm or budget B&B). If you don't fancy the climb twice, the early bus from Barrydale to Swellendam runs on the N2 (~£6) and you can ride a loop from town.

🚌Bike ~45 km; optional N2 bus Barrydale–Swellendam (~£6)

🛏Swellendam backpackers (~£20)

• →Tradouws Pass descent
• →Suurbrak village
• →Bontebok National Park trails (~£10 entry)

Roll through Overberg farmland via Bredasdorp towards Cape Agulhas, the southernmost tip of Africa (about 60 km). Cape Agulhas National Park entry is small (~£6), and the lighthouse and the 'two oceans' marker are a ten-minute walk from the car park. There's no direct public transport to Agulhas, so either ride it or book a shared shuttle from Swellendam/Bredasdorp with the local tourism office (~£15-20). Stay in Agulhas or Struisbaai (backpackers ~£20).

🚌Bike ~60 km; optional shared shuttle Swellendam–Agulhas (~£18)

🛏Cape Agulhas / Struisbaai backpackers (~£20)

• →Cape Agulhas lighthouse & southern tip marker
• →Cape Agulhas National Park (~£6)
• →Struisbaai harbour

Ride through the old Moravian mission village of Elim and the rolling farmlands to Kleinbaai (about 55 km), then take a local shared taxi or the Bredasdorp–Hermanus bus to Stanford (~£6) and on to Hermanus (~£8 total). If you're a beer person, the Birkenhead Brewery tasting near Stanford is ~£6. Arrive in Hermanus, the whale-watching capital — in season (Jun-Nov) southern right whales are visible right from the cliff path, free. Backpackers ~£22.

🚌Bike ~55 km; shared taxi/bus Stanford–Hermanus (~£8)

🛏Hermanus backpackers (~£22)

• →Elim mission village
• →Birkenhead Brewery tasting (~£6)
• →Hermanus cliff path whale spotting (free in season)

A rest day. Walk the 11 km Hermanus Cliff Path at dawn for whales (free), or book a boat-based whale-watching trip from the New Harbour if you want close encounters (~£45-55 via GetYourGuide or direct with a local operator). Alternatively do a wine tasting at one of the Hemel-en-Aarde valley estates just outside town (tastings ~£6-10; cycle there in 20 minutes). Catch up on laundry, eat well, and rest the legs for the big coastal days ahead.

🚌Walking/cycling locally

🛏Hermanus backpackers (~£22)

• →Cliff Path walk
• →Optional boat whale watching (~£50)
• →Hemel-en-Aarde wine tasting (~£8)

The long one: 90 km along the Whale Coast from Hermanus through Betty's Bay (penguin colony at Stony Point, ~£4 entry) and Gordon's Bay, then around False Bay to Simon's Town. This is a demanding day with traffic on sections of the R44 — many independent riders split it by taking the Overberg/Boland local bus for the Betty's Bay–Gordon's Bay stretch (~£6) and riding the scenic coastal segments. Simon's Town has a backpackers and a couple of budget guesthouses (~£25).

🚌Bike 60-90 km; optional local bus for part of the route (~£6)

🛏Simon's Town backpackers or budget guesthouse (~£25)

• →Betty's Bay penguin colony (~£4)
• →Whale Coast riding
• →False Bay coastal road

Take the early Metrorail or a shared taxi/uber to Cape Point Nature Reserve (~£10-12 with bike), pay park entry (~£18), then walk from the Cape of Good Hope to the old lighthouse before riding the reserve's quiet coastal roads back towards Simon's Town (about 35 km). Lunch at Boulders Beach and see the penguin colony (~£9 entry). Alternatively there's a daily Cape Point shuttle from Simon's Town if you don't want the logistics (~£12 return).

🚌Shared taxi/uber to Cape Point (~£11); bike ~35 km inside the reserve

🛏Simon's Town backpackers (~£25)

• →Cape of Good Hope & old lighthouse walk
• →Cape Point Nature Reserve cycling (~£18 entry)
• →Boulders Beach penguins (~£9)

The highlight day: ride from Glencairn over Red Hill Pass, along the old navy road to Scarborough, then the legendary Chapman's Peak Drive (toll ~£3 for bikes) to Hout Bay, up Suikerbos Ridge past Llandudno, and on through Camps Bay and the Twelve Apostles to Sea Point (~70 km). If the wind is brutal, hop the MyCiTi bus from Hout Bay back to the city (~£2). Celebration dinner at the Waterfront or a braai at your hostel (~£15). Cape Town hostel ~£20.

🚌Bike ~70 km; MyCiTi bus fallback Hout Bay–city (~£2); Chapman's Peak toll (~£3)

🛏Cape Town hostel/budget guesthouse (~£20)

• →Red Hill Pass
• →Chapman's Peak Drive
• →Camps Bay & Twelve Apostles
• →Waterfront celebration dinner

If you didn't do it on day 1, book the Robben Island ferry and tour (~£25, book ahead — it sells out and is weather-dependent), then return your bike and head to the airport. Alternatively, a Kirstenbosch Botanical Gardens visit (~£9) plus the free Bo-Kaap walk makes an easy last morning before your flight.

🚌MyCiTi/Uber to airport (~£13); walking

🛏—

• →Robben Island ferry & tour (~£25)
• →Kirstenbosch Botanical Gardens (~£9)
• →Return rental bike