Cape Town: Cape of Good Hope, Penguins & Wine Tasting Day Trip

Summary

Penguins at boulders beach, cape point wild air and constantia wines

You’ll feel Cape Town shift around you as you wander Bo-Kaap’s painted streets with your guide, drive Chapman’s Peak cliffs above crashing surf, watch penguins at Boulders Beach and taste local wine in Constantia. There are laughs with locals, salty sea air at Cape Point, maybe even a seal or two—and plenty of small surprises along the way.

What’s the experience like?

We started out from Cape Town with our guide, Sipho, who kept making us laugh about the city’s “four seasons in a day” weather. He was right — by the time we rolled through Bo-Kaap, the sun bounced off those wild colors and then suddenly a cloud swept over Lion’s Head. The air smelled faintly sweet, almost like baking bread from somewhere nearby. Sipho pointed out the oldest mosque as we dodged a film crew (apparently Americans love shooting movies here). I tried to pronounce “Bo-Kaap” right; he grinned but didn’t correct me. We wandered the cobbled streets for a bit, watching kids chase each other between art stalls.

The drive along Chapman’s Peak was honestly something else — I kept craning my neck for another angle and probably missed half of Sipho’s stories about shipwrecks and that Mercedes accident (nobody got hurt, somehow). The sea on one side looked impossibly blue and cold; on the other side, cliffs shot straight up. At Hout Bay we stopped for coffee by the harbor where seals lounged like they owned the place. Someone nearby was grilling fish — that smoky-salty smell stuck with me for hours. We skipped the ferry to Seal Island this time, but it felt good just to sit with locals chatting about soccer scores.

Eventually we made it down to Cape Point and the Cape of Good Hope. There was this wind that just cut right through you — sharp but clean, if that makes sense. Climbing up to the lighthouse took longer than I thought (I pretended not to be winded). From up there you could see forever: jagged coastline, tangled fynbos, and all these tiny white waves breaking below. A group of baboons watched us from a distance; someone behind me muttered about keeping snacks hidden. The guide talked about how pure the air is here — “breathe deep,” he said — so I did. Maybe it was just being far from everything familiar but I felt lighter somehow.

Boulders Beach was next — penguins everywhere, waddling between sun-warmed rocks or just standing there like grumpy old men in tuxedos. Kids squealed when one splashed close by; even grown-ups couldn’t help smiling at them (myself included). Simon’s Town had this faded colonial vibe and we wandered past old navy buildings and curio shops before lunch (I had snoek for the first time — still not sure what fish it actually is). Last stop was Constantia for wine tasting; I’m not really a wine person but even I could taste why people rave about South African reds. The vineyard cat tried to climb into my lap which made everyone laugh.

On the way back Sipho pointed out where Mandela was once held — just a quick glimpse from the window but it landed heavy somehow. By then clouds were rolling back in over Table Mountain and everything looked softer, more muted. I keep thinking about that moment at Cape Point: wind in my face, nowhere else to be.

Step-by-step itinerary

Day 1 — Cape Town coastal and nature sightseeing

• Visit Bo-Kaap colorful houses
• Walk Bo-Kaap art and craft shops
• Pass by Clifton Beach
• Pass by Lion's Head mountain
• Visit Camps Bay beach
• Pass by Twelve Apostles peaks
• Pass by Llandudno beach
• Visit Hout Bay harbor and shops
• Drive Chapman’s Peak scenic route
• Visit Cape of Good Hope Nature Reserve
• Hike to Cape Point Lighthouse
• Visit Boulders Beach penguin colony
• Explore Simon's Town village
• Optional wine tasting in Constantia
• Drive by Nelson Mandela prison
• Drive by first heart transplant hospital

Top questions

How long does this day trip from Cape Town take?

The full tour lasts most of a day—expect around 8–9 hours including stops.

Are park entry fees included in this tour?

Yes, entry tickets for Cape of Good Hope are included in your booking.

Is hotel pickup provided?

The tour includes pickup from your hotel or central meeting points in Cape Town.

Do you visit Boulders Beach to see penguins?

Yes—the tour stops at Boulders Beach where you can see African penguins up close.

Is wine tasting part of this itinerary?

You’ll stop in Constantia for an optional wine tasting experience near the end of the day.

What wildlife might we see besides penguins?

You might spot baboons, zebras or even whales along certain stretches if you're lucky.

Are meals included on this tour?

No meals are included but there are several places to buy lunch en route—your guide will give recommendations.

Is this tour suitable for families with children?

Yes—it’s suitable for all ages and infants can ride in prams or strollers if needed.

What’s included

Your day includes hotel pickup by a registered guide-driver, bottled water along the way, all entry tickets including Cape of Good Hope access and tolls for Chapman’s Peak Drive—all wrapped into an easygoing pace so you can focus on soaking up every moment before heading back into town together.