Safari, Whales, Cities & Wine: Our 14-Day, Multi-Generational South Africa Adventure

The big day is finally here—what we’ve been planning and dreaming about for over a year! Most flights from the Midwest to South Africa are overnight, so we came prepared with packed snacks, noise-canceling headphones, and plenty of entertainment for the little ones. When traveling with a larger group, lock in seat assignments early so younger kids are near an adult they trust.

Before you take off, I also recommend downloading offline maps of Cape Town and Johannesburg since connectivity can get spotty at times.

And one last tip: tuck some warm layers into your carry on. The plane can get chilly, and July in Cape Town brings those crisp winter temps—think 46–62°F—perfect for cozying up once you land.

Touchdown in Cape Town! We arrived feeling equal parts tired and thrilled—and instantly aware we’d landed somewhere truly extraordinary. One of the very first sights that greeted us was the iconic silhouette of Table Mountain—unforgettable, and it set the tone for everything to come.

After grabbing our bags and clearing customs, we met our pre-arranged private transfer for the ride to the hotel. With a big group (and lots of luggage!), booking transfers in advance is absolutely the way to go—smooth, easy, zero stress.

We kept our first evening intentionally low-key. After checking in and freshening up, we wandered out for dinner in the wonderful Kloof neighborhood. It’s friendly, trendy, super walkable, and perfect for groups trying to find a spot everyone agrees on.

We stayed at the Canopy by Hilton Cape Town Longkloof—clean, stylish, and in a fantastic location.

Dinner was at La Parada on Kloof Street, which worked perfectly for a big family and didn’t require a reservation.

With only four nights in Cape Town, we wanted to make the most of our time—so we booked a private highlights tour, and I highly recommend it. Our guide picked us up right from the hotel and took us south along the Cape Peninsula, home to some of the most breathtaking coastal scenery you’ll ever see.

We started the morning in the colorful Bo Kaap neighborhood before heading up Table Mountain by cable car for those iconic views. Then we continued toward Hout Bay, where we opted for a fun boat ride to see the noisy, adorable Cape fur seals up close.

From there, the route winds along the dramatic cliffs of Chapman’s Peak Drive all the way to Cape Point and the historic Cape of Good Hope. On the way back, we stopped at Boulders Beach—the ultimate highlight—where African penguins waddle freely along the boardwalk and often come right up to you. Our 4-year-old was in absolute heaven.

It was the perfect first full day. And for a group of 11, a private full-day peninsula tour is hands down the most efficient and comfortable way to see so much in just one day.

On day four, we headed into South Africa’s famous wine country—and for me, this was a must. As a longtime wine lover who’s spent plenty of time in Napa Valley, I can confidently say: if you enjoy wine even a little, this day belongs on your itinerary.

Our Winelands tour picked us up right from the hotel for an easy (and incredibly scenic) 1.5 hour drive from Cape Town. The day took us through three of the region’s most iconic areas: Paarl, Stellenbosch, and Franschhoek. Along the way, we passed the former Victor Verster Prison, where Nelson Mandela spent the final years of his incarceration—a quiet, powerful moment that adds depth to an otherwise leisurely day.

Stellenbosch welcomed us with oak lined streets, dramatic mountain backdrops, and world-class estates. Highlights included Boschendal, one of the country’s oldest farms with beautiful gardens and family-friendly open spaces, and Delaire Graff Estate, known for its stunning art collection and sweeping views. We then continued to Franschhoek, the charming “French Corner” of South Africa, celebrated for its culinary scene and relaxed elegance.

While wine tastings are reserved for adults (around $40 per person), many estates are wonderfully welcoming to kids, with open lawns, farm animals, and space to roam and even playgrounds. Perfect for a large multigenerational group!

We wrapped up the evening with a memorable 60th birthday celebration back in Cape Town at the historic Kloof Street House. This beautifully restored Victorian home is as rich in history as it is in craft cocktails. From tales of pirate visits to its past as a burlesque house—and even whispers of lingering ghosts—it’s truly a place to experience, from the food and drinks to the stories and atmosphere.

We took things slow this morning and soaked up a little more of the lovely Kloof neighborhood. It’s filled with charming boutique shops and cozy cafés—perfect for a relaxed late breakfast or brunch. And today was extra special… it was my 45th birthday, so celebration was officially on the agenda.

In true celebratory fashion, our first stop was lunch and a wine tasting at Constantia, the oldest wine estate in South Africa and one of the Cape’s most important historic landmarks. Just 25 minutes from the city, this lush, tree lined valley feels like a peaceful escape. Tastings are relaxed and approachable (around $11 per person), and the expansive gardens make it easy for kids to explore while adults savor the experience.

That evening, we headed to Gold Restaurant in Green Point—and this is far more than just dinner. It’s a full on cultural celebration and a perfect choice for milestone moments. Reservations are a must, especially for large groups. The night featured a 14-dish Pan-African tasting menu, interactive djembe drumming, traditional face painting, and live performances by incredible African dancers.

Festive, energetic, and unforgettable—it was the ideal way to celebrate surrounded by family.

After four unforgettable days in Cape Town, we packed up and headed east to Hermanus—just a scenic 1.5 hour drive away and widely known as the whale-watching capital of the world. This charming coastal town is one of the few places on Earth where we could spot whales right from shore, especially during peak season.

July is prime time, when southern right whales migrate into Walker Bay to calve, and sightings along the famous cliff path are often frequent and dramatic. After checking in, the highlight of the afternoon awaited: a 3 p.m. boat-based whale-watching excursion departing from the harbor—an unforgettable experience for all ages.

After the tour, we enjoyed a leisurely stroll through the Hermanus Cliff Path. It’s a 12km (about 7.5 miles) coastal walk, with beautiful views and local galleries and boutique shops. Unique statues line the coast and it’s super easy to grab a bite to eat at any of the local shops. The perfect way to end the day.

I’m lucky enough to have a family that’s just as adventurous as I am, so when I told them we were going shark cage diving, they all signed up!

We were picked up from our hotel in Hermanus and headed out by boat toward Dyer Island, one of the most famous great white shark habitats in the world and part of the legendary “Shark Alley.” Once at sea, the experience unfolds right from the deck as a submerged cage is lowered alongside the boat, allowing guests to safely get in the water and come face to face with these incredible predators in their natural environment. No diving experience needed, just a sense of adventure and a willingness to get very wet. And if getting in the water isn’t your thing, the action from the boat is just as thrilling.

It’s high energy and unforgettable—it became one of the most talked about moments of our entire trip. My 4-year-old was an absolute champ—wetsuit on, brave smile, and all—proving the apple truly doesn’t fall far from the tree. I feel so incredibly blessed to experience the world with him by my side.

Afterward, we worked up quite an appetite and capped off the day with dinner at Char’d Grill and Wine Bar, one of Hermanus’ most loved steak houses. Incredible food, excellent wine pairings, and the perfect ending to an epic day. Reservations are not needed but recommended, especially for a party of 11.

Finally—it was time for safari! Today we traveled from Hermanus back to Cape Town International Airport to catch our flight to Hoedspruit Eastgate Airport, the main gateway to the greater Kruger region and its legendary private reserves. In under two hours, we left the Atlantic coastline behind and landed in the heart of the African bush, where the landscape, pace, and energy shift completely.

From the airport, we drove about 2.5 hours through the Mpumalanga countryside to the absolutely incredible—and highly recommended—Elephant Plains Game Lodge. Upon arrival, we were welcomed with a refreshing drink and a brief orientation before settling into our comfortable, air-conditioned chalets. This was the perfect moment to unpack, exhale, and fully arrive before our very first evening game drive.

As the sun dipped below the horizon, we headed out in an open Land Rover with an expert ranger and tracker, scanning the bush as night fell. This is when the reserve truly comes alive—lions were heard before they’re seen, leopards moved silently through the shadows, and smaller nocturnal creatures began to emerge. It was a powerful, unforgettable introduction to safari life and a special shared moment across my family.

Elephant Plains is fully all-inclusive, covering accommodations, all meals, two daily game drives, and most beverages. Children of all ages are welcome on drives (though bush walks are reserved for guests 12 and up).

Today was a full immersion into the magic of the Sabi Sands Game Reserve—widely considered one of the best wildlife viewing areas in Africa thanks to its unfenced border with Kruger National Park and its incredible density of the Big Five: lion, leopard, elephant, buffalo, and rhino.

We set out before sunrise for our morning game drive, when the bush is most active and the light feels soft and cinematic. Our ranger and tracker were exceptional, reading fresh tracks in the red sand, listening for alarm calls from impala and hornbills, and interpreting subtle signs most of us would never notice. It felt less like a tour and more like stepping straight into a real life nature documentary.

At 4 p.m., we headed back out for the afternoon and sunset drive—one of the most magical times of day. As the landscape shifted into golden and amber tones, wildlife stirred once again. Sundowners were served in a scenic bush setting as elephants and giraffes moved across the horizon against a glowing Mpumalanga sky. It was picture-perfect!

Safari is intentionally quiet and observational, so if you’re traveling with young children, it helps to prepare them for “quiet excitement,” where stillness is part of the thrill. My 4-year-old amazed both the ranger and tracker with how well he listened and followed instructions—earning us even closer encounters with wildlife. A very proud mommy moment I’ll never forget.

While the morning game drive was always a priority today, we had also built in the option to explore one of South Africa’s most breathtaking scenic routes—the Panorama Route. Located about three hours from the lodge, this iconic drive is known for its dramatic landscapes and sweeping viewpoints. I had included it as a flexible option in case the family was ready for a change of pace from safari.

Turns out, I couldn’t have been more wrong. The entire family was completely mesmerized by the beauty and wonder of the wildlife, and there was zero interest in leaving the bush. So instead, we leaned all the way in and made this our second full day of safari.

We joined both the morning and evening game drives and even participated in guided bush walks—and we’re so glad we did. The sightings just kept getting better. Over the course of our time in the Sabi Sands, we were lucky enough to spot four of the Big Five: lions, leopards, rhinos, and elephants. The only one we missed was the buffalo… which clearly just means we need to come back for another safari someday.

After three incredible nights on safari, our bush chapter came to a close as we flew into Johannesburg, landing at OR Tambo International Airport. The shift in energy is immediate—Johannesburg is South Africa’s largest city, fast-paced, vibrant, and very much a major metro after days immersed in nature.

We stayed near the airport at Emperors Palace, which turned out to be the perfect transition after four days in Kruger National Park. Connected to a casino and the Entertainment Emporium, it feels like a miniature indoor Vegas strip, complete with restaurants, shops, arcades, and entertainment venues.

For the kids, it was a dream—video games, bright lights, and fun after being happily unplugged and wildlife-focused for days. And for the adults, it offered just as much appeal, with great dining options and a lively casino scene featuring just about every cuisine we could imagine. It was the ideal reentry into modern comforts before continuing the journey.

This was our only full day in Johannesburg, and the most convenient and insightful way to experience the city was via the Hop-On Hop-Off City Tour with the Soweto extension. It was an easy and flexible way to get our bearings while covering many of Johannesburg’s most important landmarks at our own pace.

Highlights along the route include the Nelson Mandela Foundation and Constitution Hill, which I highly recommend allowing at least an hour to explore. We also spent time at the Apartheid Museum—an absolute must—where two hours is the minimum needed to fully absorb its powerful, moving, and immersive exhibits.

If time permits, the Soweto extension adds valuable context, offering a deeper look into one of South Africa’s most historically and culturally significant communities.

After a full and thought-provoking day, we headed to the Rosebank neighborhood for a relaxed group dinner at Marble Restaurant. Known for its elevated South African grill cuisine and sweeping city views, it was the perfect spot to unwind, reflect on the day, and enjoy a memorable final evening with an amazing view of Johannesburg.

Today we packed our bags and said goodbye to South Africa.

It’s hard to put into words just how special this journey was—immersive, adventure filled, and truly celebratory from start to finish. After a year of planning, the trip exceeded everything we had hoped for, leaving us with unforgettable memories, deeper connections, and a profound appreciation for this incredible country.

Until next time, South Africa.

After a long 25-hour journey home—with a stop in Frankfurt before continuing on to Chicago—we finally arrived back where it all began.

The jet lag was real, and the transition back to everyday life took a moment, but the memories we returned with made every hour of travel completely worth it.

South Africa left a lasting impression, and it remains firmly on my list of places to return to. I already can’t wait to go back.