The one really nice thing with the Giants Cup Trail is that you can easily bail at the end of day 1, near the end of day 3 and at the end of day 4. If you have a designated driver in your group who doesn’t do the hike (or the role can be switched out halfway) - they can meet the team along the way each day, take your overnight gear for you, head to Underberg to buy supplies as required etc. (aside from night 2, where the hut isn’t accessible by car). It also means if someone isn’t coping and wants to bail, they can easily just move to the support crew.
The route is generally marked by white painted footprints, as long as you make sure you follow these, navigation is relatively easy. There are some spots where losing the route is possible, though, so make sure you know where to go. Some notes:
Day 2: the first 1km is a bit confusing. From Pholela Hut, head towards the paddocks and turn left towards Lakes Cave. After the end of the fence you’ll see a clear trail to the left that you need to take - its very easy to miss if you aren’t paying attention. The ablutions for this hut are hidden in the bushes - walk past the hut to find them. No hot water, but there is a shower and toilet. This hut also has a really nice rock pool next to it.
Day 3 has the most tricky navigation: from the hut, you will cross the suspension bridge over the river, and will soon hit a 4-way junction, go straight at this one - this will start you on the slog up Bamboo Mountain, one of the hardest ascents of the route. Once you are fairly far down the other side of Bamboo Mountain you’ll see a split to the left with a large cairn in the middle of the trail split - go left here. You’ll cross a stream almost immediately and then see a white footprint that tells you it was the correct split - a lot of people go wrong here. You’ll soon walk next to a fence for a while, and then have to cross a fence via a ladder and walk to the tarred road to Garden Castle. Turn right on the road and follow it for 2km - the spot you leave the road is below a windmill on a hill, the turnoff to leave the road is next to the Castleburn Lake sign, there are white footprints to mark it, but they aren’t on the road and are very easy to miss. You will probably lose the trail going past the windmill, but once you’re over the hill you can see the rondavels that are Wintershoek Hut, and if you aim for them, you’ll re-find the trail easily enough.
Day 4: there’s no water this day, so make sure you carry what you’ll need. The trail is mostly obvious, the T-junction near the end is signposted, you go right at this towards Swiman Hut.
Day 5: your first 1km is the last 1km of day 4, but backwards. The final downhill to the finish has a split at one point, left to the finish - right to Bushmans Nek Hut. If you get that split wrong, it adds 500m and doesn’t really matter.
As for whether or not an entirely inexperienced team should attempt this with children - it really depends on the team and the children. Don’t underestimate this trail, it has denied many experienced teams in the past. Weather could be anywhere from baking hot, thunderstorms, hail, mist, snow, wind etc. It also depends on how inexperienced - never even done a parkrun vs done plenty of day hikes but no overnight hikes would be completely different.
I used to take a youngster (11 when we first hiked together) hiking in the Drakensberg, he started hiking with me after his father picked up a back injury and couldn’t take him hiking any more. He first did the Giants Cup Trail with his father at 6, but his father was a very experienced hiker at the time. The ability of a youngster really varies from person to person, and he was definitely the exception, not the rule. He finished his first Drakensberg Grand Traverse (DGT) at 14, and did two more over the space of 16 days at 15. When he was 13 he asked me to take him on a DGT, so I took him on a 7 day evaluation hike (which incidentally included the Giants Cup Trail as part of the loop), and he didn’t cope well. A 5 day hike is no joke, and finding the balance between putting someone off hiking forever and an experience they’ll remember fondly is not easy.
Incidentally a friend of mine has been taking his kids hiking for many years. Before his kids were 10, he managed to get the entire family to the top of Mafadi. His kids are insanely fit, though. His youngest almost beat me at a parkrun when he was 6 years old - and my time was sub 28 minutes, so I wasn’t exactly the slowest person there.
Here’s the story of the time Mike did the Giants Cup Trail in a day at 16 years old: