Why Hermanus
Southern right whales come close inshore here from June to November — often metres from the cliff path, breaching and lob-tailing in front of the town. There are few places on earth where you watch whales from a paved walkway without leaving land. Peak is September–October, when the bay can hold dozens.
From the shore vs. the boat
From the cliff path is free, uncrowded before 10am, and honestly the better experience for most people — you watch at your own pace with no diesel fumes. A boat trip gets you closer and is worth it if you want the scale of a whale next to you, or if the shore sightings are quiet that day. Either way, book the boat the day before, not the morning of.
The town
Hermanus is a real town, not just a whale-viewing platform — it's the hub for the Hemel-en-Aarde wine valley, has a good Saturday craft market, and is the right base for a Whale Coast couple of days. Stay a night; the dawn cliff-path walk before the crowds is the thing.
When to go
August to October for the best chance of close, active whales. September is the sweet spot — the whales are settled, the weather is warming, and the crowds are smaller than the Christmas peak (which has no whales anyway). Bring binoculars and a windproof layer; the coast is windy even in spring.