This is a full day trip: they pick you up at your accommodation (at around 7 am) and drop you off at the same place (at around 6 pm). And it is well worth. Our guide Phil was great! At the start of our journey he showed us a map and told us the itinerary of the trip. Throughout the whole tour, he was always talking about the fun facts and curiosities. And we even had a quiz at the end (with rewards of course!). We made several stops (and Phil always made sure he would talk about the place we were at): Friendly beach, Wineglass bay lookout, Cape Tourville,Honeymoon Bay. We were fortunate to have very good weather on the day.
For the Wineglass Bay lookout you do need comfortable walking shoes (and appropriate clothing) as the 40 minutes walk can get tiring with all the steps you have to climb. (Phil was always making sure the whole group was ok though). We did not go down to the beach and preferred to go to the other places mentioned before.
This is a great trip to do in one day if you're in Hobart!