Advice for 5 day road trip from Sydney, returning to Sydney.

weather wise, by end Oct prob doesn't matter if you go north or south - north you could look at Nelson Bay area (and surrounds); south yes Batemans Bay and surrounds like Sunshine Bay. Given you only have 5 or 6 days I'd be looking at somewhere thats about 1/2 a days travel from Sydney so you have time to relax and enjoy.

I'd suggest Seal Rocks and the Myall Lake area to Forster. You could make it to Port Macquarie but plenty of interest in the first areas

It's a bit one way or the other and either north coast or south coast have their attractions, northwards certainly having a far greater population than going south and both have their beachy hits with plenty of swimming and walking opportunities, the north coast with greater population obviously having more by way of masses but also more eating opportunities though still plenty of that on the south coast too.
For north coast, you could consider places like Nelson bay as suggested, Tea Gardens/Hawks Nest, Lake Cathie just south of Port MacQuarie or going south from Sydney you have places like Kiama, Jervis Bay region for beautiful white sands, Mollymook, Ulladalla before Batemans Bay or going a bit further to Narooma or even Merimbula and Eden region, the whole south coast having more of a quieter vibe to it.
I do have more experience with it, hence knowing it better so a few places you could consider staying at for relaxation would be https://www.murramarangresort.com.au/ , anywhere around Tilba - https://tilba.com.au/accommodation/ ad stayed at https://tilba.com.au/item/central-tilba-farm-cabins/ , a hidden gem and great value, a little way from the beach and restaurants but seclusion makes up for a little travelling as would being at http://www.seahorseinnhotel.com.au/ which is hard to beat for being right on the beach.

There are two ways you can go. North to the Blue Mountains, Port Stephens (nearby at the beach you can ride camels), Newcastle and Port macquarie. Or you could take the lesser known coastal drive on the way to Melbourne. Better not consider visiting Canberra, it really is quite boring unless you like politics and historical museums. Keep in mind that the drives are quite long for Australia and you should really take your time and explore each city. For Port Macquarie you might just be lucky to see the last of the migrating whales. I was lucky in October and saw them as well as dolphins. There is also a koala shelter, beaches and great parklands.

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