Which would you say is nicer Simon? I need guidance!
Sheerness is severe - a former military town. There's Georgian cut and struck brickwork, a Martello tower, tall windows in narrow walls and some ironwork. It's dominated by the naval yard, the see wall and, far worse, the modern port. I'm not sure if the steel mill is still going. It's absolutely not pretty. Kind of savage on a wet February morning.
Maldon has a sweet town centre, with a lovely church, the Blue Boar Inn which is 600 years old (and not expensive) and some darling shop frontages. There's a hairdressers that will give you an Essex bouffant and make you feel good about it - that's you, Becs, not me. There's not much sign of the famous battle of Maldon. The quayside has a tradition of smuggling - which was still going on when I first went there in the early seventies. If you're lucky you'll get to see a red-sailed barge.
You have to use your imagination with both of them.
Maldon hasn't got a railway station, so you have to go on to Witham, or, as I say, head for Mersea (now that's something) and take a landing craft over the river. The ride to Maldon is much nicer than the ride to Sheerness, although you could enliven the Sheerness route with a trip down the Military Canal (the dead kiddies are probably too far out of the way) and, if you get an early start, the Dartford bypass is a wonder - it's next to a bird sanctuary and the birdsong is quite something.
It doesn't matter which one you go to - you'll go to the other one before too long