Remarkably difficult, assuming we’re to ignore places we had to go to through work etc. I’ll stick to places I’ve visited on vacation.
Cairns, Australia. Feeding off a steady flow of backpackers, I found it rather depressing, with a shallow and grubby getting drunk culture. There is appeal outside of it, but definitely not somewhere I’d recommend as a base to explore. I’d come in from Darwin, a quirky / oddball little city, but one that did have charm.
Milano, Italy. This a little harsh, as day trips can give a misleading impression. Highlight was rummaging in a cheap designer clothes outlet away from the centre, but the city felt aloof and pretentious, plus the insistent street hawkers were a near constant irritation. I’m sure a return visit would offer up something to enjoy, but with so many other places to choose from, this would be below hundreds of other places I’d be more keen to go to in Italy.
Siena, Italy. Not awful by any means, but absolutely underwhelmed vs. expectations. I love prep’ing food shops, enoteche, markets, etc. before going, but we had a remarkably bad success rate. The massive market was indeed massive, but ‘more’ didn’t feel like it equated to more variety, quite the reverse in fact. A decent sized co-operative food shop was dull as anything, and even the enoteca nazionale was dead / deserted and significantly failed to get close to expectations. I also tend to avoid the major tourist destinations, and it’s a combination of ignorant tourists and the businesses that suckle from them that grate. On the upside, the small farmers market in the old market square was everything I hoped for in terms of food quality, with every stall we visited impressing for their produce. I’d return for this, but that puts it in day trip territory.
Dorchester, England. This was decades ago, but we’d planned it in as part of a road trip with work colleagues. We’d found loads of lovely places en-route, so surely this historic town would be good? I can’t recall specifics, but nothing about it felt charming, plus the planned accommodation was shit. We had a quick look around for alternatives and soon realised it wasn’t likely to reveal anything decent, so we headed off elsewhere (lulworth cove IIRC)