I went in 2012, stayed in Birmingham from Thursday to Sunday and went to Cheltenham for Gold Cup Day on the Friday. Birmingham was great, especially over the weekend, which was Paddy's Day. Digbeth was jumping. The train to Cheltenham was very well organised and a good laugh. That's where the fun ended. From the minute we got off the train the day turned into an utter shambles. The town simply can not cope with the size of crowds. Took forever to get to the course on the 'shuttle bus'. In fact we ended up getting off and walking the last couple of miles. We arrived at the turnstile around an hour before the first race yet only got in just as the 2nd race was going off. Huge crushes outside and again once inside. Huge queues for a pint or burger and you could barely see the racing. Being a festival goer and having attended many huge sporting events, I'm used to crowds but this was ridiculous. Felt very unsafe and the course was way too busy. After the racing we had a few pints in town but couldn't get back to Brum quickly enough.
It was 9 years ago though and I think more enclosures have opened since then but I vowed never to return. I have mates who go year in, year out and love it but I've had much better times at Ayr, Perth, Mussy etc. I've got a few pals who go abroad for Chelts week and sit in a sunny pub watch on the telly instead and that's definitely the way to go IMHO.