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Ross, we have had a few club night photography shoots around Cheltenham. Around Montpellier is a strong area with the Rotunda and Queen’s Hotel normally floodlit. Usually in February every year many other buildings are floodlit so worth considering. There are also some floodlit modern buildings along Jessop Avenue. Getting high up is more difficult. you can go onto the top level of the car park in the Regency Arcade but no very attractive views. I have always found it frustrating in Cheltenham to find a higher viewpoint for photography so hoping that there will be some more useful replies.
Dave