Boys trip feeling worried

My husband cheated on me numerous times - serial cheating for years before I discovered it. We’re still together as I have a teenage son who has 1 year of high school left. My husband has been remorseful but has not been to therapy and has handled this by never talking about it and pretending it never happened. That’s been difficult for me as it makes me feel like I’m difficult when I need reassurance to heal. He’s also a gambling addict and that’s been difficult to handle. Overall we’ve made progress in handling the situation but there are still ALOT of red flags (Snapchat on his phone and denied it, works remote and never know where he is, deleting calls and text, changing passwords, excessive gambling and financial secrecy). He’s always been remorseful and assures me it was a terrible mistake and he’d never hurt me again. He is now going on a boys trip with male colleagues at the end of the month to a golf resort and casino. I feel weird about this trip and worry he’s taking or meeting someone there. How do I approach this without sounding paranoid? Would men cheat on their wives while with co workers?