Leaving breastfed toddler overnight?

[Victoria2002]

DS is going to be 2 this summer and I have a few hen nights and weddings coming up when I would ideally leave him with his dad or my mum for 1 or 2 nights. Part of me thinks it would be unfair/cruel to leave him while he is still breastfed. He is always with me apart from rare occasions when I have left him with DP or my mum for a few hours. They have put him down for a nap successfully but no-one else has ever put him down for the night. He normally breastfeeds at bedtime and often at nap time and around 6am (then rolls over till 7/8am). He won't drink milk/soy milk/almond milk from a bottle or cup but will drink banana milkshake! I think the comfort/snuggles is more important than the actual drink though. Anyone got any experience?
Will he be ok?
Will I need to pump?
Is it better to wean first?

I left DS1 overnight from about 6 months. If he's with his dad or grandma he'll be fine, I wouldn't wean over it (unless you want to of course). I didn't pump but it depends on how comfortable you are I guess.

I have done night shifts (out the house 8pm-10am) from 10 months and all was fine, I do about 3 or 4 nights a month, she needed a few extra dad cuddles at first (now mostly sleeps through). We don't give any other milk when I'm not there. I don't express. She is 18 months now and I would happily go away overnight and have done it to a friends a few times. Not 2 nights as yet...