The one I had the most fun with was when my siblings and I decided to send Mum to Hawaii. All of us gave her a nice piece of luggage the year prior. She was happy, but a little sad, saying the only place she ever visited was Reno. That's when inspiration hit.
We all started planning, I remember working a mess of overtime and forwarding a week of vacation (I got two at that point) so that I would have three for the following year. I complied a box of iconic Hawaiian goodies, mac nuts, a chichi in a can, postcards, and a dummy airline ticket, along with her itinerary. She spent a week on the Big Island and a week on Maui along with my MIL (My FIL told TBG that he deserved a medal for going on a trip with two mothers and a wife.
On Christmas morning, my niece was with Mum and TBG bridged us all onto the phone (my sister from South Carolina, my oldest brother from Reno with us, and my other brother in Florida. My niece took photos as my Mum unwrapped her gift with all of us on the phone with her (this was before VCRs even). Yeah, she was surprised and so excited. We even timed it so that we were there for the Merrie Monarch Festival.
*happy sigh* It was a good one.