He likes golf. Cigars. The usual man stuff. He is already getting a new phone. So iphone is out of the question. I need to find something great for under $300 USD!
If he smokes cigars, Scotch is probably high on his list, too.
A bottle of good single malt (Macallan 21) will run you less than an iPhone, as will a few lessons with a golf pro (unless your father's already quite good).
If there's something he needs for the car, or for his new phone (bluetooth hands-free headset) that might be a good idea, as well.
If your dad is single (most who play golf and smoke cigars are - now) how about a hooker? Or better yet, a hooker who plays golf along with a green fee at a nice course? Both can be had for about $300, but it would only have to be for a quick 9 holes.
No, seriously - a monogrammed set of the best golf balls they sell along with a gift certificate to a golf shop. Offer to get his clubs re-gripped (most of us hacks neglect the grip till it is almost past the no return point). Depending on where he lives, if there is a top notch PGA course nearby, score him a green fee there. Better yet, score some tickets to a PGA event nearby. Perhaps he is a wine drinker - a case of good wine can be had for around $300. Either way, he will like it coming from you. I wish I could be so lucky. All I got from my kids were some macaroni refrigerator art. I still like the golfing hooker idea though - keep it on the table anyway. :)
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