I would have to say my best trip pretty much for golf in this manner would be what i did this past february. My father visits Hawaii once a year for business, and this year my whole family was going while I sat in class in freezing Vermont.
So, to surprise my dad, I flew to Maui to play two rounds of golf with him and my brother. The trip was, either way, a two hour drive to Albany from central Vermont, an hour and a half flight to Dulles, six hours to LAX, and five and a half to Kahului, Maui, hour cab ride to hotel. He had business the first day so I play at the hotel (Kaanapali North, a waste of time) but played the next day at Kapalua Plantation, one of my favorites.
Two and a half days later, I returned to Vermont exactly how I came. So basically for a round at Plantation and three hours of snorkeling, I traveled 18 hours each way. The look on the baggage guy's face when I boarded the plane in 25-degree Albany in shorts and flip-flops was priceless.
The Middlebury legend that surpasses this is the story of four guys who, fed up at the lack of quality snow in Vermont one January, drove 24 hours straight to Vail in Colorado for one day of skiing before returning the following day for classes.