Hi Katie That's a tough one! I love both races, but since there are males and females, I will have to go with the Wine and Dine. My husband and I have done both, but I think he felt a little out of place doing the "Princess" half surrounded by mostly women. (although, I think he enjoyed that part of it too!) We did the Wine and Dine this past October with 3 other couples and it was the best! The things I liked: 1)You don't have to get up early in the morning for the race. 2) The after party was awesome at the International Food and Wine Festival at Epcot. 3) You have more running time on the course through the parks and less on the highway.
As for crowds, either race is really a great time to be at Disney. The crowd level was not an issue during either weekend. There are less runners in the Wine and Dine, so that did make the race course seem a little less crowded. I think that the fun level is at a maximum at both races, but again, I think the guys would probably enjoy the Wine and Dine more since it isn't all about princesses.
If you go to the
runDisney website and click on the race you decide upon, you will find the discount rates for resort rooms and theme park tickets on there. I HIGHLY recommend staying at one of the Disney host resorts. These resorts will offer runner discounts and most importantly, they offer free bus transportation to the expo for packet pick-up and to the start/finish lines of the race. If you are looking to be budget friendly, the Value Resorts are comparable to non-Disney chain hotels in price, and some of them will be host resorts. Every Disney resort is exceptionally clean and have fun themes. Please let me know if I can help you and your friends plan your trip!