When you are celebrating 4 friend's birthdays all at once, it ups the ante on the birthday party planning. Simply grabbing a cake and a keg won't cut it. This past friday I was a co-conspirator of a birthday party plan for a group of friends affectionately named "The 4 Horsemen". We chose to hire a Chicago Trolley to squire us around the city...what a blast. The photos don't lie
The trolley launch was 830pm outside of my place. This had the potential to be trouble, I live in Chicago, city people are horrific at arriving on time anywhere for anything. So the plan was for happy hour on the pool deck at 7pm followed by a few entertainment options pre-trolley boarding. The 4 birthday boys were excited and nervous for the entertainment, as they should have been. I had received inspiration from my fantasy baseball auction in Maine in March. The host created a powerpoint roast of the fantasy baseball owners that brought the house down. I decided to do the same thing and enlisted the help of my friend Scott to help properly roast the birthday boys.
A roast has to be done properly or it can be a fiasco. Most people have characteristics or behaviors that make them unique and endeared to all. The trick is to know the roast targets well enough to correctly jab them in a way they can also laugh at. You don't want the guests of honor to feel like crap. But you also want to get a good laugh at their expense. It is a delicate balance. The guys appeared to be laughing along with everyone else so I think the roast goal was achieved. After the roast, the different groups of friends for each birthday boy were more acquainted with the birthday boys. Everyone was warmed up and ready to party.
At this point t-shirts 
were given out to all the guests. You can't do a pub crawl on a trolley without wearing matching shirts commemorating the event. I think it might be a Chicago city ordinance that trolley crawls with shirts get fined. Everyone put on their shirts and we were off to the trolley.
Think of the Chicago Trolley as a rolling VIP room at a club with only your friends invited. 32 people driving through downtown Chicago causing a ruckus is a great way to ring in old age. The trolley allows you to byo-anything, so we had it stocked with food and various beverages for anyone's tastes. The "windows" on the Chicago Trolley are a thick soft plastic, so people can unzip them to create an open-air effect. This was key for cat-calling and harassing people on the street. The open trolley allowed us to engage in a "trolley war" with another group on another trolley. This involves roaring and screaming at the other trolley until they give up trying to out-loud you. Trust me it is much more fun that it sounds.
Despite elaborate bar hopping plans, we only ended up stopping twice. Once for a mass bathroom break which had everyone running off in different directions like ants after their ant hill got kicked over. This led to about 30 reconnaisance missions to track down everyone. The other stop was at Fulton Lounge over in the West Loop. After the first chaotic bathroom stop it was wisely decided to stop at one location that could handle 30 idiots at once rushing in for beverages and bladder relief.
There were no other trolley stops because what would've been the point? Everyone and everything needed for a great night was already on board the trolley. It is better than renting out a room, because your friends are all sequestered in the same space without distractions. Rather than hearing about some of the night's hijinks the next day at brunch, on a trolley you are most likely to be present to witness them occurring real-time. Getting a fun group of good friends to board the Chicago trolley for a night is a guaranteed great time.
Hey, you ought to be our spokesperson! Very happy to read that you had a blast. Thanks for sharing with your friends...
John Curran
Vice President, Charter Sales
Chicago Trolley & Double Decker Co.
Posted by: John Curran | July 24, 2007 at 06:52 PM