Traveling as a Group: Headache or Great Idea

Vacation Planning for the Whole Family

When my mother and I first went to Chicago to Christmas shop, we had a blast. We knew my dad and my sister were disappointed because they were unable to go. My dad had only been to Chicago once, but he loved it. My sister and brother had never been to the city. Plus, my dad had been hinting for a while he would really like to take a train ride. When I was home for Christmas, we made tentative plans. We would take the train to Chicago for a couple days as a family. My brother was not able to get the time off work, and my sister had just started and internship that may not allow her to go wither, but my parents and I decided we would still go.

Taking the train would be cheaper than the gas money and tolls to get there, plus we wouldn’t have to pay for parking. My parents did not want to drive in the city, so we would use public transportation. That would save money too.

A few months later I asked my boyfriend to come with us. When I invited him, he thought I meant we would drive to Chicago, spend the day, and then drive home that night. He was very shocked when I told him our plan. He didn’t see how the train would save money. He didn’t want the added expense of a hotel. He wanted to be able to drive around the city. To him, his idea would save money. I was afraid he really might choose to decline our offer. Our idea of what the trip looked like differed from his ideas. In the end, he agreed to come along.

2) Is everyone doing their job? If you have the planning responsibilities broken up, is everyone following through? If another person does not do what they are supposed to do, this can have major (and sometimes expensive) effects.

Because of the costs, my mother and I decided to split up the responsibilities. Initially, I was supposed to find the hotel and book train reservations (from Indy to Chicago) for my boyfriend and myself. Mom was supposed to book the train reservations (from Toledo to Chicago) for my Dad, herself and possibly my sister. Later we decided we would all be leaving from Indianapolis, so Mom was now responsible for booking all the train reservations. She had the travel vouchers and the AAA, so it just made sense.

I went online, shopped around and found a hotel. I made the reservations and followed up with the hotel to put in requests for a certain type of room. I figured my mom would have made the train reservations shortly after I had secured us a place to stay. Instead, she kept putting it off. I kept explaining to her how Amtrak works. The fuller a train is, the more expensive the train fare is. The longer she waited to make her purchase, the more it would end up costing her. Plus, I did not want to find out that the train was sold out because she waited too long to make our reservations.