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Brian Lehrer: Brian Lehrer on WNYC. To end the show each day during the membership drive, we're talking travel tips, and joining us again is Michelle Singletary, personal finance columnist for The Washington Post. She's here to talk today about the finances and some of the other dynamics of group vacations. Uh-oh, Michelle, welcome back to the show. Hi.

Michelle Singletary: Thank you so much for having me.

Brian Lehrer: Before we get started with your tips for this, we just have to ask you, are you for or against traveling with friends and extended family generally, or you have no general rule?

Michelle Singletary: I actually love traveling with family. Every couple years, my husband and I host families at different places around the world, really. I think it's a great way for families to bond, and I'm a big believer in it, but with lots and lots of rules.

Brian Lehrer: I have one of my own, which is there was a trip I was going on with-- planning with some extended family, bunch of people, and one of the relatives said, "I saw this big house that we can rent and we can all live in the house." I said, "I love you all. I want to be with you on this trip, but I want my own hotel room."

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Michelle Singletary: That's a really good rule. I actually like the big house. A couple years ago, we rented a house in Mexico, and it was about 10 of us. It was lovely. Everybody had their own room, and there was a pool there. It was such a great trip. We all got along, and it was fabulous.

Brian Lehrer: Now, one of your rules is communicate clearly your travel, traveling style, and budget. Before we get into the heart of what you really do for a living, which is personal finance and the budget side of this, I just gave you one example of my personal style. I just know I'm going to sleep better if I have really my own room. What about anybody? What are some of the big style points that you get into?

Michelle Singletary: The big thing is when you are planning a group trip, you have to communicate clearly the cost and everything and not just the lodging, which is what you were talking about. If you're going out to eat, excursions, just make sure you've got a good grasp of what everything's going to cost and clearly communicate it to everyone.

We have family meetings before the trip, and we were talking what everybody's responsibility was and how we would even negotiate if there's a conflict that comes up. We talked a great deal before the trip. Communication is just key, so everybody is clear. We sent emails, so there was nobody saying, "I don't remember you saying that." There was a paper trail of all the agreements of what we were going to do on the trip.

Brian Lehrer: My mom was just telling me a story a couple of weeks ago of a trip they took with just one other couple, but that other couple, they wanted to sit around, sit on the beach, and my parents wanted to get into the neighborhoods and stuff where they were traveling, and go do things. That's the kind of thing you have to negotiate in advance, too.

Michelle Singletary: You do. I think you should travel with people who have a similar traveling style. I love just sitting hours and hours on a beach. When I travel, that's the kind of person I would travel with. Now, if you still want to travel with that person, then that's, again, communication. Say, "Listen, we're going to go about and do things. It's okay if you just sit on the beach all day long."

The key is to know before the trip who you're traveling with and their traveling style, and that they don't kind of control you or try to guilt trip you into doing things that you don't want to do. This is your vacation. You should vacation just the way you want. There were times where some of us said, "You know what? I just want to sit by the pool. You guys can go do whatever." I think it's okay, but it becomes a problem if the expectations aren't laid out.

Brian Lehrer: On the finance track, you advise people to "lay down the law about finances before going on a group trip". What kinds of laws about what?

Michelle Singletary: First of all, the most important thing is a group trip is that you collect all the money up front. If there's a down payment or some money has to be, everybody has to put their money in before the trip starts. I was crystal clear about that. I set a deadline. If you didn't make the deadline, you are not coming on this trip. That's usually what causes a lot of friction. People come or they back out at the last minute.

In our case, we did have some family members who backed out and not give them back their deposit. I said, "I'm so sorry, because this was a trip for 12, you backed out, all of our expenses are still for 12. You're not getting your money back." They completely understood because I was clear about that. Once you give me your money, this is part of the trip. If you back out, I'm so sorry, but you're not getting the money back.

Brian Lehrer: Sounds fair. Tough, but fair. You write that you recommend designating a banker on large group vacations. I'm thinking there hasn't been a designated banker in my group since the last time I played Monopoly, right? One person gets to be the banker.

Michelle Singletary: That's right.

Brian Lehrer: What is the banker in this context?

Michelle Singletary: It's probably no surprise that I'm the banker usually, and the key is the banker has to be diplomatic, right? They have to be firm about collecting money, like making sure people pay what they're supposed to pay, but also just kind as well. As a banker, you can talk to the family. You set up rules.

For example, we had a large family, and one of the family members had two small children. Well, we're not going to split the cost with the two little ones. They don't work. The banker proposed this to the family. That was me. I said, "Hey, you all, let's split the cost for the villa, the house, among the working adults," and that really helped that couple that had the little kids. Those are the kinds of things that the banker wants to be.

For example, there are some instances where there were younger adults, people in college, or not have a lot of money. As the banker, I said, "Listen, some of us make more. We're more secure. Is it all right if we charge them a little bit less, which means we pay a little bit more?" We presented it to the group. Now, if someone disagrees, you negotiate or you say, "I understand," but the banker has to be that person, and clearly someone who's not afraid to talk about money, put things out on the table, negotiate, renegotiate, look at the cost, and plan out everything.

Brian Lehrer: Can you give me 20 seconds, 30 seconds on cost splitting? You wrote, "Compromise on cost splitting."

Michelle Singletary: Yes, like what I said, when we travel, one of our rules when we travel with our children, my husband and I, is that we get the place. You don't have to worry about that. We might even play excursions. You just pay for the airfare. That's what I mean. You look at all the costs, you look at people's financial abilities, and as a family, you decide what's fair. Fair may not be equal.

Brian Lehrer: Yes, because that's a whole other show that actually we've done in the past, which is like, don't take the people in your circle who don't have as much money as you for granted when you're making plans. Right?

Michelle Singletary: That's exactly right. You could do a trip. My husband, I've been working for years and years, and so we have more saved, and we like exposing the younger adults and family members to something that they would not necessarily be able to afford. We are okay with that. We are allowed, we're taking them on places in the world that they just couldn't afford. We love being able to do that. That's what I mean by cost sharing and looking at things.

Brian Lehrer: Michelle Singletary, we got to go, personal finance writer for The Washington Post. Thank you, thank you, thank you for these two days.

Michelle Singletary: You're so welcome.

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