Write an IOU to the kitty
We use IOU's in our kitty. My tip is when I travel with my sister or a close friend we make a kitty where we donate the same amount of money and trade keeping it safe. This helps so that only one person has to pull out money when paying for meals, cabs, etc. instead of two. This is much safer and also keeps things simplier. When the kitty runs low we toss in another equal amount. When one of us wants to purchase a trinket, they write an IOU to the kitty, until we reach an ATM or cash a traveler's check .P.S. I love Journey Woman and I recommed the site to everyone! Peace,
Colette, Minneapolis, USA

We track our spending
I just came off a marvelous trip to Alaska. As is sometimes convenient, my traveling companion sometimes paid for little things and other times I did. In order to sort things out, we track our spending and often make up the difference by treating the other to lunch or dinner after we get home. It’s a great way to recap our adventure.
Penny, Baltimore, USA

Review the trip's finances
When I travel with my travelling companion, we put our money in a kitty together each day and one person (we each take turns) pays for the days expenses as we go along. Whatever is left over goes in next day's kitty. We also keep a small notebook to log the items, just to have an idea of what things cost at the end of the trip. It's always fun to do the calculations over the last meal, which is always a big splurge. This system has always worked well with my various companions.
Christine, Montreal, Quebec

Who handles money best?
The best bookkeeper in the group takes care of the money. When my friends and I travel to Paris on our annual trip, one of the first things we do is establish a kitty from which all of our common expenses are paid. We assign one of us to manage the money and every couple of days or so we determine whether we need to replenish and how much each one needs to contribute. It saves us from individually having to pull out our wallets to pay for incidentals, subway tickets, museum fees, meals and other things we do in common. It works best if there’s a separate kitty wallet or pouch.
Eleanor, New York City, USA

Pay for your own drinks
We, too, keep a kitty but only one of us drinks wine. So, to keep things fair we pay for the wine separately (per person) and then pay for the meal from the kitty.
Evelyn, Aberdeen, Scotland

Two is cheaper than three
Actually, I often travel with two other ladies. I guess that makes this travel for three! Our adventures began in 2003, when we enrolled in a three week study abroad trip to Greece. Being nearly twice the age of our other travel mates, we choose to share a room. We were referred to by our professor and our new Greek friends as 'the ladies. Our one rule was that we would let each other know if we needed some 'alone' time. Each of us, during the three week trip, carved out some 'alone' time and it worked quite well for us. We hardly knew each other at the beginning of the trip, but became great friends in the course of three weeks. We have continued to travel together and have a never ending list of places we'd like to explore. Once we've decided where we'd like to go, we each buy different travel guides to research our destination. We have a system where each of us comes up with a list of the top five things we'd like to see or do. That allows us to do some advance planning. We are currently planning our 4th annual trip together. I highly recommend travel for three. It's economical and you can take off and do something by yourself without feeling like you're deserting your travel partner. Plus it's triple the fun!
Jeanie, Radford, USA

Match your travel style
Several ways that I have traveled successfully with two or more include: If you don’t know the person very well find out their travel style. Do they like to see and do as much as possible, or do they like to get to a place and settle down for awhile? I think this difference in travel styles can make or break a vacation.
Sharon, New York City, USA

Learn from your travel pals
When I travel with a friend or two we divide the time and take turns being the guide for the day.We each lead the others and do the thing that we most wanted from the trip. For example, on a trip to Crete, one day I led the group to the Palace of Knossos and the Archeological Museum, another day my niece took us to the beach and out for local food, and a third day my boyfriend took us for a drive over the mountains. I find that i enjoy following others to do things I wouldn't have thought to do and still get to have plenty of time to focus on my most important destination too.
Cynthia, Massachusetts, USA

Negotiate your differences
The most important thing is to voice each others assumptions at the planning stages and negotiate the differences. Such things as taxi or public transport, meal times and time alone seem essentials to discuss. A niece of mine travelled in a threesome and each place they stopped they rotated around a twin and a single room. So they knew they would have a room to themselves each third stop.
Grace, Sydney, Australia

Share and compare ideas
Sometimes my friends and I just like to do different things on a given day when we are travelling together. If we have ideas on what to do or where to go for the next day, we share and compare beforehand. If we are interested in the other person's idea, we join up, otherwise we arrange to meet somewhere later at a set time. That way we can still do what we each want to do, and then join up later to share our separate experiences.
Sherry, Dijon, France

Don't be a bunch of grapes!
We often travel in tandem with my husband's extended family. On an early trip my father-in-law taught us that 'we don't have to hang around like a bunch of grapes'. I find the philosophy comes in handy when travelling with only one other person as well. A little independence does wonders for a travel-buddy relationship. Sometimes, if we're not in a city, we even rent two cars. We each go our separate ways for an afternoon and meet up later with exciting stories to tell.
Joni, Toronto, Canada

Be in charge for the day
When traveling with one or more people, it helps if each person takes a day for accepting responsibility. During this period of time, they are responsible for planning everything (including meals) - even if it is deciding that group will rest and do nothing. It helps ease the 'complaining' aspect, since you would prefer that the others not complain about what you choose on your day. It shares the responsibility of the holiday, and if each/several of you plan the same thing, well done - go back - and enjoy it again.
Amelia, Los Angeles, USA

Do what you must do
I don't travel very often with friends but when I do it can be scary. I really enjoy being the leader of the pack but that does not always work. A small tip that my best friend and I share in our travel-making decisions is 'attachment.' We share how 'attached' we are to pursuing a certain activity. If someone is VERY attached then we usually do it. But if we are not so attached, the subject remains up for discussion. It helps us communitcate better without getting into disagreements. I hope this tip helps other women.
Jamie, Yuki, Japan

How is everybody doing?
Periodically have an evening check-in. How is everyone in your group doing? What problems are arising? What is working or not working? If this is done routinely every three or four days (or when someone needs it), it is a good time for people to talk about what’s bugging them and it prevents resentments or building frustrations
Sharon, New York City, USA