I've traveled several times with different friends and it can be stressful. Figuring out how each person likes to travel and each persons interests and blending them is a challenge. I think all my trips have gone well, no had has said they wont travel with me again... I'm sure I'm not a perfect travel partner, and to be fair my friends aren't always either. Just because your friends doesn't mean that your good travel partners. A big part of making a good trip for all parties is reasonable expectations and planning together.
Last year I went to Disney World with Terye, before the trip I probably tortured her with emails about planning. First, I was figuring out a list of restaurants that we wanted to eat at, I was sending a little synopsis of pretty much every restaurant with review information. We were able to narrow that down to a reasonable list and I went ahead and made a variety of different reservations for us for breakfast, lunch and dinner. Then we worked on a list of attractions we did and didn't want to do, but the most important was a list of our MUST DO attractions. This was the list that would allow us to leave Disney knowing that we didn't miss anything that we really wanted to do. This allowed us to make sure that while we might not get to do everything we wanted, we wouldn't leave with any real regrets. Terye and I did have one issue, it's called mornings. Terye is not a morning person, she did ok the first couple days, but towards the end... Lets just say that I had to inform her that she wasn't allowed to put the TV on in bed when I had already taken my shower. I'm sure she had some issues with me - like me nagging her to get out of bed. In the future we decided that we should go somewhere where getting out of bed in the morning is not necessary for your enjoyment - I'm thinking Las Vegas or New Orleans.
Planning my trip with Tara to Hawaii has also required a lot of planning. I started with the list of what must have been 1,000 excursions and started to break them down a bit and learn what Tara was interested in that I was also interested in. I couldn't convince her that zip-lineing would be fun, but she's agreed to take the helicopter tour. As the more experienced traveler I've tried to send her information about what to expect when flying and on the cruise. It's good for things to be a surprise, but not all surprises are good. We still need to discuss the dining options on the ship as I hear it can sometimes be hard to get into some of the restaurants.
Here are some things to keep in mind when choosing travel companions and planning a trip. What are the eating habits of the person you want to travel with? If someone is the make every meal at home type and you like to eat out a lot, then you'll want to discuss that. My sister's friend traveled with a family who wanted to make dinner every night, but they wanted to go out every night - not a good combination. If the other person is a beach person and you hate the sand - another thing to discuss. Also, what types of activities do you want to do, art musuem, history museuems, major landmarks, photography. All these things are reasons people travel, and just because someone has different interests then you doesn't mean that you can't travel together, but it means that you need to discuss these things and find out if you can each compromise so that each person can get what they want out of the trip. If you want to travel together and have some different interests then consider setting aside time to split uop. Waiting until your on your vacation to have these conversations may lead to the end of your friendship. A friend of mine traveled with a friend once and their friendship barely survived, later on he traveled with a girlfriend of his and that was how he knew they could live together.
