By Mark W, April 06, 2008 at 10:42 PM

Sometimes the decision to take a "big" vacation doesn't come easily. I took my first vacation to Europe in September 2004. The planning for it actually began in 1999.

Back in 1999, I was fresh out of graduate school, trying to keep my business running. There were a lot of long, stressful days of coding and dealing with customer issues (I was running an Internet company back then). I had an idea that I wanted to take a vacation at some point and started looking at the various options. Would I travel independently or should I travel with a tour group. A tour group had a lot of distinct advantages in that I would be with other travellers and a tour guide who had knowledge of the area.

Being my first trip internationally and my first trip solo, the idea of independent travel didn't top my list. I would easily have gotten a hotel room in London for a week and spent my time there. But that raises a lot of questions for which there weren't a lot of easy answers. Back then, the Internet wasn't as fully developed as it is now, so not a lot of robust travel forums available out there. And I never had a really great experience talking with travel agents.

My first step was to get a passport. I found a place to take a photograph, filled out my application and went to the local post office. Weeks later, it arrived. Fairly painless, back then, now a bit more of a process.

Passport in hand, I had pretty much decided that I would do a tour group on my first trip. Never having been a big traveller, I wanted to allow more of the planning on the tour company and allow myself to enjoy the sites, plus, with the right tour, I'd be able to see more of Europe on the trip. Don't underestimate the value of that decision. Had I decided to travel by myself, maybe I would have seen one or two countries. Because coordinating moving between countries takes a lot more planning. Plus, as I said before, having never been there, I wouldn't know the first thing about picking out the right place to stay.

Having decided to use a tour group, all I needed to decide was where I wanted to go, how long and which group. I don't remember how I first learned about the company I eventually decided to travel with, but I do remember that I ordered their current tour catalogs way back then. Being in their target market, there was one important factor that they offered which appealed to me: they matched solo travellers up together to avoid the single supplement.

Personally, I don't understand single supplements, but what I do know is that it can make another wise affordable vacation expensive. For example, if you haven't looked, a cruise for a single can be upwards of 75% higher. So by matching up travellers, you save money and hopefully you're roommate is cool (if not, you have great stories...like I do).

While I did look at other companies, the other key factor in my decision was that the company I picked focused on the younger generation. That way, I would be with people my own age.

That decision made, I ordered their brochures, browsed through their offerings and nothing happened.

As you might remember, around 1999/2000 the Internet ad market crashed and my business went belly up (well, I closed it before all of my finances went belly up). So with all the distractions in my life, I wasn't able to travel. Then came 9/11 and nobody was travelling.

Finally, in early 2004, I started planning again for a trip. I pulled up the website of the tour company I had looked at before and considered several different tour options. I know, at the very least, that I'd pick a tour with an asterisk next to it (meaning that the tour would stop in Munich while Oktoberfest was going on). We all have certain priorities. Also, I picked a two week tour that looped through Europe, so that I got a wide range of experience. My feeling was that when I travelled back, I'd be able to pick more focused trips to areas I wanted to visit again.

I had several calender versions of the trips planned out, trying to optimize my vacation time from work, which also meant I couldn't use any vacation time so it could build up by the time my trip came up. All that was left was to book and pay for the trip. Thank you MasterCard (I suppose there is a good debate waiting on whether you should pay for travel via debt).

Funny thing happened as my trip approached, I got a new position two weeks before I was to depart...

"We'd like to offer you a position here..."

"Great, by the way, I'll be going on a two week vacation a week after I get there."

"Um...okay."

Now, I had a vacation coming up and I had to move to central Florida (from the west coast of Florida). Two days before I moved, hurricane Charlie ripped through central Florida (luckily sparing the apartment I was moving into), but causing a lot of damage around the area.

A week before the actual flight, I started getting up earlier each day. The idea was to get myself on London time. When my plane landed in London, I had that day to see parts of London before our first tour meeting that evening.

Two days before my flight, I drove back to the west coast of Florida to leave my car at my parents and because my flight was long booked out of Tampa.

A day of frantic packing and repacking. You'd think for two weeks I wouldn't need such a large bag...I hate packing, by the way.

The day of the flight, I'm up at around 2 a.m. in sync with when my Flight will land in London 24 hours from now.

Nothing to do now but wait until the sun comes up and then wait until the airport shuttle arrives.

And then the fun begins.