As you can imagine, the worst thing you want to hear at work is that you’re being forced to take additional vacation.  Such was my lot at my full time job, where because I had so much built up vacation time, this year, I needed to take an additional week off above my standard 3 weeks.  The reason for this, the company explained in a single font, 10 point e-mail is because they care about my health and well being.

Of course, being in Finance, all of us knew that the real reason was to move stored vacation time from one line on the balance sheet to a more street-friendly line.  Get rid of all that accrued vacation.

But these days, do you really want to take vacation?  My company went through layoffs like many others did and a good bank of vacation is that much more cushion should they decide they don’t need me any longer.  Early this year, I had no plans to take a vacation because the prior September, I took a way too short trip to Munich and Paris.  But do I take vacation and sit home for a couple of weeks?  Not a chance.

Where to go, what to do?  With the global economic crunch and decline in travel, there certainly wouldn’t be a better time for deals, so I started to research possible locations.

I’ve been to Europe on several trips, so it wasn’t my initial thought to revisit there.  The first place I looked into was Iceland. The country was hurting due to the hard crash of its economy.  And there were certainly some great places to see there.  I’ve seen a few travel shows focused on Iceland so there was no doubt it would be a fantastic place to visit.

I fired up the browser and started doing some pricing via the usual suspects (Travelocity, Orbitz, Expedia, etc).  At the time of the search, the best prices that were coming up were in the neighborhood of $3k and above.  A little steep for my wallet (although I did a search just now and there are some options below $2k now for August).

Another internal question I was dealing with was whether I wanted to travel solo, booking my own hotels, airfare, etc.  On a couple of my trips to Europe, I had booked with a tour group.  There are benefits and negatives to consider when doing that.  For example, the first tour I did was 14 days, traveled to several cities in Europe, starting and ending in London.

The beauty of that trip was that I treated it as an introduction to Europe.  It gave me experience in 10 European cities.  The negative being there wasn’t a lot of time in each location to really dig deep into the culture and there was a lot of time on the bus.  I enjoyed it thoroughly and even recommended it to one of my leaders who took the tour with his wife and enjoyed it as well.

That trip was like a chef’s sample dish.  A little taste of everything and in later trips, decide what to focus on.

So, not looking at Europe this trip, one of the places I’ve got a strong desire to visit it Tokyo.  I’ve read a lot about the city from the bizarre to the truly fascinating and amazing.  A couple of friends of mine have been to both Tokyo and surrounding country side in Japan, so I had a couple of knowledge references to bounce questions off of.

So, I started doing research into Tokyo.  For 8 nights with airfare I was getting prices between $1600 and $2200.  The hotels looked like they were nice and in good areas, although honestly, I wouldn’t know one good area from another.  I knew of one or two districts that people recommended avoiding, so tried not to look at hotels in those areas.

One of the reasons I did not book immediately was the falling prices.  At the time I was looking, the economy was getting worse; tourism was declining which meant that prices for hotels may be going down as operators lowered their prices to attract people.  I wanted to see how far it would slide.

Had I booked and the price gone down, I would have been fine because I always try to find a price I’m comfortable with.  Always determine what you think is a good value for your flights, hotels and book as close as possible to that price.  If the price drops below that, sure you could have paid less, but at least at your price, it was still a fair value.  Sucks, but it’s fair.

The second delay was the language.  I don’t speak a word of Japanese and from talking with my friends, not a lot of people in Japan speak English.  While I would find it possible to communicate in Tokyo, outside of the city might prove a bigger barrier.

In Europe, I’ve had no problem wondering around a city by myself and surviving.  Sure, I’ve encountered people in Paris who didn’t speaking English, but because of the common ancestry of our languages, you can at least make out the difference between ordering pasta Bolognese and beef tartar, even if you didn’t understand anything else on the menu.

Japanese on the other hand is completely new to me.  For me, ordering from a Japanese menu would be a choice between which symbols looked the coolest.  “Hmm, I like how the lines in that one swish across those other two…”

Being that I was traveling solo, I wouldn’t have a travel partner to bounce thoughts off.  “What do you think that means?”  “I have no idea.”  “Should be do it?”  “Why not?”  You know, a second gut check.

The final event that occurred against the Tokyo trip was the U.S. State Department issuing a travel warning for people going to Tokyo to avoid bars in a certain area.  Apparently people were being drugged and robbed.

Not that it bothered me much, as I didn’t think I would be hanging out in bars that much, but when you’re parents hear the same news, the last thing you want is the spend the months before the trip listening to them wonder if it’s such a good idea to go.  “Mom, when I go out to pick up Japanese ladyboys, I’ll be sure to buy my own drinks.”

Finally, I turned back to Europe.  A couple of my prior tours had been with Contiki, a tour company that focuses on 18-35 year olds.  At this point, I’m beyond their age limits.  Their parent company, Trafalgar, however, had a series of tours call Breakaway which is for 21-38 year olds.  This is the last year I could do that.

Unfortunately, there aren’t many Breakaway tours offered, only eight.  One of them was Viva Italia, which was a 12 day tour (2 of which are travel days) around Italy.  I’ve done Italy during my initial tour, but only Rome, Florence and Venice.  This tour would give me an opportunity to get some more experience in Italy.  All I needed now were flights.

I started the search for them and they were being priced a bit higher then I wanted at $800-1200 round trip.  This annoys me.

Orlando has the third most visited tourist site in the world according to a Forbes survey, yet the only international city offering non-stop flights is London (via Gatwick).  Not Paris, not Rome.  Don’t even think Madrid or Berlin.  Nope, I usually have to go through Atlanta or Washington DC.  No wonder the state of the airline business is teetering on bankruptcy.

After a couple of weeks of research, one day I happen upon a sale by Air France on Orbitz.  Round trip tickets come out to $600 total.  Immediately, I start booking the flights and get Trafalgar on the phone to make sure I can still make the tour, I have less then two months before departure.

While I’m talking to the guy on the phone, I’m working my way through Orbitz to make sure they don’t change the price mid-booking (which unfortunately happens sometimes).  I make it to the end and my flights are booked.  I give my credit card to Trafalgar and the trip is booked.

I’m golden.

Less then two months to go and I would be in Roma!