I posted this in another blog I write for a website, Marriott Rewards Insiders mgoes2's blog:
Planning a trip is a chore most of my friends seem to dread. They just want to get there already and usually book a vacation through one of generic travel websites that advertise with cute gnomes or former star ship captains. I did this once, too, with quite unfavorable results. Not only did I not save money in the end, but I got stuck with an inferior hotel which could not be cancelled and problems with the airline which no one was responsible for solving. Worse yet, I accrued no points with any loyalty programs which could have been substantial for a two-week trip to England from Miami. You live and learn, hopefully!
It was after this fiasco that I started taking planning travel seriously. With this sort of seriousness I employ, I have found the research to be almost as much fun as the trip itself. Here's the method to my madness:
1. After determining when and where for the trip (and if there is any flexibility in the dates), I begin the search for airfares. There are several sites I like for the "big picture" of what's out there. They are ITA Software and Yapta. Unfortunately, Southwest and AirTran won't show on these searches, so you have to look at their sites separately. Once I get the picture of flight schedules and prices, I focus on trying to get the best deal I can on one of the two main airlines I seriously have frequent flyer memberships with. More often than not, the difference in price between my loyalty program airlines and least expensive airline is minimal. In that case, it's worth spending the extra $20 for the flight to get the miles.
2. Booking the hotel is generally quite easy if there's a Marriott nearby. I search my destination hotels here in the Insider site, then compare prices and Elite offers on the hotel search for which property best suits my needs. One interesting tidbit for Elites is that often, the higher end properties will end-up being a better deal with special rates offered and the freebies that come with being a Gold or Platinum such as free breakfast, internet, etc. It there's no Marriott nearby, I also have loyalty programs with several other chains as a back-up.
3. Researching the destination is always the most fun! I'm a foodie, so first thing I do is check Chowhound and Urban Spoon to see what's unique to eat or which restaurants are loved by the locals. Also, I enjoy following food trends and interesting chefs, so I keep track of whether my destination may have a noteworthy restaurant to seek out. I usually plan at least one nice dining experience on a trip and the rest, I look for reasonably priced local favorites. Rarely am I disappointed.
Once I know where I'm eating, the rest seems to fall into place. I'm not one for tourist attractions, but I love shopping, museums and exploring neighborhoods. Try specific google searches based on your interests, using " " and : to define your searches. For example: Montreal: "Lighthouses you can visit". This helps you zero in better on what you want, rather than getting pages of random ads show on your search results.
4. Keeping track of it all is just as important. I use a colored plastic legal size envelope with a wrap string closure to stash all my specific trip info in. I use colors, since I'm often planning more than one trip at a time. The plastic keeps them safe from water while traveling and the closure ensures everything stays put. I always print airline info, hotel and car reservations, as well as info sheets I create specific to the trip. The info sheets are the cut and pasted results from the destination searches which have been condensed to the smallest typeset I can read. I clip all these together in order of the trips schedule and put it into my envelope along with maps, brochures, etc. During the trip, I add receipts from places I ate and shopped, etc. to the envelope. That way, if I want to do review of the trip or make recommendations to friends it's easy to see the name of that little taqueria I found on the way to the museum that was so great.
While my methods may or may not work for you personally, the point is a little bit of planning goes a long way to making your trip enjoyable and avoiding wasting time wondering "what do we do today" or just going to the same mundane tourist traps with lines that everyone else is going to.
