Everyone imagines the ideal trip where everything goes exactly as planned—flights aren't delayed, baggage isn't lost, hotel rooms are nicer than described, the sites and restaurants aren't crowded and you packed exactly the right clothes. Okay, let's face it, how often does that really happen? However, with a little advance planning, you can greatly increase the likelihood of your travels going smoothly and be able to handle any bumps in the road more easily.
When I begin to plan a trip, the very first thing I do is research, research, research. Whether it's buying a few guidebooks, saving articles from travel magazines, or finding information online, I like to learn a little about where I am going before I ever book my hotel or flights. What sights do I want to see? What's the best neighborhood to stay in? Which restaurants do I want to try? Are there any conventions or events in town that might make things more crowded? How is the weather at the time of year when I will be there? Do I want to go to a play or sporting event and, if so, will I be able to get tickets? With all of this knowledge at hand, I can begin to plan my trip.
Before I book my flights, I like to make sure I have a great place to stay. First stop - Tripadvisor if I am staying in a hotel or Homeaway if I am hoping to rent a home or condo. I read the reviews of the various hotels and look at the user posted photos (beware of the fancy professional photo gallery posted by the hotels - they make every hotel look like the Ritz while this is often not the case).
Make sure you research the hotel's location—nothing will spoil a trip more than ending up in a bad neighborhood, being too far away from the things you want to see or being next to a busy highway. I like to use Google Maps Street View and virtually walk around the area where the hotel is located. There are even sites and apps now where you can check which rooms in the hotel are the best (Room77 for iPhone) or if they have had a problem with bedbugs (Raveable).
Once I narrow it down to a couple of hotels where I would like to stay, I search everywhere for the best deals (Expedia, hotels.com, etc.) and make sure I can find availability. I have tried all the major internet booking sites and, surprisingly, more often than not, the best deals come from the actual hotel web site. They also have the most up to date availability. You can also try calling directly - the rates usually aren't any better, but they may show rooms that are available if the web site does not.
Do you belong to a hotel loyalty club? Many only require you to sign up to receive benefits on your first stay. Small Luxury Hotels, a consortium of high end boutique hotels, offers a free upgrade on your first stay, after you join their complimentary Club. Fairmont Hotels offers complimentary membership in their President's Club which will give you free internet access, special rates and other benefits just for signing up.
If you are a family or group, consider renting a house or condo. It's nice to have the living space that a hotel room doesn't provide and it is quite often more cost effective that booking multiple hotel rooms (although you will be sacrificing the service you receive at a hotel). Homeaway and Flipkey are great places to start but you might also want to consider contacting local realtors. Usually, home rentals are by the week but if you would like to stay for a shorter amount of time, it may be possible - just ask.
Another tip—remember that the rates quoted on many internet hotel booking sites do not include tax which can add as much as 20% to the cost of the room.
Also, research any extra charges (parking, rollaway beds, resort fees) and factor them into your nightly rate. Domestically, being a AAA member usually will save you about 10%. Do you want breakfast included? Look for a Bed & Breakfast package but make sure it's worth it—it may be cheaper to pay for breakfast separately. Sometimes the best rate is a non-refundable one—however, I try to avoid these rates unless I am 100% certain of my dates and that I am definitely going on the trip. It's hard enough to change flights these days, I don't like to be on the hook for the hotel as well.
Finally, once you have booked your hotel, send a friendly e-mail to the reservations manager with your confirmation number telling them how much you are looking forward to your stay at their hotel. If you have a specific room request, ask if that room is available. A little personal contact, in an increasingly impersonal world, will go a very long way. You might just be rewarded with a nice upgrade upon arrival!
With a little information and diligent research, you are on your way to booking the "Perfect Trip"!