Probably the most important aspect of trip planning is getting your living situation figured out. Whether you're going to be out of town on a business trip for just a couple of days or leaving your condo for a month while you backpack through Peru you're going to have to book your accommodations before you leave.
Sure, it might feel adventurous to travel down to Mexico or Peru without a place to stay and sightsee around town until you find some rental or hostel that will take you in. However, that could also be very dangerous, as you'll be traveling with all your personal belongings and the potential of not having secured lodgings for the night.
Planning a trip can be like designing bungalow house plans. When coming up with house plans you need to account for every single detail of your designs such as where the master bedroom will be or how big the bathroom will be. Leaving out any detail, small or little, could potentially ruin your designs. The same goes for planning a trip. During your trip planning stages you need to book your plane ticket, figure out how you're going to get to the airport, pack your bags and book your accommodations. Forget to do one of those things and your trip won't go off according to plans.
The great thing about traveling, whether you're going to Peru or Toronto, is that you have plenty of travel accommodations to choose from for you and your traveling companion. If you have friends or family members who live in the city you are traveling to you can stay with them. That will cut down on costs and gives you the chance to spend quality time with people you love. If that's not option you can always stay in a hotel or motel, hostel, vacation rental unit or a bed & breakfast. VRBO.com is a great place to begin your search.
Your accommodations will entirely depend on your needs and budget. If you are looking to save some money and don't mind sharing a room with strangers then staying at a local hostel is an option. If you want to be pampered while staying at a beautiful resort then you might want to look into a bed and breakfast that will look after your needs. Staying at a hotel is the option many travelers take while staying away from their home because they offer rooms at reasonable rates and other features such as inground swimming pools (find image examples here) or wireless internet. The sooner you get your accommodations settled the sooner you can get excited for your trip!