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There is also a bunch of canoe trip planning advice in the trip reports right here at Loon Island Outdoors. Here are some things to think about when planning your trip.
Travel Time - Getting There and Back
The first day is usually a mix of "hurry up and get going" and "slow down and start relaxing". The most important thing is to make sure that you have a reasonable amount of time to get where you are going both on the road and on the water. It is also important to make sure you start out well rested. Lack of sleep was probably one of the factors contributing to the Lake Temiskaming tragedy. When planning the last day of your trip, remember that you still have that drive back home after you get off the water. About the longest drive home that I've had for a 4 day weekend has been the 7 hours from east side of Algonquin back to Waterloo. The Petawawa River is really beautiful, but there's a reason why my two trips to that area have been 7 years apart.
Vehicle Shuttle If you are picking a route that involves starting and ending at different locations, then make sure you plan time for the shuttle. Whether your group takes a couple of vehicles and you do your own shuttle or you hire a shuttle, the time still adds up. For example the round trip from McManus Lake to Lake Travers on the Petawawa takes about two hours while I expect the round trip from McManus Lake to Cedar Lake further up the Petawawa would take you at least 4 hours on top the rest of your drive.
Type of Route
Loops
This was the approach that we took for our first canoe trip with the kids which was in Frontenac Provincial Park. We still kept the days fairly short with only 1 portage each but got to explore something new each day, including hiking some of the trails and finding old artifacts.
Rivers
Depending on the river and the time of year, you will also need to be prepared for different hazards, many of which go along with changes in water level. The Petawawa River from Cedar Lake on down is really well known whitewater canoe route. While the portages along the route are well maintained, I definitely recommend taking a whitewater canoe course One of the most serious hazards on a river is a man made dam. Dams are important for controlling water flow and for power generation but they can also create recirculating waves that will trap anyone or anything that flows over the dam. As long as you research your route ahead of time and know where to take out above each dam you'll be in good shape.
Base Camping This approach to canoe tripping was something that I was first introduced to through a spring fishing trip. While it was the first time I was exploring that area, the folks I was with knew the area well and were there for the fishing. An early spring trip also means planning for cold weather, like the blizzard we had on the first day of that trip. By setting up a base camp and then exploring and fishing nearby lakes on day trips, the guys could get away with packing a lot more luxury items than if we were packing up and moving every day. S I used to avoid planning routes that had me repeating part of the trip because I wanted to get more exploring done. Now I find the base camping approach more relaxing because we don't have to get anywhere in particular most days. Even on the last day when I really do need to get home so I can work the next day, the base camping routine takes some of the pressure off because we'll be covering the same route on the way out that we used on the way in.
Weather and Daylight Living and working in the city, most of us are used to choosing when we do things pretty much independent of the weather or the time of day. Even when you are car camping its pretty common to set up camp in the dark. On a canoe trip you have to accept that Mother Nature is the boss.
In the summer the long days can be a blessing, giving you easily 16 hours or more of daylight. In the spring and fall the days are a lot shorter. For our spring fishing trip in early May we know it will be dark out by about 8pm but if you are taking a late September trip in Killarney the sun will be setting shortly after 7pm.
The time of year and the amount of daylight you have is going to affect the distance you can travel on any given day. I know people who have still been portaging in the dark and it isn't an experience that they want to repeat.
Experience and Skill Level The whole point of a canoe trip is to have fun. Having fun might well include challenging yourself to accomplish something - a long portage, a new route, catching a trophy fish. Or having fun might mean getting a few portages away from the crowds and then not moving for a couple of days while you relax and decompress. All those things can make for a great experience that you want to come back and do all over again.
First Aid I'm not saying that you'll need to do first aid, but I am saying that you should be prepared. I've been fortunate so far and never had a major first aid issue on a trip. I have however heard first hand stories ranging from a broken glass mustard jar (not in a Provincial Park with a glass bottle ban) to a serious back injury. Whether you are 4 hours or 4 days away from the nearest access point, you need at least basic first aid knowledge. While cellphone coverage is becoming more prevalent even in the places like Algonquin which many consider a wilderness retreat, response times will be measured in hours not minutes.
Lists, Lists and More Lists
The next list is the packing list - first the group gear and then the individual gear. Of course since some of that individual gear is the clothes we wear every day at home (underwear for example), you can't just pack it all up a week ahead of time. So as we get closer to the trip I start having lists for what needs to get packed up each day, which also takes me back to the grocery list to buy any buns, pitas or bread the day before we leave. I'll also load the canoes on the truck the day before we're leaving since it can save me 30 minutes on the night we're actually leaving. If we are camping overnight before the trip, or perhaps staying at the cottage then I'll also have a list of what needs to get packed up that morning. Since our cottage is on an island, we just take an overnight bag over with us rather than our packs and then we have stuff like toothbrushes than need to get into the canoe packs in the morning. Finally I'll have a checklist of stuff that needs to get done at the put in. Things like putting the rod holders on the canoes, strapping the yoke pads onto the yokes, putting the safety buckets in each canoe, etc.
Pamper Yourself with Going Home Clothes
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Whether you are going away for a week, a month or just a weekend the travel time to get to and from the trip can add up pretty quickly. Most of our trips have turned out to be 4 days long, which has a lot to do with how much vacation time folks have. Generally speaking I try to keep the driving time down to about 4 - 5 hours each way for these long weekend trips. Sometimes we'll drive up the night before and camp at a provincial park close to where we will be starting the trip to help get an early (OK, earlier) start on the first paddling day. Other times we'll get up at 5:30am and plan to be on the water by noon or so after taking time to pick up camping permits. 
I think most folks plan their first canoe trips looking for a loop that lets them start and end the trip at the same spot. If you are looking to cover as much ground, umm, water as possible and to explore somewhere new every day then a loop works really well. By ending the trip back where you started you can avoid the hassle and time involved in a vehicle shuttle. 
Canoeing down a river is a great way to cover a lot of distance. Even if the river isn't big and pushy it's pretty amazing how much the current can help move you along. You will need to plan for a vehicle shuttle but that's usually pretty manageable. 
before planning a whitewater trip. The Grand River near home is notorious for being really low in the summer. Low enough that you might be walking more than paddling. Keep the water level in mind when deciding between your nice light kevlar canoe or the beat up old plastic one. 
ince then, I've really become a big fan of the base camp routine. Many of my trips have been one on one with each of my kids in turn. Now the kids are great canoe trippers and have always done their share of the work, but when they were 8 or 10 years old I was definitely doing the heavy lifting on portages. One of our best base camping trips was the one that Madeline and I took to 
Wind and lightening are usually the most important weather considerations. While a nice tailwind can speed you along, a headwind can add hours to your paddling day. Lightening should keep you off the water entirely and while we've paddled through plenty of rain over the years, we do head to shore for a thunderstorm. On our Temagami trip we had delays from both thunderstorms and from wind. Each time we had to wait out the weather until it was safe to continue on. 
When planning your canoe trip make sure you include a buffer to sit out bad weather. Depending on where you are going that can be a bigger or smaller risk. For example, the small lakes in Frontenac Provincial Park are fairly well sheltered from wind but if you head out through the 
Pick a route that matches the skill level and experience you have today. If you haven't been canoeing before then don't hesitate to take a course. In Ontario look for an ORCKA certified course. Load up the canoe and get out for a few hours or a day trip ahead of time. Before we took the kids to Frontenac for their first "real" canoe trip, we did a 'dry run' at the cottage. We also had them practice dumping the canoe and getting back in so they would be comfortable with it if anything did happen on the trip. 
Perhaps the most important thing you can do in planning your trip is to get organized and make sure you don't forget anything, especially at the last moment. I think the first list we make for most of our trips is the menu. That sounds easy enough but then the menu turns into a shopping list and the shopping list turns into 'food to get ready' list. The 'food to get ready' list is the one where we dehydrate anything that needs dehydrating, measure out the ingredients for what we are taking with us and get all the food packed up to go. And somehow we still always seem to end up with extras. 
This was another idea I learned from those spring fishing trips. In late April or early May, I'm not doing too much swimming. Especially not if the ice just went out the week before. So by the end of the trip I'm plenty ready for a hot shower at the comfort station near the takeout followed by some nice clean clothes for the ride home.