Lately I've become a fan of making slideshows of our various trips and events. Ever since we skipped out on presents last Christmas and bought the fancy camera instead, there are so many good pictures to share. Not to mention that between two sets of families, friends, Facebook, etc. there are so many people to share them with. Slideshows just seemed like the easiest way to accomplish that.
I have absolutely no technical advice on the subject. Windows Movie Maker came free with both our little netbook as well as our desktop and I've just been learning as I go. Like most scary technical stuff these days, it's actually pretty user friendly if you just click around and experiment. So I'll leave the technical stuff between you and your own software, but I've figured out a few helpful things that will streamline the process for you.
Gather all pictures - To have the best selection of photos you need to have everyone's pictures, not just your own. We started doing this just with our west coast family when they would visit - before they left we'd upload all of their pictures to our computer, and vice versa if they owned a laptop. We also did this recently with our local family by bringing our netbook on vacation with us and grabbing all of the photos before we left.
Segregate and delete - Both of our recent trips to Cape Cod yielded around 300 photos. But both 5 minute slideshows I made (and even that is a pretty long montage) only contained 100 pictures. That's a LOT of deleting. A lot. It took me most of a day to whittle down the pictures to a manageable number.
The easiest way to accomplish this is not to attempt to choose the good pictures, but rather to delete the inferior ones. Take all of the pictures you've gathered and copy them into a new folder marked "Slideshow." This way you can go through and delete with abandon. It'll take several rounds of editing before you have a final grouping. But remember...
Keep in the non-person shots - 5 minutes of looking at the same 6 faces is boring, even to the 6 faces. It's a nice break for the eye to see a nature shot. Also, it will give a sense of place, which is key to making people understand what your trip really felt like. Keep this in mind when you're actually taking the pictures too. Take pictures of your surroundings: where you're staying, the spot you're visiting, the stuff you're buying, etc. This will help significantly when you put together your story.
Arrange - Your slideshow needs to make sense to people who weren't there and it won't have the benefit of captions. This is where order becomes crucial. (This also relates to editing as well, so keep the overall story in mind when you're deleting pictures)
First choose a beginning and ending shot. I always have my first picture as some kind of non-person representation of the trip because that's the picture I overlay the title onto (for the first beach slideshow I used a picture of the house we were renting, and for the second I used a picture of the beach). For the last picture, any one you like will be fine. I just make sure to end on a really great one from the end of the trip.
The best way to use your non-person shots is as introductions. Start with a global view, then get specific: start with a picture of the beach you're at, then move to all the shots of the kids in the sand; start with a picture of the maple syrup shop, then move to the picture of you illegally sucking the sap out of the tree tap. This will help your trip feel more like a series of events (which it was), and less like a series of 100 nice but confusing photos.
Choose a song - This was difficult for me because I'm not a music person. I have no idea who sings what, what artists are in what genre, who the upcoming singer/songwriters are, etc. Despite that, I was able to find two songs for the Cape Cod montages that I really liked (Beautiful World by Colin Hay and Better Together by Jack Johnson)
I started with Google searches and it was totally useless. Every search yielded the same grouping of songs, all of which were cheesy and snappy and not at all what I wanted. We're not the Griswolds. We weren't on a slapstick road trip to a closed theme park. These specific trips were calm and relaxing and I wanted that reflected in the slideshows.
It worked much better to first go through our own iTunes music collection (that's how I got the first song) and then to move on to some more targeted internet searching (that's how I got the second song.) Instead of searching for "vacation slideshow music" I started searching for things like "upbeat acoustic songs." They're harder to come by than you'd think.
All of those song suggestions weren't right either, but I did get a few artists that were frequently mentioned, so I was able to go through their catalog of songs and find something that fit (hence, Better Together). The song you choose sets the tone for the whole thing, so it's important to get the tone right.
It can be a time consuming project, but it's something you'll have forever and they're SO wonderful to revisit from time to time. Much nicer than just clicking through pictures.