How about making the person in the canoe going over the cliff the tray holder (just a thought that came to mind; unless you are training extreme butlers this might come across wrong). I like the idea of a hiker's silhouette pulling a rolling suitcase; it's a good example of combining the elements you are trying to express in your mark.
Make a matrix of ideas, and try to think of different ways to combine them. Try to list the different ways you can visually represent these ideas to come up with new styles of conveying the image. From a strong vocabulary you will be able to draw strong visual impressions to use for different concepts.
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