You are probably going to want ~4000 calories per day, as you will burn a lot while paddling. More if you are paddling flat water (so currents not helping you achieve that 50 miles a day - truthfully 50 would be a big stretch for flat water).
Clif and Power Bars are maybe 200 calories each, so breakfast and lunch would get you 600 calories. You may want to look at meal replacement bars instead of regular energy bars. Only slightly larger than an energy bar, but twice the calories. I like ProBar.
That said, even switching to a meal bar for breakfast and 2 for lunch will barely scratch your caloric needs.
High caloric, but low volume, foods:
- look for pastas with no hollow space. Tube pastas (macaroni, ziti, etc.) should be non go - lots of wasted space in them. Strait pasta could be Ok, as it is relatively efficient. Grain style pasta, like orzo or cous cous, are best.
- nuts are high energy, but they often have a lot of air space between them due to odd shapes. One way to make them smaller is have them in butter form - peanut butter, almond butter, etc.
- eat dried grains, like instant oatmeal.
- you can dehydrate lots of stuff if you have a dehydrator (or just use your oven, but that is less efficient). I think there was a recent article on this site on dehydrating foods. Some is available dehydrated (guess you could call jerky dehydrated meat).
Harvesting foods en route can save you space and provide variation for meals. Had lots of blackberries on a pair of trips I did in the Pacific Northwest. Even just getting a kelp salad added to the meals along the CA coast. Read up on what is in your area and bring some gear (like basic fishing gear). You could stick to safe stuff (so no mushroom harvesting if there are dangerous ones in the area you will be), and still find a lot. Fish, shellfish, wild rice, berries, etc.
4-place Boat Trailer
Hardshell Kayak Sail Rigs
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