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A medium looked like the max size for my tour pack, was a perfect fit, any bigger box would not have fit. There was plenty of room left for the order of wings!
Yep a 14" will fit in the box. A large French Bread across the rack.
Saddle bags =2 gallons of milk, large liquid laundry detergent, and everything smaller. Sometimes if I buy too much I have to take everything out the bags and spread them around then when I get home put everything back in the bags to carry inside.
I'd think that you'd be okay as long as the large wasn't loaded with toppings ... You know, GVW ratings might come in to play ... and hold the anchovies too ...