As other's have said, the difference between inside/outside is almost 100 NM, with inside being the shorter. If you had crew, great weather, and the desire to explore. I may have said outside.
Going around, you really don't have a lot of "duck in ports" for weather. Hyannis and Martha's Vineyard are probably the last ones on the upper cape. Dennisport maybe could take you if you have a shallow draft. Harwichport is tiny and not really a suitable place. Chatham is doable if you can negotiate the ever changing sand bars/shallows. Not easy to get into if you need to in a hurry. After Chatham, your basically on your own, 40 NM, until Provincetown (P-Town), but there you need to basically do almost a complete 360 as you need to go around all the way around Race Point/P-Town to get into the harbor which is on the Bay side.
Using the Canal (inside), once through you have a lot more options for weather. Sandwich on the Bay (east) end oft he canal, Plymouth, Scituate (a favorite of mine) are within a few hours of the canal. P-Town is only 25 NM or so from the canal.
If your goal is not to circumnavigate Cape Cod, I really don't see any reason to go outside. Inside is easier to navigate, safer, quicker, and has more weather options.
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