nolatom is right, you want to choose your weather and conditions very carefully for this trip, in such a boat...
I'd strongly caution against making it with any significant swell running, or in the aftermath of any real weather out of the E-NE... Pollock Rip Channel is so named for a very good reason, and while ideally it's nice to ride the ebb out of there, it will get dangerously riled up if there's any sea in opposition to the wind or current...
ELDRIDGE should be your guide for planning around the currents, and be mindful of the fact that the times of the current changes listed for Pollock Rip are counter-intuitive. In other words, when the "Ebb Starts at Pollock Rip", that's when the current actually begins to
FLOOD into Nantucket Sound from seaward... Weird, I know, but that's because what the tidal current chart for that area is really indicating is the flood into Buzzards Bay and Vineyard Sound...
Those waters to the E of Nantucket Sound and the Cape can get pretty messy... By far the largest, and most confused seas I saw all summer, were on my final approach to the Great Round Shoal Channel near Nantucket at the end of my passage across the Gulf of Maine from Shelburne. It was blowing pretty good from the NE, and about 20 miles out I ran into the ebb out of Nantucket Sound. For about 6 hours I had a very chaotic and uncomfortable sea state, lots of breaking crests, would definitely not have wanted to have been on a Beneteau 235...

No way to avoid it, it was the price I had to pay to sneak in before it was forecast to really begin blowing, and catch a fair tide across Nantucket sound over to the Vineyard...
In short, the currents and the way they meet with the rapidly shoaling bottom in that area can produce some very impressive effects. Then, the proximity of the shipping lanes into Boston can serve to pin you in closer to Cape Cod than you might like to be. A fair amount of fishing boat activity out there, as well, you really don't want to be doing that trip if there's any chance of fog...
having said all that, it can be a very pleasant and benign trip in ideal conditions... However, I'd suggest you check carefully the comparative distances between going outside, and going thru Woods Hole and the CCC... It's a long way down around the bottom of Monomoy Point from Chatham, and a long way all the way around Race Point, and back up into P-town, so the difference in total mileage may not be quite as much as you've initially thought... Plus, if you have the time to play the tides, and catch a fair current over to Woods Hole, and then up Buzzards Bay and thru the Canal, that time differential can be reduced considerably... Not to mention, plenty of very nice stops along that route, if you're not in too much of a hurry...