Finalized our plans. We are driving from Chicopee, MA straight to Cape Cod. We will have most of that day to sightsee since we are arriving so soon in the day. Staying in Dennis for 1 night. Spending the next day finishing up what we want to see at the Cape. Drive up to Plymouth, look around there and staying there for the night. Next day drive to Boston for the day, check in to our hotel in Salem that night. Sightsee in Salem the next day until mid afternoon, then head to the airport.
Thank you all very much for your input. It helped a great deal. I know I am still cramming a lot into our time, but we want to see and get a feel for these areas and where to return to in the future.

Please keep in mind that you will be on the Cape in peak season so it will be slow moving around, even on those days, it will be very crowded. Dennis is a good place to stay being mid-cape but it is around an hour out to P-town due to traffic. What looks like short drives can be time-consuming.

I hope you enjoy your trip

Skybus went out of business. No New England trip for us. I appreciate all of the input all of you gave me. I've kept all of the info and will hopefully rebook another trip in the near future. Take care!

Why not look into Southwest? They fly into Hartford, Manchester and Providence. I looked quick and found Round Trip tickets for $200 per person into Manchester. This would put you closer to Boston.

Too bad about skybus!!! I was just about to post a warning for you - that week in Provincetown is Carnival. The normal hectic Summer pace goes into a fever pitch such that by parade day on Thursday, there is no parking in town and thousands are dressed in full summer regalia/costumes. (Park at the seashore or take a shuttle bus)This year it is to be "Wild Wild West" - Ptown goes from it's sleepy Winter population of about 2,000 to well over 50,000 on parade day!!! It's a great party for anyone in the area this year.