Itinerary help for Boston and Islands
 

Let me know how this will work:
Day 1-3 Boston, Day 4 - Rent car drive coast to Plimouth Plantation then on to Chatham and spend night
Day 5-6 - Nantucket
Day 7- ferry over to Martha's Vinyard (spend night and leave from there next day or go back to Nantucket? Will have to compare prices of ferry, room rate etc.
Day 8- Ferry back to Hyannis to get car. Drive to Newport RI for night. See the mansions, etc.
Day 10 drive to Boston airport for departure
Questions: It could be cheaper to fly from Boston to Nantucket, no rental, no parking. Skip Newport and fly back to Boston . Sounds like a lot of hopping around while the car is just sitting in parking lot.
Any other suggestions? Maybe go north instead of south. Want to spend as much time seeing the beauty of Mass. while I'm there. We are in good physical shape and I know what activities I'd like to do and where to stay but am concerned about the itinerary.
Thanks

Don't go all the way to Newport for just one night. Spend another night in Chatham, there is plenty to do and see on the Cape and you've got virtually no time there in the above plan

This is going to sound a lot more complicated than it is. If you have a real road atlas, its greater scope will let you see the whole route better than your phone or google maps.

Day 1-3 Boston
Day 4 P&B bus from South Station to Hyannis Transportation Center, free
Steamship Authority shuttle (free phone) to Lewis Bay Steamship Terminal
Ferry to Nantucket
Day 5 Nantucket
Day 6 Cape Air from Nantucket to Martha's Vineyard (spectacular 20 minute flight)
Day 7 Vineyard, fly Cape Air to Hyannis late in day. Rent car in Hyannis, drive to
Chatham for night
Day 8 Outer Cape in morning, drive to Newport mid afternoon
Day 9 Newport
Day 10 Boston car return, catch flight

You are missing Plimoth Plantation. I don't think you can reasonably do Plimouth Plantation and Newport on this trip.

I personally would save Newport for another time and spend Day 9 exploring the quaint Kings Highway (MA 6) from Brewster to Sandwich in the morning and doing Plimoth Plantstion in the PM. Spend the night in Plymouth unless you have an early flight. Eat at a clam/lobster shacks on the town pier.

This saves you three days of car rental and about $150 in parking and adds two quick hops in small planes for about the same money. Public transportation and bus tours eliminate the need for cars on either island.

The traffic to Boston will be very heavy until maybe 10 AM. Allow lots of time.

Thank you!

Just a slight correction to the above post: the Kings Highway between Brewster and Sandwich is route 6A. The highway is route 6.

I like Ackislander's trip for you. It totally eliminates the cost of renting a car in Boston and paying for it and parking while it is sitting in a lot for your trip to the islands.

Another option would be to take the ferry from Boston to Provincetown. Then either renting a car there, exploring the cape and islands and returning it to Town and either flying or ferry back to Boston.

Thank you. I guess the only reason for the rental was to take the coastal highway from Boston to Hyannis, but in the above plan I can do that on the way back. This is a great source! Helped me plan my whole trip to Germany a couple years ago!