Tom:

I have done that trip many times, first as a middle aged couple on our first long distance cruise up the coast. Here is what we did with alternate stops along the way based on our subsequent trips:

Onset through the Cape Cod Canal to Marblehead, Ma- This is a pretty long leg, about 60 NM so you can break it up with stops in Boston, Scituate or P Town. Make sure that you time your trip considering the currents through the canal. They can run up to 3-4 kts. Hail one of the yacht clubs in Marblehead and pick up a mooring. The moorings aren't cheap, but Marblehead is a serious sailing town and shouldn't be missed. Good provisioning at the little grocery a few blocks from the town dock.

Marblehead to Goucester- A short hop, but Gloucester is an interesting little town where you can buy all sorts of seafood. Drop your hook in the small anchorage inside and dinghy up to the seafood market.

Gloucester through the Annisquam River to Biddeford- Anchor outside in Wood Island Harbor or pick up a mooring inside the pool. You can break up this run with a stop at Isle of Shoals and then on to some of the best of Maine- Jewell Island for example.

From Biddeford, the possiblities are endless.

David