I would say Boston up to Newburyport, Isles of Shoals, or Portsmouth on day 1. Head to Gloucester and go through the Annisquam River (very cool experience and saves a bit of time from going around Cape Ann), then to either of the three destinations above. Newburyport is a great city and waterfront, though you will want a dock or mooring due to the current. Isles of Shoals is great, but moorings are first-come/first-serve and a member of the Portsmouth Yacht Club could ask you to leave if all are full. Holding is poor. Perkins Cove in the entrance to Portsmouth has plenty of moorings and I think good holding too. I may end up in any of these three places over the weekend. Should be a 6-8hr day from Boston. The next good stop is really Kennybunkport, which is another ~3 hrs.
Day 2 would be ~8-10hr run up to Booth Bay.
ANZ154 Cape Elizabeth Me To Merrimack River Ma Out To 25 Nm- 1015 Am Edt Tue Jun 11 2013
.small craft advisory in effect through Wednesday morning...
This afternoon..E winds 15 to 20 kt...becoming ne 10 to 20 kt. Seas 4 to 6 ft. Rain early...then a chance of showers. Areas of fog early...then patchy fog. Vsby 1 to 3 nm early.
Tonight..N winds 10 to 15 kt with gusts up to 20 kt. Seas 4 to 6 ft. Rain likely...mainly in the evening. Areas of fog. Vsby 1 to 3 nm.
Wed..N winds 10 to 20 kt with gusts up to 25 kt. Seas 3 to 5 ft. Areas of fog in the morning. A chance of showers. Vsby 1 to 3 nm.
Wed night..N winds 5 to 15 kt with gusts up to 20 kt...becoming nw 5 to 10 kt after midnight. Seas 2 to 4 ft.
Thu..NW winds around 5 kt...becoming se in the afternoon. Seas 2 to 3 ft. A chance of showers in the afternoon.
Thu night..E winds 10 to 20 kt...becoming ne 15 to 20 kt after midnight. Gusts up to 30 kt. Seas 3 to 5 ft. Showers likely.
Fri..N winds 10 to 20 kt. Seas 4 to 6 ft. A chance of showers.
Fri night..W winds around 10 kt. Seas 3 to 5 ft.
Sat..W winds around 10 kt. Seas 2 to 4 ft.
Sat night..W winds around 10 kt. Seas around 2 ft
-Donny