Two weeks ago (You know that fun week with all the rain and fog, made for an interesting trip. Especially when the GPS crapped out entering the Plymouth channel with less then 100 foot visibility. Had to go all the way in on dead reckoning.) we did the opposite trip to relocate our new to us Catalina 310 from Warwick, RI to Hingham, MA.
We overnighted at the Sandwich Basin. Brand new bathrooms and showers that were great. From the Mass Bay side I believe you can make the basin in any tide. So you might consider Salem to Sandwich, overnight to wait for a good tide and then head into Buzzards Bay.
I would second some of the others that mentioned the long trip in and out of Plymouth. It is a nice stop but it takes a good amount of time off of your trip.
Here are a couple of links that we found helpful in planning our trip:
- Good source of general information and reviews of marinas and anchorages
- Another good source for marinas
-US Army Corps. Canal Navigation
-Canal Tides and Currents
- pdf format
Salem to Boston is a quick trip and I would recommend saving that for another trip. The winds in the Harbor can get shifty due to the buildings and you can get a lot of chop on the weekends due to the power boaters. A good, short overnight trip for you might be Salem to Boston and stay at Spectacle Island or on the hook at Portuguese Cove.
Good luck with your trip and remember to be prepared for anything in Buzzards Bay. The weather can change quickly on you there and can be very different from what is predicted. On our trip it was predicted to be 10-15 kts winds and 2 foot seas. When we got out there it was 25 kts winds with gusts to 35 kts and 5 to 10 foot seas.