I was around boats quite a bit growing up. I have taken classes on the basics. This is my first boat and the area is new. The boat will handle most conditions I'd try (wind < 12, seas <= 2ft) between here (Falmouth) and Martha's Vineyard. So far we've been from Hyannis down past Woods Hole with no problems. Seems to be a lot of boats around our size or smaller. My wife is getting tired of just driving around, wants to spend some time on Martha's Vineyard, ...
We don't know how long you have owned the boat, what type of boat, your experience, the shape the boat is in, your emergency gear, how you react in an emergency, etc., etc. I hate to say it, but most of these questions are from guys that shouldn't be doing what they are asking about
Headed to MV there is Bishop & Clerk's which is a rocky shoal south of Pt. Gammon, be sure to stay clear as there are some huge boulder there that will ruin your day. Continuing west, Horshoe Shoal has an area where there are exposed rocks, also stay clear, other than that it won't be bad. There are shoals as you head west from the Shoe, should be enough water, but if the tide is pullin' against the SW wind, it could be hairy
just an fyi if coming from falmouth and going to OB be carefull coming around the corner near vineyard haven. gets a little choppy there to. you can always try and time it right and run behind the high speed ferry. nice smooth ride as long as you can hang with him.
Know the circumstances.... and even if you are wrong (within reason), you have an hour of "every wave in the face" misery to withstand... no one has died from it. But it could really turn off a rookie crew.
So here is the bottom line... go slow. Push things just a bit at a time. Learn as you go. Take your poundings in stride and be safe and have fun
Check your charts, tides, and weather conditions. It could be 2 mph winds in morning with the sound being flat as glass then come afternoon the SW wind comes in at 12 mph and if the tide is going out during this time you are going to have some chop and a wet hairy ride back. All it takes is one good wave