When will you be taking this trip?
Alan is correct that you can take whale watching trips from Boston as well as various spots on Cape Ann and Cape Cod. Depending on the other interests of your group, we can advise on where might be most enjoyable to stay. So, what else are you interested in doing/seeing while here?
Yes I did see that whale watching is available out of Boston. We were wanting to get out of the city which we will be exploring for several days and see something different. We are from Florida and want to see a different coast. We were looking for quaint towns to explor with pretty coastline-again something different than what we see in Florida. We are open to hiking, kayaking, or just exploring around town. There are so many different towns and was not sure which would have decent accommodations as well as things to do and see
Regardless of where you decide to stay, you can easily explore the general area and in addition, won't be far from the NH and southern ME coast. You can rent kayaks in Rockport, Essex, and Ipswich (and perhaps elsewhere), for example. I think you'll find the greatest variety of accommodations in Gloucester.