are you renting? My fam usually does 3-one for the boys, one for the girls, and then one for bride/parents of bride. My wedding party is too big to get us all into 2 limos, but i really don't know if i want a third one!
Have you considered a trolley? I am having everyone go in one trolley since it holds 50 people. The company I am using is called A Perfect Limo, they are out of Shrewsbury but are traveling to Peabody, Stoneham, and Atkinson NH so I'm sure they would travel to your locations as well.
I did a trolley (back in 2001) (My first wedding) I used Beantown Trolly Tours. Church was in Woburn Reception Sheraton in Danvers. So the travel part was not an issue. There are a few companies in Boston that have the traditional trollies and there are some white ones some with music and disco balls. Check them out, the price I paid was ver reasonable and if my memory serves me cheaper. Hope this helps and good luck
Re: How many limos....