Most common license is a 6-pack (even my nephew has one) which is restricted to 6 passengers as the name implies and uninspected vessels (your typical charter or small boat). With 7 you need someone with a Master's license, there's one more possible. It's the Spirit, 50' boat, I'd try to contact them direct, rather than going thru Dana Wharf.
SPIRIT SAILING CHARTERS
Surprised Curlew isn't available, thought they were even having scheduled sunset cruises recently.
A hired captain wouldn't be a loophole, it would actually be him performing an unethical and/or illegal act.
Anyone could do it for free, licensed or not, compensation of any kind would make it illegal.
(They may be suggesting that the captain could claim one of you is crew)