Re: Trip to Block Island...
I would suggest not making your first trip during prime time. Mid-week or off season weekends are wonderful.
This might provide you the chance to get a town mooring. At prime time the anchorage can be full, the holding is OK, but not great, and depending on the spot you might need lots of scope. Honestly, the anchorage can be a nightmare or a non-event. The biggest problem can be depth and idiots who don't put out enough scope and/or anchor on top of you.
The prevailing SW winds make the mooring field and marinas fairly calm, even in a blow as they are protected by the land mass. As the wind comes up over that land mass it tends to build a bit across the pond making the wind and chop worse the farther out into the anchorage you get. A lovely anchorage but the dinghy ride in can be long, wet and windy.
I think The Oar has some of the best food on the Island as far as price vs. quality and selection. The Mohegan is also great, it's a brew pub and the food portions are huge.
Use the dinghy dock in front of the Oar. Showers are available in town or at the town beach.
'88 C&C 30 MKII