I was in a mono, both in December and in June, and didn't find it rolly in the anchorages much, except, as Mike said, in Saline Bay on Mayreau - and it still wasn't as bad as some of the norther anchorages in the BVI's during a swell.

There are places to eat at every stop except for Petit Nevis just south of Bequia and the Cays.

Some places only have one choice, but most have a few you can choose from.

Admiralty Bay, Bequia and Clifton Harbour, Union Island have lots of choices within a few blocks area of the docks.

Most of the other anchorages have one or two places close by the docks, and a few farther away, which might entail a long walk or taxi ride.

I never made it to Chatham Bay, Union Island, but there are several beach bbq places (are they restaurants now?) along the beach.

I was never concerned with where to eat or drink, even in the off season there were plenty of choices.