Over several visits we've done the eastern Caribbean chain from Barbuda to Grenada.. It's 'open ocean' sailing, often in pretty solid trades between islands - and the fetch starts in Africa.. Still, it's pretty nice sailing, mostly reaching, and 40-50 miles in distance so a nice daysail at 7-9 knots in most boats. Squalls are frequent, as are rainshowers, they can slam you pretty good but you can usually see them coming.
Most islands (save Saba) have decent lee side anchorages and harbours.
The non-french islands have a strong 'boat boy' culture which you can choose to utilize or not.. understand that it's a good part of their economy and I believe there's a certain amount of 'security' inherent is using them - and possibly the opposite if you don't.
I think in the past decade St Vincent has been a less than popular stop, but we stopped at Wallalaboo without incident some years back. The Tobago Cays are spectacular, Les Saintes off Guadaloupe is a pleasant place to visit, and we would put Bequia on the list too. Depending on how far south you want to go, Carriacou is a delight; no cruise ship influence and very friendly people.
You do have to deal with customs officials often, as nearly every island is a new country.
