On Nevis, I recommend Sunshines which is in front of the moorings just north of Charlestown. Food is great, but be careful of Sunshine's famous rum punch called the "Killer Bee". A couple of our crew got "stung" and slept through dinner.
A really good tour on Montserrat is provided by Sunny and you can contact him at [email]sunnykristina@yahoo.com.[/email] I took their tour and they were were recommended by fellow TTOLers.
I'll also vote for Isles des Saintes for a couple of days.
In Dominica, you can pick up a mooring from Seacat just south of the capital of Roseau. Seacat also gives really great tours and a trip to one or more of the beautiful waterfalls and other areas is definitely worth staying over a couple of nights here. We also ate at a really good restaurant about a 5 minute dinghy ride from the mooring at Dive Dominica.
Finally, since no one has mentioned the Tobago Cays, I think it's a must stop in the Grenadines.
Fred