There's so much variety available that it's hard to know what to recommend without knowing what you and your crew will be interested in doing. You mentioned preferring out of the way places, and enjoying Anegada
and the Tobago
Cays. That would lead me to conclude that you're not looking for glitzy nightlife and fancy restaurants. I can relate to that.
Here are some thoughts. There are a number of other members here with a lot of experience to share, so I'm sure they'll chime in, too.
Out of the way anchorages:
In the shallow lagoon
below Spanish Point, inside the Palaster Reef on Barbuda. Doyle's guide tells you how to get in and the cautions you need to exercise. We were the only boat in sight, anchored in 10 ft of gin-clear water
over white sand. Dolphins
and turtles messing around, some coral
heads to snorkel, and endless peace and quiet. This is about as out of it as you can get in the eastern Caribbean
Ditto Special Delivery
: Great Bird Island, a remote
island among the reefs
on the north side of Antigua. After the few day-trippers left, we had the place totally to ourselves. Nice little hiking trail on the island, and some snorkeling opportunities. We left there and threaded our way out through the reef to head
north to Barbuda. Exciting!
Ile Fourchue, west of St Barths, looks like a volcanic crater that's open on the south side. There will probably be a few boats there for lunch, snorkeling, and a hike ashore, but not enough to make you feel crowded.
Pinneys Beach on Nevis will usually have enough boats to make the beach bars interesting, but not so many that you feel like you're in a herd. The beach is three miles of uncrowded, soft sand. Free WiFi
at the Double Deuce and maybe others.
White House or Majors Bay on the southeast peninsula of St Kitts. A few boats, not much on shore. Good spot if the northerly swells are rockin' and rollin'. Skip Basseterre Harbour.
Ditto Special Delivery
: Anse de Columbier, on the western end of St Barths. Very pretty spot. Hiking ashore over to the Atlantic side.
Tintamar Island, off the north coast of St. Martin, is uninhabited and pretty.
Don't miss Grand Case on St. Martin--the restaurants are fantastic (French), and they have an open air barbecue
going, as well. It's a bustling little village, but not over-powering. Good snorkeling around Creole Rock.
Here's a link to Chris Doyle's website. It's got articles, sketch charts
and photos. Not as detailed as the guidebooks
, but helpful for getting the flavor of the islands.