travelzoo.com Great Deals on fairmont.com Royal Pavillion
Been to both several times Barbados bigger more variety also have Stayed at the Crane good. Antigua great beaches smaller dodgier in some areas not as safe. Travel.state.gov for advisories. St James Club was nice for me there last several years back.
luxurylink.com other good options.

Happy Hunting!

I'd recommend Grenada, it has what you are looking for.

I would look at Turks and Caicos or Grand Cayman. Barbados has great nightlife.

thanks so much for your suggestions! Any advice for what islands have the stereotypical pastel colored buildings in the little towns? (not looking for a big city by any means)

Gustavia, St Barts; Willemstad, Curacao; St Georges, Grenada is a nice town to walk through, Marigot, St Martin, some areas of St Johns in Antigua has nice renovated buildings, not necessarily pastel coloured.

I live in Antigua and I think is a great place to be, however the things you are looking for aren't here, or better, we have a large number of beaches but the "Pirate Vibes" is more in Grenada, so I suggest you look at that one too. Barbados very big and Bridgetown very nice. Every Island has a different vibe and feeling to itself. I love living it here coz it's very safe, qwovadis watch too much television, like any other place the little crime is present but faaaaar from being a un-safe place to be. Antiguan are very friendly and you'll find no hassler around, it's quite obvious that anybody will find trouble when they looking for it... lol
Back to your first Caribbean Holiday, make sure you pick the right one and I guarantee you'll get a sort of Caribe Addiction which will make you want to visit all of the island. Think St.Lucia, or for the perfect beach (and beach only) no Island can beat Anguilla....

Now is your choice, whatever you do have fun and stay Irie.

Nat

"Any advice for what islands have the stereotypical pastel colored buildings"

Curacao and Aruba. Neither will have lush vegatation or Planations. Curacao, think Arizona with a beach. Aruba, flat with palms trees, much better beaches than Curacao, but tons of nightlife.

St. Lucia and Jamaica come to mind for those. Better beaches in Jamaica, but not really any "towns" to walk through.

I agree with Grenada or maybe Nevis or St. Kitts.