Weddingbee boards

Well, Anguilla is flat, with a ton of beaches but there is honestly not going to be a lot of activity- day or night.  You can take the ferry to St. Martin, but that is about it.  I was thinking that Anguilla wasn't really big on the AI, so I think that might be a good fit.  You really wouldn't need to switch hotels as the island is easily driveable (and taxis are expensive).  There are so many wonderful restaurants on the island, you would never get bored with trying all the different places out, even the beach bars had great lunches.  I wish I had pics from when I was there one February, beach everywhere, and like 10-15 other people.  There were huge stretches where there was no one, except for the people walking the beach.  If you wanted a little adventure, you could take the ferry over to St. Martin.

St. Lucia is absolutely gorgeous, very lush, but very mountainy, so you have to have someone who has the stomach to drive the roads.  Travel is slow, so it will take you to get from one area of the island to another.  There are a few amazing hotels on the island, but I would probably stay put.  I was in St. Lucia for a shorter time, so I can't comment on the restaurants so much.  The beaches I saw were nice, but St. Lucia was better.  I'm guessing they'd have more to offer activity wise, especially since it is a cruise port.  I don't know that I saw anything amazing in the water at either location, but sometimes a few fish are ok too.

Either island- the people are friendly and take a moment to get to know some locals.  They can fill you in on the good stuff.  Just me, while St. Lucia is beautiful, the roads make me feel ill and so I feel like I'm confined to where I'm at.  Anguilla I had more freedom with driving, and I'm a beach lover, so I'd go back to Anguilla first. 

Cap is gorgeous and no kidding about the nightly rate.  If you go to Blanchard's for dinner, the cracked coconut is amazing for dessert, I make it to impress company and it always works.  I had a great dinner at Mango's, listening to the crashing waves, as well.  There is a great artist on the far end of the island, near the turn to Blanchard's, her name is Carol.  And if you run in to Raymond, the beach rental chair guy on Shoal Bay (whose job inspired my next career), say hello and make sure he gives you a good rate, even though you already have a beach companion!

Ladera in St Lucia is amazing!! I would highly recommend it. And Jade Mountain has been #1 on Travel & Leisures Gold list for a couple of years.

Another more affordable option would be Anse Chastenet. We've used it several times, and the guests always come home happy.