As between the two, I would choose Anguilla -- but are they the only two you are considering? And when are you planning to go? I would argue -- having been to Anguilla, Grand Cayman and Provo -- that there are equal or better beaches elsewhere, such as Barbuda and many of the Bahamian Out Islands.

But if you're looking only at Anguilla and Grand Cayman, in Anguilla's favor are (a) several beaches that, while not as long as Grace Bay, are as beautiful and populated by fewer people and fewer resorts than either Grace Bay or 7 Mile Beach, (b) in general, a far less congested and developed destination, (c) exceptional dining, and (d) the second-best beach bar culture in the Caribbean (with the BVI coming in first ... if you care about such things).

The Bahamas are not really an option if you are planning to go December - March (I find it too chilly), and if you are seeking "glamor" they might not suit either (unless you define "glamor" as I do in the sense of utter seclusion).

Callaloo thanks for the analysis.

I am leaning towards Anguilla as well, but since 7 Mile was voted best beach by Caribbean Travel magazine it must be considered no? (Grace Bay was runner up).

Glamor to me means the same to you. Seclusion, total chill, but good local drink culture. Soggy Dollar and CGB are some of our favorites.

Which out islands would you recommend?

As far as Out Islands go (at least the ones I've been to), Cat Island wins for stunning, secluded beaches. I've heard great things about Cape Santa Maria on Long Island as well, but haven't been there (yet). The Exumas have fantastic beaches, but the best way to access many of them is by boat (if you stay at Staniel Cay Yacht Club, your lodging comes with a Whaler). The Abacos and Eleuthera are great, too.

As you might guess, I love 'em all. Check out my trip reports -- they have photos as well as descriptions, because each Out Island has a slightly different personality and vibe, and some are easier to reach than others. (www.islandtime.homestead.com). But the Out Islands are more rustic than Anguilla, which is pretty high end. Of course, if you love the Soggy Dollar (one of my personal favorites), the Out Islands might be just your speed.

Anguilla is my favorite island!! Though I got married on Grand Cayman so I like that too (and snorkeling is great there). But strictly for beaches, Anguilla can't be beat. The sand is amazingly soft and powdery (like T&C). The restaurants are the best we have found in the Caribbean. And the people are so friendly. The only disparaging thing I can say about the island is that the snorkleing isn't very good. But it does exist and you can take an excursion to Prickly Pear for example if snorkeling is important to you. But the beaches, food and people more than make up for it.

we went to T&C two years ago and loved it. we went to Anguilla almost 4 years ago and loved it. I found that my love for the 2 was almost equal, but i think Anguilla has the edge. I fell in love with it, the beaches, the food, the laid back atmosphere... This spring we are trying Grand Cayman. I don't have anguilla expectations, but i hope we love it. I can't wait to return to anguilla.

Agree with all of the above...especially the comments by callaloo re the out islands...we love LI, Eleuthera and Exuma. Have not hit Cat yet but thats next...flights to get there are very inconvinient for us
We love Anguilla as well and between turks and Anguilla, Anguilla certainly in our eyes is the winner because of the seclusion factor

It has been many years since I was on Provo, after Anguilla I never went back to TCI. Anguilla's beaches and restaurants are better. I have been to Grand Cayman, and although 7 Mile Beach was nice, I think Maunday's Bay, Shoal Bay East, Cove Bay, Shoal Bay West and Mead's Bay are all nicer. Grand Cayman reminded me of Florida, with better beaches. I like Florida, but when I go to the Caribbean, I want Caribbean islands, not mainland US. The year I went to Abaco, it was the coldest November in years. Too cold to get in the water, but the restaurants and the people were great

We went to Grace Bay the last 3 yrs. and do love it, but we also loved Shoal Bay East on Anguilla----fantastic!

TCI is easier to get to than Anguilla, so that has been a factor.

7 Mile beach on Grand Cayman was very nice, but most of it far too crowded for us, so if you go there, choose your place to start with a good map.