We recently retired and have never been to the Caribbean. There are a lot of islands, but how do we decide which one fits us the best. Obviously want ocean beaches. But, don't care to have too many people immediately available. Would like good restaurants. Historical sites, if possible.

I've never been, but immediately Cuba jumps to mind. I would imagine it's pretty rife with historic sites and great restaurants (in Havana particularly) and I've heard (not verified) that the beaches can be pretty fantastic. However, if you are an American it can be pretty darn tricky to get there.

St. Vincent and the Grenadines

Cuba is not a realistic option for Americans, so let's just put that one off the table until the U.S. changes its policies.

Your interests could fit with many different islands. Grenada is one. But there are isolated resorts at almost any island. If you have a lot of money to spend (at least $3000 per person), then you have innumerable choices at high-end resorts throughout the Caribbean in the off-season. There is also often a lull (and dip in prices) in January right after Christmas and New Year's (except for the Martin Luther King holiday weekend).

Maybe OP isn't American? But I do understand, it's not the best idea to encourage people to break the law on a public forum and that wasn't my intent -- I promise!

Puerto Rico comes to mind & from there it iseasy to 'hop' to other islands as well. San Juan is busy but very historical but PR is still very Americanized so if you have any trepidations, it may be a good place to start.

St John

We were there for our honeymoon and LOVED it. GORGEOUS beaches and scenery, nice restaurants, wonderful selection of villas (great privacy), a bit of shopping, and easy to travel to.

Have fun planning!

Barbados is a wonderful introduction to the Caribbean. It has some of everything the Caribbean has to offer, except for a volcano. Lovely people with a (formerly) British-Caribbean culture, wide range of hotels, beaches, restaurants, sightseeing, history, nitelife. See www.barbados.org