Montego Bay

Turks and Caicos is great.

I loved St Croix, with the added bonus that you don't need a passport and it's the US. I appreciated that the divide between the tourists and locals was not SO wide that we needed to be fenced in somewhere.

Vieques. Direct flights from DC to San Juan, then you take a little plane to Vieques. Rent a house and a jeep for everyone to share. Stunning beaches, very casual, mostly inexpensive, but still nice. There is also a W for spa treatments and a more upscale experience. It's a great place.

Anonymous wrote:Isla Mujeres

does that meet any of OP's criteria at all?

Where do your friends live? It will be easier to get a connection to an affiliated island (re: French Caribbean, Dutch Antilles, BVI etc.) Also, do they prefer casinos and nightlife, culture/music, nature and scuba?
St. Barts is wonderful but requires a connection in either Miami or PR and then St. Maarten. And you have to fly in and out during the day on a tiny plane. It might be depressing to be there without your significant other.

Isla Mujeres

I think it depends a lot on where your friends are coming from, because it can be a pain to get to some places in the Caribbean.

For example, Grenada and Barbados have direct flights from London, so that might bump them up the list (there was a nice NYT article recently on Grenada-- you can visit spice and chocolate plantations, and Bridgetown, Barbados is a decent city if that's what you want).

Grand Cayman
Barbados
Bermuda (not technically the Caribbean, but easy flights and tropical atmosphere)

The food in St. Barth is fantastic. But expensive.

St. Martin/Maarten? Easy direct flights from lots of places, and with 2 countries sharing the island lots of food options. Plus you can take a ferry to Anguilla or St. Barths.

Anguilla has a ton of good restaurants, but no real "city" to speak of.

I do an annual trip with a group of very close girls friends that have moved overseas. Because everyone is scattered around the world, we try to meet somewhere that is convenient for all. This year we have decided to meet at an island in the Caribbean. We would prefer somewhere with a small town/city nearby to appreciate a little more of the island's culture. Good food is a huge plus. Any ideas??? We haven't ruled out an all inclusive resort, but would prefer not to do that if we have access instead to nice, yummy restaurants. The DR and Curacao are out.

I appreciate any suggestions! Thanks!