Hey folks. After a year+ of hiatus we are gearing up for another trip and can use some advice between Anguilla and St. Barths. Some key points/criteria for our island choices:

- BEACHES - quiet, calm, and the fewer people the better
- we prefer villas over hotels/resorts
- fine dining and nightlife not a major thing, as we like to cook at the villa
- great local watering holes and street food we like very much
- local bands/fish frys we do try to hit
- cost of groceries/supplies - I know its Euros at St. Barth's so that worries us
- cheap rum and beer a must!! = )

We are planning to go in the May time frame, right after peak season, and intends to rent a car.

Any suggestions and advice are welcome!

IMHO, if you don't want wonderful food and if you are looking for cheap anything, St Bart's is not a good option. The local watering holes are tres chic. Anguilla is a quieter destination.

Both are expensive and hard to get to. We love the French influence of St. Bart's and driving around the island but it is one of the most (if not THE MOST) expensive islands we've been to.

Anguilla has gorgeous beaches. We stayed on Shoal Bay East and loved it. Next to Grace Bay, TCI, the best beach we've been on. Several beach bars---Uncle Ernie's and Gwen's in particular. But aside from the bars themselves you can have your quiet, stunning beach. Johnno's had great music a bit of a drive away. There is a huge grocery, liquor store. Prices were comparable to most islands, not cheap but doable.

I can't comment on stand alone villas as we stayed at Shoal Bay Villas
http://sbvillas.ai/

It is as close to the beach as you can get. A bit older but it will remain as one of our favorites. The only reason we haven't returned is that it takes too long to get there. We've been going to TCI for the last 4 years. Before that we've been to 20+ islands so have a good comparisson.

Have fun planning. Fodorites will help you all the way.

I just have to say, why pick 2 of the islands best known for excellent restaurants, the best in Caribbean, and decide to cook in your villa?

Defeats your choices.

Having said that, sounds like Anguilla meets your requirements better than St. Barts

St Barts does not meet the requirements at all, it's not quiet and calm, it is all about the fine and/or expensive dining (so many celebs and well off people holiday on this island), street food - I can't imagine it but might exist. St Barts is St Tropez in the tropics.
I've only seen Fish Frys on Barbados/Antigua/St Lucia and Tobago, not on French islands. But the fish markets should be very good and the supermarkets with produce from France. I agree with the other posters, why stay on St Barths and cook in your villa?

I think Anguilla much better meets your wishes than St. Barth.

- BEACHES - Anguilla has some of nicest ones in the Caribbean, and there's plenty of room for you to find one that you won't have to share with many people, especially if you have a car.

- Villas -- can't answer that one, as we'd either stayed on a boat or at a hotel.

- Actually, Anguilla is quite a good fine dining destination for when/if you do choose to go out. You many not want to cook when you see all the choices for fine and casual dining, but if you do, I recall there being decent (not great) grocery stores to get what you need. (Much better choices in St. Martin, if you transit through there, but I don't know what the rules are for bringing food over.)

- As for great local watering holes, I found that Anguilla was second only to the BVI when it comes to great beach bars. And those beach bars come with great food. Gwen's and Nate's (Palm Grove) come to mind.

- Can't speak to local bands; we tend to fade after dark. But I think there is some decent action at Road Bay some nights.

- Cost of groceries/supplies - well, it will be cheaper than St. Barth. But still, Anguilla is a costly destination, so you won't be finding much on the cheap. They blend Pyrat rum on the island; you might be able to find some at the factory at a cheaper price than in the US (where it runs about $30/bottle).

Anguilla is actually not that difficult to reach. Fly to SXM and take a ferry over. Much easier and cheaper than trying to get a flight to AXA.