Which Island is for us?
 

We are trying to figure out which Caribbean island to go to this winter. We've been to Mexico (4 times), DR, Jamaica, Hawaii, cruise to BVI & St. Martin.

What's important to us is:

1. Beach - has to be close to perfect.
2. Ability to walk a lot and get to shops, etc.
3. A quaint feeling, not too Miami or touristy.
4. Friendly locals and ability to do a lot on your own, without tours.

We will always return to the Mayan Riviera of Mexico, as that is my favourite yet, but want to try different areas in between.

Thanks for your help.

St. John, Virgin Islands

Anguilla or Provo (doesn't meet your shopping requirement, but it meets your others!)

One of the things you are going to find is that most resorts that are on beautiful beaches are not near "shops, etc." which tend to be in the towns. The towns are usually in protected harbors with lots of boat traffic while the beaches are on other parts of the island. This is especially true on "quaint islands".

As Blamona points out St. John (US Virgin Islands) come pretty close to what you are seeking. If you don't mind taking some type of ground transportation to reach shops, etc. you might want to check out St. Kitts or Nevis. St. Martin has a lot of shopping and plenty of restaurants within walking distance of many of its hotels and resorts but it is a very busy island and probably doesn't meet your definition of quaint.

Bequia (in the Grenadines) has a small town which is located adjacent to a very nice beach. It's the quintessential "old world Caribbean" island - quiet, laid back, friendly locals, not touristy. If you are looking for "quaint" this is certainly the place.

I love Abacos, Bahamas- Hope Town (Elbow Cay)
Fly into Marsh Harbour and take a ferry boat to Hope Town (lighthouse)

I would second Abacos especially elbow cay based on your criteria. Quaint town, great beaches and friendly locals. Bit difficult to get to but worth it.