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How to choose an island??

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I have found some very useful information in these forums however, it seems that most people are looking for something a little different. My husband and I are in our mid 50's and are planning a late June, early July trip to the caribbean. We will be traveling with at least one other couple our age. We are pretty much open to any of the islands. We have been to many of them but only from a cruise ship perspective - so have only seen the sights where cruise ships go.

These items are absolute must haves:
1. Clean, clean, clean
2. Safe (I'm probably a little more nervous in unfamiliar areas than most)
3. Beachfront with crystal clear water and sandy beaches
4. Great pool area - although I want to LOOK at the ocean I will primarily be spending my time at the pool (lol)
5. Great food (would love to hear pros/cons of AI), we are not obsseesed but do try to eat a little healty and would not be opposed to eating breakfast and lunch in our rooms if there is a place to buy groceries and we have a ref in the room. We are perfectly fine with yogurt, cereal, salads & sanwiches. My husband is diabetic.
6. The purpose of this trip is total relaxation. Don't really want to be in an area that is predominantly loud children or teenagers

These items are "would likes"
1. Casino
2. Spa
3. Shopping

These items are not necessary at all:
1. Night clubs/Alcohol
2. Night entertainment

Hope that gives you some idea as to what we are looking for. If you have any questions, please do not hesitate to ask. I appreciate all advice. I forgot to mention that it is our 35th anniversary but we would have taken the trip even if it wasn't.

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    Hopefully people will reply with some specific suggestions and personal experiences. But honestly from your list, except for casino/gambling, I think pretty much every island has places that would check all your boxes.

    Generally speaking often "great food" and "AI" don't go together, unless you get into the more expensive resorts. I'd encourage you to go not-ai but with a frig in your room as you mentioned, near a town so you can easily shop.

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    Let me first make some general comments that address some of your concerns:

    1) Most islands are "clean" but do expect to occasionally see more littler along the roads than you find "back home". It's pretty much a fact of life in the Caribbean.
    2) Most islands are safe if you use the same common sense precautions you do "back home".
    3) With the exception of a couple of islands like Saba and St. Eustatia you can find beachfront accommodations with clear water and sandy beaches on any island.
    4) A lot of the better resorts have small pools or even no pools but you should be able to find some resorts with nice pools on any island.
    5) In general AI's are not noted for having "great food", plentiful food, yes, great food, no! You'll generally have to venture off resort to get "great food". If you are serious foodies look at St. Bart's, St. Martin and Anguilla - they have some best restaurants in all of the Caribbean. By the way, there are grocery stores on every island so you can purchase yogurt, cereal, the makings for salad & sandwiches.
    6) June & July are "Low Season" in the Caribbean so it is traditionally "uncrowded". While you might encounter some families you can easily avoid resorts that cater to families.

    To address your last few points:
    1) Not every island has casinos so you'll have to decide how important that is to you.
    2) You can find spas (both on and off resort) on just about every island and almost all resorts will offer some type of spa service. There are a number of resorts that have full service spas but the tend to be more "high end" properties.
    3) Some islands have better shopping than others.

    So what islands should you look at?

    St. Martin might fill your bill, lot's of great restaurants, nice beaches, plenty of shopping on both the Dutch and French sides of the island, casinos & access to spas.

    For a more upscale island look at St. Bart's - think of it as the Paris of the Caribbean - some of the finest restaurants in the Caribbean, fantastic "boutique and fashion shopping, plenty of nice beaches, very few families, many, many spas but no casinos. This is a very upscale island so cleanliness, & safe is not an issue.

    Anguilla - 35 fantastic white sand beaches, 80+ restaurants, plenty of upscale resorts with exceptional spas, no casinos and no real shopping other than the ubiquitous trinket shops - you can, however take a short 25 minute ferry ride to St. Martin for your shopping fix.

    Grand Cayman - wonderful beaches, calm clear waters, good shopping, plenty of full service resorts with on-site spas.

    As for specific recommendations for resorts it would help if you could give us some idea of your budget for accommodations and another for your daily food it will be easier to steer you in the right directions. Try to be specific as terms like "not too expensive", "Affordable" or "won't break the bank" are meaningless without an actual dollar point of reference.

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    Turks and Caicos comes closest. Clean, safe, no vendors on the beach (total relaxing) terrific restaurants, best spas in Western Hemisphere, (Regent Palms spa voted #1 in Conde Nast Traveler March 2013 issue, #2 in all the Americas!) there's a small casino, (does the job), no crowds, bright turquoise long beaches, great pools, awesome views even from some restaurants, different price points, mostly condos with full kitchens, but just a little bit of shopping.

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    My first thought would be Aruba. Describes everything that you are looking for. Look at the Bucuti, Divi, Amsterdam Manor and Manchebo on Eagle Beach. Some rooms have kitchenettes. There is a grocery store in the Eagle Beach area and if you want to pay the extra you can shop on-line and they will deliver to your hotel.

    If you don't drink alcohol than AI would probably not be the route to go. Aruba has tons of great restuarants in all price ranges and an excellant public transportation system. There are several casinos on the Island and the Downtown area as well as the Palm beach area have good shopping options.

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