Too many choices.....
 

Could someone help narrow down Caribbean islands for a 4 day get away for two couples in their forties (leaving children at home!) that has great beaches and snorkeling, awesome seafood, cute local shopping towns preferably walking distance, and unique swimming holes/waterfalls. If you also have oceanfront resort recommendations for those specific islands that would be great! Traveling in February 2015 on a moderate budget. Thanks so much!!

Define "moderate budget" in actual dollars as we have no idea what "moderate means to you. Tell us too if that budget includes airfare and if so where you are flying from. Without knowing how much money you have available for accommodations it's very difficult to make meaningful resort recommendations.

FYI - February is "High Season" in the Caribbean so expect to see the highest room rates of the year - no such thing a a "bargain" at that time of year.

In the mean time look at St. Thomas or St. John in the USVI's or Tortola or Virgin Gorda in the British Virgin Islands. All those island have nice beaches, good snorkeling, places where you can shop and are relatively easy to reach making them ideal for a short 4 day getaway 9if you are traveling from the US) however they lack waterfalls and swimming holes (which are normally found on the more mountainous islands..

Great! I will look more closely at those islands. After researching a little last night looks like most islands have some accommodations in our price range so that isn't going to be an issue. Other islands on my radar that you didn't mention are St. kitts, St. Lucia and Barbados. How do you think those compare? One thing I didn't mention that might be helpful is that we aren't gamblers or looking for a busy night life. Thanks for your help!

There's only a limited amount of snorkeling on St. Kitts & St. Lucia and compared to the USVI's & BVI's snorkeling on those islands leaves a lot to be desired. Those islands are much more "lush" with dense rain forests plus St. Lucia has the waterfalls you are seeking. I don't think there's any waterfalls on St. Kitts but there might be a couple very deep in the rainforest (think 1 to 2 hour hike to reach). St. Lucia is the biggest island on your list with lot's of twisty, narrow & steep mountainous roads so driving can be a bit of a challenge - factor that into your decision. Both St. Kitts and St. Lucia have smaller "cove like" darker sand beaches than the ones you'll find in the USVI's & BVI's.

There's no gambling in the USVi's, BVI, or St. Lucia. There is some gambling on St. Kitts but it's easy to avoid so it should be an issue. I wouldn't worry about "nightlife" as that too can be avoided on any island if you don't want to participate.

I'm not all that familiar with the snorkeling around Barbados so I'll leave the comments about that island to others. The island does have nice beaches and a decidedly "British feel".

You'll find "towns for shopping" on all islands - whether or not they will be within walking distance of your hotel depends on the hotel you choose. For the most part though, in the Caribbean the more popular resorts are not near towns so be prepared to make a concession on that desire.

Keep in mind 4 days really only gives 2 full days.

So really leaves out Barbados, at kitts, definitely St Lucia

You're pushing it with Virgin Islands too, especially St. John and Virgin Gorda were you get what you're looking for

You might want destination where you take advantage of less travel, think maybe Caymans?

I agree that the short duration of the vacation is worth considering first and foremost. What places you can get too most quickly and easily from your home airport. So you don't waste half of your 4 days getting to and from.

Travel time is definitely something to think about that I hadn't considered. I have already been to the Caymans and was looking for an island with more local island character and less commercialized. We have also been to TCI. Loved it but we were encouraged to stay on the resort for safety reasons which was a little scary. So sounds like I should focus on the Virgin Islands. My friends have stayed at Caneel on St John and really liked it but don't want to go to the same place twice since there are so many neat places to see and we have so little time.

For such a short visit, Aruba and Puerto Rico are worth considering. They can often be reached via a direct flight. If you need to get a connecting flight ( even if it's just a 45 min flight), you lose several hours of your day because the second flight doesn't leave the minute you get off the first flight. Plus, you have greater chances for delays and problems. So with only four days, you should go wherever you can get a direct flight from your home city. All other factors are secondary.