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Which islands would you rate better than the USVI given a choice, based on FF award seats available?

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This is going to be a broad set of open-ended (and probably naive) questions, but I am seeking some expertise from those of you who know multiple destinations in the Caribbean.

We are planning a week-long vacation for our family of six (parents, daughters in early 20's plus one son-in-law) for the last week in May, partly as a graduation celebration.

For those of you (perhap only a few) who know me from the Europe forum, this is a change of heart from a previous plan to go to Nova Scotia in May. Wrong time of year, we decided.

The tentative plan is to fly into St. Thomas, stay four or five nights there, return via San Juan (PR) and take advantage of the opportunity to make a free layover (probably two nights) there, as part of the FF award travel (on American).

The decision to choose St. Thomas was very, very tentative and proposed after a very minimal amount of research. None of us has traveled in the Caribbean to any significant extent). Not all destinations are available to us as award travel. Barbados seems to be out, for example. But many other destinations are still available, even at the 30,000 mile award level: Aruba, Curacao, St. Lucia and Trinidad, and probably others.

Personally, I would favor going to the furthest away destinations since this is free travel. I might never choose to spend the money to go to the further away islands as paid travel. And I like the idea of the warmest possible water temperatures (i.e., further south) for snorkeling or scuba (SNUBA?) in bathing suits without a wet suit (novices to never-tried-its).

The trip is not necessarily intended to be an all-beach vacation. Shopping, or history, or "exotic" culture, or jungle or eco-tourism, or other opportunities will be viewed as a plus. At least one daughter thinks that Aruba is too small and not enough else to do. They, as a group, have the idea that they are not really interested in Mexico (Yucatan/Mayan Riviera) or Central American ("isthmus") countries. A preference for predominantly English-speaking setting over non-English (thus, maybe not Dominican Republic?)

What do you recommend, given these parameters? Is the two-night layover in PR a good idea? or a loss of "other island" time (we are not adverse to relocating once, for example... by boat... from USVI to BVI, just to mention one possibility - - or maybe just daytripping).

Thanks in advance for all replies... and...

Best wishes,

Rex
(from the Europe forum)

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