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When June/July are the only time you can visit the caribbean....

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...and given that one (meaning me and family) have little experience regarding any of the caribbean islands AND given that we are still trying to figure out how we can choose our next destination, what are our options? Let me be more specific. So, here we are my wife and I with our 3 little kids (one is infant) and probably will have with us a 'parental unit' (my mother-in-law more than likely this time) and thinking of going to another carib island. We visited TCI (stayed at the sands and loved it), and grand cayman (stayed at the lacovia, but were unimpressed...on a scale 1-10 probably a 5 was our experience). Now, I have to be clear; we are somewhat 'boring' and don't do much real island activities such as snorkeling, as we are kind of limited in our roaming around with a breast fed infant and "pumbing" that my wife has to do every 2-1/2 to 3 hours. Though, in our next travel, more than likely we will not be as limited, as I am pretty sure my wife will be done with pumbing, and our little guy will, by then, be about 16-17 months old we should be more 'mobile.'
We would like to be somewhat
1) centrally located, although renting a minivan is something we will do anyway,
2) have access to either an on site, or very near by good restaurant and venture to other great restaurants
3) access to super market
4) kids activity venues or generally options
5) crystal clear waters (like the provo in tci),
6) not too isolated or too 'cosmopolitan' either (in other words grand cayman was OK in that regard)
The above we have experienced already in TCI and in Grand cayman, now we would like to see..
7) a little bit more of local flair/culture,
8) more kids activities options
9) probably look in to a villa this time despite the fact that resort is high on priority as my wife feels more 'secure' with such an option in case of an emergency EVEN THOUGH, she wants to venture on the villa option :).
I have been reading a lot of good things about Virgin Gorda, but there seems to be a problem of 'accessibility' as you can only get there through other destinations (or am I wrong on this one?) -- we are flying out of boston.
Keep in mind we would like to keep the TOTAL travel time at a max of maybe...8 hours or so (I know this limits many options) and ALSO avoid Miami (prefer charlotte, philadelphia, or NY for layovers). I also see (through the forum's posts) US VI as an option, but St. Thomas does not seem to get great reviews...St. Johns seems to be a preferred destination, but only through st. thomas (how far is by ferry/boat from St. J.?)
If bahamas is an option (I know I know ...many of the fodorites may cringe on this one) which island?
Before I forget, budget is not so much of an issue, although we would rather not spend on a 7-9 day vacation more than 6000 for lodging it should not be the deal breaker if the budget goes to say 7K.
Also, weather....I realize that June - July is the rainy month season for many carib islands (though we had excellent weather when at TCI, the same was not the case at the cayman...5out of 7 days we had on and off rain throughout the whole day). So, although no one can predict the weather, statistically speaking, what is the likelihood to have better chances for good weather choosing a specific destination? Or does this not matter as all the islands may have the same weather during June-July?
In addition, this time we may be better able to explore little cays/coves, do more driving around, and probably swim at different beaches, we hope we can hit something like those pictured in many of the islands, secluded, small, clear waters, no big waves, etc. type of beaches.
I have a sneaking suspicion I am omitting pertinent information so you can better help out here, but please accept my apologies and let me know what other additional info might be helpful in helping me decide again...
Thank you all

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    OK, I'll try to ally some of your concerns:

    1) Weather in the Caribbean during June and July is going to be essentially they same no matter where you go - day time temps in the mid-to-high 80 F. with lots of sun - only a couple of degrees different between the very northern islands and the southernmost islands. It is not "rainy season" but it is in what is know as the Atlantic Hurricane Season which runs from June 1 thru November 30. Now, that does not mean there are major storms swirling around the islands all that time. It merely means storms are possible. the most active period for storms is usually between late August and the end of October (give or take a week or so). If there's no major storms the weather is some of the best of the year. Even if there is a major storm the odds of it striking a specific island are small. For instance, so far this year there were some 18 named storms in the Caribbean/Atlantic and only one or two have actually affected St. john or Virgin Gorda. In June and july you can expect an occasional short (5 or 10 minute) shower every once in a while but all day rains are rare. All that being said no one can give you any assurances when it comes to predicting the weather.

    2) You are correct that Virgin Gorda is difficult to get to from the US. Generally speaking you'll have to fly into San Juan or St. Thomas and then either fly to VG or take a series of ferries.

    3) When you say "St. Johns" I suspect you mean St. John (no "s"" as St. John is the island in the USVI's and St. Johns is the Capital of Antigua). If so, the only way there is to fly into St. Thomas and take one of the ferries from either Charlotte Amalie or Red Hook. I believe the CA ferry takes about an hour while the RH ferry is only about 20 minutes however, you have to factor in taxi time from airport to ferry dock which negates some of the time differential.

    Based on what you are seeking I'd suggest you concentrate on St. John. It's not that difficult to get to, there are plenty of rental villas, it's a very safe island, has numerous calm water beaches to visit that will be perfect for your kids, it's relatively small so nothing will be far from your villa (if you don't go the villa route look at Caneel Bay Resort which should be in your budget range during June/July).

    Virgin Gorda would be a close "second" although you may find it too difficult to get to with three kids and a mother-in-law in tow, however, with that many people in your group you may find you can fly into San Juan or St. Thomas from Boston and take a private Charter flight to Virgin Gorda for about the same cost as taking a commercial commuter flight and/or ferries. If you do choose Virgin Gorda check out Little Dix Bay (for a resort option) or villa rentals on Mahoe Bay (seclude 1/2 mile long calm water beach with crystal clear water, very good walk-in snorkeling and only a 10 minute drive from Spanishtown.

    I'd skip the Bahamas, the Out-Islands may be too "quiet" for you.

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    RoamsAround: THANK YOU! So much and great info! I really appreciate this. Now, a 'stupid' question....why do you rule out the bahamas? Also, the total travel time that I mentioned, am I being realistic with those islands mentioned (and indeed I meant St. John USVI) or are there other options you may recommend?

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    As I said, Bahamas Out-islands may be too quiet for you unless you are going to Nassau or Grand Bahamas which are very commerce. Also, the out-islands are often difficult to get to - often requiring you to first fly into Nassau then on to the out-island. Save those for when you and your spouse are more "seasoned" island travelers and it's just the two of you.

    As for travel time, from Boston you should be able to get to St. John in well under 8 hours. Getting to Virgin Gorda may take a bit longer but might be doable if the scheduling gods are on your side.

    Lastly, I'm somewhat in the minority on this forum but I never understood why people seem to have an aversion to connecting through MIA. I been flying to/from the Caribbean via MIA multiple times a year for well over 10 years. I never have any problems clearing immigrations and customs, always get through the TSA checkpoint fairly quickly (no longer than at any other airport) and experience flight delays (either when departing or arriving) no more often than at other airports. Regardless of my experience, you should use the routing that offers you the most convenience and gives you the least overall travel time. The only caveat I have is no matter what routing you take make sure you allow yourself adequate layover time between connecting flights.

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