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First time to the Caribbean Islands

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My family of 4 - two adults and two teenagers (14 and 17) would like to go to the Caribbeans in early June. After skimming through a few guide books, we have narrowed it down to Aruba, Dominican Republic, and Jamaica. Please help provide input. We're are looking for a relaxing vacation and love beautiful beaches. We don't care for golf, shopping, or casinos. We are also trying to keep the cost down. We are from the San Francisco Bay area. Here are some of our questions:
-Which island would best meet our needs?
-Is 5 days/4 nights long enough?
-What is the best way to book our vacation? Is CheapCaribbeans a good source?
-Should we go for all inclusive?
-Is early June early enough to avoid the risk of hurricanes?

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    In general Dominican Republic and Jamaica will be less expensive than Aruba and somewhat easier to reach from San Francisco (but it will be a long haul no matter where you go in the Caribbean). Airfare will probably be lower to Dominican Republic and Jamaica vs. to Aruba.

    5 days/4nights is OK if you mean mean actual time "on island". It's going to take you at minimum of 13 hours (and possibly as much as 24 hours depending on routing and days of travel) flying time just to get there and a similar amount of time to get back.

    You'll find picturesque beaches on all three island but the sand will be "whiter" on Aruba. The sand on Jamaica and the Dominican Republic will have more of a light gold tint.

    Many people book through Cheap Caribbean and are pleased with the results but you have to do your research to be sure the deal you are getting is a good one. Others book travel directly with hotels/resorts and airlines and get just as good or even better deals. You have to price out the various alternatives to see what works best for your situation. There's no "one size fits all" answer when it comes to pricing airfares and hotel packages. Check your airline of choice's website for package deals they may be better than those offered by Cheap Caribbean. Look at hotel/resort websites for pricing info.

    Whether or not you go All inclusive is a personal choice. If you don't mind taking all (or most of your meals) at the resort and the adults in your party like to drink a lot of alcoholic beverages then going AI makes a good deal of sense. If, on the other hand, you like to "dine around' and/or you don't drink a lot then AI might not be for you. FYI - There are lots of AI's in the Dominican Republic and Jamaica so the competition is stiff meaning lower prices vs. Aruba.

    Hurricanes in June are very rare in the Caribbean - While there are never any guarantees when it comes to predicting the weather it's not not a big issue so I wouldn't worry about it.

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