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Choosing the Right Island

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Hi Everyone! My husband and I are looking to plan our next 5-6 night vacation and I was hoping to get some advice on which island would best suit us. We don't have any set dates yet - these are flexible depending on whatever time is best for the island we end up choosing.

We are looking for something relatively easy to get to from the Philadelphia/NJ/NY area and would like to keep the trip (airfare/accommodations/food) under $5,000. We are in our early 30's and have never been to the Caribbean. We would like this vacation to be mostly relaxing on beautiful beaches with turquoise waters, with some exploring around the island mixed in. Snorkeling off the beach is important to us, but having "the best" snorkeling will not make or break our trip. We are not fans of all-inclusives and would prefer staying at a nice hotel/villa with a pool that is on or generally close to the beach where we have the opportunity to come and go as we please. We are definitely looking for something laid back, but love good food and would like to be able to do something in the evenings. We aren't looking for crazy nightlife, but grabbing a drink or two and listening to some live music, or walking around a little downtown area would be perfect.

We are open to any suggestions, but so far we are seriously considering the following: St. John, Bermuda (I know this technically isn't in the Caribbean), Anguilla, Virgin Gorda, and Exuma (swimming pigs sounds like fun!). Grenada also sounds interesting. I know these islands are all fairly different from one another, but I'd love to hear your thoughts on which may be the best option for us and when would be the best time to go. Thank you for your help!

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