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Which Caribbean Island for vacation??

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My husband and I are planning a week long Caribbean vacation in May with two other couples. We were thinking about renting a villa, but after doing research, still not sure where to go. We are looking for nice beaches, activities during the day, nice restaurants, and modest nightlife. We would also like a safe island where we can rent a car and explore or just walk around. Any advice is appreciated! Thanks!

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    It's always helpful if you can give us a budget. That way we can recommend places in your price range.

    Now, what you describe (a rental villa on a island with nice beaches, activities during the day, nice restaurants, and modest nightlife) is available on just about every island so my suggestion is you do some basic research to choose a destination that appeals to your group. Once you do that finding a villa on that particular island should be relatively easy.

    Among the islands that have lots of rental villas are Providenciales (in the Turks & Caicos), Anguilla, St. Thomas, St. John, St. Barts, Virgin Gorda, Nevis and St. Martin (and that's just for starters). There are literally tens of thousands of rental villas in the Caribbean so we need more info from you to help narrow down your choices.

    So start by using the "Destinations" link at the top of this page. Click your way through to the "Caribbean" then read the descriptions of the islands I mentioned. Pick two islands that most appeal to your group. Do google searches using such topics as "Things to do on Name OF ISLAND" to learn more about what that particular has to offer. If what you read interests you do another google search for "Rental Villas on NAME OF ISLAND". You'll find links giving you info and photos of the rental villas on that island. Choose a couple you like and you can come back here with the villa names to see if contributors have stayed there. Or you can go to TripAdvisor and check out recent reviews for those particular villas.

    Besides your budget tell us where you'll be flying from, whether or not you want a destination you can reach non-stop from your nearest international gateway airport or if you are willing to take one of more connecting flights and/or ferries to reach your destination. Tells us if you want a beachfront villa (they are often in short supply and/or very expensive) or are you OK with beach access or even mountainside (but within a reasonable driving distance of the beach). Let us know if you would rather be on a larger or smaller island. Clarify what type of activities your group is seeking. Have you been to the Caribbean before? if so, where did you go, what did you like and dislike about the destination you visited? The more you can tell us about you, members of your group and your likes and dislikes the easy it will be to steer you in the right direction.

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    Thanks you for the feedback, I appreciate it!
    -For a budget we are thinking around $4,000 a couple for airfare, villa, and car rental and then another $1,000 to $1,500 for food and excursions, and obviously if we spend less, that's great.

    -The number of connections doesn't matter to us (from Cleveland Ohio).

    - For the location of the villa, we are looking for a nice place with a pool and great ocean views. As long as we have those things and it is within reasonable driving distance to the beach, we will be happy.

    - The size of the island doesn't matter to us. Bigger may seem to imply that there is more to see and do, but I'm not sure that is the case.

    - Activities we would enjoy would be snorkeling, shopping, boating, golfing, driving/walking around, or doing anything different that the island has to offer.

    - We have all been to many of the islands in the caribbean before, but we were there on cruises, so we were only there for a few hours and usually doing an excursion, so we never really had the chance to experience the whole island. The only dislike we had about some of them was that the people were pushy. Trying to sell you things and literally following you, so if we could avoid that it would be great.

    If it helps, our favorite vacations spot is Maui Hawaii. We enjoy the beautiful scenery, nice dining options, the feeling of safety, the ease of renting and driving a car, and the multitude of things to do and see.

    We have been doing lots of research, but because they all sound so wonderful, we are having a hard time deciding, so any recommendations will be helpful.

    Thanks again!

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    With that Budget, I think you could find an great villa in St John. The island is safe to venture out and explore the many different beaches, great snorkeling, excellent restaurants, moderate nightlife, the only drawback for your wishlist would be the golf...which I don't think St John has. Everything else is there waiting, and the villas can be very affordable when split 3 ways.

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    Check out rental villas on Virgin Gorda's Mahoe Bay - upscale villas, almost all with pools that are either beachfront or beach access (no more than a 2 to 3 minute walk). Very good walk-in snorkeling reef that starts just 100' or so off shore and runs entire length of the 1/2 mile long golden sand beach. Fantastic views of neighboring islands and cays and the setting sun. Rental properties don't get much better anywhere in the Caribbean. Topography of island is similar to Maui, plenty of hiking and interesting things to do. No golf and only a few shops but you can take a ferry to nearby Tortola for your shopping fix.

    Not every island has golf. On those that do, it can be quite expensive (think in terms of greens fees in the $200 to $300US PP range). If golf is high on your list of things look at villas on St. Thomas - island also has good beaches, the shopping you crave, many points of interest.

    You'll find lots of golf on Puerto Rico but there will be many more rental "condos" rather than rental villas.

    Providenciales has some nice rental villas and golf but not too much shopping.

    Likewise, Nevis - lots of rental villas, golf available at the Four Seasons Resort (about $250 Green Fees) not much shopping and snorkeling is almost non-existent.

    No golf on St. Barts but has everything else you are seeking.

    I'll confirm - no golf on St. John.

    Anguilla - has one golf course (now operated by Cuisinart Resort - $230 Green fees) and a good selection of rental villas. Combine that with 35 white sand beaches and over 80 restaurants and you just may have the island you are seeking. There's no real shopping but you'll be just a short 25 minute ferry ride from St. Martin where you'll find all the shopping you'd ever want (warning, St. Martin is a major cruise ship port so you'll find a few "pushy" salespeople there).

    St. Martin has the shopping you want, great restaurants but the golf there is nothing more than a "cabbage patch" with some flags and holes. NO ONE, repeat, NO ONE goes to St. Martin for the golf.

    Now you mentioned "pushy people" - you'll tend to find those types in the shops near the cruise ship ports in Cancun, Costa Maya, and similar destinations so simply avoid going to the shops right near the ports on those islands. FYI - there are very few or in some cases no cruise ships calling on St. John, Nevis, Provo and St. Barts so "pushy people' don't really exist.

    Hope this helps.

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    i think you should consider barbados. it is safe, has 6 golf courses, shopping, some snorkeling, tons of dining options, some calm palm lined beaches on west coast & dramatic rocky beaches on east coast, as much nightlife as you choose in 'the gap', lots of things to do in daytime as well as a plethora of rental villas. for your budget you should find beachfront with pool and full staff (cleaning & meals of your choice). all the big rental companies list them, plus bajanservices.com is a great local company or vrbo or homeaway.
    american has a 6:10am flt - in 7 hrs with return lving a 7am that lands at 6pm both through miami
    kayak.com makes it easy to find out where it's reasonable to fly to.

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