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Which Caribbean island and when to go?

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It's our 25th wedding anniversary next year and want a special trip. So, am thinking about Caribbean island but no idea how to choose between them. Don't want a purely beech holiday. Enjoy walking, restaurants, visiting architecture, museums and shopping. In our 50s so don't want noisy, party atmosphere. Which island best fits the bill, please? Don't want to go when heat is massive or in the hurricane season. What does that leave as the best season to aim for. Look forward to your thoughts. Thanks

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    The best way to narrow your choices is to do some basic research to learn the differences between the islands. Start by clicking on the "Destinations" link at the top left side of this page, then click on the different "islands" and read the descriptions. You should then be able to choose 3 or 4 that most appeal to you so you can do more inept studies. Keep in mind there are big islands, small islands, lush mountainous islands and flat arid islands. Every island is different and has it's own appeal and no one island "has it all".

    Now with the exceptions of a few larger islands you are not going to find many "museums" on most islands and those you do find will be quite small. Instead you'll find historical sites like old fortresses, sugar plantation ruins, lookouts, ramparts, etc.

    Hurricane season in the Caribbean runs from June 1 through November 30 with the peak time for storms being late August through the end of October so you are pretty safe traveling anytime except September and October.

    Average temperatures in the Caribbean don't vary more than about 5 degrees between summer and winter months. You can expect daytime highs in winter to be in the low to mid-80's F. and in the mid to high-80's in summer. There are less breezes and higher humidity in summer so it will feel "warmer". FYI - the Bahamas are not actually in the Caribbean and can be much cooler, especially during the winter months.

    High Season in the Caribbean runs from around December 15 until the week after Easter - expect to see the highest room rates and most tourists during this time period. Shoulder Season runs from the Week after Easter until mid-to late June and again from around Thanksgiving to December 15 - expect to see a drop in both room rates and the number of tourists. The remainder of the year is Low season with the lowest room rates and least number of tourists. FYI - some resorts, restaurants and tour operators close during late August through the end of October/middle of November.

    In order for the regular contributors here to make meaningful suggestions it would help if you tell us where you are traveling from, how long a trip you are planning, what your tolerance level is for travel (i.e. are you willing to take one or more connecting flights and/or ferries or even an overnight stop to reach your final destination or do you want some place you can reach in a short non-stop flight from your nearest International Gateway Airport? Also, give us an idea of what type of budget you have for airfare, accommodations, food and excursions. Give an actual dollar range not some nebulous term like "affordable" or "won't break the bank" as we have no idea what they mean to you.

    If you don't want a "party atmosphere" avoid traveling during Spring Break or President's week and you'll probably want to avoid much of Cancun, Cozumel, Parts of the Dominican Republic and many, if not most, of the lower tier All Inclusive Resorts.

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    "Enjoy walking, restaurants, visiting architecture, museums and shopping"

    Well when I read this sentence, Puerto Rico came to mind as Old San offers all of these activities and of course there are beaches all over the island. If you want the best Caribbean beaches, then Puerto Rico is not the best choice for you. However, if you want beaches and these other things (there is also a rain forest and casinos in case that is appealing) PR is worth looking into.

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    Thanks to both for sound advice and useful pointers but we've had to change plans and are now not in a position to go the Caribbean after all. Headed for Canada instead. Thanks for your time.

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