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Anniversary in May, need resort suggestions

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We are celebrating our 25th in May and my wife and I would like to spend about a week in the Caribbean. We're looking for something that would combine a secluded feel with a night life, or fun things to do. We like to try different things. I'm looking for specific resort suggestions (someplace you've been!), as searching resorts, even by island, online hasn't been very helpful. Thanks,

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    These types of questions are difficult to answer because you haven't given us enough information.

    First & foremost we need to know your budget. You have to give us a specific dollar range and not use nebulous terms like "affordable", "won't break the bank", etc. as they are meaningless without a pint of reference - we don't know what you can afford. If you can try to give us separate values for accommodations, food, activities and airfare. It makes no sense for contributors here to make recommendations for places that are out of your budget.

    Tell us what you mean by "fun things to do", in other words describe some of the things you like to do and activities that interest you - everybody has different tastes and what might be fun for me may not be fun for you.

    What type of island do you think you'd like to visit? If you include the Bahamas there are more than 800 different islands and cays in the Caribbean - each has it's own appeal and no one island "has it all". Likewise, there are literally 1,000's or resorts & hotels in the Caribbean. Asking us to tell you which island and/or hotel or resort is right for you without any real input from you is a daunting task.

    Describe what type of night life you are seeking - "secluded resorts" don't offer a lot of night life so that could be a tradeoff.

    Tell us where you are traveling from and how much elapsed time you re willing to endure to reach your destination. Some "secluded resorts" take a full day or even an over-night layover to reach. Are you willing to take one or more connecting flights and/or ferries to reach your destination or do you want an island you can reach non-stop from your nearest International Gateway airport?

    What "activities" are important to you - snorkeling, hiking, sailing, fishing, diving, casinos, etc. Give us your "wish list" in order of preference as not every island has all those activities and you'll have to make some concessions.

    What type of resort experience are you seeking - All inclusive, full service luxury, boutique, mid-range, bed & breakfast, etc.????

    What type of island - flat, arid scrubby limestone & coral based islands with long strands of white sand beaches & bright turquoise waters, hilly islands with smaller cove like beaches and multi-hues waters, or mountainous islands with lush rain forests, dark sand beaches and deeper blue waters? Also, do you want a large island with a combination of cities and country life, small islands with little villages and no real infrastructure, or perhaps something in-between?

    The more you can tell us about your likes & dislikes the easier it will be for us to steer you in the right direction.

    in the meantime you might want to start by using the "Destinations" link at the top of tho page. Click your way through to the "Caribbean" and then read the descriptions of each island. Choose one or two that most interest you than look at resorts on those islands . You should be able to narrow down your choices to several different resorts. You can then come back and post specific questions about those island and resorts.

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    Well, I'm not being smart, but having never been there before,, and if I knew answers to all the questions you raise, well I imagine I'd know just where to go.

    It's our anniversary, so it's kind of a big deal. I won't say money is no object, but I was thinking a splurge for us might be around $5000.

    We like adventures--meaning we aren't so set in our ways that we necessarily HAVE to know exactly what to expect. Our favorite vacations have always had an element of surprise. I don't mean to be a smart-*** but it sounds like you and I take completely different approaches. Anyway, how many resorts have you personally been to? Are there some that you would definitely recommend, some you would not? That's the kind of help I need.

    I'm looking for recommendations for someplace nice...I imagine like anyplace, the Caribbean has places that are nice and places that are not. I'm not looking to book a travel agent, just some honest opinions from people who've help us narrow this down.

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    Not trying to sound smart either, but there are many islands in the Caribbean. Roams around has not only been to quite a few, but also lives there.

    Every island has a nice resort. Every island has not so nice. There are 1000s of places.

    Every island has a fan. Every island has a someone who doesn't go back. Here's the thing, tastes are relative.

    We know nothing about you except your budget. We don't know what you like. For example, roams around knows Turks and Caicos is one of my favorite islands. Actually he probably never needs to return. Yet we both love the Caribbean.

    To help us guide you, you need to tell us what you want and what you're looking for. Excursions? Romance? Nightlife? Shopping? Happy just at a beach or need more? Adventure?

    Maybe to see what grabs you more, check out Fodor's Caribbean 2014. It has chapter overviews of every island in Caribbean. Then you can see what interests you, what doesn't. It can help narrow down, so when you come back to ask you can say, "well, such island doesnd impresse me but these 2 do" for example.

    Just Bahamas has 800 little islands. Caymans has 3. Turks and Caicos has 9 habited ones. Virgin islands has many among them.

    Every island has nice resorts and something to offer.

    If we told you about every single one, you'd just get more confused. And we have no idea what your tastes are!

    And yes, I've been to about 80% of the islands, and still wouldn't know how to answer you!

    Please be as specific as possible about what you like, we would love to make suggestions!


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    Well, to answer your question - I've been traveling to the Caribbean for over 30 years (multiple times in some years) and have stayed in perhaps 50 different resorts/hotels and even though I now have a retirement home in the Caribbean I still visit at least one or two other islands each year. So yes, there are a lot of resorts I can recommend but based on your $5,000 many are well out of your price range (and that assumes the $5,000 is just for accommodations). There are also many I wouldn't go back to again.

    Now, I'm guessing your $5,000 budget is for accommodations, airfare, food and excursions/activities. If that's the case we need to know where you are flying from as airfare could use up a significant potion of your budget. For instance, R/T airfare from some East Coast cities to some of the larger islands could be in the $500 to $600 PP range but over a $1,000 PP to some of the smaller islands which require connecting flights. If you live in the mid-west or on the west coast airfares could be in the $1,500 PP range. So you see, your $5,000 budget really means you have under $4,000 (probably closer to $3,500) to spend on accommodations, food and activities.

    The reason I ask you to clarify your budget is it will make a big difference on which resorts people recommend. If you read through many of the threads on this forum you'll find a large number of them are questions asked by first time (Caribbean) travelers. The ones that get the most responses are the ones where the OP supplies much of the same information I suggested you give us.

    Everybody wants "someplace nice" and you are correct, you can find "nice resorts" on just about every island. The thing is "nice resorts" come with a price and your budget (after airfare) is not going to get you the best of the best. Even going in May (when room prices are at their lowest) you are looking at mid-range resorts.

    That said, you'll find you'll find you'll get the most bang for your travel dollar at destinations such as the Dominican Republic, Jamaica, Cozumel, Cancun, Playa del Carmen so you might want to concentrate your search to those places.

    I'd avoid Grand Cayman, the Turks & Caicos, St. Barth's, Anguilla as they are among the most expensive destinations in the Caribbean.

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    Anyone can answer your question with their favorite Island or resort, which may or may not be what you are actually looking for. The regular posters on this forum, who continually answers questions such as these, know that. We want to be able to assist in the best way that we can.

    Everyone here that regularly posts brings what they know to the table. In my case, we have been to several Caribbean Islands, but we mainly travel to AI resorts in Mexico. We are also budget minded travelers, which means I don't hardly ever spend $5,000 for air and hotel. We have been to Grand Cayman and T & C for around $3,000 air and hotel. I have not traveled to St. Barth's or Anguilla as $3,000 is usually at the top of my budget that I want to spend. Hawaii and Alaska were great exceptions to that budget.

    If you are interested in AI's, you get the most bang for your buck in Mexico, Jamaica and the Dominican Republic.

    If you are interested in white sand beaches and crystal clear water; Bahamas, Turks and Caicos, Grand Cayman, Aguilla, St. Barts, and Antigua.

    Islands with tropical flora, fauna, mountains and waterfalls; Jamaica, St. Lucia, Grenada, Dominica, Puerto Rico and Costa Rica.

    Do nothing but chill: Turks & Caicos, St. John, USVI, Cozumel, Grand Cayman.

    Nightlife; Aruba, St. Martin, Puerto Rico, Playa del Carmen, Cancun, Barbados.

    Adventure; Costa Rica, St. Lucia, Mexico, Jamaica

    Shopping; St. Thomas, USVI, St. Martin, Aruba.

    Just to name a few. We spent our last Anniversary in Key West, FL. Not great for a beach vacation, but lot of things to see and do, great pool opportunities, great nightlife and some wonderful food.

    We have always found the 2nd/3rd week of May to be very good regarding lower prices and lower crowds. You will want to avoid the week/weekend of Memorial Day. Picking a hotel that is either adult's only, more secluded and higher priced will keep the families with children at bay if that matters to you since it's an anniversary.

    If you could provide a few of the most important things you want to see and do and things you are completely not interested in, we can probably point you in the right direction.

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    I know it can seem overwhelming to pick an island so some specific suggestions can be helpful. I have not travelled extensively in the Caribbean but based on what you are seeking, St. Martin seems like an option. You can do some research on it but below is my experience of the island.

    My wife and I went to St. Martin (French side) and stayed at the Radisson Blu hotel a few years ago and really liked it. The hotel is secluded in Anse Marcel and has a very nice beach and beautiful pool area. There are a few restaurants in walking distance but to go to the really great dining options you need to drive or take a cab to Grand Case, which is about 10 minutes away. You could also stay in Grand Case to be closer to all the wonderful restaurants. There is a beach there too.

    Recently there has been some concern about safety in Grand Case however many people seem to go without concern and have a wonderful time. I just mention it as something you should be aware of if you decide to go there. We also ate at a restaurant near the Radisson called Sol e Luna and it was a wonderful experience.

    Orient Beach is another area of the island which is very active and has beachside bars and restaurants. You could stay there but it's not very secluded. It's also a nice place to just go for the afternoon.

    The Dutch side is much more built up but has casinos and many more restaurant and nightlife options.

    We have also done a day trip to St. Barth's which is fun and you can take a day trip to Anguilla. These islands are very different than St. Martin and it's nice to have both experiences. Travel Talk on Line (TTOL) is a good forum for St. Martin/St. Maarten.

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    For beginners to the Caribbean, I would recommmend Barbados because it looks like how you imagine a Caribbean island to be. Palm trees, beautiful white sand beaches and calm clear water on the west coast. It has a good tourist infrastructure. You may not get that secluded feel though unless the hotel you choose has large grounds. There is some nightlife and plenty of upmarket shopping. There are interesting things to see outside the hotel, historical buildings etc. The question is whether it can be done in your budget and if you can get there easily.

    Grenada is another really beautiful island with something of everything. Stunning beach at Grand Anse, several very good hotels, rainforest in the centre, very friendly people, little bit of snorkelling, excursions available around the island. Again flight options might be limited.

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    For some breaks on the budget, and to get a better idea of what kinds of things you can get for the money, join travel-zoo and look at some of the specials in the Caribbean. The specials are usually kind of last minute, but you may find something interesting to research.

    OK, know you are asking about an AI island resort, but with the budget, have a look at a cruise. Vacationstogo 90 days sticker is informative. Just as with resorts, and islands, you would have to learn a bit about the ships, lines and itineraries, etc. but that is easy to do. Look at cruise #10317, Royal Caribbean Jewel that departs from San Juan and visits five other islands. You might have to plug in your dates for this cruise to come up, since it is not within the 90 days. It is not secluded, but does everything else you want and is within budget. By May, many ships have left the Caribbean for the summer to cruise the Med, so choices are limited, but I specifically looked for 7-day, at least 4&1/2 star, non-party oriented ships/cruises that visited several islands.

    OTOH, Barbados would be lovely if you can make the budget work.

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