I had been trying to convince my boyfriend that our next vacation should be to South America, but he really wants to just relax, so we have decided on the Caribbean the third week of May 2007. Cruise are not of interest to us, and we just don't know what island would fit our needs. If anyone has any suggestions I would welcome this. Here are our criteria:

1. Good value -- we are recent college grads with good jobs, but definitely not looking to drop $500 a night. We are hoping to spend $1000 each for air (from the Midwest)and hotels for a week. Luxury not important.
2. Very close, if not on, a beach
3. Not overly crowded feeling, especially feeling overrun by families (although couples only not necessary)
4. Not Cancun or Puerto Rico (I have already been there)

My initial ideas are Dominican Republic and Cozumel, but I am worried that DR is dangerous and Cozumel too much like Cancun.

Another big question: when should we look for deals? We are thinking of doing a package (not sure all inclusive or not). I know May isn't high season for the Caribbean, so should we wait until 2007 to book? Or are prices not likely to drop much?

Thanks for any response!

To clarify: $1000 means air + an AI, which is what you seem to imply? If you are just looking for air + hotel, then you can easily do a small inn somewhere, and there are a few on almost all islands that are on or near the beach.

The only choice in the Caribbean may be the Dominican Republic. $1000 from the Midwest is a fairly low budget for a week at an AI anywhere in the Caribbean. You might also be able to get a cheap rate at a very mediocre resort in Antigua. You will have absolutely no safety problems in the DR, particularly if you stay at an AI, which is almost a hermetically sealed environment, so I don't think that shoudl be a concern for you.

If you will consider Cozumel (and it's not like Cancun if you choose your resort carefully), then you can also do that for your budget.

I want to be very clear about what you should expect for this kind of money. You will not find a place that doesn't have a crowded feeling because the only places available to you will be big AIs, and most of the low- to mid-range AIs are family-oriented.

If you go the route of a small hotel or inn, you could look in St. Lucia around Gros Ilet, in Barbados in The Gap, in St. Maarten almost anywhere, in St. Croix (but few of the small inns are on or near the beach), and perhaps in St. John if you want to do Maho Bay Camps. Be sure to set yourself a budget for food, which is rather expensive in the Caribbean and (depending on the island); plan on at least $40 a day per person for food and are willing to eat very modestly, more if you expect to go out to nice restaurants. Also think of budgeting for a rental car, which will add at least $250 to your costs.

In terms of timing, it's impossible to predict when you'll see the best prices. Focus on when you see an airfare sale because those prices are going to fluctuate more than the cost of the hotel or AI. If you see a great deal you can afford, jump on it whenever you see it ... anytime between now and next March.

Thanks for the response. To clarify: If we were at an all inclusive, we would be willing to go beyond $1000. Actually, we are realistic in knowing that we will go beyond that probably no matter what. However, I figured for $500 each for airfare and $150 for a room per night that would be realistic, and bring us to $1000 each. I definitely spent under that in Puerto Rico and Cancun, but I realize the islands are probably more upscale.

The small inn idea seems like a good idea to me. We have no real desire to rent a car as we are under 25 and don't want to pay for it.

We will keep our eyes open for sales. Thanks for the advice.

hi lizzy, as doug said if you have any interest in leaving your resort domican republic is not for you.
the further south you go in the islands the higher the air rates and travel time can be 9-24+ hours.
my suggestion is that you consider the maya riviera area which is appox 45 mins south of cancun, a/or a world away. i will use the akumal beach resort as an example, as i have friends who have been once and found it comfortable, clean and fun. it is ai, and beachfront. a standard rooom next may is $469/pp or $938 for the 2 of you including food and drinks. you should be able to find air for $1000 and the resort will come pick you up in cancun so your only other expenses would be excursions and trinkets. take a look at www.locogringo.com if this interests you at all.
or, in boston there are 2 charter companies tnt and gwv that have some amazing prices so you could find out if there are any similiar companies in your area.

I would suggest Grenada to you as a destination in May.

If you would like romantic seclusion on a gorgeous beach, take a look at www.lasagesse.com for a place with extremely nice rates that offer a good value. The beach is a real tropical beauty, the restaurant on site offers excellent seafood, and you can use their sea kayaks, boogie boards, or walking trails if you want to seek a physical diversion. This place is extremely secluded--no other restaurants within walking distance, but if you just want peaceful relaxation, with maybe one day spent on an island tour and one nice meal out one evening (both of which would require taxis), this could be your place.

If you want to be a little closer to what passes for the action on Grenada, pick a place on the 2-mile long Grand Anse beach. As of this past summer, the Grenada Grand was offering hotel rooms for under $100/night on sites like www.hotels.com. There's also the Flamboyant on the far end of Grand Anse beach, which has their rack rates starting at around $100. These places are within walking distance of a few restaurants. Public transport would be easy from these places, and taxi rides wouldn't be very expensive within this area, either.

Grenada is a beautiful island, with a stunningly lush mountainous interior and many beautiful beaches. The island itself has a nicely balanced tourist infrastructure without being Americanized, in my opinion.