3-4 grad students, spring break (1 week) - where to go? (PR, DR, StM, VI, etc?)

I'm completely new to the idea of traveling to anywhere but Europe, so I figured I would finally venture out and ask around on FT before I do. A few of my friends (25-29 y.o. guys) and I are looking into (relatively) inexpensive options March 16-24. I was thinking a budget of $2,000 or so for the week, preferably all-inclusive. Any kind of advice or past experiences welcome (especially advice on booking websites!), I'm open to most suggestions - especially if they somehow help me get to St. Maarten (wanted to check out the beach by the landing strip). Just kidding, though - while I'm slightly biased towards that island, I'm open to all kinds of suggestions. Oh, one thing - I would prefer non-stop flights (out of the Washington, DC area) if at all possible.

I did check out the other thread here, but that one is geared more towards families with small kids, plus it only has two replies.

If you want a Las Vegas type place on steroids look at Pattaya Thailand.

I think Pattaya would be the ultimate destination for a bachelor party.

We don't. This is why I pointed out our age. Not fans of all-out college-type blowouts, nor is anyone getting married. Just want to relax after two years of school.

Besides, Thailand is not in the Caribbean. Let's keep this on topic, please.

You might start by looking at www.vacationstogo.com

You can look by area and they have all-inclusives.

A quick check at Expedia vacation packages, airfare and hotel included will yield following results for the dates you are looking:
SJU from $700
SDQ from $600
SXM from $1200

None of the trips are direct for this rate, they start from BWI, I do not think there are any direct flights to any Caribbean Island from your location. the lower priced options for your destinations are NOT all inclusive type hotels. Dominican Republic offers the best option for all inclusive starting at $850. SJU all inclusive are a bit away from metro area, and go upwards of $1300, SXM, will be about $2000 for your dates. I was born and raised in Puerto Rico and travel there a lot. I've been to both, SDQ and SXM, I prefer SXM overall, but it is quite pricey. I enjoy SJU also, but that is because I know the area and its home for me. SDQ is very similar to SJU in regards to the beaches, sights, nightlife, and language. SXM offers lots of adult beaches, two sides Dutch and French, different cultures and sights.
Whatever your decision, keep in mind also the extra expenses, casinos, nightlife, tours, etc. that could eat up into your budget.

Aren't those just cruises? Not really interested in those.

No, if you will actually look at the website they have everything including all-inclusive packages like I said in my original post. if you are looking for other people to do all the work for you then find a good travel agent and pay them their fees.

I did look at the website. Clicked on "First time here?" and saw nothing but cruise adverts. That website isn't what you would call intuitive (the text search for "all-inclusive" took me somewhere to the bottom of the page to "one of our other pages") - so instead of moralizing, I'd have appreciated it if you actually pointed me to where on it I should have looked (the address was actually www.resortvacationstogo.com which I am researching right now). But I understand if that was too much trouble.

Thanks! There are some direct flights from IAD (like to PR) but they are few and far between. SXM will probably end up being outside of my price range since the flights themselves are over $700 for my dates. However, I'm considering going to SJU and then taking Jet Blue for $46 to SXM for a couple days - is that worth considering or am I better off just staying in one location?

I guess I was more looking for people's impressions of different islands since I haven't been there at all before. The logistics are important, but secondary - going cheaply to a destination we won't enjoy isn't exactly ideal.

I mean, all three destinations offer beach, casinos, nightlife, golf, etc. You mentioned your preference towards all inclusive, I personally do not like them, as I feel that I'm missing out of something. With all inclusive you tend to spend time on the resort, all your food and drinks are included as some of the activities, there is no reason to venture outside. However, on the flip side, the advantage of all inclusive is that you do not spend time going out to eat, drink, if you do not know the area. Its give and take I guess.
SJU hotels are known for the "party" like atmosphere in the lobby, everyone dresses up and hangs out in the lobby bars.
SDQ is cheaper overall, your money will go longer.
SXM is my favorite, but it is expensive overall. You might also think on St Thomas, I enjoy it also.

St John in usvi is close and a flight to st Thomas then ferry
So flights are relatively cheap to st Thomas but st John is less commercial, lots of great beaches, casual restaurants and maybe you can rent a house for the week (see VRBO) and avoid restaurants for breakfast lunch some dinners

About the time you want to go you should be able to get airfare for about 400 and change to Aruba, plenty of hotels on the beach (holiday inn, occidental etc.) have all inclusive. Aruba has all you are looking for and weather is more reliable than St Martin

I echo going through St Thomas and catching a ferry to either St John or Tortola. Did that a few years ago (Tortola) for spring break and had a blast -- and not too expensive.

30 minute flight, a few minutes to get through customs.. not bad at all. This is a regular weekend trip for me now that I have friends on the island and don't need to pay for a hotel.

However the $46 fares are closer to $140 all in, with advance purchase. I just booked a flight for the 17th, and it came to $197 all-in. Spring break dates I've seen as high as $500 all-in for a 30 minute flight.

You might want to check Insel Air as well.