I have plenty of time to plan but I really would at least like to find an island and a hotel for my destination wedding in April 2008. I expected the planning to be a little difficult but I'm having major trouble just finding an island/hotel that is what I want but also affordable to my guests. My fiance does not want a wedding at home due to his large italian family, plus mine would have a guest list of over 350. He is back in school and I'm just finishing paying off my student loans so we will not have lots of money to spend. Our budget would be under $5000 for 1-2 weeks in the Caribbean. I would have loved Hawaii or South Pacific but that is too far for family to travel so we decided on the Caribbean. I would prefer a lush, mountainy island with nice beaches, snorkeling/diving-my fiance wants to try it. We would prefer a smaller resort/hotel-I do not want a typical holiday inn feel however-I want the romance of it. This has been hard to find that would be affordable to our family. We plan on under 30 people coming, possibly a few very young children. This has been the problem partly. I found a few resorts I liked in St. Lucia-Ladera, Tikaye but they do not permit kids under 12. Plus we are coming from Pennsylvania and flight time is a little bit of a concern. To St. Lucia with lay overs, it is saying online that it would be 8-10 hrs-pretty far for a 3 yr old.
So I guess my question is now that I gave some background. Can anyone suggest an island that has the things we want and a hotel that would be under 200 or so a night with a romantic feel to it. And will some hotels give a good rate for groups-like have the price be per room not per person. Thanks, any input would be appreciated.

Your requirements will sharply limit your options. The only island that I can think of that may satisfy your island desires, budget, and need for a short flight is Jamaica. Perhaps the Montego Beach Resort (the old Jack Tar Resort) would work. There are many mid and low priced Jamaican resorts but the Montego Beach Resort has the advantage of being near enough to the airport so that you wouldn't have to deal with a long drive to Negril or some other arguably more popular Jamaican destination site. One suggestion, no matter where you decide to go, would be to schedule your wedding for the second half of April when most resorts institute low season rates.

I got married in Antigua in 2003, and while it is not mountainous and lush, it's not flat & arid either, like the typical coral-based island. It's western topography is fairly lush and hilly, falling short of mountainous, and the east coast is more arid, but still with hills and cliffs.

With our group of 42 people, we chose the Long Bay Hotel on the east coast as being family friendly and a good value economically. We were given a special rate for the 3 night/4 day long weekend in which we took over the entire hotel. They worked with us to give us both a per person discount for those traveling solo, and a per family discount for those with many kids (the best deal was for a family of 6, who got to stay there for $300/night because they elected to stay for a whole week). The rates included breakfast, dinner, water sports, taxes and gratuities, so it ended up being a fantastic deal. Long Bay is a very casual resort that lacks many modern ameneties like air conditioning or television, but it is a much beloved place with it's extremely high percentage of repeat guests.

You're going in the right direction by keeping your guests' cost and travel time in mind. If you can travel at the second half of April, most places will have kicked into their low season rates and you will save a bundle over traveling in the first half of April.

Keep in mind that the larger islands with bigger airports that can facilitate the larger jets will have lower airfare costs than the others, so think Jamaica, St. Thomas, St. Maarten, Dominican Republic, Puerto Rico, and Antigua. Incidentally, these are all fairly northerly in the Caribbean, so travel time is definitely cut down.

Thank you all for your replies. We chose April just for the fact that it would be getting into the cheaper rates. I would have liked January, but my fiance talked me into waiting for the rates. Besides what's a few more months after a 2 year engagement right.
The island does not have to be mountainy per say, just not flat like I picture Aruba being. Seeing pictures of the USVI seem nice too. I've been to Jamaica so I'd prefer not to go again-though it was very lovely and what I like as far as lush. Many people say it has a lot of crime though and you can't really leave the resorts. I was there for a day on a cruise and did the Dunn's falls.
So any more suggestions for hotels that I can look into would be great. I'll look into Long Bay. Thanks.

I helped my friend plan a fantastic wedding at the Hyatt Grand Cayman 6 years ago. About 25 people. The Hyatt will probably be pretty pricey, but there are cheaper hotels for other guests. They did the rehearsal dinner on the same catamaran as the Sunset Cruise/Stingray city boat. It was awesome as was the food and the steel drum (but played good music) band. Good luck. You may want to also try Turks & Caicos. There's a reasonable comfort inn for your guests right in town.