Heather thanks!
Hi Lkb01,
Sorry I did not get to you right away had a destination wedding this past week that had allot of last minute add ons, changes and weather related concerns. Hopefully I can still give you a hand.
First of all the best place to start is with the two of you. Sit down, turn off the TV and cell phone, then each person right down a list of what you want for your wedding, then another what you want out of a resort and lastly what you feel your guests will be comfortable with. Then look at what you have similar and go from there. For an example you would like to walk down an aisle created on the beach with flower petals while the sun lowers into the ocean, but you want to make sure that your guests who the majority are first time travelers outside of the United State have a place that will take care of them for a moderate budget and not spend all day on an airplane. Now if that was the case that would narrow down your choices to a very few choices within the Caribbean. That's the best way to start, what you want and work you way through the wishes.
Secondly, find a budget that you feel would be comfortable for your guests to travel and your wedding details. Then what you can do is honestly compare what resort's wedding package fits you or if you want a wedding outside of the place you are staying or at a villa. If you really want a cocktail party and a private sit down wedding dinner, look for ones that include this or one that does not have 5 - 7 weddings per day. Whatever is your concerns they should fit your wedding day. Personally I am not a lover of the resorts that act like a wedding factory because I have stay there and seen brides, yes I said brides passing each other. Plus if you plan on having guests this is not a real great place to private the reception.
Another item allot of couples have been doing over the past year is comparing the wedding packages. Some have found lower priced wedding packages at higher priced resort. So what they did was pay a set amount on the guests travel. I have one right now that is paying for one night for their guests, another paid for three nights and another is just giving each room $200. They figure if the wedding package was $1500 at a resort that had a $1000 3 night stay, but a resort that costs $500 to stay and a $3000 wedding package, they would help their guests have a better quality resort. Yes, they want to save but they also want their guests to be well taken care of too.
Lastly, travel time! You do not want your guests who might stay shorter stays to spend all day on a plan traveling to and from the destination. This is especially true with people who have guests who have not traveled allot. With the Caribbean you have to be careful due to the time of year. Many of the airlines put better flight schedules during the winter months then from after Easter to Christmas. Destinations like Antigua, Grand Cayman, British Virgin Islands, even St Lucia can have trying flight schedules out of the majority of the cities in the United States.
You ask how do I know about the nights my guests are going to take. The best guide is to use the date you pick. Over the past 10 years with the weddings that I have done and I know with the other consultants here, we tend to see guests looking for longer stays between January - first part of May. That is when we get allot of 7 night requests for guests. Around the middle of May to Christmas time it is usually 3 or 4 night trips where people are making it a long weekend.
On to your next question who to pick to help you with this quest. Ok, full disclosure here I am partial because I am the owner of a destination wedding company, but I do hear your confusion. I myself don't like the way the destination wedding industry is handle today.

Too many different choices. My company is different because we are a travel agency and wedding planners in one that has been doing this for 10 years.

We did not buy a website address, we do not look up vendors off the internet with no track record and we do not book the travel and send you an email address to get the wedding done. Our best asset is to help couples like yourself because you do not know where you are going. We can provide not only travel information on various destinations but also the wedding information, all in one email address. All because we have created a working relationship with these companies they know our email when we come a calling for a couple.
Basically we can keep everyone together on the travel to find the discounts, we have a staff of people to book their travel plans, wedding details and your coordinator here oversees all of the organization. We even set up a webpage either on our site or with a company including all of the travel information like details and pictures about the resort so the bridal couple does not get asked all the time for things. We take care of the questions, just easier for you to sit back and enjoy!
There are too many avenues like you stated to take, but one thing I will state, don't go it alone!

Find someone to bounce ideas off, who has had weddings there in the past, personally seen the places you are going to and has done a wedding from start to finish, travel to wedding.
The best thing to do for a destination wedding is to have communication open and to relax. You know that 100% satisfaction for everyone is not going to come because you cannot control everything. And that is a big thing, you cannot control it like a local wedding. There could be rain or a floral shipment did not come in on time. A destination wedding is like a free fall in allot of cases because there is many items that local brides spend months planning ahead of time floral arrangements, cake flavor and menu. You have to be willing to trust the resort that does this all the time. If they are an all inclusive resort then look at the reviews for their food, because it will be the same for your wedding dinner. And don't be afraid to ask for changes. I just had a wedding at an all inclusive which I alerted the wedding planner, pastry chef and Head chef to the groom's food allergies. The mother of the bride told me that the waiters knew this request.
With our company I must admit that we work with certain resorts because of 10 years track record. And these resorts know that. They want you to have a great time so the outside vendors like florists and live music have to be good otherwise they would get rid of them. Otherwise it would reflect back to their business name, which translates to no business. That is the same reason we suggest certain resorts to people. You are going to remember our name vs. the resort if something goes wrong.
Sorry went on a little bit long, but I want to make sure you cover all angles. This is your destination wedding, not your family, not whatever wedding planner or travel agent you use. The two of you is what this event is all about! Your love coming together and on to the next step in your relationship. Always keep in mind!
Best Wishes on your special day!
Lindsay