Guide to Planning a Destination Wedding in the Carribbean

For those who have been following my posts over the past 6 years, I have tried to capture and share my experiences in traveling and trip planning. In 2021, I may have helped plan my most logistically challenging trip yet. A Caribbean destination wedding… during the Covid-19 Pandemic. And even though we had many setbacks throughout the year of planning, I wanted to share with you all of our lessons learned through the wedding planning process.

Step 1: Set Goals & Expectations

This can be the hardest part of planning any wedding, let alone a destination wedding. You have to be brutally honest with you and your partner about what your expectations are for the wedding. For example, if you want as many people as possible there, a destination wedding might not be for you. We went into this wedding planning with the following goals: To get married on the beach, okay with having just our parents and bridal party there at a minimum, and a cost comparable to having one in Utah. We really just came down to us wanting to celebrate our wedding, over many days with our friends and family, in the form of an international trip.

For us, a destination wedding was easy to justify, because in our case, both sides of our families live back east and a flight + lodging in Utah would be just as much, if not more, than just having a destination wedding on an island.

Step 2: Narrow Down Your Search Criteria

A list of criteria that we looked into, in attempt to narrow down the list of 97 Caribbean resorts we looked at in a gigantic excel spreadsheet, was as follows: Cost/Night, All Inclusive, Airport Shuttle, Capacity >50, Calm Waters, Beach Access, Multiple Pools, Vilas, Adult Only, Jungle Vibes, Multiple Restaurants, Hosts Weddings, Private Reception, Beach Wedding, Flight Prices, and Non-Stop Flights available.

Obviously, the most important input was cost, for both my wife and I, as well as our guests. We had to be considerate of them looking at the cost of flights from Philadelphia & New York, cost per night at the all-inclusive resort, and any additional costs that might come along with the travel. Beyond travel cost, we had to look at the costs of the ceremony, reception, rehearsal dinner, and any other group events we wanted over the weekend. We picked an all-inclusive resort because we assumed that since everyone is paying for food & drinks each day, the wedding events would be mostly free (except for the setup costs). We couldn’t have been more wrong. As it turns out, most resorts will charge you for the full ceremony, reception (food + drinks), and any other group events at a rate you’d expect for any stateside wedding. And that made no sense to us since everyone was already paying for the resort’s amenities.

Step 3: Down-selecting Your Resorts

How do you even begin this process? With so many options and so many variable, where do you even start? For this, I took an engineering approach to this and created a decision matrix, which are used to help visualize a clear winner between all the different options. How this works is you take each resort/destination, and rank them based on category. If you have 10 resorts, the best one would be ranked a 10 and the worst a 1. Then you apply a ranking of importance to each of your categories (I.E. cost = 5, Resort size=2, wedding venue=4, Number of Pools=1). Then you multiply the ranking by the category value to get a scaled score for each of the resorts. Next, sum up all the scaled scores for a resort total score. Lastly, rank each of the resorts based on their total score. From there, you will get your answer about which resort you should get married at.

Step 4: Contacting Resorts

So now you have the resorts narrowed down, based on whatever selection criteria you’ve used. I’m sure one of the resorts is great on costs but lacks the other intangible aspects of a wedding, and other resorts have amazing scenery and amenities, but is higher on cost. Next step is to contact the resorts and reach out to the wedding planner. This step may be the most critical, because the relationship you can build with a wedding/resort personnel is going to make-or-break your wedding and trip experience.

As an aside, please scour the internet for many more wedding resources from sites that are dedicated to this topic. Just as an example, this site offers dozens of helpful tips and questions to ask. But back to the steps.

Face it, you will not be able to micro-manage your destination wedding as if it were happening in your home town. You will have to trust them and know that this isn’t their first rodeo and that their job is dependent upon providing great experiences for their guests. We ran into this issue a lot, that is, lacking trust for the wedding planner thinking they were always on “island time”. But we couldn’t have been more wrong. They ended up going above and beyond for us and made our destination wedding more memorable than we could have ever hoped.

Step 5: Picking Your Destination Wedding

Once you’ve got a warm, and fuzzy feeling, about the resort to host you, your friends, and family, you have to make the most committing decision yet. You either have to take a trip to visit the place for yourself, book the entire wedding blind without ever seeing the place, or, for a third option, get lucky by having your family friends be sailing around the Caribbean with your Fiance’s parents and coincidently be able to stop by and check the place out. We were beyond fortunate to be able to go with option 3, which we are forever indebted to Radeen and Hayden for this. Realistically, it’ll all depend on your budget if you’ll be able to visit the resort prior to having your wedding there. I’ll admit though, not having been there, and seeing the resort for the first time on our wedding was more than worth it, especially since it far exceeded every expectation we had!

Last Tip: Do What Makes You Happy

Whatever you decide, just remember, it’ll all go way too fast. So try to plan a destination wedding with your closest friends and family so that you can spend the most amount of time with them individually. And also, don’t forget that this is YOUR wedding. Do what makes you and your partner happy, because that is all that matters.