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Tips & Tricks for a Destination Wedding - All the details

Updated: Feb 27, 2023


When Hayden and I got engaged, even though I was SO excited to marry him, I was absolutely dreading wedding planning. I wanted to elope. All I wanted was Hayden. That’s it. Just my person, forever! Simple. But no, wedding planning is so much work, and I found it annoying that all the work was falling on me.


And as it turns out, wedding planning is as absolutely miserable as I assumed it would be…but I have no regrets on choosing to have a destination wedding! I highly recommend just inviting your inner circle and running away to paradise!


I’m going to get into some of the not-so-fun things about planning a destination wedding. I don’t mean to sound negative, but these are things I wish I would have known, so I want to put them out there to hopefully help out the next bride-to-be. So bear with me as I try to be as transparent as possible.


Looking back, I wouldn’t change a thing about our wedding day. I didn’t get the elopement I hoped for, but what I did get was pure magic! We had the most wonderful day. It was better and more beautiful than I could have ever dreamed! We ran away to paradise and got to claim forever together in front of 25 of our favorite people. We invited our wedding party and our parents to join us in our amazing celebration. So if you’re planning a wedding, hang in there—in the end you will have everything you need….Your person!


You can read all about the resort we choose in our post, but let’s dive into destination wedding details and recommendations.

First and foremost…

If you are planning a destination wedding, understand that not everyone will want or be able to come. This can be a hard pill to swallow, but it is the reality of the situation. Expenses, travel, PTO, and childcare are all big obstacles, and it’s a huge request to make of people. We took the stance from the start that there was really no pressure. If Costa Rica was not a destination they were interested in, or it just wasn’t in the cards, we understood. It wasn’t always easy to hear the bad news if someone couldn’t make it, but in the end we were so happy with how many people wanted to be there on our big day!


Step 1: Find an agency

A destination wedding agency will come in handy for two major things– 1. Finding the resort you want to use. 2. Allowing you and your guests to pay for the trip under a payment plan. Trying to find the perfect resort can be very overwhelming, so having an agency’s portfolio to look through made it a lot less daunting. Not having to front the whole balance of your stay will make it more practical for you and your guest to be able to make the trip work. An agency can also help with booking transportation from the airport to the resort. But before booking flights, make sure you reach out to the resort directly to see what routes they recommend.

Step 2: Pick a resort & wedding package

When you’re filtering through resorts and falling in love with all the beautiful destinations, be sure to take a peek at their wedding packages too. When we were looking at resorts, I never thought to look at the wedding packages, I was just looking at the resorts as a whole. I just figured that if the agency used these resorts, they must have good wedding packages. You will need to budget for both your stay and the package cost. I recommend taking a look at how many hours of photography and images are included, number of guests included, and what floral is included. These are the things that added up quickly for us. Before you fall completely in love with a resort, reach out to the wedding department and ask what other projected costs are typical for weddings there. Get as much information as you can prior to signing the contract and paying a deposit.


Step 3: Prepare for emails

Our whole wedding was booked with one phone call and about one million emails. You really need to just trust the process. I am going to say that again…TRUST. THE. PROCESS. I am sure every resort is different, but I had to pick the majority of our wedding details out of a catalog. I also had to send “inspiration photos” for several things and just hope for the best. Everything worked out absolutely beautifully, but it is stressful when you have never seen the venue before and don’t get to work with the vendors directly. I followed the resort's wedding page on Instagram, and when they would share or tag brides, I would message those ladies! I asked how the big day went and if they had any tips, and they all were so kind and let me know that everything went according to plan. It might sound kind of weird, but I recommend doing this if you are looking for first hand experiences.

The things that caught us off guard

Although everything was smooth sailing on our wedding day, we hit some bumps in the road leading up to the day. Just know you will run into some unexpected costs. It is bound to happen, and everyone we talked to who has planned a wedding confirmed this. Leave plenty of wiggle room in your budget and just expect the unexpected.


The wedding package we chose was the “high end” of our resort’s offering for our number of guests. It included a bunch of really great perks, but there were a lot of things we needed to add on. Here are the two examples I have for you: #1 We had to pay for the lights at our wedding venue. It was outside and they had to hang string lights to light the space for the dinner and reception. We had to pay per strand of light, and they were outrageously expensive. #2 The package came with one hour of photography and 50 images. We were looking for a lot more coverage of this special day and knew we would have to pay for anything additional. The photography packages the resort offered were significantly more than we were planning for or had seen in any wedding budget estimator.


Honestly, I didn’t fully love the agency we used. After we booked with them, they didn’t do much else to help us and were hard to get a hold of. Plus, they had us use a third party transportation company to get to and from the resort that turned out to be unreliable for multiple people in our party. Once we were in Costa Rica, we talked to the resort about the transfer issues our group was having. They recommended we take taxis, and that ended up being significantly cheaper than the transportation our agency set up. Communicate with the resort from the start and ask them for help and suggestions directly.


I’m not telling you all this to be scary or daunting, I just want to be transparent. I think the wedding world is really missing transparency. Make sure you know what is important to you on your big day so you know what you’re willing to splurge on.


Think of paradise

Whenever you’re sick of emails, stressing over not being able to sample the food, or ready to cry stressing over how it will all turn out, just think about how all your favorite people will be by your side in paradise! We got the most magical wedding day and the best beach vacation with an amazing group of people. It made all the stress and countless emails worth it.

It’s not over yet…

Plot twist…The planning didn’t stop there! We are having a rather large reception (think beer & dancing) in Wisconsin this spring with all our friends and extended family. (That is a planning nightmare story for another time...) Be on the lookout for our Happily Ever AFTER-PARTY recap this spring!


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