How to Plan a Destination Wedding?

Today’s post comes from Mrs. Distilled Dollar! She writes about a topic that has been top of mind for us over the past few months following our engagement. She shares our approach to planning a destination wedding.

How to Plan a Destination Wedding?

No, seriously — what the hell do we do? This article isn’t a step by step recipe for a perfect getaway wedding. This article is me asking how to actually plan one.

We’ve done the hardest part, which is setting a date. Now we have something to say when everyone and their mom asks us when the big day is. But alas, we are naive, and we thought that would get us off the hook.

Negative. Turns out if you can get past setting the date, the next question everyone asks is, “Have you picked a venue?”

Venue. Venue? VENUE??!?!?


Okay. Let’s start with what we DO know:

  1. We want to get married — half the battle right there, amirite?
  2. Our dream location is far away from people who would show up for the “open bar”.
  3. We want to get married on the first of the year for a plethora of reasons only significant to us and because we want to be difficult..
  4. The first of the year is dead cold in Chicago and we ain’t havin’ no winter wedding ‘cause this bride wants to feel her toes walking down the aisle.
  5. Our big goal is to have the wedding paid for in cash. We don’t want to wake up after the wedding with a big credit card bill.

Great! Caribbean Wedding on a budget it is. If only there was a magical hassle-free package we could “Add to Cart” that would cost less $10K while wining and dining a 100 people.

I actually had my first call with a Wedding Coordinator who specializes in booking Caribbean Destination Weddings. She flat out told me it’s going to be a pain the ass to find a resort willing to have an event on New Year’s Day. But, lucky for us, it wouldn’t be impossible either.

As someone who has spent years working in the hospitality industry myself, I can tell you for a fact that hotels and resorts work on January 1st and often for time and half wages. Not sure why a venue would not want to book a wedding if they’re open and working ANYWAY, but hey — that’s just me and my common sense over here.

Regardless — we’re 2 years out, and since our date is not flexible, we have to lock down a venue as soon as possible.

Any Distillers have ideas or suggestions for venues? Let us know about your Destination Wedding experiences and if you have any helpful tips to share!

Happy Holidays to All!

– Future Mrs. Distilled Dollar

6 comments… add one
  • The Green Swan Dec 12, 2016, 7:09 am

    Sorry I’m not much help on destination weddings, but I wanted to stop by and tell you how much of a proponent I am of them. They are great for having close family and friends (the folks you care about!) come to the wedding and for it to also serve as a vacation for them. And for you folks, a lot of the planning (tedious and hard stuff…) is taken care of by the resort who specializes in these things and do them all the time. It is definitely an easy and great way to get married!

  • Mrs. Picky Pincher Dec 12, 2016, 9:43 am

    Congratulations! Oh, thank god you have two years to plan! For a second I thought you meant New Year’s THIS year and I was going to commend you for your courage, haha!

    Mr. Picky Pincher and I almost opted for a destination wedding, but it wasn’t the right choice for us. However, there are still a lot of things we did to save money that can be applicable to any wedding.

    1. We asked for honeymoon donations instead of wedding gifts.
    We already lived together when we got engaged, so we didn’t need to set up a household. Instead of getting 13 blenders, we asked everyone for donations to our honeymoon. We didn’t have to spend much of our own money and we went to Disney World, which is infamously expensive. Our parents also contributed quite a lot of cash to our already-modest celebration, so it was affordable for us.

    2. I bought a dress off the rack.
    I bought a sample dress with cash after saving up for six months. I paid $100 to get it altered and that was that!

    3. We negotiated a cash price for our rings
    If you’re already engaged, this might be too late, but we walked into the jeweler with cash in hand. We got about $200 off our rings because of that!

  • Danielle Dec 12, 2016, 4:15 pm

    I had a destination wedding 2 years ago in Costa Rica and it was the best. It definitely ensures that the people who attend are there because they want to be there for you and not because they want to attend a “party.” The best advice I can give is to book your trip around 4 months out for the best prices. They seem to be higher the longer out you go and get cheaper the closer to the date up to a point, and then get higher again. I went to several travel agencies and no one could find prices better than what I found on my own online, they only could ensure flight seating and rooms were closer together. The last week of December and the first week of January are the most expensive time of the year for any warm destination and start to increase in price starting November 1. Also remember that everyone wants the holidays off, so even if hotels and restaurants are open then, excursions are more limited if your guests are into that. As well it is much cheaper to get married by your local courthouse first and then just have a renewal of vows service at the destination because of the legal fees involved, your guests generally won’t know that the service they are attending is not the legal one. Also a wedding dress idea is to look at prom dresses in white for a huge savings, and much less heavy for the hot weather. Good luck and congrats.

  • Tawcan Dec 13, 2016, 9:59 am

    We got married 3 times, once was in Denmark, did that count as a destination wedding?

    What about getting married locally in Chicago with a small group of family & friends then have a destination reception and invite only a small group of people? Asking money to pay for honeymoon instead of gifts is very common nowadays.

  • AustralianDividendInvestor Dec 14, 2016, 3:19 am

    You’re brave! My favourite weddings have all been destination weddings. An added bonus… the hangers on won’t make the trip!

    I have literally no usable advice, other than the best money I spent at my wedding was to get someone to take care of all the details on the day (rather than my wife worrying about them). Good luck!

  • Sylvia @ Miss PF Dec 15, 2016, 10:06 am

    Saw this and thought of this post:

    I don’t know if you guys use travel credit cards, but it’s another one of my hobbies, so thought I would share it with you to lessen the cost of travel for you (and your guests.) 🙂

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