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Planning a Destination Wedding in Few Months

A checklist and some insight

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Sam Livingston
Mar 17 2020 | min read
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A checklist and some insight


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Planning a wedding in about five months turned out to be… not as daunting as it sounds. We got engaged at the end of March (2019) and there ultimately wasn’t a need for us to wait well over a year to get married the following summer. Neither of us particularly thrives in the heat and the odds of getting hit with a 90ºF day from June through August was all too real. We also didn’t want to spend a year and a half planning a wedding when we knew we wanted something small and fairly low-key.



We technically had a seven-month engagement, but we didn’t get any actual details locked down until about two to three months in, hence planning in four to five months. It was a bit stressful at times, but in hindsight, I would definitely do the whole process over again. It ultimately panned so perfectly!



Naturally, we went back and forth on where we wanted to have the wedding, how many people to have attend and then available dates that lined up with our photographers and videographer, locations and our bridal parties’ personal schedules. You can’t please everyone or make everything work, but you can sure get close.

We decided on more of an elopement in Marfa, TX, one of our most cherished places, with our immediate families and a handful of close friends. It ended up being 25 of us in total! Which, as I may reiterate several times throughout the course of this post, was absolutely the way to go. All of the pressure was taken off— there was no chaos or rush from the moment we got there to the moment we left. Everything just felt so peaceful and relaxed.


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We also decided on having a party in Portland so we could invite other family members and friends to celebrate with us— we had about 55 guests at this one. Interestingly, it felt pretty overwhelming for me and I didn’t really know what to do with myself because I wanted to make sure I got to talk to everyone and barely even made a dent. That said, though, it was quite serendipitous to have so many loved ones in one room from all over the country and the world, but I could not be more grateful that we chose to have everyone come to a completely separate party.



We booked a beautiful room in one of our favorite restaurants and bars in town, had an excellent jazz trio play all night, and enjoyed an amazing meal with everyone. Really good food was a top priority, so keeping it small allowed us to create the menu we wanted. We had a sweet friend give a speech, and otherwise, it was all party, no formalities (or garter belt tossing), and was truly the most fun. Narrowing down guests is so difficult: definitely the hardest part about planning. We could have easily invited 200 friends, but did our best to keep it intimate and allow ourselves the space to attempt to share part of the night with everyone there. Also, the most common regret I hear about weddings is that couples wish they would have made it smaller - having photographed many a wedding, myself - I was primed to make this decision if it was the last thing I did, haha.


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Let’s jump into our wedding planning checklist.


Month 1

  • Decide on a budget

  • Choose several wedding dates that work (you may have to plan around preferred vendors’ schedules based on the shorter notice. We chose four dates that would have worked.)

  • Create a guest list

  • Choose a venue or location, tour it if needed, and book

  • Choose and book a photographer and/or videographer

  • Choose a restaurant, caterer or decide what you’ll do for dinner

  • Choose your music situation, start building playlists


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Month 2

  • Once you know your location, book airbnbs or hotels

  • Invite your bridal party and/or friends

  • Finalize your guest list

  • Decide on florals: bouquets and decor

  • Create save the dates and/or invitations

  • Send out save the dates (We did everything on Typeform. My husband designed a really beautiful wedding website and we collected RSVP’s this way. It was so efficient.)

  • Make plans for your rehearsal dinner if you’re having one

  • Create wedding website and registry

  • Order wedding invites

  • Decide on wedding ceremony outfits

  • Choose wedding bands

  • Decide on bridal party attire

  • Write vows (I chose to do this right after we got engaged, before stress and finite details of planning were at the forefront of my mind and then I added on to them as the day got closer. Highly recommend this!)

  • Book flights to destination


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Month 3

  • Plan and book honeymoon if applicable: I use Scott’s Cheap Flights for everything. (I never pay more than $400 for international flights this way)

  • Figure out what’s necessary for a marriage license at your destination

  • Finalize playlists and music selections

  • Finalize decorations and florals

  • Ceremony outfit alterations

  • Decide on menus, programs, place cards/etc. (I used Artifact Uprising for everything.)

  • Make changes to menu for reception and rehearsal dinner

  • Book rental cars

  • Create seating charts

  • Make wedding weekend timeline and share with family, bridal party, vendors

  • Purchase gifts for bridal party


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Month 4

  • Purchase gifts (or experiences) for each other

  • Write cards for family and friends

  • Make final touches to vows

  • Pack a carry-on with essential items (in case your checked bag gets lost)

  • Pack less-essential items in checked bag

  • Write down a long list of everything you’ll need to do once you get to your destination, plan out the travel day, grocery list, etc. and share with your friends

  • Get married (!!!)



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Not that bad, right? It really wasn’t too overwhelming, considering we essentially had to choose a field on the side of the road to say our vows in and then choose a restaurant to have dinner at afterwards. 

If all of the finite details like place cards and menus don’t need to be immaculate, then there’s really not all that much to be done. It’s a fairly manageable planning schedule, I think. :)

I really hope that this guide was helpful for you if you’re in the elopement or tiny-wedding planning phase at the moment. For other wedding-related posts, go here.



Disclosure: I may earn a commission at no extra cost to you if you decide to buy any of the products I refer to & promote. All opinions are my own.