How to Plan a Destination Wedding in Three Months

While remaining (relatively) sane

By Zarya Alexandra Rubin

When people ask me when I actually got engaged, I’m not sure whether I should answer with the practical proposal that took place while looking at a calendar three months before my wedding, or the romantic, hearts-and-flowers-and-a-ring proposal that took place at the restaurant where we had our first date, a month later.

Like most women, I had dreamed about my wedding and all the trappings since early childhood, including the dress, the ring, the groom, and being swept off my feet. Of course, the sweeping took a good 15 years longer than I had anticipated, as I didn’t meet my prince charming until I was almost 40 years old.


The good news? I was mature, together, knew what I wanted, and financially solvent enough to actually pay for it myself.

The bad? I didn’t want to wait. When you’ve waited this long, any longer seemed ridiculous, and if I had any hope of having children without a shotgun ceremony, I had no time to waste.

Here’s how it all came about, how I did it in less than three months (without a wedding planner), and still managed to have the happiest, most stress-free day of my life.

  1. Save the Date: the date of your wedding is the most important part, as it sets the tone for the location and type of wedding you will have. Make sure to take into account weather, national and religious holidays, work events, and any other curveballs life throws you. I don’t like the cold, but I also got engaged in July and didn’t want to wait until the following May. My sister was living in Australia at the time and was about to give birth. Not conducive to attending a U.S.-based wedding, but I knew they were planning to return to North America in early October. My husband is from Oregon, and we decided it would be very special if we got married out there (even though we were living in Atlanta, and I had never been!). So between the fall creeping in and my sister’s impending arrival, October 6th was the one date that worked. The fact that it was Columbus Day weekend didn’t deter me, as it’s certainly not a major holiday.
  2. A Family Affair: the guest list is a tough one, and one of the earliest decisions you and your fiancé will have to make. Do you want a small wedding or a large one, and what can you afford? A long guest list means $$$. Keep in mind that a significant number of folks will be no-shows, especially if it’s a destination event. After adding your immediate and extended family, close friends and work colleagues, you may have to whittle down ruthlessly. Don’t feel obligated to invite everyone you know nor everyone who has ever invited you to your wedding (however if you did attend, you might want to consider adding them to the list). In the end, we invited 100 people and 70 attended. It was the perfect number for socializing with everyone we cared about without feeling overwhelmed or that we never got to spend time with folks.
  3. Save-The-Virtual-Dates: according to most timelines, by the time we got engaged, we really almost had to send out our invitations. I’m an aesthete and a perfectionist and had long drooled over intricate lace overlay, deckle-edged, embossed invites, letter-pressed, hand-stenciled, etc…SIGH…but there was no time. One of the biggest compromises and best decisions I ever made was to use Paperless Post for my save-the-dates as well as my invitations. An online “freemium” service (initially free to send basic cards, but certain designs and features require upgrades and minimal payment), Paperless Post lets you track all aspects of the invite process, request RSVPs, allows guests to comment, and was easy as pie to use.oregon-destination-wedding
  4. Trying The yes, seriously, go ahead and sign up. I thought I was above all that bridezilla fray, I wanted my own indie-style wedding, I didn’t need to commune with other whiny brides in their early 20s complaining about cake toppers, but it wasn’t at all what I expected. It’s free, it’s easy to navigate  and there are a number of excellent resources from vendors and regional directories to articles and the essential Checklist! Ok, the checklist did stress me out because I was already woefully behind before I even started, but once I eliminated the non-essential items (beauty rituals months before the wedding???) and checked off as much as I could, it was a lifesaver.
  5. Say Yes to the Dress: naively, I thought three months was a substantial amount of lead time to find a wedding dress. No problem! I’ll go to some larger stores, some boutiques, some high-end places, some consignment shops, some trunk shows, and eventually I’ll find the dress of my dreams! I quickly had a rude awakening when I learned that most dresses take SIX MONTHS to order!!! Most high-end bridal shops will smirk disdainfully at you while giving you the Pretty Woman treatment (“I’m afraid we don’t have anything for you here, darling”) when they learn of your impending nuptials (people will also stare suspiciously at your midsection). I swallowed my pride, went to David’s Bridal, and literally bought the third dress I tried. And I could not have asked for anything more breathtaking. If I hadn’t gotten so lucky, I would have tried sample sales and other off-the-rack options, or shops that re-purpose used wedding dresses and donate proceeds to charity. I know a friend who bought her dress that way and looked absolutely stunning. Make sure you factor in undergarments and exorbitant alterations into your overall dress price.
  6. destination-wedding-outdoor-mountainsLocation, Location, Location: once you have a date and an idea of your guest list, the most important piece that needs to fall into place is the location. Decide if you want indoor or outdoor (risky, but in my mind, a non-negotiable); religious or secular; and whether or not you want the ceremony, location, and accommodations to be in the same place. This may be the area you have to compromise on the most, or, in my case, a change in perspective means you end up with exactly what you dreamed of. See, I love wine and always wanted to get married at a winery. The vines, the vino, the rustic romance…and Oregon seemed like the perfect place to live out my Pinot Noir fantasies. Unfortunately, wineries are popular destinations, and the over 20 that I tried had no availability. The more I investigated and came up empty, the more I realized I actually did NOT want a wedding at a winery. First of all, they often don’t hold many guests, they don’t have on-site catering, and very few have hotel facilities. This would mean drunken guests would have to drive back in the wee hours to their B&B, myself included, and this didn’t sound great. In the end, my fiancé remembered attending a conference at a high-end mountain lodge on the Washington-Oregon border, Skamania Lodge, and suggested we take a look. Miraculously, they had our date available (although earlier in the day than we had planned, but, again, compromise is the name of the game!), and provided full service: guest accommodations, catering, table linens, bar, lighting, audio-visual set-up, and the most attentive and thoughtful wedding planner. I could not have asked for a better location or better service.
  7. Bridesmaids Was a Great Movie: I love my girlfriends more than almost anyone, but the thought of forcing them to all dress alike and line up in a row just seemed, well…unnecessary. When you have really tight timelines, you just have to decide which aspects of your wedding are essential, and which are extras that you can live without. For some folks, a coordinated bridal party may not fall into that category, but for me, this one didn’t make the cut. That’s not to say I didn’t have three best girls and my sister up there looking gorgeous (and, oddly, wearing matching colors despite several continents and countries separatingwedding-cake-fall-flowers them).
  8. Let Them Eat Cake: I made a trip out West to visit family, but also to find vendors, visit the wedding venue, and generally feel calmer about the fact that this was all taking place 3,000 miles away. I highly recommend a site visit and tastings wherever possible. We didn’t end up tasting the food, but selected the menus, but did find an incredible artisanal bakery in downtown Portland, La Joconde where I had the most delicious and elegantly understated wedding cake, complete with real flowers. I wasn’t willing to compromise on the quality or taste of the food, being a foodie and having lived in New York City for a decade.
  9. Flower Power: yes, flowers are an important part of any event, particularly a wedding, but they can also add many, many figures to your budget. I decided to go light on the flowers, instead relying on the natural beauty of my venue, and opting for a traditional Jewish huppah, or arbor, that added just the right touch to the ceremony. The table settings were simple and spare, with antique multi-sized vases and seasonal field flowers that matched my autumnal bouquet. I didn’t want anything fussy or frilly or overdone, and luckily Bloomsbury Florist, a tiny local storefront in Stevenson, Washington, fit the bill perfectly! They understood my vision and my budget, and even though the florist and I never met we managed to connect over email and phone to ensure we were on the same page.
  10. A Picture is Worth a Thousand Words: your wedding photographer may be the most important vendor you hire. Long after the band has finished playing and the cake has been consumed, your photos and your memories are what remain to memorialize this one incredible day. I also learned quickly that photographers aren’t cheap and they book up really fast during wedding season. Luckily, they all have gorgeous websites that display their work, so you can decide if you like their aesthetic and overall approach to capturing the event – journalistic, classic/traditional, or some combination of the two. Another thing I learned is how tight the wedding photographer community is, and each time I came up against a booked shutterbug, they would refer me to trusted colleagues who might be available. It was through this method that I happened upon Jennifer Boyle a Seattle-based photographer who had been living in New York, and somehow agreed to shoot my Oregon/Washington wedding! Not only were Jenny’s photos magical, technically brilliant, told a story and captured the emotional moments, she was also there for me during my mini-meltdown the week before my wedding when the weather forecast looked grim. You can’t ask for more in a wedding photographer. The one regret I have is that I never had time for engagement photos, which is often part of the package that your wedding photographer will offer, but the fairytale of my wedding day more than made up for it.outdoor-destination-wedding
  11. Etsy, Pinterest, and Amazon, Oh My!: the Internet is your friend when planning a wedding on the fly. For every special, unique, individual touch I wanted, I went to Etsy, a repository of quirky crafts and quirkier vendors. I lost many, many hours ordering blue “I Do” stickers for the bottom of my shoes, a gorgeous raw silk guestbook, and a custom-made lace bolero from Israel that was a fraction of the price and infinitely more beautiful than anything I found in stores. Pinterest is the ideal place to make a wedding look-book and idea board, view other brides’ pins, and keep track of those cool shoes you saw on some website you can’t remember. I didn’t get much on Amazon despite doing most of my everyday shopping there, but I did end up getting my hair accessories at a fraction of the price of more boutique vendors. I also used a really cool website to create a custom wedding color palette for free! Sounds overboard, but really helped set the tone of the overall design theme.
  12. It Takes Two to Tango: one of the most important lessons of wedding planning is: don’t forget your groom. While men are genetically disinterested in almost every aspect of the prep, leaving the lion’s share of agonizing and color-matching to the bride, find things that do matter to your fiancé and put him in charge of those items. My husband picked the band, took care of the wedding rings, and weighed in on the menu, cake, table stationery and photographer. And we wrote our own vows (well, I wrote mine, and he winged his, which left not a dry eye in the house). Ultimately, the devil is in the details, and after months of planning, it goes by so fast. Things will go wrong (the bottom of my dress was almost irreparably crushed during our planes, trains, and automobiles journey), but you won’t remember them; the only thing that really matters at the end of this one incredible day, is that you will be husband and wife.


All photos courtesy of Jennifer Boyle.

Thanks for doing such a great job with the article/photos! I hope it inspires brides and would-be brides everywhere!