Planning a Destination Wedding Like An Expert | Willow & Oak Events

Planning a Destination Wedding Like An Expert

Planning a destination wedding can be equal parts exciting and nerve-racking, especially if you’re unsure of the variables you should consider or the questions you should ask. Use this list as a guide to navigate the murky waters of planning a destination wedding, no matter where in the world you’re thinking! Our hope is that you will feel equipped to make informed decisions along the way and feel confident you’re laying the best foundation possible for the celebration of your dreams. Ready to dive in?

Determine A Location

Every destination will come with its own unique set of benefits and challenges, so it’s great to at least narrow in on a single country, region or type of destination before you start planning anything else. Close your eyes and envision every little detail of your dream celebration. Are you with your guests across multiple days? Are there certain destinations that would complement your style loves or the mood you have in mind? What season is it?

As you start to weigh the pros and cons between different destinations, do some research on the weather, seasonality, cultural barriers, budgetary considerations. Ensure the destination is accessible to the guests that are most important to you, not only financially, but considering travel time + logistics as well.

A few good questions to ask in this filtering process include:
1. What locations hold significance for us?
2. Is this location prone to hurricanes, monsoons, blizzards, unbearable heat + humidity…?
3. Will this location be over‑crowded during peak season? Will it be eerily empty during off‑season?
4. How difficult is this location to get to? Consider this from the point of view of your oldest guest all the way down to your youngest guest.

Hire A Planner & Set A Realistic Budget

Early planning can be chock full of stressors around setting a realistic budget, choosing a venue, hiring a vendor team, determining your guest count and more. A local Planner or one who specializes in destination weddings can guide you through this process with ease, helping you lay a solid foundation for the entire planning timeline and wedding weekend from the start.

Not only can they help you define your true wedding vision, they will maximize your financial investments for the entire wedding, often saving money in the long‑run (which you can then invest in the honeymoon, new home, etc). Seasoned planners will gain a solid understanding of your priorities and recommend budget allocations accordingly, always keeping the nuances of your destination + the way they impact the bottom line in mind.

We may be a little biased, but hiring a Planner is a must for destination weddings where the logistical challenges and cultural barriers are heightened.

Say Yes To a Venue That Checks All The Boxes

With a destination selected and a Planner at the helm, you’ll want to confirm your wedding venue next. By now, your Planner will have understood your vision in depth and advised you on a realistic budget accordingly. You’ll want to narrow down to the top 3‑5 venues that align with your style, budget and needs for in‑person site tours. Take some time at each to consider how you feel in each part of the property. Finding the right fit for you is so much more than capacities and curfews, so take some time at each property to consider how you feel in the space.

We share a free guide to choosing the perfect wedding venue that walks you through the most important questions to ask and helps you to filter down to the top choice based on a variety of factors. You can grab the download via our website!

Hire Your Dream Team

The next step is to hire your A‑team of wedding vendors! Start with those vendor categories who book up the quickest and who are only available once per day/weekend (photography, cinematography, entertainment, food & beverage). It can be helpful to spread these bookings out as most will require a 30‑50% deposit to hold your date, though don’t wait too long as many of the top vendors book up 12‑16 months out. Next, you’ll want to secure your floral designer, hair & makeup artists, officiant, cake designer, stationer, calligrapher, transportation, rentals, lighting and so on. Keep in mind that with the design‑based vendors, you’ll need to have a good idea of the deliverables when you reach out for quotes, as their pricing will be based on inventories, scope of work, specific design/variety requests, etc.

With destination weddings, we highly encourage you to hire local vendors wherever you can! Not only does it cut down on travel fees and thus the carbon footprint of your celebration, it’s a wonderful thing to support the local economy of the destination you’re getting married in! Just be mindful that there will often be cultural barriers beyond the language alone, so having a point‑person/coordinator on the ground, at the very least, will save you much time, stress and expense.

Plan Site Visits

You will want to conduct at least one more site visit to the venue at least 3‑5 months before the wedding to get a sense of the space with more concrete design ideas formed. You’ll need to take down many more measurements than you ever thought necessary, understand where every outlet and see how the light falls on certain spaces at the times of day your wedding events will take place (for photography!). If you have a Planner, they typically manage this site visit to take all the nitty gritty out of your planning experience, leaving you to return for the fun bits. Cue: Menu Tasting!

Jasmine climbing on the historic residences of State Street in Charleston
Photo by Hannah Alyssa

Check Major Requirements For Your Destination

Do your research on everything that will be required for getting to your destination (I.e. specific passports/visas, vaccinations, etc). Put simply, making a marriage legal in destinations outside your home country can be a serious hassle, requiring all sorts of paperwork from birth and medical certificates to letters of intent to proof of residency. For this reason, many couples choose to forego this potential headache by having a civil ceremony prior to their departure, but that is certainly not for everyone and by no means the only answer! Just give yourself plenty of time to do your due diligence and make the right decision for you.  

It’s a great practice to mentally walk yourself through the wedding weekend from the moment you pack to the moment you land back home, and make a checklist of every potential hiccup along the way so you can prepare yourself in advance with a little bit of Google! For example, you’ll want to talk to your bridal salon about traveling with your dress and looking through various airline policies to find those that align with your needs before you book your transportation.

Get Inspired

The most memorable destination weddings are those that blend the natural beauty of the destination and the local culture with the personal stories, passions and styles of the couple + their families. You can read our Instagram Guide on finding your Wedding Style for more details on this topic, but for destination weddings in particular, spend some time on your site visits soaking up the location as authentically as possible.

Ask your venue coordinator for their recommendations on restaurants, shops, hiking trails, shows, experiences… Find out what the locals are proud of and what traditions/recipes/musical styles have stood the test of time. Be open to everything and journal as you go. You’d be surprised what you can incorporate into your wedding design both subtly and significantly.

Prepare For Logistical Challenges

A seasoned planner will take the burden of cultural barriers and logistical challenges off your shoulders. They’ll be able to anticipate common misconceptions international production teams might have for custom builds, prepare for shipping challenges from the get‑go so you aren’t missing important decor elements like quality linens and put out any fires before you even get there the week of the wedding. And these are just a few examples! You’ll also want to have a solid understanding of the route your transportation company will take to ensure the roads are wide enough for shuttles, learn about any special permits or inspections required for tents or installations, research the specs + loading capacities of elevators any rentals will need to travel on, etc.

Jasmine climbing a small house with blue shutters in the historic district of Charleston, SC
Photo by Hannah Alyssa

Prioritize Guest Communication

Over‑communication is paramount for weddings where guests will be traveling internationally. You can expect between 40‑60% of your invitees to RSVP Yes for a destination wedding, and the farther in advance you can provide details about your very special celebration in a very special destination, the better. Plan to send Save‑the‑Dates out between 8‑12 months before the wedding, and be sure to provide a digital resource they can turn to for more details as they plan their travel, accommodations, etc. Even if you prefer a sense of mystery for your guests, you can have a password‑protected wedding website that’s well‑designed and shares important timings, addresses, room block details, dress code, advice on where to fly in + out/how to get around once they arrive, recommendations for local restaurants, activities, shops, etc.

We love to include welcome packets in Wedding Welcome Gifts reiterating details like the weekend itinerary, transportation schedules, dress code reminders and a sweet note from the couple thanking them for traveling all this way to celebrate with them. It sets the tone for an energetic weekend filled with warmth, fun and thoughtfulness all around.

It’s always a nice touch to reach out to your guests 2‑3 weeks before the wedding with important reminders to help mitigate the risk of anyone texting you when you’re just trying to enjoy a cooking class in Tuscany with your VIPs a couple days before the official festivities begin. Many wedding websites enable you to send a single e‑blast to all your guests at once, and you can add the contact info for the point person they can get in touch with should they have any questions between now and then.

Managing all guest communication is what we do for our couples, and it is truly a game changer. From collecting guest addresses to sending out these important reminders to communicating time sensitive updates the wedding weekend due to unforeseen events, having your planner step into this role on your behalf sets you and your guests up for success in all the right ways.

Plan An Epic Itinerary & Celebrate!

Anticipate hosting a couple different events for a destination wedding. With your guests traveling such a far distance, it’s nice to kick things off with a Welcome Dinner at the very least! One of the perks of destination weddings is that the day of week matters a little less if your guests are already taking more than a “weekend off”, so you can often negotiate better rates for events happening on weekdays. If you can, give your guests some opportunities to hang with you outside of the wedding events too! Maybe you have a couple different options for group activities like a sunrise hot air balloon ride or horse riding on the beach. Don’t feel obligated to fill every second of their time in the destination, as you’ll want some breaks to recharge and be on your own, but throwing a few bones here and there can make the wedding experience feel that much fuller.

Explore some of our favorite destinations to wed (and our recommended venues in each) here next!

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