How To Plan Your Destination Wedding Itinerary - Willow & Oak Events

How To Plan Your Destination Wedding Itinerary

When it comes to planning a multi-day destination wedding itinerary, there are a few key things to remember. In fact, it wouldn’t hurt to scribble these reminders on sticky notes you plaster everywhere from your office nook to your coat rack. 

01 || Pace is everything

02 || Quality over quantity 

03 || Experience is more memorable than decor

Whether your guests are well-traveled or not, the pace of events will ultimately make or break their experience. Schedule your festivities too close together, and they may fall victim to burnout before the main event. Create too much of a lag in activities, and the antsy will win over anticipation… a mood no one wants their guests to feel before the wedding day. 

In our experience, the sweet spot is this: 

Day 1: Welcome Event 

At the very least, we’d highly recommend hosting some sort of welcome cocktail party that allows your guests the opportunity to say hello to you, settle into the spirit of the destination and mingle + nosh with the other guests they may not have met before. It’s the perfect ice breaker! Especially if you have some sort of group activity or excursion opportunities planned in the days to follow. 

While your loved ones are traveling to the destination because they are eager to celebrate you and hey, they will probably get to piggyback a vacation of off this… it’s important to remember that this is a significant investment of their time and money. So even if you can’t host a full-blown Welcome Event, having some sort of planned moment where they can spend some quality time with you (and vice versa) is worth its weight in gold. 

That being said, we are 100% in the camp that believes a knock-your-socks-off Welcome Event can set the tone for the entire weekend. And honestly, if you have to choose between this and a farewell brunch/activity, the Welcome Event always prevails. More on the why shortly. 

For us, the makings of an unforgettable Welcome Event involve the following:

01 || An invitation for everyone on the wedding guest list 

02 || A laidback, playful and footloose fancy-free vibe

03 || Unique entertainment (Bonus Points if it’s a surprise moment during the party!) 

04 || Great food + drink with fun presentation

05 || Subtle opportunities for guests to break the ice

This event doesn’t need to be a carbon copy of the Wedding Day. No one wants to attend the same event two days in a row, and let’s face it, the Welcome Event shouldn’t overshadow the actual wedding day! Instead, think about how you can play up the destination a bit more or follow a theme that relates to your couple story/shared passions. The Welcome Event should still feel cohesive with the weekend as a whole, but you absolutely have permission to color outside the lines a little bit for this one. 

We could go on forever about how to plan an epic Welcome Event that’ll have you + your guests grinning from ear to ear, but for now we’ll leave it at this: Consider how you want your guests to feel during the wedding weekend from start to finish. Ask yourself how you can craft an experience that builds from one part to the next. How can you lay out the timeline, the decor, the entertainment, the speeches, etc. to achieve these feelings in each moment so that they culminate in a wedding night finale that has everyone floating on Cloud 9? 

Day 2: Guest Free Day +  Rehearsal Dinner for the VIPs only 

If you’re going all out for a Welcome Event, it’s always nice to provide an intermission of sorts that allows your guests to recover from a fantastic night of partying. Not to mention the jet lag they’ll probably be combating at this stage as well. We find that most destination wedding guests want some time to themselves during the weekend anyways. They love having time to themselves to explore the surrounding areas + activities that interest them the most, without a feeling of obligation or fear of missing out on something you’ve planned. 

If the thought of leaving guests to their own devices makes you sweat a little, it’s perfectly acceptable to arrange 1-2 excursion opportunities that you do or don’t participate in yourselves. This isn’t something you should feel obligated to pay for by any means. Whether it’s a group outing to the bustling village market, a vineyard tour + tasting or a cooking class with a renowned chef, we’ve often had couples mention excursion opportunities on the wedding website with brief details about the timing, what it will entail, the price per person and the deadline/instructions for securing their spot. This doesn’t need to happen on Day 2 either. Anytime during the wedding weekend is fair game! It ultimately depends on the official events you decide to host in the end.

Meanwhile, you + the VIPs will likely be conducting a Ceremony Rehearsal at the venue on this day. The time of day will depend on a number of factors, not the least of which is the venue’s availability for the rehearsal. But typically, having the Rehearsal take place in the late afternoon/early evening when it’s a little bit cooler and everyone has had the opportunity to sleep in/do what they want during the day is great. The Rehearsal can be followed by a formal or informal rehearsal dinner for the VIPs only, which gives you that quality time you’ve been craving with your most important people now that everyone has settled into the destination and weekend’s flow a bit more. 

This can be a great opportunity to indulge in a bit more personalization than you might be able to for the larger guest count, so if you’ve had your eye on extra special table decor, florals or hand-calligraphed elements, this is a great time to treat your people! If you’d prefer not to have this full day break between wedding events for your guests, it’s perfectly fine to have a VIP only festivity like this the day before the main events for all the guests kick off instead. 

Day 3: Wedding Day 

Pretty self-explanatory! The wedding day timeline will ultimately depend on the venue’s rules (not only for the party curfew, but also for parameters around setup/load-in time for vendors and the like). You’ll also want to factor in things like sunset time, which will have a huge impact on the photography. Be sure to discuss the best options with your Planner and Photographer based on all the elements you’ve got lined up for the wedding! On average though, we typically see a minimum timeframe of 8-10 hours for your wedding guests to be ). It’s a full day indeed!

Making sure you keep your guests comfortable + informed throughout every part of the day is of the utmost importance. They may not remember the specific hors d’oeuvres or the flower varieties at the ceremony, but they will absolutely remember the FLOW. Your vendor team can and should guide you + your guests through the wedding day moments, so no moment every feels awkward, stagnant or rushed, but it’s always a great idea to discuss this priority with them throughout the process so they know they have your permission to keep the timeline flexible as needed. There are many factors they will be considering in addition to guest comfort levels, from vendor contracts + overtime rates to hard curfews and even how the weather (rain, wind, unbearable heat, snow flurries, etc), so as they weigh these variables affecting timeline adjustments against the “in the moment feeling”, rest assured that they are in your corner always!  

Day 4: Farewell Activity

We hesitate to say brunch because in our experience, the sendoff brunch tends to feel obligatory for guests, even if it’s not. And let’s face it. If you’ve thrown a really great party the night before, your guests will be exhausted… and probably a little bit hungover too. The last thing they’ll want to do is roll out of bed, put on some makeup and go to another meal where they feel obligated to converse. It’s just the truth! So if there’s one thing you take away from this convo, it’s this: Give your guests ample time to recover! 

You don’t have to leave without saying goodbye, by any means! We simply suggest organizing something extremely low-key and later in the day if you’re going to follow up the wedding day with an encore of sorts. Activities they can participate in are perfect. So whether it’s a casual pool hang out they can literally roll out of bed for, an afternoon lazing away on sailboats in Capri or a non-obligatory invitation to join you for drinks at your favorite beach club, keep this day simple! 

Overall, keeping the complexities of your wedding events to a minimum will win you a lot of points in the guest experience department. Go all-in for those wow moments you have in mind, but don’t feel like you have to do it all. And while we are ALL for thoughtful, beautiful and layered designs that are bursting with storytelling symbolism, at the end of the day, your guests will remember the moment they were surprised by a strolling jazz band during the Welcome Dinner than the number of floral arrangements on the table. 

There are a lot of ways to create really impactful moments throughout your day, without spending anything extra. Brainstorm different ways that you can use the musicians to transition guests from one part of the event to the next (i.e. a second line from Cocktail Hour to Dinner). Think about who your guests are + what they enjoy. Are they older or younger? Do they like to dance? Do they prefer deep conversation? Are they big foodies? How well do they already know each other? How many of them will be flying solo? What kinds of ice breakers can you provide so that no one ever feels awkward or left out?

We hope this sheds some light on how you can craft a multi-day wedding experience that keeps your guests comfortable, engaged and fresh for every moment you have planned. Use our email scripts for wedding guests to keep them informed in the months leading up to the celebration and discover some of our favorite guest excursions in Provence via our Instagram Guide here next! 

Happy planning! 
Haley

PHOTOGRAPHY: Flora & Grace // PLANNING & DESIGN: Willow & Oak Events // FLORAL DESIGN: Floraison Paris // VENUE: Bastide de Gordes // PAPER GOODS: Who Drew // HAIR & MAKEUP: Ylva Langenskiold // GOWNS: Cara Cara and Lela Rose // TABLETOP RENTALS: Maison Margaux // FURNITURE RENTALS: Be Lounge // PRODUCTION RENTALS: D&X Events // WELCOME DINNER BAND: The Gypsy Queens // STRING TRIO: Wedding Music in France // COCKTAIL HOUR & DINNER MUSICIANS: Jazz Around Midnight // PARTY BAND: Brightlights 

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