Awkward (But Necessary) Questions to Ask Your Guests When Planning a Destination Wedding
(+ How Other Couples Are Navigating Them with Grace)
Planning a wedding abroad is a dream come true—sunshine, jaw-dropping views, and that holiday buzz in the air. But it’s not quite the same as planning a one-day celebration at your local countryside manor. From travel logistics to multi-day events, a destination wedding brings a different pace, mindset, and skill set.
Let’s be honest—while planning the big day is joyful, there are some awkward conversations you’ll need to have with your guests. The kind that feel a little cringey but are absolutely essential if you want to avoid misunderstandings and make sure everyone has a fab time!
Here are the ten slightly uncomfortable questions to ask (plus how other couples are handling them with confidence and kindness):
1. “How do you feel about travelling to our wedding destination?”
Why ask: You might assume your nearest and dearest will be over the moon to jet off for your big day—but travel isn’t always easy for everyone. Budget, health, and time off work can all play a part.
Top tip: Chat casually over coffee or dinner. Most guests will be flattered you’ve considered their opinion. Start the convo early—ideally before you’ve paid big deposits.
2. “Would you be able to contribute to the cost of your accommodation?”
Why ask: If you’re hiring an exclusive-use venue like a Tuscan villa, the price tag can add up fast. Many couples now ask guests to chip in for their rooms, and most guests are happy to do so.
How to handle it:
Create a clear bedroom list or use a travel agent or planner to collect payments. Some couples even open a separate Revolut or Monzo account just for the wedding. If you’re hosting at a hotel, negotiate a group discount so guests can book and pay the hotel directly.
3. “Would you be okay with a ‘cash bar’ after a certain time?”
Why ask: In the UK, it’s perfectly normal to provide a few welcome drinks and wine with dinner, then switch to a cash/paid bar. But in other cultures, that might feel odd or even rude! Know your audience!
Keep it clear:
Set expectations on your wedding website or invites. Many destination venues offer bar packages, so you can tailor the drinks offering to your budget and your guests’ expectations. If you are organising a paid bar, perhaps include ‘bar menu’ on your website with prices of the drinks.
4. “Are you up for a multi-day celebration?”
Why ask: A destination wedding is often more than a single day—it’s a few days of relaxed fun, meals, and maybe a pool party thrown in.
Think about:
What will your guests genuinely enjoy? A laid-back pizza night the day before? A farewell brunch? Consider how much “organised fun” your guests are up for—and how much your budget allows.
5. “Would you be willing to use your annual leave for our wedding?”
Why ask: Most weddings abroad take place midweek, when venues are more affordable and available. But that often means guests will need to use their holiday allowance.
Solution:
Give people as much notice as possible—ideally 12+ months. This gives them time to plan, save, and turn your wedding into their own little getaway.
6. “Will you be bringing the kids?”
Why ask: Children are adorable—but at a destination wedding, they add layers of planning. Think: child-friendly accommodation, travel logistics, meal preferences, and even a babysitter or nanny.
Our advice:
Decide early if your wedding will be family-friendly or adults-only. Communicate it with kindness. If children are invited, consider hiring a nanny for the day or creating a play area (away from the pool)!.
7. “Does anyone have mobility or accessibility concerns?”
Why ask: Many wedding venues abroad are historic—beautiful, yes, but full of steps, cobblestones, and uneven pathways.
Ask before you book:
Check with guests who might need easier access, and ask your venue or planner about layout, walking distances, and bathroom facilities.
8. “Are you happy sharing a villa or apartment with other guests?”
Why ask: Group stays are fun and cost-effective, but not everyone wants to share bathrooms or do communal cooking on holiday.
How to handle it:
Create guest groups with similar vibes—families, uni friends, couples—and give them the option to opt out. Add a few helpful notes about what shared living might involve (like taking turns with breakfast duties, or driving to the local shop for ingredients).
9. “Do you have a valid passport?”
Why ask: It sounds obvious, but expired passports have ruined more than one guest’s plans. And with some countries requiring six months' validity beyond the travel date, it’s worth double-checking.
Include in your comms:
Reminders on your website, save-the-dates, or info packs. Include passport rules, visa info (if needed), and airport recommendations.
10. “Would you like help with travel bookings?”
Why ask: Not all guests are confident travellers. Some will love sorting their own flights and hotels, while others would appreciate guidance or even help booking transfers.
What works well:
Offer a few recommended flight options, group transfer details, and hotel booking links. At WedAwai, we also offer concierge-style travel support, so if your guests want to turn your wedding into a proper holiday, we can help them do just that. Follow our Travel link here.
Final Thoughts
It might feel awkward asking some of these questions, but honesty and clarity go a long way. Most guests are just thrilled to be invited to your wedding abroad, and they’ll appreciate being kept in the loop. Sort out the above questions, and you are on the way to booking your dream wedding venue, where everyone is happy too!
So don’t shy away from the uncomfortable stuff—it helps you plan a stress-free, joy-filled celebration that works for everyone.
At WedAwai, we help couples like you plan destination weddings that are beautiful, practical, and unforgettable. From venue sourcing to guest travel support, we’ve got your back.
Ready to start planning your dream wedding abroad? Let’s chat!
