If you’re considering a destination wedding, one of the bigger decisions you’ll make early on is WHEN to have your wedding!

Some engaged couples come to me with a very set-in-stone date – maybe their anniversary, a specific set of dates they have off of work, a meaningful date to their families or their relationship, etc.  That’s totally fine if they do!

Other couples come to me with a general window of time like “spring” or “when it’s not too hot, and not too cold.” 

That’s great, too!

With all of my couples, I talk through the different factors to consider when setting a destination wedding date, because this “small detail” can make a huge difference in the quality of your experience. And my whole job is to make sure you and your guests have a fantastic wedding experience – from travel days, to the vacation and relaxation part of the week/end, to the main event – your wedding!!

So today I want to talk about some of the biggest factors you should consider when choosing a date for your destination wedding – let’s dive in!

Factors To Consider When Setting Your Destination Wedding Date

Let’s start out with factors that you have absolutely no control over.

Weather in the Destination

Depending on your destination, there’s likely a hurricane season to avoid, a rainy/wet season to potentially avoid, “peak” or “high” season when it’s slammed. Warm weather, HOT weather, cooler weather, etc.   Depending on your preferences and needs, weather is a big deal, and you should plan accordingly.  (during our call, ask me about my brother-in-law who sweated through the legs of his linen pants for his destination wedding photos  .. spoiler: they did not consult me)

Peak Season vs Shoulder Season

All destinations have seasons with a huge influx of travelers (peak / high season), mid-level seasons, and low level or “shoulder” seasons. Together, we’ll pick the season that best fits your needs, preferences, and budget (because yes, the season affects the price!)

Holidays

Local holidays in the destination, and often US holidays will also affect your ability to have a destination wedding. First, travel is almost always more expensive during the holidays – so flights, rooms, and more will all cost more. Yuck.  Then most resorts often have ‘black out dates’ where they will not allow events to take place and/or groups to hold rooms over holiday weekends. So a 4th of July wedding or New Years Eve wedding? Sorry, but probably not doable at a resort.

Now here are some more factors to consider when setting your destination wedding date. They’re still ones you can’t control, but are more about the actual resort or property itself.

Wedding Venue Availability

Obviously, the wedding venues you want will need to be available on your chosen dates. Availability changes constantly, and the most popular venues tend to sell out quickly, ESPECIALLY for Saturday / Friday  / Sunday wedding dates. For the best shot at getting what you want (especially if you want a weekend wedding), booking early is the best plan.

Resort Room Availability

Most resorts are pretty large, and tend to have decent availability for wedding groups. However, things like corporate groups, other wedding groups, holidays, peak season, spring break, and more can all affect the availability of actual rooms for you and your guests. This is one of the biggest reasons we utilize a room block contract for groups – to ensure you and your guests will definitely have a room for your chosen dates. I also check on resort availability BEFORE you commit to a wedding date to avoid any availability issues.

Next, let’s dive into YOUR preferences. What’s important to you and your guests? Dates, days of the week, time off, and any other constraints you may want to consider.

Weekend vs Weekday Weddings

Like I said, weekends are the most popular, and for good reason. You and your guests can spend less of your PTO on the trip and take advantage of the weekend! But that also makes weekend weddings a) in greater demand, and b) often more expensive. Some of my couples will opt for a weekDAY wedding, to save a bit of money on the wedding, and get better availability at their preferred wedding venues.

PTO – Time off for you, your family, and your VIP guests

Lots of engaged couples or their VIP guests (read: the most important people who they MUST have present for their wedding) have strict rules about PTO or other big schedule constraints, and need to plan accordingly. If you or anyone on your VIP list (immediate family, BFFs, etc.) is one of those folks, talk to them about their availability in advance!

Significant dates to you or your family

If there are any important dates (numbers, days of the week, anniversaries, etc.) that are significant to you two, your relationship, your family, etc., make sure you mention those during our planning sessions!

Giving enough lead time to save money

For most of us mere mortals, money doesn’t grow on trees. So it’s best to give your guests as much time as possible to decide if they can take PTO, save up, and make payments toward their trip. (thank you DIY payment plan for rooms!). Plus, most of your wedding costs will need to get paid in the last couple of months leading up to the big day. So the earlier you set a date, the longer you ALL have to save and pay!

How to Organize Your Thoughts & Set A Date

Yes, you should consider these factors when choosing your date. But please don’t go on a stressful research spree, cross-referencing all of these factors with your PTO, your brother-who’s-a-teacher’s spring break, Dad’s knee surgery, and more..  

You literally have an expert on your team (that’s me).  Ask for help. Share your constraints.

We’ll work together to find the best possible date for your big day! 

For now, just keep a list of dates that will NOT work, so we know we can rule those out. And start thinking of a general time when you might want to tie the knot!!

Remember, getting too locked in to a specific date can lead to a lot of frustration down the line (lack of availability, etc.). So leaving yourselves open to a window of time is the best bet to find something that works for you and doesn’t stress you out along the way!

I hope that’s helpful!! And remember, I’m here whenever you’re ready to start planning your big day in paradise!

P.S. if you’re considering a destination wedding in 2026, well, the best time to start planning was last year, but the second-best time is NOW!! Don’t delay, so you can still get your pick of gorgeous venues, and you and your guests will have time to take PTO, save, and pay for the trip.  Just click the button below to get started!